Pentamethine cyanine dyes with alkynyl group as perspective structure for conjugation with targeting moiety

• Published in: Bioorganic & medicinal chemistry letters Vol. 115; pp. 130025 - 130030
• Main Authors: Uspenskaia, Anastasiia A., Doroshenko, Irina A., Popovicheva, Kseniia A., Shmychkov, Nazar V., Pryakhina, Ekaterina V., Shafikov, Radik R., Skvortsov, Dmitrii A., Beklemishev, Mikhail K., Zaborova, Olga V., Podrugina, Tatiana A., Machulkin, Aleksei E., Beloglazkina, Elena K.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.01.2025; Elsevier
• Subjects: Alkynes - chemical synthesis; Alkynes - chemistry; Antigens, Surface - chemistry; Antigens, Surface - metabolism; Asymmetric carbocyanine; Azides - chemistry; Carbocyanines - chemical synthesis; Carbocyanines - chemistry; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Click reaction; Cyanine dyes; Cycloaddition Reaction; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Glutamate Carboxypeptidase II - antagonists & inhibitors; Glutamate Carboxypeptidase II - metabolism; Humans; Life Sciences & Biomedicine; Ligands; Male; Molecular Structure; Pharmacology & Pharmacy; Photochemistry; Physical Sciences; Prostatic Neoplasms - drug therapy; Science & Technology; Cyanine dyes; PSMA; Click reaction; Asymmetric carbocyanine; DCL; ICG; DMF; Photochemistry
• ISSN: 0960-894X; 1464-3405; 1464-3405
• DOI: 10.1016/j.bmcl.2024.130025

[Display omitted] •An asymmetric carbocyanine for the [3+2] cycloaddition reaction was obtained.•A triazole ring does not affect the photophysical properties of the fluorophore.•The conjugation to the vector molecule does not abolish the selective binding. We report a modified carbocyanine-based asymmetric fluorescent dye, suitable for the azide-alkyne cycloaddition reaction, that possesses promising photochemical properties (Φfl = 0,49). As an example of usage of the new fluorophore, it was conjugated to a ligand targeting prostate-specific membrane antigen (PSMA), one of the widely utilized prostate cancer markers.