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  2. Design, synthesis and in vitro biological evaluation of short-chain C12-sphinganine and its 1,2,3-triazole analogs as potential antimicrobial and anti-biofilm agents

Design, synthesis and in vitro biological evaluation of short-chain C12-sphinganine and its 1,2,3-triazole analogs as potential antimicrobial and anti-biofilm agents

  • Eur J Med Chem. 2016 Aug 8;118:98-106. doi: 10.1016/j.ejmech.2016.04.020.
T Vijai Kumar Reddy 1 A Jyotsna 1 B L A Prabhavathi Devi 2 R B N Prasad 1 Y Poornachandra 3 C Ganesh Kumar 3
Affiliations

Affiliations

  • 1 Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
  • 2 Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India. Electronic address: prabhavathi@iict.res.in.
  • 3 Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
Abstract

A conceptual synthetic approach of short-chain C12-sphinganine 1 and a small library of its 1,2,3-triazole analogs 2(a-f) has been accomplished using the commercially available and inexpensive 10-undecenoic acid as a starting material. Miyashita's C-2 selective endo mode azidolysis and Huisgen click reaction was employed for the synthesis of the designed analogs. Based on biological evaluation studies of all the synthesized compounds, it was observed that, (2S,3R)-2-(4-(3-hydroxyphenyl)-1H-1,2,3-triazol-1-yl)dodecan-1,3-diol (2b) exhibited promising antimicrobial and Antifungal activities. Furthermore, compound 2b was able to inhibit the biofilm formation of Candida albicans MTCC 227, Micrococcus luteus MTCC 2470 and Staphylococcus aureus MTCC 96 with IC50 values of 1.9, 2.1 and 2.9 μg/mL, respectively. Compound 2b increased the levels of Reactive Oxygen Species (ROS) in C. albicans MTCC 227.

Keywords

1,2,3-Triazole; Anti-biofilm; Antimicrobial; Click reaction; Reactive oxygen species; Short-chain sphinganine.

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