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4-[2-Allylsulfanyl-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-2-amino-butyric acid: evaluation as topoisomerase inhibitor using in vitro assay and molecular docking study

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Abstract

A new compound 4-[2-allylsulfanyl-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-2-amino-butyric acid (ASAB) bearing allyl group was synthesized and characterized by spectroscopic (FTIR, NMR, & LC–MS) methods. ASAB showed significant antibacterial activity against gram-positive (S. aureus) and gram-negative (E. coli) bacteria. ASAB was screened for interaction with type I and II DNA topoisomerase activity via in vitro supercoil relaxation assay. ASAB was found to be a strong inhibitor for topoisomerases; with much more significant inhibition for topoisomerase II than topoisomerase I. Furthermore, DNA binding properties of ASAB with pBR322 DNA was investigated by fluorescent spectra which revealed its DNA binding ability. Molecular docking study was performed to elucidate the specific binding site in the active site of topoisomerase I & II.

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Authors and Affiliations

  1. Laboratory of Bioprocess and Engineering, Department of Biochemistry, Periyar University, Salem, 636 011, Tamil Nadu, India

    Pachamuthu Pratheebaa & Thayumanavan Palvannan

  2. Structural Biology Lab, Department of Bioinformatics, Bharathiar University, Coimbatore, 641 046, Tamil Nadu, India

    Perumal Perumal & Narayanan SundaraBaalaji

  3. School of Biotechnology and Genetic engineering, Bharathiar University, Coimbatore, 641 046, Tamil Nadu, India

    Jayaraman Angayarkanni

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  1. Pachamuthu Pratheebaa
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  2. Perumal Perumal
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  3. Jayaraman Angayarkanni
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  4. Narayanan SundaraBaalaji
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  5. Thayumanavan Palvannan
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Correspondence to Thayumanavan Palvannan.

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Pratheebaa, P., Perumal, P., Angayarkanni, J. et al. 4-[2-Allylsulfanyl-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-2-amino-butyric acid: evaluation as topoisomerase inhibitor using in vitro assay and molecular docking study. Med Chem Res 24, 1893–1900 (2015). https://doi.org/10.1007/s00044-014-1263-y

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  • DOI: https://doi.org/10.1007/s00044-014-1263-y

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