DOCSLIB.ORG

Imidazole and Triazole Coordination Chemistry for Antifouling Coatings

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Imidazole and Triazole Coordination Chemistry for Antifouling Coatings Chalmers Publication Library Imidazole and Triazole Coordination Chemistry for Antifouling Coatings This document has been downloaded from Chalmers Publication Library (CPL). It is the author´s version of a work that was accepted for publication in: Journal of Chemistry (ISSN: 2090-9063) Citation for the published paper: Andersson Trojer, M. ; Movahedi, A. ; Blanck, H. (2013) "Imidazole and Triazole Coordination Chemistry for Antifouling Coatings". Journal of Chemistry, vol. 2013 pp. Article ID 946739. http://dx.doi.org/10.1155/2013/946739 Downloaded from: http://publications.lib.chalmers.se/publication/185391 Notice: Changes introduced as a result of publishing processes such as copy-editing and formatting may not be reflected in this document. For a definitive version of this work, please refer to the published source. Please note that access to the published version might require a subscription. Chalmers Publication Library (CPL) offers the possibility of retrieving research publications produced at Chalmers University of Technology. It covers all types of publications: articles, dissertations, licentiate theses, masters theses, conference papers, reports etc. Since 2006 it is the official tool for Chalmers official publication statistics. To ensure that Chalmers research results are disseminated as widely as possible, an Open Access Policy has been adopted. The CPL service is administrated and maintained by Chalmers Library. (article starts on next page) Hindawi Publishing Corporation Journal of Chemistry Volume 2013, Article ID 946739, 23 pages http://dx.doi.org/10.1155/2013/946739 Review Article Imidazole and Triazole Coordination Chemistry for Antifouling Coatings Markus Andersson Trojer,1 Alireza Movahedi,1 Hans Blanck,2 and Magnus Nydén1,3 1 Applied Surface Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, 412 96 Goteborg,¨ Sweden 2 Department of Biological and Environmental Sciences, University of Gothenburg, 405 30 Goteborg,¨ Sweden 3 Ian Wark Research Institute, University of South Australia, Adelaide, SA 5001, Australia Correspondence should be addressed to Markus Andersson Trojer; [email protected] Received 29 April 2013; Accepted 9 July 2013 Academic Editor: Suleyman Goksu Copyright © 2013 Markus Andersson Trojer et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Fouling of marine organisms on the hulls of ships is a severe problem for the shipping industry. Many antifouling agents are based on five-membered nitrogen heterocyclic compounds, in particular imidazoles and triazoles. Moreover, imidazole and triazoles are 2+ + strong ligands for Cu and Cu , which are both potent antifouling agents. In this review, we summarize a decade of work within our groups concerning imidazole and triazole coordination chemistry for antifouling applications with a particular focus on the very potent antifouling agent medetomidine. The entry starts by providing a detailed theoretical description of the azole-metal coordination chemistry. Some attention will be given to ways to functionalize polymers with azole ligands. Then, the effect of metal coordination in azole-containing polymers with respect to material properties will be discussed. Our work concerning the controlled release of antifouling agents, in particular medetomidine, using azole coordination chemistry will be reviewed. Finally, 2+ an outlook will be given describing the potential for tailoring the azole ligand chemistry in polymers with respect to Cu adsorption 2+ + and Cu → Cu reduction for antifouling coatings without added biocides. 1. Introduction are based on acrylic or methacrylic copolymers. The active substance (TBT) is covalently attached to the carboxylic A major problem for the shipping industry is fouling of group of the polymer, which is hydrolytically instable in marine organisms, such as algae, mussels, and barnacles on slightly alkaline conditions (as in seawater) [1, 4, 6]. Toxic ship hulls [1–5]. As the ship moves through the water, the copper pigment is also included in the TBT-SPC paint hull is subjected to form drag and skin friction drag.Since fouling increases the surface roughness, the skin friction drag systems, which in combination with TBT, provides protection is increased, which subsequently results in increased fuel against the entire spectrum of fouling organisms since some consumption and reduced manoeuvrability [3]. Traditional algae are tolerant to TBT but not to copper and vice versa countermeasures against marine fouling are coatings con- [7]. As the use of TBT containing paints increased, marine taining antifouling toxicants that have had severe environ- life in the vicinity of harbours and marinas was severely mental consequences on marine ecosystems. The most well- affected [8, 9]. The hazardous nature of TBT for the marine known examples are organometallic paint systems (compris- environment is ascribed to its weakening of fish immune ing lead, arsenic, mercury, etc.) which met the market in the systems, causing imposex and sterility in female gastropods early 1960s. The notorious tributyltin self-polishing coating (atsuchlowconcentrationas1ng/L)aswellasitsbioac- (TBT-SPC) was developed in the 1970s [1, 6]. The reason for cumulative properties in mammals [1, 4, 6]. Starting with the success of the TBT-SPC paints is that the rate of release TBT ban for pleasure craft in France 1982, TBT-contain- can be controlled on a molecular level. Generally, these paints ing paint systems were successively phased out in the 1990s 2 Journal of Chemistry and finally banned by IMO (the International Maritime medetomidine [29](seeScheme1)whichisbasedonimi- Organization) [10, 11]. dazole for antifouling purposes [30–32]. Medetomidine is A number of tin-free alternatives have been developed exceptionally efficient against fouling barnacles33 [ ], which due to the restrictive legislation regarding TBT paints. These isoneofthemostproblematicfoulantsinthenorthAtlantic, can crudely be divided into biocide-release and biocide-free yet, without seriously affecting nontarget organisms34 [ –37]. antifouling systems. Biocide-free approaches are dominated Inthisreview,wewillsummarizeadecadeofresearch by paint systems called foul-release coatings.Theantifouling concerning azole (primarily imidazole) coordination chem- mechanism lies in the low surface energy and smoothness istry for antifouling coatings. The work spans a variety of ofthecoating.Thebindersinthesecoatingsaresilicone chemistry disciplines including molecular modelling [38, 39], polymers, for example, PDMS (polydimethylsiloxane) and to surface and colloidal chemistry [40–43], controlled release some extent fluoropolymers, with both possessing very low [30, 31, 40–42, 44–46], coordination chemistry [39, 40, 47], surface energy. polymer synthesis [47–50], and material science [39, 47]. In tin-free SPC paints, tin is replaced by other elements Some references from other groups will be provided; how- such as copper, zinc, and silicon. Even though the side group ever, it is important to note that very few studies have of a few tin-free SPC paint binders also possess biocidal addressed azole coordination for antifouling purposes, and properties, no alternative is nearly as effective as TBT [4, 6]. the area is still rather unexplored. The azole coordination To provide full and long-term fouling protection, it is now approaches implemented by us with respect to antifouling necessary to add other biocides, so called boosters, generally coatings can be divided into three main categories: (1) antifoulant immobilization, (2) triggered release and (3) in combination with copper. The most frequently employed 2+ + boosters are conventional agrochemicals, some of which, Cu /Cu mediated antifouling as described later. for example, irgarol, have been under scrutiny due to low rate of biodegradation as well as toxicity towards nontarget 1.1. Antifoulant Immobilization. Booster biocides, including organisms [1, 4, 6, 10–18].Sincealsotheuseofcopperhas the azole-based molecules already mentioned, are typically been under debate recently, a number of other pigments are small molecules which are molecularly dispersed in the used such as Zn(II), Fe(III), and Ti(IV) oxides [1, 3, 4, 6]. antifouling paint [3, 51]. As a consequence, the biocides leach A generic problem with tin-free SPC paints is premature out from the coating within a couple of weeks (diffusive leakage of the booster biocides [3]. These are not anchored release from thin coatings ∼100 m) [52]. This results in a pre- tothebinder,asTBTis,andarehencesubjectedtofreedif- mature loss of fouling protection which is a severe problem fusion within the paint matrix. The immediate consequence since the desired lifetime of a marine coating is ∼5years[3, of premature leakage is loss of antifouling effect prior to the 4]. However, when the biocides are immobilized on macro- hydrolysis-dependent lifetime of the coating. molecules or colloids (with negligible diffusion coefficients A lot of research and development has been conducted on given there large sizes), the effective diffusion coefficient SPC paints from an environmental perspective. For instance, will be reduced by the magnitude of the stability constant the antifouling substances secreted by marine organism, that for immobilization [53]. We have explored the possibility is,
Load more

Recommended publications
  • Structure-Based Design, Synthesis, and Biological Evaluation Of
    Structure-Based Design, Synthesis, and Biological Evaluation of Triazole-Based smHDAC8 Inhibitors Dmitrii Kalinin, Sunit Jana, Maxim Pfafenrot, Alokta Chakrabarti, Jelena Melesina, Tajith Shaik, Julien Lancelot, Raymond Pierce, Wolfgang Sippl, Christophe Romier, et al. To cite this version: Dmitrii Kalinin, Sunit Jana, Maxim Pfafenrot, Alokta Chakrabarti, Jelena Melesina, et al.. Structure-Based Design, Synthesis, and Biological Evaluation of Triazole-Based smHDAC8 Inhibitors. ChemMedChem, Wiley-VCH Verlag, 2019, 15 (7), pp.571-584. 10.1002/cmdc.201900583. hal- 02999295 HAL Id: hal-02999295 https://hal.archives-ouvertes.fr/hal-02999295 Submitted on 23 Nov 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Distributed under a Creative Commons Attribution| 4.0 International License Full Papers ChemMedChem doi.org/10.1002/cmdc.201900583 1 2 3 Structure-Based Design, Synthesis, and Biological 4 5 Evaluation of Triazole-Based smHDAC8 Inhibitors 6 [a, b, c, d] [c, e] [c] [f] 7 Dmitrii V. Kalinin, Sunit K. Jana, Maxim Pfafenrot, Alokta Chakrabarti, [g]
    [Show full text]
  • Triazole Fungicide Residues and Their Inhibitory Effect on Some Trichothecenes Mycotoxin Excretion in Wheat Grains
    molecules Article Triazole Fungicide Residues and Their Inhibitory Effect on Some Trichothecenes Mycotoxin Excretion in Wheat Grains Tamer M. A. Thabit 1,2, Eman M. Abdelkareem 3,* , Nahla A. Bouqellah 4 and Shokr A. Shokr 1 1 Central Agricultural Pesticides Laboratory (CAPL), Agricultural Research Center (ARC), Giza 12611, Egypt; [email protected] (T.M.A.T.); [email protected] (S.A.S.) 2 Saudi Arabia Grains Organization (SAGO), Riyadh 11471, Saudi Arabia 3 Plant Pathology Research Institute, Agricultural Research Center (ARC), Giza 12619, Egypt 4 Biology Department, Collage of Science, Taibah University, Al-Madinah Al-Munawarah 344, Saudi Arabia; [email protected] * Correspondence: [email protected] Abstract: Wheat is one of the global strategic crops and ranks third in terms of cereals production. Wheat crops are exposed to many fungal infections during their cultivation stages, some of which have the ability to secrete a number of toxic secondary metabolites that threaten the quality of the grains, consumer health, producer economics, and global trade exchange. Fifty-four random samples were collected from wheat which originated from different countries. The samples included 14 types of soft wheat to study the extent of their contamination with deoxynivalenol (DON) and T-2 toxin by auto-ELISA technology and r-biopharm microtiter plate. All samples were contaminated with −1 DON toxin except one sample, and the values ranged between 40.7 and 1018.8 µg/kg . The highest contamination rates were in Lithuanian wheat and the lowest was in Indian wheat. Meanwhile, the Citation: Thabit, T.M.A.; highest average level of T-2 toxin contamination was in Lithuanian wheat grains with 377.4 µg/kg−1, Abdelkareem, E.M.; Bouqellah, N.A.; and the lowest average was 115.3 µg/kg−1 in Polish wheat.
    [Show full text]
  • 1,4-Disubstituted-1,2,3-Triazole Compounds Induce Ultrastructural Alterations in Leishmania Amazonensis Promastigote
    International Journal of Molecular Sciences Article 1,4-Disubstituted-1,2,3-Triazole Compounds Induce Ultrastructural Alterations in Leishmania amazonensis Promastigote: An in Vitro Antileishmanial and in Silico Pharmacokinetic Study Fernando Almeida-Souza 1,2,* , Verônica Diniz da Silva 3,4, Gabriel Xavier Silva 5, Noemi Nosomi Taniwaki 6, Daiana de Jesus Hardoim 2, Camilla Djenne Buarque 3, 1, , 2, Ana Lucia Abreu-Silva * y and Kátia da Silva Calabrese y 1 Pós-graduação em Ciência Animal, Universidade Estadual do Maranhão, São Luís 65055-310, Brazil 2 Laboratório de Imunomodulação e Protozoologia, Instituto Oswaldo Cruz, Fiocruz, Rio de Janeiro 21040-900, Brazil; [email protected] (D.d.J.H.); calabrese@ioc.fiocruz.br (K.d.S.C.) 3 Laboratório de Síntese Orgânica, Pontifícia Universidade Católica, Rio de Janeiro 22451-900, Brazil; [email protected] (V.D.d.S.); [email protected] (C.D.B.) 4 Faculdade de Ciência e Tecnologia, Universidade Nova de Lisboa, 2825-149 Caparica, Portugal 5 Rede Nordeste de Biotecnologia, Universidade Federal do Maranhão, São Luís 65080-805, Brazil; [email protected] 6 Núcleo de Microscopia Eletrônica, Instituto Adolfo Lutz, São Paulo 01246-000, Brazil; [email protected] * Correspondence: [email protected] (F.A.-S.); [email protected] (A.L.A.-S.) These authors equally contributed to this work. y Received: 26 June 2020; Accepted: 14 July 2020; Published: 18 September 2020 Abstract: The current standard treatment for leishmaniasis has remained the same for over 100 years, despite inducing several adverse effects and increasing cases of resistance. In this study we evaluated the in vitro antileishmanial activity of 1,4-disubstituted-1,2,3 triazole compounds and carried out in silico predictive study of their pharmacokinetic and toxicity properties.
    [Show full text]
  • Synthesis of 1,2,3 Triazole-Linked Benzimidazole Through a Copper-Catalyzed Click Reaction Purification [17, 18]
    Heterocycl. Commun. 2019; 25: 122–129 Research Article Open Access Mohammad Bakherad*, Ali Keivanloo, Amir H. Amin and Amir Farkhondeh Synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction https://doi.org/10.1515/hc-2019-0016 purification [17, 18]. A majority of published procedures for Received January 28, 2019; accepted April 25, 2019. the CuAAC reactions favor simple copper salts like CuI, Abstract: An efficient method has been developed for the Cu(AcO)2, and CuSO4 as the catalysts [19-23]. Other copper(0) synthesis of 1,2,3 triazole-linked benzimidazole through and copper(I) catalysts such as copper nano-size powder [24], a copper-catalyzed click reaction in ethanol at 50°C. copper nanoparticles adsorbed onto charcoal [25], and copper A broad range of aromatic azides were successfully reacted nanoclusters [26] have also shown good catalytic activities. with n-propynylated benzimidazole via copper-catalyzed In view of the biological importance of benzimidazole azide-alkyne cycloaddition reactions in the absence of a and 1,2,3-triazoles; synthesis of the 1,2,3-triazole linked ben- ligand. This method offers many advantages including zimidazole pharmacophore via efficient copper-catalyzed short reaction times, low cost, and simple purification click reactions would produce novel molecular templates procedures. that are likely to exhibit interesting biological properties. Kulkarni et al. have reported the synthesis of 2-mercapto- Keywords: 1,2,3-triazole; Benzimidazole; Click reaction. benzimidazole-linked coumarinyl triazoles as anti-tubercu- lar agents [27]. Eppakayala and co-workers have carried out the synthesis and biological evaluation of benzimidazole- Introduction linked 1,2,3-triazoles as potential anti-cancer agents [13].
    [Show full text]
  • Estonian Statistics on Medicines 2016 1/41
    Estonian Statistics on Medicines 2016 ATC code ATC group / Active substance (rout of admin.) Quantity sold Unit DDD Unit DDD/1000/ day A ALIMENTARY TRACT AND METABOLISM 167,8985 A01 STOMATOLOGICAL PREPARATIONS 0,0738 A01A STOMATOLOGICAL PREPARATIONS 0,0738 A01AB Antiinfectives and antiseptics for local oral treatment 0,0738 A01AB09 Miconazole (O) 7088 g 0,2 g 0,0738 A01AB12 Hexetidine (O) 1951200 ml A01AB81 Neomycin+ Benzocaine (dental) 30200 pieces A01AB82 Demeclocycline+ Triamcinolone (dental) 680 g A01AC Corticosteroids for local oral treatment A01AC81 Dexamethasone+ Thymol (dental) 3094 ml A01AD Other agents for local oral treatment A01AD80 Lidocaine+ Cetylpyridinium chloride (gingival) 227150 g A01AD81 Lidocaine+ Cetrimide (O) 30900 g A01AD82 Choline salicylate (O) 864720 pieces A01AD83 Lidocaine+ Chamomille extract (O) 370080 g A01AD90 Lidocaine+ Paraformaldehyde (dental) 405 g A02 DRUGS FOR ACID RELATED DISORDERS 47,1312 A02A ANTACIDS 1,0133 Combinations and complexes of aluminium, calcium and A02AD 1,0133 magnesium compounds A02AD81 Aluminium hydroxide+ Magnesium hydroxide (O) 811120 pieces 10 pieces 0,1689 A02AD81 Aluminium hydroxide+ Magnesium hydroxide (O) 3101974 ml 50 ml 0,1292 A02AD83 Calcium carbonate+ Magnesium carbonate (O) 3434232 pieces 10 pieces 0,7152 DRUGS FOR PEPTIC ULCER AND GASTRO- A02B 46,1179 OESOPHAGEAL REFLUX DISEASE (GORD) A02BA H2-receptor antagonists 2,3855 A02BA02 Ranitidine (O) 340327,5 g 0,3 g 2,3624 A02BA02 Ranitidine (P) 3318,25 g 0,3 g 0,0230 A02BC Proton pump inhibitors 43,7324 A02BC01 Omeprazole
    [Show full text]
  • Application to Add Echinocandins to the Essential List of Medicines for Treatment of Fungal Diseases
    APPLICATION TO ADD ECHINOCANDINS TO THE ESSENTIAL LIST OF MEDICINES FOR TREATMENT OF FUNGAL DISEASES 1 1 Table of contents 1 Table of contents 2 2 Summary statement of the proposal for inclusion, change or deletion. 5 3 Relevant WHO technical department and focal point (if applicable). 7 4 Name of organization(s) consulted and/or supporting the application. 8 5 International Nonproprietary Name (INN) and Anatomical Therapeutic Chemical (ATC) code of the medicine. 9 6 Dose forms(s) and strength(s) proposed for inclusion; including adult and age-appropriate paediatric dose forms/strengths (if appropriate). 10 6.1 ANIDULAFUNGIN 10 6.2 CASPOFUNGIN (AS ACETATE) 10 6.3 MICAFUNGIN (AS SODIUM) 10 6.4 DOSING 11 7 Whether listing is requested as an individual medicine or as representative of a pharmacological class. 14 8 Treatment details, public health relevance and evidence appraisal and synthesis. 15 8.1 TREATMENT DETAILS 15 (requirements for diagnosis, treatment and monitoring). 15 8.2 INDICATIONS FOR ECHINOCANDINS 17 8.3 THERAPEUTIC DRUG MONITORING AND DRUG-DRUG INTERACTIONS AFFECTING EFFICACY 20 8.4 DOSING 22 2 9 Information supporting the public health relevance. 23 9.1 EPIDEMIOLOGICAL INFORMATION ON DISEASE BURDEN 23 9.2 ASSESSMENT OF CURRENT USE 28 9.3 TARGET POPULATIONS 32 9.4 LIKELY IMPACT OF TREATMENT OF THE DISEASE 33 10 Review of benefits: summary of evidence of comparative effectiveness. 35 10.1 IDENTIFICATION OF CLINICAL EVIDENCE 35 10.2 SUMMARY OF AVAILABLE DATA FOR ECHINOCANDINS 35 10.3 SUMMARY OF AVAILABLE ESTIMATES OF COMPARATIVE EFFECTIVENESS FOR ECHINOCANDINS 36 international, randomized, double-blind trial 40 Prophylaxis in patients with haematologic malignancies 46 Invasive aspergillosis in allogeneic haematopoietic stem cell transplant patients 48 11 Review of harms and toxicity: summary of evidence of safety.
    [Show full text]
  • Synthesis and Biological Evaluation of Benzimidazole-Linked 1,2,3-Triazole
    Harkala et al. Organic and Medicinal Chemistry Letters 2014, 4:14 http://www.orgmedchemlett.com/content/4/1/14 SHORT COMMUNICATION Open Access Synthesis and biological evaluation of benzimidazole-linked 1,2,3-triazole congeners as agents Karna Ji Harkala1, Laxminarayana Eppakayala1* and Thirumala Chary Maringanti2 Abstract Background: Benzimidazoles and triazoles are useful structures for research and development of new pharmaceutical molecules and have received much attention in the last decade because of their highly potent medicinal activities. Findings: A simple and efficient synthesis of triazole was carried out by treatment of 2-(4-azidophenyl)-1H-benzo[d] imidazole (6) with different types of terminal alkynes in t-BuOH/H2O, sodium ascorbate, and Zn(OTf)2,screenedfor cytotoxicity assay and achieved good results. A series of new benzimidazole-linked 1,2,3-triazole (8a-i) congeners were synthesized through cyclization of terminal alkynes and azide. These synthesized congeners 8a-i were evaluated for their cytotoxicity against five human cancer cell lines. These benzimidazole-linked 1,2,3-triazole derivatives have shown promising activity with IC50 values ranging from 0.1 to 43 μM. Among them, the compounds (8a, 8b, 8c,and8e) showed comparable cytotoxicity with adriamycin control drug. Conclusions: In conclusion, we have developed a simple, convenient, and an efficient convergent approach for the synthesis of benzimidazole-linked 1,2,3-triazole congeners as agents. Keywords: Benzimidazole; Clic reaction; Cytotoxicity Findings Some of benzimidazole derivatives have also exhibit anti- Cancer is one of the terrible diseases which cause uncon- microbial [4,5], antitumor [6], anti-inflammatory [7], anti- trolled growth of group of cells.
    [Show full text]
  • Good Practice Recommendations on Use of Triazole Antifungal Agents in Chronic Respiratory Disease
    Good Practice Recommendations on Use of Triazole Antifungal Agents in Chronic Respiratory Disease Purpose of this guidance The Scottish Antimicrobial Prescribing Group (SAPG) Antifungal Stewardship group have developed these recommendations through consultation with clinical specialists, to provide practical advice for Antimicrobial Management Teams and specialist clinicians for the appropriate and safe use of anti- fungal agents in chronic respiratory disease. The guidance adheres to the principles of Realistic Medicine: To minimise anti-fungal treatment associated harm and waste To minimise variation in prescribing practice across Scotland To promote shared decision making and individualised patient care. They are intended to be used to inform/supplement local guidance for managing patients with Allergic bronchopulmonary aspergillosis (ABPA) and Chronic pulmonary aspergillosis (CPA). These recommendations do not replace clinical judgement, which should be influenced by individual patient risk factors. Clinicians should be mindful of the potential for harmful polypharmacy and increased risk to adverse drug reactions in patients with multiple co-morbidities or frailty. Background Chronic respiratory disease Allergic bronchopulmonary aspergillosis (ABPA) is a hypersensitivity lung disease resulting from exposure to Aspergillus fumigatus and occurring primarily in people with asthma or with cystic fibrosis. Disease is characterized by a variety of clinical and immunologic responses to A. fumigatus antigens. Clinical manifestations include
    [Show full text]
  • New-Generation Triazole Antifungal Drugs: Review of the Phase II and III Trials
    Review: Clinical Trial Outcomes New-generation triazole antifungal drugs: review of the Phase II and III trials Clin. Invest. (2011) 1(11), 1577–1594 In this article, the pharmacological, microbiological and clinical development Corrado Girmenia†1 & Erica Finolezzi1 progress from Phase II and III clinical trials with the new generation triazoles 1Dipartimento di Ematologia, Oncologia, albaconazole, isavuconazole, posaconazole, ravuconazole and voriconazole Anatomia Patologica & Medicina Rigenerativa, are reviewed. These drugs exhibit a favorable toxicity profile and possess high Azienda Policlinico Umberto I, Via Benevento 6, activity against resistant and emerging fungal pathogens. Pharmacokinetic 00161, Rome, Italy †Author for correspondence: may be affected by variability in metabolism and/or gastrointestinal Tel.: +39 0685 7951 absorption. Only voriconazole and posaconazole have been adequately Fax: +39 0644 241 984 investigated and are now indicated in the treatment and prophylaxis of E-mail: [email protected] invasive fungal diseases. Other triazoles; albaconazole, isavuconazole and ravuconazole are under development; therefore, their future use is unknown. Keywords: albaconazole • antifungal prophylaxis • antifungal therapy • isavuconazole • Phase II and III trials • posaconazole • ravuconazole • triazoles • voriconazole Opportunistic invasive fungal diseases (IFDs) are a major cause of morbidity and mortality in immunocompromised patients, particularly those affected by hematological diseases and cancer, and those undergoing transplant procedures or prolonged immunosuppressive therapy. Considerable progress in treating systemic mycoses has been achieved in recent years through better use of old antifungal agents and through development of new drugs in association with more advanced diagnostic procedures. The search for new antifungal strategies has been mainly focused on the reduction of toxicity, enhancement of bioavailability, improvement of the antifungal spectrum and counteraction of resistance.
    [Show full text]
  • Process for Preparing Latex Paints Containing Biocides
    (19) TZZ __T (11) EP 2 217 667 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C09D 5/02 (2006.01) C09D 17/00 (2006.01) 27.12.2017 Bulletin 2017/52 (86) International application number: (21) Application number: 08856379.6 PCT/US2008/082931 (22) Date of filing: 10.11.2008 (87) International publication number: WO 2009/073309 (11.06.2009 Gazette 2009/24) (54) PROCESS FOR PREPARING LATEX PAINTS CONTAINING BIOCIDES AND GRIND PHASE FOR LATEX PAINTS VERFAHREN ZUR HERSTELLUNG VON BIOZIDE-ENTHALTENDEN LATEXFARBEN UND MAHLPHASE FÜR LATEXFARBEN PROCÉDÉ DE PRÉPARATION DE PEINTURES À BASE DE LATEX CONTENANT DES BIOCIDES ET PHASE DE BROYAGE POUR PEINTURES À BASE DE LATEX (84) Designated Contracting States: • HENNING, Mark, A. AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Barrington HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT IL 60010 (US) RO SE SI SK TR • QUINN, John, W. Skokie (30) Priority: 30.11.2007 US 991315 P IL 60077 (US) (43) Date of publication of application: (74) Representative: Beck Greener 18.08.2010 Bulletin 2010/33 Fulwood House 12 Fulwood Place (73) Proprietor: Dow Global Technologies LLC London WC1V 6HR (GB) Midland, MI 48674 (US) (56) References cited: (72) Inventors: WO-A-2004/018565 WO-A-2007/026004 • ANNIS, Ioana WO-A-2007/078598 US-A- 6 133 300 Mundelein IL 60060 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations.
    [Show full text]
  • Essentials of Heterocyclic Chemistry-I Heterocyclic Chemistry
    Baran, Richter Essentials of Heterocyclic Chemistry-I Heterocyclic Chemistry 5 4 Deprotonation of N–H, Deprotonation of C–H, Deprotonation of Conjugate Acid 3 4 3 4 5 4 3 5 6 6 3 3 4 6 2 2 N 4 4 3 4 3 4 3 3 5 5 2 3 5 4 N HN 5 2 N N 7 2 7 N N 5 2 5 2 7 2 2 1 1 N NH H H 8 1 8 N 6 4 N 5 1 2 6 3 4 N 1 6 3 1 8 N 2-Pyrazoline Pyrazolidine H N 9 1 1 5 N 1 Quinazoline N 7 7 H Cinnoline 1 Pyrrolidine H 2 5 2 5 4 5 4 4 Isoindole 3H-Indole 6 Pyrazole N 3 4 Pyrimidine N pK : 11.3,44 Carbazole N 1 6 6 3 N 3 5 1 a N N 3 5 H 4 7 H pKa: 19.8, 35.9 N N pKa: 1.3 pKa: 19.9 8 3 Pyrrole 1 5 7 2 7 N 2 3 4 3 4 3 4 7 Indole 2 N 6 2 6 2 N N pK : 23.0, 39.5 2 8 1 8 1 N N a 6 pKa: 21.0, 38.1 1 1 2 5 2 5 2 5 6 N N 1 4 Pteridine 4 4 7 Phthalazine 1,2,4-Triazine 1,3,5-Triazine N 1 N 1 N 1 5 3 H N H H 3 5 pK : <0 pK : <0 3 5 Indoline H a a 3-Pyrroline 2H-Pyrrole 2-Pyrroline Indolizine 4 5 4 4 pKa: 4.9 2 6 N N 4 5 6 3 N 6 N 3 5 6 3 N 5 2 N 1 3 7 2 1 4 4 3 4 3 4 3 4 3 3 N 4 4 2 6 5 5 5 Pyrazine 7 2 6 Pyridazine 2 3 5 3 5 N 2 8 N 1 2 2 1 8 N 2 5 O 2 5 pKa: 0.6 H 1 1 N10 9 7 H pKa: 2.3 O 6 6 2 6 2 6 6 S Piperazine 1 O 1 O S 1 1 Quinoxaline 1H-Indazole 7 7 1 1 O1 7 Phenazine Furan Thiophene Benzofuran Isobenzofuran 2H-Pyran 4H-Pyran Benzo[b]thiophene Effects of Substitution on Pyridine Basicity: pKa: 35.6 pKa: 33.0 pKa: 33.2 pKa: 32.4 t 4 Me Bu NH2 NHAc OMe SMe Cl Ph vinyl CN NO2 CH(OH)2 4 8 5 4 9 1 3 2-position 6.0 5.8 6.9 4.1 3.3 3.6 0.7 4.5 4.8 –0.3 –2.6 3.8 6 3 3 5 7 4 8 2 3 5 2 3-position 5.7 5.9 6.1 4.5 4.9 4.4 2.8 4.8 4.8 1.4 0.6 3.8 4 2 6 7 7 3 N2 N 1 4-position
    [Show full text]
  • Estonian Statistics on Medicines 2013 1/44
    Estonian Statistics on Medicines 2013 DDD/1000/ ATC code ATC group / INN (rout of admin.) Quantity sold Unit DDD Unit day A ALIMENTARY TRACT AND METABOLISM 146,8152 A01 STOMATOLOGICAL PREPARATIONS 0,0760 A01A STOMATOLOGICAL PREPARATIONS 0,0760 A01AB Antiinfectives and antiseptics for local oral treatment 0,0760 A01AB09 Miconazole(O) 7139,2 g 0,2 g 0,0760 A01AB12 Hexetidine(O) 1541120 ml A01AB81 Neomycin+Benzocaine(C) 23900 pieces A01AC Corticosteroids for local oral treatment A01AC81 Dexamethasone+Thymol(dental) 2639 ml A01AD Other agents for local oral treatment A01AD80 Lidocaine+Cetylpyridinium chloride(gingival) 179340 g A01AD81 Lidocaine+Cetrimide(O) 23565 g A01AD82 Choline salicylate(O) 824240 pieces A01AD83 Lidocaine+Chamomille extract(O) 317140 g A01AD86 Lidocaine+Eugenol(gingival) 1128 g A02 DRUGS FOR ACID RELATED DISORDERS 35,6598 A02A ANTACIDS 0,9596 Combinations and complexes of aluminium, calcium and A02AD 0,9596 magnesium compounds A02AD81 Aluminium hydroxide+Magnesium hydroxide(O) 591680 pieces 10 pieces 0,1261 A02AD81 Aluminium hydroxide+Magnesium hydroxide(O) 1998558 ml 50 ml 0,0852 A02AD82 Aluminium aminoacetate+Magnesium oxide(O) 463540 pieces 10 pieces 0,0988 A02AD83 Calcium carbonate+Magnesium carbonate(O) 3049560 pieces 10 pieces 0,6497 A02AF Antacids with antiflatulents Aluminium hydroxide+Magnesium A02AF80 1000790 ml hydroxide+Simeticone(O) DRUGS FOR PEPTIC ULCER AND GASTRO- A02B 34,7001 OESOPHAGEAL REFLUX DISEASE (GORD) A02BA H2-receptor antagonists 3,5364 A02BA02 Ranitidine(O) 494352,3 g 0,3 g 3,5106 A02BA02 Ranitidine(P)
    [Show full text]