Oliveira Et Al-2018-Chemistryopen
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DOI:10.1002/open.201700135 Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes:ADual- Color Flag Elisabete Oliveira,[a, b] Emilia BØrtolo,[c] Cristina NfflÇez,[d] Viviane Pilla,[e] HugoM.Santos,[a, b] Javier Fernµndez-Lodeiro,[a, b] Adrian Fernµndez-Lodeiro,[a, b] Jamila Djafari,[a, b] JosØ Luis Capelo,[a, b] and CarlosLodeiro*[a, b] ChemistryOpen 2018, 7,9–52 9 2018 The Authors. PublishedbyWiley-VCH Verlag GmbH &Co. KGaA, Weinheim Red and green are two of the most-preferred colors from the the fieldsofbio-, chemo- and nanoscience. The review focuses entire chromatic spectrum,and red and green dyes are widely on fluorescent dyes containing chromophores such as fluores- used in biochemistry,immunohistochemistry,immune-staining, cein, rhodamine, cyanine,boron–dipyrromethene (BODIPY), 7- and nanochemistry applications. Selectivedyes with green and nitobenz-2-oxa-1,3-diazole-4-yl,naphthalimide, acridine red excitable chromophores can be used in biological environ- orange, perylene diimides, coumarins, rosamine, Nile red, ments,such as tissues and cells, and can be irradiated with naphthalene diimide, distyrylpyridinium, benzophosphole P- visible light withoutcell damage. This critical review,covering oxide, benzoresorufins, and tetrapyrrolicmacrocycles. Metal aperiod of five years, provides an overview of the most-rele- complexes and nanomaterials with thesedyes are also vant results on the use of red and green fluorescent dyes in discussed. 1. Introduction histochemistry,immunostaining, and nanochemistry.For exam- ple, translational applications have arisen in the field of imag- Due to their sensitivity,technical simplicity,and fast response ing of biological tissues to minimize cellular autofluorescence time, fluorescent probes, also known as fluorescent chemosen- and colocalization in confocal microscopy in multicolored sors, have emerged as very useful tools in analytical sensing experiences.[5,6] and opticalimaging.[1] The main parts of afluorescent probe To achieveabetter understanding of how biological systems are the signalingunit (chromophore), the spacer(chemical work, researchers need to be able to visualize and quantify bridge), and the binding unit (receptor);manipulating these eventshappening at the cellular level with high levels of spa- three key componentsallows the design of probes specifically tial and temporal resolution.[7] Despite great advances in the tailoredtoparticulartargets.Organicdyes that absorb light in field, creatingselectiveand sensitive fluorescent probesre- the visible region of the spectrum (l=400–700nm) can be mains achallenge and generally requires along process of trial used as chromophores. These dyes can contain different auxo- and error.There are many requirements that afluorescent chromes andfunctional groups such as amino, carboxylic acid, probe must meet to be used in biological systems, such as carbonyl, hydroxy,sulfonic acid, and nitro groups, which nontoxicity,specificity,and solubility in aqueous solutions. modify the ability of the chromophoretoabsorb light.[2] These Moreover,probes to be used in intracellular labeling need to auxochromes can increasethe intensity of the color and/or be able to cross plasma membranes.[8] Theoretical modelsspe- shift the emitted color in the spectra as well as increase the cific to particular chromophores have been created to facilitate solubility of the dye.[3,4] Selective probes with red and green the design of better probes, for example, to design boron–di- emission, two of the most-desired colors from the entire elec- pyrromethene (BODIPY)[9] and benzothiazole derivatives.[10] The tromagnetic spectrum,are used in biochemistry,immuno- majority of the current fluorescent probeshave been designed by using alimited number of core chromophores, with cou- [a] Dr.E.Oliveira, Dr.H.M.Santos, Dr.J.Fernµndez-Lodeiro, marin, BODIPYs, cyanines, fluoresceins, rhodamines, and phe- [11,12] A. Fernµndez-Lodeiro, J. Djafari, Prof. Dr.J.L.Capelo,Prof. Dr.C.Lodeiro noxazines among the most-popular ones. The most-stud- BIOSCOPE Group, UCIBIO-LAQV-REQUIMTE ied green dyes are fluoresceins,[13] Oregon green 488 and Departamento de Química, Faculdade de CiÞncias eTecnologia 514,[14] perylene diimide,[15–19] the rhodamine green family,[20] Universidade NOVAdeLisboa [21] [22] 2829-516 Lisboa (Portugal) chlorophyll, and eosin. Red dyes typically come from rhod- [20,11] [23] [24,25] E-mail:[email protected] amines, porphyrins, and corroles. [b] Dr.E.Oliveira, Dr.H.M.Santos, Dr.J.Fernµndez-Lodeiro, Red and green pigmentshave long attracted the interest of A. Fernµndez-Lodeiro, J. Djafari, Prof. Dr.J.L.Capelo,Prof. Dr.C.Lodeiro researchers. For example, the ability of primates to discriminate Proteomass Scientific Society,Rua dos Inventores between redand green has been linked to foragingadvantag- Madan Park, 2829-516 Caparica (Portugal) es, allowing animals to detect more easily ripe fruit and young [c] Prof. Dr.E.BØrtolo Biomolecular ResearchGroup, School of Human and Life Sciences leaves against maturefoliage. Research also suggestsitmay Canterbury Christ Church University,Canterbury CT1 1QU (UK) help intraspecies sociosexual communication in primates by [26] [d] Dr.C.NfflÇez aiding them in the selection of their reproductive partner. Research Unit, Hospital Universitario Lucus Augusti (HULA) The primaryfunctionofpigments in plants is the process of Servizo Galego de Safflde (SERGAS), 27003, Lugo (Spain) photosynthesis, in which chlorophyllsplay akey role.[27] Chlor- [e] Dr.V.Pilla ophylls are agroup of natural pigmentsbased on achlorin Instituto de Física, Universidade Federal de Uberlândia-UFU Av.Jo¼oNaves de vila 2121, Uberlândia, MG, 38400-902 (Brazil) magnesium macrocycle ring that absorbs yellow and blue [28,29] The ORCID identification number(s) for the author(s) of this article can wavelengths and reflects green color. Chlorophyll is pres- be found under https://doi.org/10.1002/open.201700135. ent in photosynthetic organisms(e.g. plants, algae, and cyano- 2017 The Authors. Published by Wiley-VCH Verlag GmbH &Co. KGaA. bacteria).[30] Other red and yellow pigments can help chloro- This is an openaccessarticleunder the termsofthe Creative Commons phyll capture light and convert it in energy.There are many Attribution-NonCommercial-NoDerivs License, which permits useand colored natural plant pigments, such as porphyrins, anthocya- distribution in any medium, provided the original work is properly cited, [31] the use is non-commercial and no modifications or adaptations are nins, carotenoids, and betalains. In the food industry,em- made. phasis hasbeen placed on replacing synthetic colorants with ChemistryOpen 2018, 7,9–52 www.chemistryopen.org 10 2018 The Authors. PublishedbyWiley-VCH Verlag GmbH &Co. KGaA, Weinheim Elisabete Oliveira graduated in 2006 in Viviane Pilla received her Ph.D. degree in Applied Chemistry from FCT-University Applied Physics Sciences in 2001 from NOVAofLisbon (Portugal), obtained her the University of S¼oPaulo (Brazil). She Master’s degree in Biotechnology in performed postdoctoral research in Ap- 2007, and completed aPh.D. degree in plied Physics in Nonlinear Optics at the Biotechnology in 2010 at the same uni- Federal University of Pernambuco (Brazil) versity.In2013, she obtained asecond and State University of Campinas (Brazil). Ph.D. degree in Food Science and Tech- She later completed apostdoctoral nology from the Science Faculty of Our- period in Physical Chemistry Applications ense Campus in the University of Vigo in the BIOSCOPE research group at the (Spain). Her scientific interests are fo- University NOVAofLisbon (Portugal). Cur- cused on the synthesis of new bioin- rently,she is Adjunct Physics Professor IV spired emissive peptide as fluorescence at the Physics Institute in the Federal Uni- chemosensors;supramolecular chemistry versity of Uberlândia UFU (Brazil) and re- (photophysics and photochemistry);mul- searcher of the group of Optical and tifunctionalapplication of chemosensors in vitro (solution and solid Thermal Properties of Materials of thePhysics Institute UFU (Brazil). Dr. studies) and in vivo (cell-imaging studies);the synthesis of new emis- Pilla has experience in the optical and spectroscopic properties of ma- sive nanomaterials, such as quantum dots and silica for drug delivery; terials, acting mainly on the followingsubjects: photothermal effects and biomarker discovery in biological samples. and thermo-opticalcharacterization of different materials as quantum dots for biological applications;crystal and glasses;and biomaterials (biofluids, naturaldyes, and dental resin composites). Emilia BØrtolo is aPrincipal Lecturer Hugo M. Santos graduatedinApplied (Chemistry) at Canterbury Christ Church Chemistry from UniversityNOVAof University (CCCU, UK)and previously Lisbon (Portugal)and completed aPh.D. worked in the DepartmentofMaterials, degree in Biochemistryfrom the same ImperialCollege London (UK). She ob- university in 2010. During his time as a tained her Ph.D. and B.Sc. degrees in Ph.D. candidate, he spent six months at Chemistry (Inorganic)from the University the Turku Centre for Biotechnology (Fin- of Santiago de Compostela (Spain). Addi- land) working with state-of-the-art mass tionally,she obtained her M.Sc. degree in spectrometry(MS) instrumentation for Environmental Technology from Imperial biomedical research. He worked as a College London (UK). She also has aPost- postdoctoral researcher at the University graduateCertificate in Learning and of Vigo (Spain) followed