CHEM2021 Online Conference Program July 12-13, 2021
Sponsored by Welcome
We acknowledge the Wurundjeri people of the Kulin Nation on whose unceded lands the RACI Victorian Branch is located and on which we live and work. We pay our respects to their Elders, past and present, and to First Nations people attending this event. ______
Welcome to CHEM2021! Welcome to CHEM2021, the Royal Australian Chemical Institute (RACI) Victorian Branch’s first ever conference run for early-mid career chemists by early-mid career chemists. This is a conference to highlight the outstanding work and achievements of early-mid career chemists working in Victoria. Our aims are to provide an opportunity for EMCR chemists to speak about their work, network and make connections with their peers, and to celebrate the diversity of Victorian chemists and their work in different fields of chemistry.
Our plans for an in-person conference in 2020 were dashed, but we see the benefits of a virtual platform that reduces costs for the conference – and therefore attendees – and allows more people to attend who might otherwise find it difficult to travel, or spend several days attending a conference in person. We hope that the virtual interactions at this conference lead to better connections and even collaborations between attendees, as well as offering inspiring insights into the variety and quality of the work being done by EMCR chemists in Victoria.
Thank you for joining us at CHEM2021. We hope to see you in person at future events.
Chem2021 Organisers: Katie Ganio, Manuela Jörg, Anitha Kopinathan, Susan Northfield, Rajesh Ramanathan, Claire Weekley
Harassment and Bullying Policy The RACI is dedicated to providing a harassment-free conference experience for everyone regardless of gender, gender identity and expression, sexual orientation, disability, physical appearance, body size, race, age or religion. The RACI will not tolerate harassment of conference participants in any form. Conference participants violating the RACI Anti-Harassment Policy may be sanctioned or expelled from the conference without a refund at the discretion of the conference organisers.
If you experience any of the behaviour described and/or you feel uncomfortable or unsafe at any time throughout CHEM2021 please contact one of the conference organisers.
Diversity and Inclusion Policy This conference is organised in accordance with The RACI Diversity and Inclusion Policy. We recognise that people come into chemistry from diverse cultures, backgrounds and experiences. We invite and welcome a diverse community of talented people to this conference with a culture of mutual respect. We aim for transparency, reflection and learning and encourage suggestions and feedback (to the organisers or to RACI) for improving the accessibility, inclusion and diversity of this conference.
1 Sponsors
The RACI is the professional body for the chemical sciences in Australia. The mission of the RACI is to be the voice of chemistry in Australia and to advance the professional interests of its members. You can find out more about upcoming RACI events here and more about the Victorian Branch here.
You can also find RACI on Twitter, LinkedIn, Facebook and Instagram.
We are Merck, a vibrant science and technology company. Science is at the heart of everything we do. It drives the discoveries we make and the technologies we create. The passion of our curious minds makes a positive difference to millions of people’s lives every day.
In Healthcare, we discover unique ways to treat the most challenging diseases, such as multiple sclerosis and cancer. Our Life Science experts empower scientists by developing tools and solutions that help deliver breakthroughs more quickly. And in Electronics, we develop science that sits inside technologies and changes the way we access, store, process, and display information.
Everything we do is fueled by a belief in science and technology as a force for good. A belief that has driven our work since 1668 and will continue to inspire us to find more joyful and sustainable ways to live.
We are curious minds dedicated to human progress. Experience our products at: www.sigma-aldrich.com | www.merckmillipore.com
CSIRO is Australia’s national science agency and innovation catalyst, collaborating to boost Australia's innovation performance. At CSIRO, we solve the greatest challenges through innovative science and technology.
2 CHEM2021 Conference Program
Merck Virtual Poster Session, from July 5
The website link will be made available to all registered participants on July 5.
Conference Day One, Monday July 12, 09.30 - 13.45 AEST
The link to the Zoom Webinar will be made available to all registered participants. This session features oral presentations by Plenary Speakers and Speakers Selected from Abstracts.
09:30 - 09:45 Welcome and Open – Dr Susan Northfield
09:45 - 10:15 Plenary Speaker – Dr Katherine Locock
Physicochemical properties of protein-protein 10:15 - 10:30 Dr Jessica Holien interaction modulators Probing chirality with supramolecular 10:30 - 10:45 Dr Carol Hua systems 10:45 - 11:15 Morning Tea Ionic liquids and plastic crystals utilising the 11:15 - 11:30 Dr Colin Kang oxazolidinium cation: the effect of ether functionality in the ring
11:30 - 11:45 Laena D'Alton DIY medical diagnostics and health testing
11:45 - 12:00 Debjani Ghosh Efficient production of xylooligosaccharides
Lubricin (PRG4): a versatile protein for 12:00 - 12:15 Dr Saimon Silva electroactive surfaces 12:15 - 13:00 Lunch Break
13:00 - 13:30 Plenary Speaker – Dr Shane Devine
13:30 - 13:45 Poster Celebration Information
Merck Virtual Poster Celebration, Monday July 12, 19.00 - 20.00 AEST
This session will feature flash poster talks, the award of poster prizes and a presentation by Professor Emeritus Frances Separovic.
The link to the BlueJeans Webinar platform will be made available to all registered participants.
3 CHEM2021 Conference Program
Conference Day Two, Tuesday July 13, 09.30 - 13.45 AEST
The link to the Zoom Webinar will be made available to all registered participants. This session features oral presentations by Plenary Speakers and Speakers Selected from Abstracts.
09:30 - 10:00 Plenary Speaker – Dr Yuning Hong
10:00 - 10:15 Dr Moya Hay Ligand tuning in cobalt complexes for valence tautomerism
10:15 - 10:30 Arpita Poddar Metal-organic-frameworks as non-viral gene delivery vectors Optimisation of 5-substituted 10:30 - 10:45 Dr William Nguyen 2-acylaminothiazoles as potential HIV-1 latency reversing agents 10:45 - 11:15 Morning Tea Quantification of pharmaceuticals in surface 11:15 - 11:30 Dr Benjamin Long waters and riparian flora of a south eastern Australian river system
11:30 - 11:45 Amy Thomson Synthesis of interchain dicarba insulin analogues
11:45 - 12:00 Dr Wenyue Zou Polyoxometalates for colorimetric sensing applications Painters, puzzles and phosphorescence: 12:00 - 12:15 Dr Tim Connell understanding triplet excited states in iridium(III) complexes 12:15 - 13:00 Lunch Break
13:00 - 13:30 Plenary Speaker – Professor Oliver Jones
13:30 - 13:45 Awards and Close – A/Prof Rajesh Ramanathan
RACI Victorian Branch Trivia Night, Tuesday July 13, 19.00 - 21.00 AEST
Conference registration includes the Branch Trivia Night! The link to the Zoom meeting and Kahoot! Quiz platform will be made available to all registered participants.
4 Plenary Speakers
Dr Katherine Locock, CSIRO
Dr Katherine Locock is a Senior Research Scientist in the Manufacturing Business Unit of the CSIRO in Melbourne, Australia. Her research focuses on the development of biologically active polymers, based on CSIRO’s patented RAFT technology. Her current work is focused on new polymer-based antimicrobial therapeutics. This patented technology is highly effective against a broad spectrum of virulent bacteria and fungi, even several strains that show resistance to common antibiotics.
Prior to the CSIRO, Katherine held a position as an Associate Lecturer in Pharmacology at the University of Sydney, where she focused on rational drug design to develop GABA analogues as potential treatments for Alzheimer’s disease and mood disorders.
Katherine is also committed to encouraging more Indigenous Australians to take up STEM education. Katherine was selected as the AIPS Victorian Young Tall Poppy of the Year Award in 2016, received a Julius Career Development award in 2016 and CSIRO Staff Association Women in Science award in 2013.
5 Plenary Speakers
Dr Shane Devine, Monash University
Dr Shane Devine received his Bachelor of Science (Honours) from La Trobe University, Australia and undertook his PhD there under the guidance of Dr Les Deady studying novel heterocyclic systems. He then moved to Monash Institute of Pharmaceutical Sciences (MIPS), where his research has included the design and synthesis of G protein-coupled receptor ligands, including the adenosine and muscarinic receptors and novel anticancer agents. More recently, his focus has shifted to antimalarials inhibiting the essential protein target, apical membrane antigen 1 and antimalarial compounds that act via unknown mechanisms of action. During his time at MIPS, Shane has gained significant experience (>15 yrs) in synthetic medicinal chemistry, culminating in >30 peer-reviewed publications. Alongside his research, Shane actively enjoys teaching to undergraduate and postgraduate students at Monash and co-supervises five PhD students involved in his malaria and cancer based research projects.
6 Plenary Speakers
Dr Yuning Hong, La Trobe University
Dr Yuning Hong is a Senior Lecturer in the Department of Chemistry and Physics at La Trobe University. She received her Ph.D. in Nano Science and Technology (2011) from Hong Kong University of Science and Technology (HKUST) under the supervisor of Prof. Ben Zhong Tang. She held postdoctoral positions in biophysical chemistry in Prof. Ekaterina V. Pletneva’s group at Dartmouth College, US, as Research Assistant Professor in HKUST, and as McKenzie Fellow at the University of Melbourne. She is an ARC DECRA Fellow (2017-2020) and the recipient of RACI Rita Cornforth Lectureship award (2018). Her research focuses on developing new fluorescent probes for the study of protein misfolding and proteostasis in neurodegenerative diseases.
7 Plenary Speakers
Professor Oliver Jones, RMIT University
Oliver Jones is a Professor of Analytical Chemistry at RMIT University. He obtained his PhD from Imperial College in 2005 and then worked at Cambridge University and the University of Durham before moving to RMIT in 2012 to get a ‘few years’ experience working aboard; nine years later he is still there. Professor Jones’ work focuses on tracking the fate and behaviour of pollutants in the environment and reducing their impact. He has developed many new methods, particularly in Chromatography and NMR for this purpose. He is also very keen to communicate science to the public and tweet regularly as @dr_oli_jones
8 Plenary Speakers
Professor Emeritus Frances Separovic AO FAA, University of Melbourne
Frances Separovic is a Biophysical Chemist based at the Bio21 Institute, University of Melbourne, where she studies the structure and dynamics of molecules in biomembranes. Frances joined the University in 1996 and became the first woman professor of chemistry (2005) and Head of School (2010). She is currently president-elect of the Biophysical Society (USA), Council member of International Union of Pure & Applied Biophysics (IUPAB) and Division I member of IUPAC. Frances has had several senior roles in professional societies, including General Treasurer of Royal Australian Chemical Institute, RACI. She is a Fellow of the Biophysical Society, an ISMAR Fellow and the first female chemist elected to the Australian Academy of Science (2012). She is recipient of the 2019 RACI M Sheil Leadership Award, an IUPAC Distinguished Woman of Chemistry, member of the Victorian Honour Roll of Women and an Officer of the Order of Australia (2019).
9 Oral Presenter Abstracts
Jessica Holien Physicochemical properties of protein-protein Medicinal Chemistry RMIT University interaction modulators
Carol Hua Probing chirality with supramolecular systems Inorganic Chemistry University of Melbourne
Ionic liquids and plastic crystals utilising the Colin Kang oxazolidinium cation: the effect of ether Materials Chemistry Deakin University functionality in the ring
Laena D’Alton Analytical Chemistry, DIY medical diagnostics and health testing La Trobe University Electrochemistry
Chemical Debjani Ghosh Efficient production of xylooligosaccharides Engineering, Monash University Polymer Chemistry
Saimon Silva Lubricin (PRG4): a versatile protein for Analytical Chemistry, Swinburne University of electroactive surfaces Electrochemistry Technology
Moya Hay Ligand tuning in cobalt complexes for valence Inorganic Chemistry University of Melbourne tautomerism
Arpita Poddar Metal-organic-frameworks as non-viral gene Chemical Biology, RMIT University delivery vectors Materials Chemistry
William Nguyen Optimisation of 5-substituted Walter and Eliza Hall 2-acylaminothiazoles as potential HIV-1 Medicinal Chemistry Institute of Medical latency reversing agents Research Benjamin Long Quantification of pharmaceuticals in surface Analytical Chemistry, Federation University waters and riparian flora of a south eastern Environmental Australia Australian river system Chemistry
Amy Thomson Synthesis of interchain dicarba insulin Organic Chemistry, Monash University analogues Peptide Chemistry
Wenyue Zou Polyoxometalates for colorimetric sensing Analytical Chemistry RMIT University applications
Painters, puzzles and phosphorescence: Tim Connell understanding triplet excited states in Inorganic Chemistry Deakin University iridium(III) complexes
10 Oral Presenter Abstracts
Physicochemical properties of protein-protein interaction modulators
Jia Truong, Ashwin George and Jessica K. Holien
School of Science, STEM College, RMIT, Melbourne, VIC, Australia [email protected] @jessholien
Despite the important roles played by Protein-Protein Interactions (PPIs) in disease, they have been long considered as ‘undruggable’. However, recent advances have suggested that the PPIs may not follow conventional rules of ‘druggability’. We sought to document the physicochemical properties of all the small molecule PPI modulators on the market, in clinical trials, and published, to explore which of these physicochemical properties are essential for a PPI modulator to be a clinical drug.
Overall, our analysis suggested that those compounds currently on the market had a larger range of values for most of the physicochemical parameters whereas those in clinical trials fit much more stringently to standard drug-like parameters. This observation was particularly true for molecular weight, cLogP and total polar surface area where aside from a few outliers, most of the compounds in clinical trials fit within standard drug-like parameters.
This implies that the newer PPI modulators are more drug-like than those currently on the market and when designing new modulators PPI specific screening libraries should remain within standard drug- like parameters in order to obtain a clinical candidate. PPI modulators are the latest frontier of small molecule drug discovery and this research is a vital step in the design of future drug discovery campaigns.
11 Oral Presenter Abstracts
Probing Chirality with Supramolecular Systems
Carol Hua1, Hui Min Tay1, Shannon Thoonen1 and Aditya Rawal2
1The University of Melbourne, Parkville, Victoria, Australia 2The University of New South Wales, Kensington, New South Wales, Australia [email protected] @_CarolHua
Chirality is prevalent throughout nature with most biologically important molecules being chiral, including DNA and proteins. The chirality of drug molecules is particularly important as each enantiomer may interact with metabolic and regulatory processes in vastly different ways. The development of new methods for determining the chiral purity of molecules is very important to the pharmaceutical, agrochemical and food industries with 56% of drugs in use containing chiral molecules.
Coordination polymers (CPs) and Metal-Organic Frameworks (MOFs) are crystalline materials containing inorganic nodes bridged by multidentate ligands. The high porosity and tunability of CPs enable the systematic modification of pore chemistry and size. Tailored chiral environments can be designed, making these materials well-suited to act as chiral selectors as they can encapsulate guest molecules in a manner similar to natural enzymes. The development of CPs as analytical chiral sensors and probes is attractive for determining chiral purity due to their simplicity and convenience.
This presentation will detail the synthesis of chiral CPs incorporating 1,2-trans- diaminocyclohexane1 and amino acid derived ligands2 where integral role of host-guest interactions in the application of these chiral CPs as solid state chiral sensors and probes will be highlighted. The discrimination of 13 4− chirality in amino acids by C solid state NMR using [Mg2(S-dobpdc)] (dobpdc = 4,4′-dioxidobiphenyl-3,3′-dicarboxylate) will be discussed.3
References 1. H. M. Tay, C. Hua, “Co(II) coordination polymers constructed from a bent chiral linker: controlling framework topology using co-ligands”, CrystEngComm, 2020, 22, 6690-6698. 2. H. M. Tay, C. Hua, “Chiral Cd(II) coordination polymers based on amino acid derivatives: the effect of side chain on structure”, Cryst. Growth Des., 2020, Cryst. Growth Des., 2020, 20, 5843-5853. 3. H. M. Tay, A. Rawal, C. Hua, “Chiral elucidation of amino acids with S-Mg2(dobpdc)”, 2020, 56, 14829-14832.
12 Oral Presenter Abstracts
Ionic Liquids and Plastic Crystals Utilising the Oxazolidinium Cation: The Effect of Ether Functionality in the Ring
Colin S. M. Kang1, 2, Ruhamah Yunis1, Haijin Zhu3, Cara M. Doherty4, Oliver E. Hutt2, Jennifer M. Pringle1
1Institute for Frontier Materials, Deakin University, Burwood, VIC, Australia 2Boron Molecular, Noble Park, VIC, Australia 3Institute for Frontier Materials, Deakin University, Geelong, VIC, Australia 4Commonwealth Scientific and Industrial Research Organisation (CSIRO), Manufacturing, Clayton, VIC, Australia [email protected] @ColinKang_
The advancement of safer, long-lasting energy storage technologies is paramount for the transition into a clean renewable energy economy and sustainable future. To envision this approach, at least in part, relies on the development of new electrolytes that i) are safe, reliable, and ii) can support next- generation battery technologies that have higher energy densities (e.g. alkali metal, metal-air batteries); both of these requirements are necessary to sustain the ever-growing demand for energy usage, that today’s Li-ion batteries cannot solely achieve. Whilst current battery electrolytes utilise organic solvents that are volatile and flammable, both ionic liquids (ILs) and organic ionic plastic crystals (OIPCs) are promising electrolyte candidates as they exhibit negligible vapour pressure, non- flammability, and are thermally stable at high temperatures. OIPCs, very similar to ILs in structure, differ in that they are solid-like materials at above ambient temperatures with plastic-like mechanical properties, yet exhibit appreciable ionic conductivities.[1] To further enhance the development, and thus utilisation, of these electrolytes depends on increasing our fundamental understanding of the structure and dynamics of emerging cation/anion families.
+ This work describes the synthesis and characterisation of a range of oxazolidinium ([C1moxa] )-based + ILs and OIPCs. These [C1moxa] -based OIPCs are found to be highly disordered and exhibit a wide + conductive phase. Interestingly, the [C1moxa] -based OIPCs studied have been found to exhibit higher + ionic conductivities than their equivalent pyrrolidinium ([C1mpyr] ) counterparts. We also probe the ion transport dynamics of the cation/anion species via solid-state NMR experiments and study the free volume in these salts through Positron Annihilation Spectroscopy.
References [1] D. R. MacFarlane, M. Forsyth, P. C. Howlett, M. Kar, S. Passerini, J. M. Pringle, H. Ohno, M. Watanabe, F. Yan, W. Zheng, S. Zhang, J. Zhang, Nat. Rev. Mater. 2016, 1, 1–15.
13 Oral Presenter Abstracts
DIY MEDICAL DIAGNOSTICS AND HEALTH TESTING
Laena D’Alton1, Serena Carrara1, Gregory J. Barbante1 and Conor F. Hogan1
1Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Victoria 3086, Australia [email protected] @hogansheroeslab
Proactive health testing, such as early disease diagnosis, saves lives, but can be difficult to implement en-mass given rising costs, and traditional pathology’s need for specialised facilities and trained technicians. Affordable, simplified and point-of-need alternatives to laboratory-based bioanalysis are needed. Electrochemiluminescence (ECL), light emission following a cascade of electrochemically initiated chemical reactions, promises ultra-low detection limits suitable for early disease diagnosis. However, the simplicity of ECL is rarely reflected in the instrumentation used. Here we describe a semi-portable, low-cost alternative, the Raspberry Pi-O-Sensor. This device is built from a Raspberry Pi (a single-board computer) and a photomultiplier tube (PMT), and can apply a potential across a sensor to initiate ECL while also detecting and recording light emission. We demonstrate how it can be combined with low-cost sensors to outperform traditional instrumentation at a fraction of the price.
14 Oral Presenter Abstracts
Efficient production of xylooligosaccharides
Debjani Ghosh1, Anil B. Vir 2, Gil Garnier2, Antonio F. Patti1 and Joanne Tanner2
1 School of Chemistry, Monash University, Clayton, VIC, 3800, Australia 2 Bioresource Processing Research Institute of Australia, Department of Chemical Engineering, Monash University, Clayton, VIC, 3800, Australia [email protected]
Xylooligosaccharides (XOS) are naturally occurring high value biochemicals with potential applications in the food, pharmaceutical and fine chemical industries. They are typically produced and purified from a variety of biomass resources in expensive and inefficient multi-step batch processes, and this high cost of production is a significant barrier to their commercial adoption. A flow-type microreactor was used as a novel and green approach to intensify and increase the efficiency of enzymatic XOS production from beechwood xylan. The xylan hydrolysis performance was compared with the same reaction performed under typical batch conditions. Over 80 g XOS per 100 g xylan was obtained in less than one minute of residence time at the optimum conditions tested in continuous flow experiments. The enzymatic xylan hydrolysis performance was improved, product selectivity was observed and xylan to XOS conversion was three times higher under optimised flow conditions compared to a conventional batch process.
With the increasing commercial development of high-throughput systems, microreactor combined with enzymatic hydrolysis therefore represent a continuous, easily controlled, scalable process to deliver sustainable, high quality XOS. The produced XOS can be utilised as prebiotics or upgraded to other valuable products such as surfactants, hydrogels, food additives, or food packaging materials.
15 Oral Presenter Abstracts
LUBRICIN (PRG4): A VERSATILE PROTEIN FOR ELECTROACTIVE SURFACES
Saimon Moraes Silvaa,b,c and Simon E. Moultona,b,c aARC Centre of Excellence for Electromaterials Science, Faculty of Science, Engineering and Technology, Swinburne University of Technology, Melbourne, Victoria 3122, Australia. bThe Aikenhead Centre for Medical Discovery, St Vincent’s Hospital Melbourne, Melbourne, Victoria 3065, Australia. cIverson Health Innovation Research Institute, Swinburne University of Technology, Melbourne, Victoria 3122, Australia. [email protected] @moraes_saimon
A major issue faced by electrochemical surfaces that needs to function in biological fluids remains the biofouling of electrode surface. In this presentation, it will be demonstrated how lubricin (LUB) can mitigate the biofouling issue. LUB is a cytoprotective glycoprotein present in synovial fluids and coating cartilage surfaces in articular joints.1 LUB displays a distinguishing chemistry, conformational and molecular structure, and also the ability of self- assembling in a well-organized manner on substrates of different materials.2 When attached to a conductive surface, LUB presents the capability of preventing biofouling and at the same time allowing good electrochemistry with the advantage of a simple and one-step coating preparation.3 This makes LUB an interesting surface coating for bionic implants and electrochemical biosensors. In this presentation, I will present how our research program has progressed in the last three years; and the versatility of lubricin to be used as antifouling coating in different biomedical applications will be discussed.
1. S. M. Silva, A. F. Quigley, R. M. I. Kapsa, G. W. Greene, S. E. Moulton, Chemelectrochem 2019, 6, 1939- 1943. 2. M. Y. Han, S. M. Silva, W. W. Lei, A. Quigley, R. M. I. Kapsa, S. E. Moulton, G. W. Greene, Langmuir 2019, 35, 15834-15848. 3. M. J. Russo, M. Y. Han, A. F. Quigley, R. M. I. Kapsa, S. E. Moulton, E. Doeven, R. Guijt, S. M. Silva, G. W. Greene, Electrochim Acta 2020, 333.
16 Oral Presenter Abstracts
LIGAND TUNING IN COBALT COMPLEXES FOR VALENCE TAUTOMERISM
M. A. Hay1, J. T Janetzki1, R. W. Gable1, A. Starikova2, and C. Boskovic1
1School of Chemistry, The University of Melbourne, Parkville, Victoria, Australia. 2Institute of Physical and Organic Chemistry, Southern Federal University, Russian Federation. [email protected] @moyaahay
Molecules that can switch between distinguishable stable states by application of an external stimulus have promise in the development of new functional molecular materials. Those which display valence tautomerism (VT) are promising candidates for such materials as the stimulated electron transfer between a ligand and a metal is accompanied by a change in their magnetic, optical and structural properties.1 Cobalt-dioxolene complexes are well studied examples of VT however alternative N-donor based redox active ligands with cobalt have been comparatively unexplored. A promising candidate is investigation of the bis(aryl-imino)acenapthene (Ar-BIAN) ligand family which has been shown to induce VT in vanadium and ytterbium complexes. 2-4
Here we present the preparation and in-depth study of a series of homoleptic octahedral Co(II) complexes with Ar-BIAN ligands in different oxidation states. Through redox tuning of the Ar-BIAN ligand via variation of the aryl substituents, the impact on the electronic structure has been investigated. The understanding of the electronic structure of Co-BIAN systems obtained in this study will facilitate the design of new VT systems.
1T. Tezgerevska, K. G. Alley, C. Boskovic, Coord. Chem. Rev. 2014, 268, 23–40. 2I. L. Fedushkin, O. V. Maslova, A. G. Morozov, S. Dechert, S. Demeshko, F. Meyer, Angew. Chem – Int. Ed. 2012, 51 (42), 10585-10587. 3J. Bendix, K. M. Clark, Angew. Chem – Int. Ed. 2016, 55 (8), 2748-2752. 4A. G. Starikov, A. A. Starikova, V. I. Minkin, Russ. J. Gen. Chem. 2017, 87 (1), 104-112.
17 Oral Presenter Abstracts
METAL-ORGANIC-FRAMEWORKS AS NON-VIRAL GENE DELIVERY VECTORS
Arpita Poddar1,2, Cara Doherty2, and Ravi Shukla1
1 Ian Potter NanoBiosensing Facility, NanoBiotechnology Research Laboratory (NBRL), School of Science, RMIT University, Melbourne, VIC, Australia 2 CSIRO Manufacturing, Clayton, VIC, Australia [email protected]
Gene therapy is a powerful modality that can not only treat, but also cure a disease at its root; with efficiency depending fundamentally on the gene delivery system used[1]. Current gene delivery is limited by a lack of suitable carrier (i.e. vectors)[2]. So far, viruses are used as vectors, but they have limited applications due to safety concerns and high production costs[3]. Non-viral vectors are safer, non-immunogenic, inexpensive, can carry large quantities of DNA and can be easily modified[4]. However, only 0.24% of gene delivery research focused on non-viral vectors[5]. The work we present[6] addresses the lack of sufficient research by demonstrating Metal-Organic-Frameworks (MOFs) as novel non-viral vectors for gene delivery. MOFs, composed of metal ions and organic ligands, are a new class of hybrid materials in nanotechnology ligands[7].
We investigate physiological synthesis of biocompatible MOFs with minimal/no cellular toxicity. The MOF subtype ZIF-8 are found to successfully encapsulate not just short chain nucleic acids, but entire genes in a one pot synthesis method. Material characterisations, transfections and confocal microscopy proved encapsulation and release do not damage the gene or, importantly, its function. Soft X-ray tomography showed cellular uptake of the gene encapsulating MOFs by revealing cytoplasmic and endosomal presence. A gradual expression of the delivered gene occurred over 96 hours.
The results obtained established the use of MOFs for gene delivery for the first time. ZIF-8 based MOFs deliver functionally intact genes in a non-cytotoxic manner with gradual release; features essential for a suitable gene therapy delivery system.
References [1] H. Yin, R. L. Kanasty, A. A. Eltoukhy, A. J. Vegas, J. R. Dorkin, D. G. Anderson. Nat. Rev. Genet. 2014, 15, 541. [2] G. A. R. Gonçalves, R. d. M. A. Paiva. Einstein (Saõ Paulo). 2017, 15, 369. [3] N. Yang. Int. J. Pharm. Investig. 2015, 5, 179. [4] S. Chira, C. S. Jackson, I. Oprea, F. Ozturk, M. S. Pepper, I. Diaconu, et al. Oncotarget. 2015, 6, 30675. [5] C. Hidai, H. Kitano. Diseases. 2018, 6, 57. [6] A. Poddar, J. J. Conesa, K. Liang, S. Dhakal, P. Reineck, G. Bryant, et al. Encapsulation, Visualization and Expression of Genes with Biomimetically Mineralized Zeolitic Imidazolate Framework-8 (ZIF-8). Small. 2019, 15, 1902268. [7] H. C. Zhou, J. R. Long, O. M. Yaghi. Chem Rev. 2012, 112, 673.
18 Oral Presenter Abstracts
OPTIMISATION OF 5-SUBSTITUTED 2-ACYLAMINOTHIAZOLES AS POTENTIAL HIV-1 LATENCY REVERSING AGENTS
William Nguyen,1, 2 Jonathan Jacobson,3 Kate E. Jarman,1, 2 Helene Jousset Sabroux,1, 2 Sharon R. Lewin,3 Damian, F. Purcell,3 Brad E. Sleebs.1,2
1The Walter and Eliza Hall Institute for Medical Research, Victoria, Australia. 2Department of Medical Biology, University of Melbourne, Victoria, Australia. 3Department of Microbiology and Immunology, Peter Doherty Institute of Infection and Immunity, University of Melbourne, Victoria, Australia. [email protected]
Combination antiretroviral therapy (cART) has proven effective in temporary suppression of HIV- 1 replication, reducing morbidity and mortality. However, these therapies don’t eliminate latent viral reservoirs within infected T cells so continual infection and rapid development of multidrug resistant strains remain a major challenge.
The “shock and kill” strategy employs epigenetic modifying drugs to stimulate viral replication, eliminating these latent reservoirs. Used in conjunction with cART, this strategy could eradicate the virus within an infected individual.
Tat is the master regulator for HIV gene expression and targeting Tat expression in the residual latent HIV-infected reservoir is important for achieving complete HIV remission. We used insights into the Tat footprint during latency to develop a screening assay using a dual Luciferase reporter cell line (HEK293.IRES-Tat/CMV-CBG/LTR-CBR) to identify compounds providing synergistic activating signals upon the HIV LTR relative to a non-specific reporter. This dual reporter platform was employed to screen a library of 114,000 drug-like molecules and identified the 2-acylaminothiazole class (EC50 ~24 μM) capable of selectively activating HIV gene expression.
Medicinal chemistry efforts including investigation of SAR, bioisosteric substitution and core hopping to optimise the 2-acylaminothiazole class will be discussed. The optimised compounds displayed enhanced HIV gene expression in HEK293 and Jurkat 10.6 latency cellular models and increased unspliced HIV RNA in resting CD4+ T cells isolated from HIV-infected individuals on cART, demonstrating the potential of this class as latency-reversing agents.
References 1 W.Nguyen et al., J. Med. Chem., 2019, 62, 5148−5175 (cover article). 2 W.Nguyen et al., Eur. J. Med. Chem., 2020, 195 (2020), 112254.
19 Oral Presenter Abstracts
20 Oral Presenter Abstracts
QUANTIFICATION OF PHARMACEUTICALS IN SURFACE WATERS AND RIPARIAN FLORA OF A SOUTH EASTERN AUSTRALIAN RIVER SYSTEM
Benjamin M. Long1, Nicholas Schultz1, and Samantha Harriage1 1Federation University Australia, Mt Helen, Victoria, Australia, 3350 [email protected] @doc_blong
Pharmaceuticals and personal care products are environmental contaminants of emerging concern. There is building evidence that these pharmaceutical pollutants widely exist in ng/L quantities in human influenced surface waters both nationally and internationally.1,2 Globally, there is limited knowledge of the ecological impacts of pharmaceutical contamination upon the environment.3 This case study consisted of 5 sites spanning 150 km of a dynamic river system positioned in western Victoria, Australia. The concentrations of three pharmaceuticals (Carbamazepine, Tramadol and Venlafaxine) were measured in surface water and in native Australian riparian flora (Phragmites australis, azolla spp., and Vallisneria spp.) as a measure of bioconcentration. Surface water and flora samples were prepared through solid phase extraction and solvent extraction, respectively, then quantified using high performance liquid chromatography tandem mass spectroscopy operating in multiple reaction monitoring mode with isotope dilution. Pharmaceuticals were found to persist through all 5 sites (e.g. Carbamazepine maximum - 499 ng/L, minimum - 35.1 ng/L) and to bioconcentrate in the leaves of the studied flora (e.g. Carbamazepine in V. australis - 27.0 ng/g dry weight). This work further characterizes the pharmaceutical pollution problem in Australia while highlighting potential for the use of native flora in phytoremediation. 1. P.D. Scott, M. Bartkow, S.J. Blockwell, H.M. Coleman, S.J. Khan, R. Lim, J.A. McDonald, H. Nice, D. Nugegoda, V. Pettigrove, L.A. Tremblay, M.S. Warne, F.D. Leusch. J Environ Qual. 2014, 43, 1702-1712. 2. M.S. Kostich, A.L. Batt, J.M. Lazorchak. Environ Pollut. 2014, 184, 354-359. 3. K.E. Richmond, E.J. Rosi, D.M. Walters, J. Fick, S.K. Hamilton, T. Brodin, A. Sundelin, M.R. Grace. Nature Communications. 2018, 9, 1, 4491-4500.
21 Oral Presenter Abstracts
SYNTHESIS OF INTERCHAIN DICARBA INSULIN ANALOGUES
Amy L. Thomson1 and Prof. Andrea J. Robinson1
1School of Chemistry, Monash University, Clayton, VIC 3800, Australia [email protected]
One hundred years of insulin research has led to many landmark discoveries, including the observation of a long-predicted conformational switch between the peptide hormone’s solution stable form and its bioactive conformation for receptor binding.[1] Although receptor-bound and free insulin structure have been well characterized by X-ray crystallography[2] and Cryo-EM,[3] how the peptide undergoes the dynamic transition between these states remains unknown. Our research aims to investigate the potential role of insulin’s three disulfide bridges (A6-A11, A7-B7 and A20-B19) in influencing conformational change of the peptide structure between inactive and bioactive conformations. Replacing flexible native cystine linkages with structurally rigid and metabolically inert C-C motifs offers a library of bridging geometries through variable hybridization (sp3, sp2, sp), which can be used to probe the conformation required for bioactivity.[4] This has been achieved to date with insulin’s A6-A11 intrachain disulfide bridge in which comparison between cis- and trans-alkene, and native bridge demonstrated a key conformational transition facilitated by bridge geometry.[5] Interchain dicarba bridge replacement presents a significantly greater synthetic challenge, whilst retaining the added challenge of overcoming deleterious peptide aggregation, a common problem in insulin analogue synthesis. This requires the development of several new interconnected strategies to facilitate cross metathesis, including use of aggregation disrupting dehydroamino acid residues, preformed bridging motifs and protecting group free conditions. Development of a library of conformationally restricted analogues allows us to probe the structure function relationship of insulin and promote development of more efficient therapeutics.
[1] J. G. Menting, Y. Yang, S. J. Chan, N. B. Phillips, B. J. Smith, J. Whittaker, et al. PNAS. 2014, 111, 33, E3395. [2] F. Weis, J. G. Menting, M. B. Margetts, S. J. Chan, Y. Xu, N. Tennagels, et al. Nat. Commun. 2018, 9, 1, 4420. [3] G. Scapin, V. P. Dandey, Z. Zhang, W. Prosise, A. Hruza, T. Kelly, et al. Nature. 2018, 556, 7699, 122-125. [4] A. Belgi, J. V. Burnley, C. A. MacRaild, S. Chhabra, K. A. Elnahriry, S. D. Robinson, et al. J. Med. Chem. 2021, 64, 6, 3222-3233. [5] B. van Lierop, S. C. Ong, A. Belgi, C. Delaine, S. Andrikopoulos, N. L. Haworth, et al. Sci Rep. 2017, 7, 1, 17239.
22 Oral Presenter Abstracts
POLYOXOMETALATES FOR COLORIMETRIC SENSING APPLICATIONS
Wenyue Zou1, Ana González2, Rajesh Ramanathan1, José M. Dominguez-Vera2 and Vipul Bansal1 1NanoBiotechnology Research Laboratory (NBRL), RMIT University, Melbourne, VIC, Australia 2Universidad de Granada, Granada, Spain [email protected] @Dr_WenyueZOU
Polyoxometalates (POMs) have been widely explored in catalysis due to their intriguing photoredox chemistry. However, these materials have seen limited applicability in other areas. A particularly exciting property of POMs is their ability to be reduced by single or multiple electrons, leading to a family of mixed-valence species with a characteristic deep blue colour (“heteropoly blues”). Light irradiation such as ultraviolet (UV) can also be used to assist the reduction of POMs in the presence of a suitable sacrificial electron donor. The strong colour generated by reduced POMs can be detected either by spectroscopy or even with naked-eye. This opens the opportunity of using POMs for colorimetric sensing as: (a) different molecules have distinct abilities to donate electrons to POMs, and (b) different irradiation energy and exposure time have distinct influence on the reaction, both of which affect the colour generation, leading to diverse intensities of colour. We investigated the photoredox reaction of different POMs with potential electron donors and have used them to develop colorimetric sensors to solve real-world problems. These include: (1) a low- cost personalised wearable UV sensor to help people manage their UV exposure, thereby reducing skin cancer rate1; (2) an enzyme-free reusable sensor for real-time detection of alcohol in sweat and saliva to provide a convenient on-site self-monitoring tool for drivers, thereby improving road safety2; (3) a colour-based lactic acid sensor for rapid diagnosis of bacterial vaginosis to offer point-of-care (POC) vaginal health monitoring, thereby benefitting female population3; and many more applications are on the way.
References 1. W. Zou, A. González, D. Jampaiah, R. Ramanathan, M. Taha, S. Walia, S. Sriram, M. Bhaskaran, J.M. Dominguez-Vera, V. Bansal. Nat. Commun. 2018, 9, 1, 3743. 2. M Sánchez, A. González, L. Sabio, W. Zou, R. Ramanathan, V. Bansal, J.M. Dominguez- Vera. Mater. Today Chem. 2021, [In Press, MTCHEM-D-21-00109R1] 3. W. Zou, A. González, R. Ramanathan, D. Tyssen, G. Tachedjian, C. Bradshaw, J.M. Dominguez-Vera, V. Bansal. [Communicated]
23 Oral Presenter Abstracts
Painters, Puzzles and Phosphorescence: Understanding triplet excited states in iridium(III) complexes
Timothy U. Connell,1 Stephen DiLuzio,2 Stefan Bernhard2 1School of Life and Environmental Sciences, Deakin University, Waurn Ponds, VIC, Australia 2Mellon College of Science, Carnegie Mellon University, Pittsburgh, PA, USA [email protected]
Luminescent transition metal complexes, especially those with a d6 electron configuration such as iridium(III), exhibit unique optical properties attractive across a wide range of applications, including: light emitting diodes (LEDs), oxygen sensing, organic photocatalysis, bioimaging, photodynamic therapy, and solar fuel generation.1 Whilst emission colour can be controlled through judicious tuning of the frontier molecular orbitals, achieved by altering the metal’s coordination environment, the structural parameters that affect emission lifetime remain poorly understood. Lifetime is often critically linked to application; short lifetimes prevent phosphor degradation in LEDs and the intrinsic bi- molecular interactions in synthetic photocatalysis benefit from long-lived excited states. Conventional approaches (either experimental time-resolved spectroscopy, or intensive computational analysis) towards understanding the triplet excited state of individual transition metal complexes are both time-consuming and expensive. Extrapolating these results across entire phosphor classes is further hindered by a lack of standardized analytical procedures between different research groups. Is it possible that an inverted approach, combining automated synthesis and data collection with statistical analysis, yields greater fundamental understanding without the need for arduous experimentation?
We tested this idea by preparing and measuring an unprecedented combinatorial library (>1,400 discrete complexes) of heteroleptic iridium(III) complexes consisting of diverse cyclometalating (C^N) and diimine ancillary (N^N) ligands. Automated analysis of only the emission spectra and excited state lifetime of each complex yielded both a predictive model for emission colour (determined by ligand substituents) and insight into the factors that govern excited state lifetime.
References 1Iridium(III) in Optoelectronic and Photonics Applications; Zysman-Colman, E. (ed.), John Wiley & Sons; Hoboken, 2017
24 Poster Presenters
Tania PhI(OTf) does not exist (yet) Inorganic Chemistry La Trobe University 2
Low-Temperature Hydrogen Sensor: Ebstam Alenezy Enhanced Performance Enabled through Applied Chemistry RMIT University Photoactive Pd-Decorated TiO2 Colloidal Crystals Kyle Awalt The Development of Biased Bitopic Ligands
Monash Institute of Acting at the A1 Adenosine Receptor as Medicinal Chemistry Pharmaceutical Sciences Cardioprotective Agents
Porous Crystalline Materials for Hydrocarbon Computational Ravichandar Babarao Separations: Integrating Modeling and Chemistry; Materials RMIT University Experiments Chemistry
Fluorescence Based Aptasensors for the Gayatri Bagree Detection of Neuro-pathological Protein Chemical Biology RMIT University Conformers
Samridhi Bajaj A novel approach for the determination of Electrochemistry La Trobe University homogeneous kinetics using FT-ACV
Lei Bao Metallo-nanodroplets For Catalysis And Analytical Chemistry; RMIT University Nanostructure Fabrication Physical Chemistry
Lachlan Barwise Electrochemistry; Mediated Electrosynthesis of AuIII Dichlorides La Trobe University Inorganic Chemistry
Iain Currie Walter and Eliza Hall Synthesis of Acyl Phosphoramidates Medicinal Chemistry; Institute of Medical Employing a Modified Staudinger Reaction Organic Chemistry Research Computational studies of a novel whey Computational Kevion Darmawan protein-based nutraceutical and its interaction Chemistry; Physical RMIT University with the peptidoglycan component of lactic Chemistry; Food acid bacteria Chemistry Evaluation of Electrocatalytic Activity of Oshadie De Silva Phase Controlled Cobalt Hydroxide and Electrochemistry; RMIT University Porous Cobalt Oxide on Oxygen Evolution Nanochemistry Reaction Conversion of γ‐Valerolactone to Ethyl Valerate over Metal Promoted Ni/ZSM‐5 Chemical Jampaiah Deshetti Catalysts: Influence of Ni0/Ni2+ Engineering; RMIT University Heterojunctions on Activity and Product Materials Chemistry Selectivity Building a New Fluorescent Reporter for Analytical Chemistry; Siyang Ding Measuring Carbonylated Proteins in Chemical Biology; La Trobe University Autophagy and Neurodegenerative Diseases Peptide Chemistry
25 Poster Presenters
Nimrod Eren Tribulations and uses of lithiated allylic Organometallic Monash University phosphines (and oxides) Chemistry
Biochemical and structural characterisation of Katie Ganio the Haemophilus influenzae PsaA ortholog, Chemical Biology University of Melbourne HIPsaA Manuela Jörg When Chemistry meets Structural Biology: Monash University and The first X-ray Structure of the Adenosine A1 Medicinal Chemistry Newcastle University Receptor (UK) A Simple RP-HPLC Method for the Joel Johnson Analytical Chemistry; Simultaneous Determination of Citrulline and CQUniversity Food Chemistry Arginine in Australian Cucurbits
Jomo Kigotho Alternate Synthesis & Structural Elaboration Medicinal Chemistry; Monash Institute of of 2-Aminobenzimidazole Antimalarials Organic Chemistry Pharmaceutical Sciences
Jaewon Kim Ultrasonic spray pyrolysis of tin oxide thin Materials Chemistry RMIT University films for transparent electrodes
Expanding the peptide synthesis toolkit to Qingqing Lin produce bicyclic peptide mimetics for drug Peptide Chemistry University of Melbourne discovery
Irreversible Inhibition of Peroxidase-mimic Piyumi Liyanage Activity of 2-dimensional Ni-based Analytical Chemistry RMIT University Nanozymes in the Presence of L-cysteine Chemical Control Over the Reaction in Ag Prisms with Sanje Mahasivam Engineering; Au+ Ions Through Plasmon-mediated RMIT University Materials Chemistry; Chemical Reaction (PCMR) Physical Chemistry Pyria Rose Divina Nanozymes as an Alternative Antibacterial to MariaThomas Applied Chemistry Antibiotics RMIT University
Sanjeedha Mubarak Iron Regulation by C. Elegans Ferritins Inorganic Chemistry University of Melbourne
Non-invasive detection of glucose in human Sanjana Naveen Prasad urine using a color-generating copper Analytical Chemistry RMIT University nanozyme
Susan Northfield Peptide BDNF mimetics with central and Peptide Chemistry University of Melbourne peripheral nervous system actions
26 Poster Presenters
Crystal structure of a complex between the Environmental Nilakhi Poddar electron-transfer partners arsenite oxidase Chemistry; Structural University of Melbourne and cytochrome c552, from the arsenite Biology respiring bacterium Rhizobium sp. NT-26 ZIF-C for targeted RNA interference and Suneela Pyreddy CRISPR/Cas9 based gene editing in prostate Materials Chemistry RMIT University cancer
Rajesh Ramanathan Nanozyme sensor array for prediction of Analytical Chemistry RMIT University Staphylococcus aureus strains
Chemical Peter Sherrell From Polarisation and Friction to Electricity - Engineering; University of Melbourne Mechanical Energy Harvesting in Polymers Materials Chemistry
Patrick Taylor Tuning the Band Alignment of Van Der Waals Computational RMIT University Heterostructures with Ferroelectric Materials Chemistry
Ian Thomas Chemical IF Thomas & Associates The 1974 UK Flixborough Disaster Engineering
Shannon Thoonen Chiral Detection with Fluorescent Inorganic Chemistry University of Melbourne Coordination Polymers
Transthyretin as a novel target for the Computational Jia Quyen Truong development of new drugs against Chemistry; Medicinal RMIT University demyelination diseases Chemistry
Perovskite-Inspired High Stability Hayden Tuohey Organometal Antimony(V) Halide Thin Films Materials Chemistry RMIT University by Post-Deposition Bromination
Structure Transformations and Responsive Martin van Koeverden Inorganic Chemistry; Properties of Porous Iron-based University of Melbourne Materials Chemistry Mixed-valence Frameworks
Inhibiting Glutathione Transferase P1 Claire Weekley Medicinal Chemistry; (GSTP1) With Ruthenium-based University of Melbourne Inorganic Chemistry Metallodrugs: Do They Work as Designed? A Simple Computational Approach for Computational Fathima Zahra Zahir Predicting Transition Chemistry; Inorganic University of Melbourne Temperatures in Valence Tautomeric Chemistry Complexes
27 Organisers and Contact Information
Dr Katie Ganio University of Melbourne
Dr Ganio is a protein biochemist and research fellow in the Department of Microbiology and Immunology at The Peter Doherty Institute for Infection and Immunity. She investigates the roles of metal-binding proteins in disease using inorganic mass spectrometry techniques.
Dr Manuela Jörg Monash Institute of Pharmaceutical Sciences
Dr Jörg is a Monash–Newcastle University research fellow in medicinal chemistry located at the Monash Institute of Pharmaceutical Sciences. Her research interest includes the development of small molecular drugs and pharmacological tools.
Dr Anitha Kopinathan Monash Institute of Pharmaceutical Sciences
Dr Kopinathan is a research fellow in medicinal chemistry at the Monash Institute of Pharmaceutical Sciences. Her research interests include fragment-based drug design as a high-throughput methodology for the development of novel small molecular drugs.
28 Organisers and Contact Information
Dr Susan Northfield University of Melbourne
Dr Northfield is a peptide and medicinal chemist in the Department of Biochemistry and Pharmacology. Her research interests include the development of peptides as chemical biology tools and therapeutic leads and the study of peptide pharmacokinetics.
A/Prof Rajesh Ramanathan RMIT University
Dr Ramanathan is a Materials Chemist and an Associate Professor in the School of Science. His research interests include creating new nanomaterials and fine tuning their properties for applications in chemical and biological systems.
Dr Claire Weekley University of Melbourne
Dr Weekley is a bioinorganic chemist and research fellow in the Department of Biochemistry and Pharmacology. She applies X-ray techniques to study proteins, metallodrugs and metals in biology.
29