Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation

Khan, Faiz Ahmed and Ahmad, S and Kodipelli, N and Shivange, G and Roy, Anindya (2014) Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation. Organic and Biomolecular Chemistry, 12 (23). pp. 3847-3865. ISSN 1477-0520

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Ianthelliformisamines A-C are a novel class of bromotyrosine-derived antibacterial agents isolated recently from the marine sponge Suberea ianthelliformis. We have synthesized ianthelliformisamines A-C straightforwardly by the condensation of (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid and the corresponding Boc-protected polyamine followed by Boc-deprotection with TFA. Further, using this reaction protocol, a library of their analogues (39 analogues) has been synthesized by employing 3-phenylacrylic acid derivatives and Boc-protected polyamine chains through various combinations of these two fragments differing in phenyl ring substitution, double bond geometry or chain length of the central spacer of the polyamine chain (shown in red color). All the synthesized compounds (ianthelliformisamines A-C and their analogues) were screened for antibacterial activity against both Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) strains. All synthetic analogues of ianthelliformisamine A showed bacterial growth inhibition against both strains (Escherichia coli and Staphylococcus aureus), having MIC values in the range of 117.8-0.10 μM, while none of the synthetic analogues of ianthelliformisamine C as well as the parent compound showed any detectable antibacterial activity. Interestingly, some of the synthetic analogues of ianthelliformisamines A and B exerted a bactericidal effect against both E. coli and S. aureus strains, decreasing viable bacterial count by 99% at concentrations as low as 2 × MIC

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IITH Creators:
IITH CreatorsORCiD
Roy, Anindya
Item Type: Article
Uncontrolled Keywords: Bacteria; C (programming language); Chains; Escherichia coli
Subjects: Others > Biotechnology
Divisions: Department of Biotechnology
Depositing User: Team Library
Date Deposited: 19 Dec 2014 09:33
Last Modified: 21 Sep 2017 07:18
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