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Medicinal Chemistry Research

, Volume 24, Issue 5, pp 1893–1900 | Cite as

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

  • Pachamuthu Pratheebaa
  • Perumal Perumal
  • Jayaraman Angayarkanni
  • Narayanan SundaraBaalaji
  • Thayumanavan PalvannanEmail author
Original Research

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.

Keywords

ASAB Antibacterial activity Docking Topoisomerase I & II Supercoil relaxation 

Supplementary material

44_2014_1263_MOESM1_ESM.doc (582 kb)
Supplementary material 1 (DOC 582 kb)

References

  1. Arjmand F, Parveen S, Afzal M, Shahid M (2012) Synthesis, characterization, biological studies (DNA binding, cleavage, antibacterial and topoisomerase (I) and molecular docking of copper(II) benzimidazole complexes. J Photochem Photobiol B 114:15–26CrossRefPubMedGoogle Scholar
  2. Champoux JJ (2001) DNA topoisomerases: structure, function and mechanism. Annu Rev Biochem 70:369–413CrossRefPubMedGoogle Scholar
  3. Cho HJ, Jung MJ, Kwon Y, Na Y (2009) Oxiranylmethyloxy or thiiranylmethyloxy-azaxanthones and –acridone analogues as potential topoisomerase I inhibitors. Bioorg Med Chem 19:6766–6769CrossRefGoogle Scholar
  4. Chowdhury AR, Sharma S, Mandal S, Goswami A, Mukhopadhyay S, Majumder HK (2002) Luteolin an emerging anticancer flavonoid poisons eukaryotic DNA topoisomerase I. Biochem J 366:653–661CrossRefPubMedCentralPubMedGoogle Scholar
  5. Chu Q, Ling MT, Feng H, Cheung HW, Tsao SW, Wang X, Wong YC (2006) A novel anticancer effect of garlic derivatives: inhibition of cancer cell invasion through restoration of E-cadherin expression. Carcinogenesis 27:2180–2189CrossRefPubMedGoogle Scholar
  6. Chu Q, Lee DT, Tsao SW, Wang X, Wong YC (2007) S-allylcysteine, a water-soluble garlic derivative, suppresses the growth of a human androgen-independent prostate cancer xenograft, CWR22R, under in vivo conditions. BJU Int 99:925–932CrossRefPubMedGoogle Scholar
  7. Eldridge MD, Murray CW, Auton TR, Paolini GV, Mee RP (1997) Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes. J Comput-Aided Mol Des 11:425–445CrossRefPubMedGoogle Scholar
  8. Filomeni G, Rotilio G, Ciriolo MR (2008) Molecular transduction mechanisms of the redox network underlying the antiproliferative effects of allyl compounds from garlic, American Society for Nutrition. J Nutr 138:2053–2057PubMedGoogle Scholar
  9. Fukuda M, Nishio K, Kanzawa F, Ogasawara H, Ishida T, Arioka H, Bonjanowski K, Oka M, Saijo N (1996) Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells. Cancer Res 56:789–793PubMedGoogle Scholar
  10. Gapter LA, Yuin OZ, Ng KY (2008) S-Allylcysteine reduces breast tumor cell adhesion and invasion. Biochem Biophys Res Commun 367:446–451CrossRefPubMedGoogle Scholar
  11. Ishikawa H, Saeki T, Otani T, Suzuki T, Shimozuma K, Nishino H, Fukuda Se, Morimoto K (2006) Significance of garlic and its constituents in cancer and cardiovascular disease aged garlic extract prevents a decline of NK cell number and activity in patients with advanced cancer. J Nutr 136:816S–820SPubMedGoogle Scholar
  12. Janovec L, Kozurkova M, Sabolova D, Ungvarsky J, Paulikova H, Plšikova J, Vantova Z, Imrich J (2011) Synthesis, DNA binding and molecular modeling. Bioorg Med Chem 19:1790–1801CrossRefPubMedGoogle Scholar
  13. Kang DH, Kim JS, Jung MJ, Lee ES, Jahng Y, Kwon Y, Na Y (2008) New insight for fluoroquinophenoxazine derivatives as possibly new potent topoisomerase I inhibitor. Bioorg Med Chem Lett 18:1520–1524CrossRefPubMedGoogle Scholar
  14. Lazaro ML, Cordero CM, Bermejo A, Cortes D, Ayuso MJ (2001) Cytotoxic compounds from Annonaceus species as DNA topoisomerase I poisons. Anticancer Res 21:3493–3497Google Scholar
  15. McKenna DJ, Jones K, Hughes K, Humphrey S (2002) Botanical medicines, the desk references for major herbal supplements, 2nd edn. The Haworth Herbal Press, New YorkGoogle Scholar
  16. Mundo NH, Adaya DS, Maldonado PD, Galván-Arzate S, Martinez LA, Cruz VPDL, Chaverri JP, Santamaria A (2006) S-allylcysteine prevents the rat from 3-nitropropionic acid-induced hyperactivity early markers of oxidative stress and mitochondrial dysfunction. Neurosci Res 56:39–44CrossRefGoogle Scholar
  17. Ng KTP, Guo DY, Cheng Q, Geng W, Ling CC, Li CX, Liu XB, Ma YY, Lo CM, Poon TP, Fan ST, Man K (2012) A garlic derivative, S-allylcysteine (SAC), suppresses proliferation and metastasis of hepatocellular carcinoma. PLoS One 7:1–9Google Scholar
  18. Nishimura H, Mizutani J (1975) Photochemistry and radiation chemistry of sulfur-containing amino acids. New reaction of the 1-propenylthiyl radicals. J Org Chem 40:1567–1575CrossRefPubMedGoogle Scholar
  19. Nitiss JL (1998) Investigating the biological functions of DNA topoisomerases in eukaryotic cells. Biochim Biophys Acta 1400:63–81CrossRefPubMedGoogle Scholar
  20. Park K, Kim J, Lim S, Han S (2003) Topoisomerase II-α (topoII) and HER2 amplification in breast cancers and response to preoperative doxorubicin chemotherapy. Eur J Med Chem 39:631–634Google Scholar
  21. Pommier Y, Leo E, Zhang H, Marchand C (2010) DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chem Biol 17:421–433CrossRefPubMedGoogle Scholar
  22. Shahabadi N, Falsafi M, Moghadam NH (2013) DNA interaction studies of a novel Cu (II) complex as an intercalator containing curcumin and bathophenanthroline ligands. J Photochem Photobiol B 122:45–51CrossRefPubMedGoogle Scholar
  23. Tabassum S, Afzal M, Arjmand F (2012) New heterobimetallic CuII—Sn2 IV complex as potential topoisomerase I inhibitor: in vitro DNA binding, cleavage and cytotoxicity against human cancer cell lines. J Photochem Photobiol B 115:63–72CrossRefPubMedGoogle Scholar
  24. Tang FY, Chiang EP, Chung JG, Lee HZ, Hsu CY (2009) S-allylcysteine modulates the expression of E-cadherin and inhibits the malignant progression of human oral cancer. J Nutr Biochem 20:1013–1020CrossRefPubMedGoogle Scholar
  25. Tang FY, Chiang EP, Pai MH (2010) Consumption of S-allylcysteine inhibits the growth of human non-small-cell lung carcinoma in a mouse xenograft model. J Agric Food Chem 58:11156–11164CrossRefPubMedGoogle Scholar
  26. Threlfall EJ, Fisher IST, Ward L, Tschape H, Gernersmidt P (1999) Harmonization of antibiotic susceptibility testing for Salmonella Results of a study by 18 national reference laboratories within the European Union-funded Enter-Net group. Micro Drug Resist 5:195–199CrossRefGoogle Scholar
  27. Walker RD (2000) Antimicrobial susceptibility testing and interpretation of results. In: Prescott JF, Baggot JD, Walker RD (eds) Antimicrobial Therapy in Veterinary Medicine. Iowa State University Press, Ames, pp 12–26Google Scholar
  28. Wang JC (1996) DNA topoisomerases. Annu Rev Biochem 65:635–692CrossRefGoogle Scholar
  29. Welch C, Wuarin L, Sidell N (1992) Antiproliferative effect of the garlic compound S-allyl cysteine on human neuroblastoma cells in vitro. Cancer Lett 63:211–219CrossRefPubMedGoogle Scholar
  30. Wu WB, Ou JB, Huang ZH, Chen SB, Ou TM, Tan JH, Li D, Shen LL, Huang SL, Gu LQ, Huang ZS (2011) Synthesis and evaluation of mansonone F derivatives as topoisomerase inhibitors. Eur J Med Chem 46:3339–3347CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Pachamuthu Pratheebaa
    • 1
  • Perumal Perumal
    • 2
  • Jayaraman Angayarkanni
    • 3
  • Narayanan SundaraBaalaji
    • 2
  • Thayumanavan Palvannan
    • 1
    Email author
  1. 1.Laboratory of Bioprocess and Engineering, Department of BiochemistryPeriyar UniversitySalemIndia
  2. 2.Structural Biology Lab, Department of BioinformaticsBharathiar UniversityCoimbatoreIndia
  3. 3.School of Biotechnology and Genetic engineeringBharathiar UniversityCoimbatoreIndia

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