Oligothiophene Isothiocyanates as a New Class of Fluorescent Markers for Biopolymers

• Published in: Journal of the American Chemical Society Vol. 123; no. 47; pp. 11600 - 11607
• Main Authors: Barbarella, Giovanna, Zambianchi, Massimo, Pudova, Olga, Paladini, Vanessa, Ventola, Alfredo, Cipriani, Francesco, Gigli, Giuseppe, Cingolani, Roberto, Citro, Gennaro
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 28-11-2001
• Subjects: Antibodies, Monoclonal - chemistry; Biopolymers - analysis; CD8 Antigens - immunology; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Immunoconjugates - chemistry; Isothiocyanates - chemical synthesis; Isothiocyanates - chemistry; Serum Albumin, Bovine - chemistry; Spectrometry, Fluorescence; Thiophenes - chemical synthesis; Thiophenes - chemistry
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja011209v

The regioselective synthesis of fluorescent oligothiophene isothiocyanates is described. The isothiocyanates were reacted with bovine serum albumin (BSA) following standard procedures and the optical properties of the oligothiophene-BSA conjugates were analyzed as a function of oligomer concentration, time, and irradiation power. The oligothiophene-BSA conjugates were chemically very stable and their photoluminescence characteristics persisted unaltered for several months. Photoluminescence data relative to the conjugate of an oligothiophene-S,S-dioxide isothiocyanate with monoclonal anti-CD8 antibody are reported. No fluorescence quenching was observed following the binding of the isothiocyanate to the antibody and the conjugate displayed high chemical stability and photostability.