Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity

Hamada H.H. Mohammed, El Shimaa M.N. Abdelhafez, Samar H. Abbas, Gamal A.I. Moustafa, Glenn Hauk, James M Berger, Satoshi Mitarai, Masayoshi Arai, Rehab M. Abd El-Baky, Gamal El Din A. Abuo-Rahma

Research output: Contribution to journalArticle

Abstract

New N-4-piperazinyl ciprofloxacin-triazole hybrids 6a-o were prepared and characterized. The in vitro antimycobacterial activity revealed that compound 6a experienced promising antimycobacterial activity against Mycobactrium smegmatis compared with the reference isoniazide (INH). Additionally, compound 6a exhibited broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative bacteria compared with the reference ciprofloxacin. Also, compounds 6g and 6i displayed considerable antifungal activity compared with the reference ketoconazole. DNA cleavage assay of the highly active compounds 6c and 6h showed a good correlation between the Mycobactrium cleaved DNA gyrase assay and their in vitro antimycobactrial activity. Moreover, molecular modeling studies were done for the designed ciprofloxacin derivatives to predict their binding modes towards Topoisomerase II enzyme (PDB: 5bs8).

Original languageEnglish (US)
Article number102952
JournalBioorganic Chemistry
Volume88
DOIs
StatePublished - Jul 1 2019

Fingerprint

Triazoles
Ciprofloxacin
Assays
Smegma
DNA Gyrase
Type II DNA Topoisomerase
DNA Cleavage
Ketoconazole
Molecular modeling
Gram-Negative Bacteria
Bacteria
Derivatives
DNA
Enzymes
In Vitro Techniques

Keywords

  • Antibacterial
  • Antifungal
  • Antimycobacterial
  • Ciprofloxacin
  • DNA cleavage assay
  • Molecular docking

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

Cite this

Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity. / Mohammed, Hamada H.H.; Abdelhafez, El Shimaa M.N.; Abbas, Samar H.; Moustafa, Gamal A.I.; Hauk, Glenn; Berger, James M; Mitarai, Satoshi; Arai, Masayoshi; Abd El-Baky, Rehab M.; Abuo-Rahma, Gamal El Din A.

In: Bioorganic Chemistry, Vol. 88, 102952, 01.07.2019.

Research output: Contribution to journalArticle

Mohammed, HHH, Abdelhafez, ESMN, Abbas, SH, Moustafa, GAI, Hauk, G, Berger, JM, Mitarai, S, Arai, M, Abd El-Baky, RM & Abuo-Rahma, GEDA 2019, 'Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity', Bioorganic Chemistry, vol. 88, 102952. https://doi.org/10.1016/j.bioorg.2019.102952
Mohammed, Hamada H.H. ; Abdelhafez, El Shimaa M.N. ; Abbas, Samar H. ; Moustafa, Gamal A.I. ; Hauk, Glenn ; Berger, James M ; Mitarai, Satoshi ; Arai, Masayoshi ; Abd El-Baky, Rehab M. ; Abuo-Rahma, Gamal El Din A. / Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity. In: Bioorganic Chemistry. 2019 ; Vol. 88.
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