title: Rigid-core fluorescent oligothiophene-S,S-dioxide isothiocyanates. Synthesis, optical characterization, and conjugation to monoclonal antibodies.
abstract: In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.
authors.affiliation: Consiglio Nazionale Ricerche-ISOF, Via Gobetti 101, 40129 Bologna, Italy.
authors.forename: Giovanna
authors.initials: G
authors.lastname: Sotgiu
authors.forename: Massimo
authors.initials: M
authors.lastname: Zambianchi
authors.forename: Giovanna
authors.initials: G
authors.lastname: Barbarella
authors.forename: Fabio
authors.initials: F
authors.lastname: Aruffo
authors.forename: Franco
authors.initials: F
authors.lastname: Cipriani
authors.forename: Alfredo
authors.initials: A
authors.lastname: Ventola
mesh_terms: D000911:Antibodies, Monoclonal / Q000737:chemistry*; D017252:CD3 Complex / Q000276:immunology; D016827:CD8 Antigens / Q000276:immunology; D002384:Catalysis; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D018796:Immunoconjugates / Q000737:chemistry; D017879:Isothiocyanates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000911:Antibodies, Monoclonal; D017252:CD3 Complex; D016827:CD8 Antigens; D005456:Fluorescent Dyes; D018796:Immunoconjugates; D017879:Isothiocyanates; D013876:Thiophenes