Rigid-core fluorescent oligothiophene-S,S-dioxide isothiocyanates. Synthesis, optical characterization, and conjugation to monoclonal antibodies.
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.
Sotgiu
Giovanna
G
Consiglio Nazionale Ricerche-ISOF, Via Gobetti 101, 40129 Bologna, Italy.
Zambianchi
Massimo
M
Barbarella
Giovanna
G
Aruffo
Fabio
F
Cipriani
Franco
F
Ventola
Alfredo
A
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
D000911:Antibodies, Monoclonal; D017252:CD3 Complex; D016827:CD8 Antigens; D005456:Fluorescent Dyes; D018796:Immunoconjugates; D017879:Isothiocyanates; D013876:Thiophenes