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      https://www.ias.ac.in/article/fulltext/jcsc/129/06/0663-0677

    • Keywords

       

      L-Tyrosine; N-fatty acyl-L-tyrosine; fatty acids; α-Lipioic acid; cytotoxicity; carbohydrates.

    • Abstract

       

      In the present study, a series of fatty acids-based (short, medium and long unsaturated chains) glycosylated N-fatty acyl-L-tyrosines and N-lipoyl-L-tyrosine methyl esters were synthesized and evaluated for their cytotoxic and antimicrobial activities. The aglycone moiety was synthesized using different chemicalreagents. The glycosylation of aglycone moiety with different carbohydrates was performed using the Lewis acid, BF3.Et2O. All the synthesized compounds were tested against a panel of four cancer cell lines. The glycosylated N-fatty acyl-L-tyrosines showed moderate activity against all the cell lines and the IC50 values were in the range of 15.6−45.6 μM. However, the oleic acid analogues (10a, 10d) exhibited IC50 values of 15.6, 17.6 μM, respectively, against MDA-MB-231 cell line. Glycosylated N-lipoyl-L-tyrosine methyl esters (6b–6d) showed promising activity against all the tested cell lines and the IC50 values ranged between 9.4−13.8 μM. The compound 6d exhibited significant cytotoxicity and IC50 values were 10.5, 9.4, 10.9 and 12.1 μM against A549, PC3, MDA-MB-231 and HepG2 cell lines, respectively. Moreover, the nonglycosylated N-fatty acyl-L-tyrosine and methyl N-fatty acyl-L-tyrosinate derivatives showed excellent and moderate antimicrobial activity against some of the tested bacterial strains.

    • Author Affiliations

       

      SRIKANTH VUDHGIRI1 2 R B N PRASAD1 2 Y POORNACHANDRA3 2 C GANESH KUMAR3 2 E ANJANEYULU1 K SIRISHA3 2 RAM CHANDRA REDDY JALA1 2

      1. Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India
      2. Academy of Scientific and Innovative Research, New Delhi, India
      3. Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India
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