title: 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.
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.
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: T
authors.initials: T
authors.lastname: Vijai Kumar Reddy
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: A
authors.initials: A
authors.lastname: Jyotsna
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India. Electronic address: prabhavathi@iict.res.in.
authors.forename: B L A
authors.initials: BL
authors.lastname: Prabhavathi Devi
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: R B N
authors.initials: RB
authors.lastname: Prasad
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Y
authors.initials: Y
authors.lastname: Poornachandra
authors.affiliation: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: C
authors.initials: C
authors.lastname: Ganesh Kumar
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018441:Biofilms / Q000187:drug effects*; D002176:Candida albicans / Q000166:cytology / Q000187:drug effects / Q000378:metabolism / Q000502:physiology; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D042541:Intracellular Space / Q000187:drug effects / Q000378:metabolism; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects / Q000502:physiology; D017382:Reactive Oxygen Species / Q000378:metabolism; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects / Q000502:physiology; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D017382:Reactive Oxygen Species; D014230:Triazoles; D013110:Sphingosine; C005682:safingol
keywords: 1,2,3-Triazole; Anti-biofilm; Antimicrobial; Click reaction; Reactive oxygen species; Short-chain sphinganine