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Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

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Clickable conjugates of bile acids and nucleosides: Synthesis, characterization, in vitro anticancer and

Devesh S Agarwal¹, Vagolu Siva Krishna², Dharmarajan Sriram²

¹Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India.

|September 22, 2018

Abstract:

A series of clickable bile acid-nucleosides conjugates linked directly or via amino acid linker were synthesized, and characterized by spectroscopic techniques such as ¹H NMR, ¹³C NMR, FT-IR, HRMS and HPLC. The synthesized compounds 6a-p were screened for their in vitro anticancer property against a panel of three cancer cell lines (PC-3, MCF-7, IMR-32). In addition, the synthesized derivatives were also tested for their antimycobacterial activity against Mycobacterium tuberculosis H₃₇Rv (ATCC 27294 strain). Among the screened compounds, cholic acid-uridine clicked conjugate (6c), and cholic acid-uridine clicked conjugate liked via phenylalanine moiety (6m) were found to be most active against MCF-7 and IMR-32 exhibiting an IC₅₀ value of 8.084 and 8.71 µM, respectively. The antimycobacterial study of the synthesized conjugates revealed all the conjugates to be active with MIC values in the range of 4.09-15.41 µM. Deoxycholic acid-adenosine clicked conjugate (6b) showed most promising antituberculosis property with MIC value of 4.09 µM. Most of the synthesized conjugates were found to be safe at 50 µM against normal human embryonic kidney (HEK 293 T) cell line.

Keywords:

Anticancer Antimycobacterial Bile acid Nucleosides Triazoles

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