Synthesis of Fluorescent C-C Bonded Triazole-Purine Conjugates

Aleksejs Burcevs; Armands Sebris; Kaspars Traskovskis; Han-Wei Chu; Huan-Tsung Chang; Justina Jovaišaitė; Saulius Juršėnas; Māris Turks; Irina Novosjolova

doi:10.1007/s10895-023-03337-6

Synthesis of Fluorescent C-C Bonded Triazole-Purine Conjugates

J Fluoresc. 2023 Jul 18. doi: 10.1007/s10895-023-03337-6. Online ahead of print.

Authors

Affiliations

¹ Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga, LV-1048, Latvia.
² Institute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga, LV-1048, Latvia.
³ Department of Biomedical Sciences, Chang Gung University, Taoyuan, 33302, Taiwan.
⁴ Graduate Institute of Biomedical Sciences, Chang Gung University, Taoyuan, 33302, Taiwan.
⁵ Center for Advanced Biomaterials and Technology Innovation, Chang Gung University, Taoyuan, 33302, Taiwan.
⁶ Division of Breast Surgery, Department of General Surgery, Chang-Gung Memorial Hospital, Linkou, Taoyuan, 33305, Taiwan.
⁷ Institute of Photonics and Nanotechnology, Faculty of Physics, Vilnius University, Saulėtekis av. 3, Vilnius, LT-10257, Lithuania.
⁸ Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga, LV-1048, Latvia. irina.novosjolova@rtu.lv.

PMID: 37460821
DOI: 10.1007/s10895-023-03337-6

Abstract

A design toward C-C bonded 2,6-bis(1H-1,2,3-triazol-4-yl)-9H-purine and 2-piperidinyl-6-(1H-1,2,3-triazol-4-yl)-9H-purine derivatives was established using the combination of Mitsunobu, Sonogashira, copper (I) catalyzed azide-alkyne cycloaddition, and S_NAr reactions. 11 examples of 2,6-bistriazolylpurine and 14 examples of 2-piperidinyl-6-triazolylpurine intermediates were obtained, in 38-86% and 41-89% yields, respectively. Obtained triazole-purine conjugates expressed good fluorescent properties which were studied in the solution and in the thin layer film for the first time. Quantum yields reached up to 49% in DMSO for bistriazolylpurines and up to 81% in DCM and up to 95% in DMSO for monotriazolylpurines. Performed biological studies in mouse embryo fibroblast, human keratinocyte, and transgenic adenocarcinoma of the mouse prostate cell lines showed that most of obtained triazole-purine conjugates are not cytotoxic. The 50% cytotoxic concentration of the tested derivatives was in the range from 59.6 to 1528.7 µM.

Keywords: CuAAC; Fluorescence; Fluorescent purines; Sonogashira reaction.