title: Oligothiophenes as fluorescent markers for biological applications.
abstract: This paper summarizes some of our results on the application of oligothiophenes as fluorescent markers for biological studies. The oligomers of thiophene, widely known for their semiconductor properties in organic electronics, are also fluorescent compounds characterized by chemical and optical stability, high absorbance and quantum yield. Their fluorescent emission can be easily modulated via organic synthesis by changing the number of thiophene rings and the nature of side-chains. This review shows how oligothiophenes can be derivatized with active groups such as phosphoramidite, N-hydroxysuccinimidyl and 4-sulfotetrafluorophenyl esters, isothiocyanate and azide by which the (bio)molecules of interest can be covalently bound. This paper also describes how molecules such as oligonucleotides, proteins and even nanoparticles, tagged with oligothiophenes, can be used in experiments ranging from hybridization studies to imaging of fixed and living cells. Finally, a few multilabeling experiments are described.
authors.affiliation: Istituto per Sintesi Organica e Fotoreattività, Consiglio Nazionale delle Ricerche, Via Gobetti 101, Bologna 40129, Italy. capobianco@isof.cnr.it
authors.forename: Massimo L
authors.initials: ML
authors.lastname: Capobianco
authors.forename: Giovanna
authors.initials: G
authors.lastname: Barbarella
authors.forename: Antonio
authors.initials: A
authors.lastname: Manetto
mesh_terms: D001483:Base Sequence; D015415:Biomarkers / Q000378:metabolism; D057930:Click Chemistry; D015342:DNA Probes / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D018796:Immunoconjugates / Q000737:chemistry; D008214:Lymphocytes / Q000378:metabolism; D053758:Nanoparticles / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D011119:Polynucleotides / Q000737:chemistry; D011506:Proteins / Q000737:chemistry; D013194:Staining and Labeling / Q000379:methods*; D013876:Thiophenes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D015415:Biomarkers; D015342:DNA Probes; D003853:Deoxyribonucleosides; D005456:Fluorescent Dyes; D018796:Immunoconjugates; D011108:Polymers; D011119:Polynucleotides; D011506:Proteins; D013876:Thiophenes