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Synthesis of Fluorescent C–C Bonded Triazole-Purine Conjugates

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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 SNAr 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.

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Acknowledgements

The authors thank the Latvia-Lithuania-Taiwan joint grant “Molecular Electronics in functionalized Purines: fundamental Study and applications (MEPS)” for financial support and Dr. chem. Kristine Lazdoviča for IR analysis. A.B. thanks the European Social Fund within Project No. 8.2.2.0/20/I/008 “Strengthening of PhD students and academic personnel of Riga Technical University and BA School of Business and Finance in the strategic fields of specialization”.

Funding

The Latvia-Lithuania-Taiwan joint grant “Molecular Electronics in functionalized Purines: fundamental Study and applications (MEPS)”. The European Social Fund within Project No. 8.2.2.0/20/I/008.

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Authors and 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

    Aleksejs Burcevs, Armands Sebris, Māris Turks & Irina Novosjolova

  2. Institute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga, LV-1048, Latvia

    Kaspars Traskovskis

  3. Department of Biomedical Sciences, Chang Gung University, Taoyuan, 33302, Taiwan

    Han-Wei Chu & Huan-Tsung Chang

  4. Graduate Institute of Biomedical Sciences, Chang Gung University, Taoyuan, 33302, Taiwan

    Huan-Tsung Chang

  5. Center for Advanced Biomaterials and Technology Innovation, Chang Gung University, Taoyuan, 33302, Taiwan

    Huan-Tsung Chang

  6. Division of Breast Surgery, Department of General Surgery, Chang-Gung Memorial Hospital, Linkou, Taoyuan, 33305, Taiwan

    Huan-Tsung Chang

  7. Institute of Photonics and Nanotechnology, Faculty of Physics, Vilnius University, Saulėtekis av. 3, Vilnius, LT-10257, Lithuania

    Justina Jovaišaitė & Saulius Juršėnas

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  1. Aleksejs Burcevs
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  6. Justina Jovaišaitė
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Contributions

M.T. and I.N. contributed to the study conception and design, and supervision. A.B. and A.S. performed the synthesis and analysis of purine derivatives, and wrote the experimental part. K.T., J.J. and S.J. performed the photophysical studies and analysis of data. H.W.C. and H.T.C. performed cytotoxicity experiments and analysis. The first draft of the manuscript was written by I.N. and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Irina Novosjolova.

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Burcevs, A., Sebris, A., Traskovskis, K. et al. Synthesis of Fluorescent C–C Bonded Triazole-Purine Conjugates. J Fluoresc 34, 1091–1097 (2024). https://doi.org/10.1007/s10895-023-03337-6

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