Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives

Hamada H.H. Mohammed, Samar H. Abbas, El Shimaa M.N. Abdelhafez, James M. Berger, Satoshi Mitarai, Masayoshi Arai, Gamal El Din A.A. Abuo-Rahma

Research output: Contribution to journalArticle

Abstract

Abstract: Herein we report the synthesis of new N-4-piperazinyl thiadiazole and oxadiazole ciprofloxacin derivatives and their antibacterial and antimycobacterial activities. Although thiadiazole ciprofloxacin derivatives compound showed broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative organisms, the oxadiazole derivatives exhibited weaker antibacterial and antimycobacterial activities than thiadiazole derivatives against most of the tested strains compared with the reference ciprofloxacin. Moreover, the antimycobacterial screening revealed that compounds which containing thiadiazole scaffold potently inhibited Mycobacterium smegmatis at MIC of 1.56 and 3.13, respectively, and modestly inhibited the drug-resistant strains. DNA cleavage assay revealed that thiadiazole ciprofloxacin derivatives inhibited supercoil relaxation, albeit to a lesser extent than ciprofloxacin, and it also increased the amount of nicked substrate produced. Graphic abstract: [Figure not available: see fulltext.].

Original languageEnglish (US)
Pages (from-to)1809-1824
Number of pages16
JournalMonatshefte fur Chemie
Volume150
Issue number10
DOIs
StatePublished - Oct 1 2019

Fingerprint

Thiadiazoles
Oxadiazoles
Ciprofloxacin
Assays
Derivatives
DNA
Scaffolds
Screening
Substrates
Pharmaceutical Preparations

Keywords

  • Antibacterial
  • Antimycobacterial
  • Ciprofloxacin
  • DNA cleavage assay
  • Oxadiazole
  • Thiadiazole

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Mohammed, H. H. H., Abbas, S. H., Abdelhafez, E. S. M. N., Berger, J. M., Mitarai, S., Arai, M., & Abuo-Rahma, G. E. D. A. A. (2019). Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives. Monatshefte fur Chemie, 150(10), 1809-1824. https://doi.org/10.1007/s00706-019-02478-4

Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives. / Mohammed, Hamada H.H.; Abbas, Samar H.; Abdelhafez, El Shimaa M.N.; Berger, James M.; Mitarai, Satoshi; Arai, Masayoshi; Abuo-Rahma, Gamal El Din A.A.

In: Monatshefte fur Chemie, Vol. 150, No. 10, 01.10.2019, p. 1809-1824.

Research output: Contribution to journalArticle

Mohammed, Hamada H.H. ; Abbas, Samar H. ; Abdelhafez, El Shimaa M.N. ; Berger, James M. ; Mitarai, Satoshi ; Arai, Masayoshi ; Abuo-Rahma, Gamal El Din A.A. / Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives. In: Monatshefte fur Chemie. 2019 ; Vol. 150, No. 10. pp. 1809-1824.
@article{bdcd7b1cdbec444693753fb3470af986,
title = "Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives",
abstract = "Abstract: Herein we report the synthesis of new N-4-piperazinyl thiadiazole and oxadiazole ciprofloxacin derivatives and their antibacterial and antimycobacterial activities. Although thiadiazole ciprofloxacin derivatives compound showed broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative organisms, the oxadiazole derivatives exhibited weaker antibacterial and antimycobacterial activities than thiadiazole derivatives against most of the tested strains compared with the reference ciprofloxacin. Moreover, the antimycobacterial screening revealed that compounds which containing thiadiazole scaffold potently inhibited Mycobacterium smegmatis at MIC of 1.56 and 3.13, respectively, and modestly inhibited the drug-resistant strains. DNA cleavage assay revealed that thiadiazole ciprofloxacin derivatives inhibited supercoil relaxation, albeit to a lesser extent than ciprofloxacin, and it also increased the amount of nicked substrate produced. Graphic abstract: [Figure not available: see fulltext.].",
keywords = "Antibacterial, Antimycobacterial, Ciprofloxacin, DNA cleavage assay, Oxadiazole, Thiadiazole",
author = "Mohammed, {Hamada H.H.} and Abbas, {Samar H.} and Abdelhafez, {El Shimaa M.N.} and Berger, {James M.} and Satoshi Mitarai and Masayoshi Arai and Abuo-Rahma, {Gamal El Din A.A.}",
year = "2019",
month = "10",
day = "1",
doi = "10.1007/s00706-019-02478-4",
language = "English (US)",
volume = "150",
pages = "1809--1824",
journal = "Monatshefte fur Chemie",
issn = "0026-9247",
publisher = "Springer Wien",
number = "10",

}

TY - JOUR

T1 - Synthesis, molecular docking, antimicrobial evaluation, and DNA cleavage assay of new thiadiazole/oxadiazole ciprofloxacin derivatives

AU - Mohammed, Hamada H.H.

AU - Abbas, Samar H.

AU - Abdelhafez, El Shimaa M.N.

AU - Berger, James M.

AU - Mitarai, Satoshi

AU - Arai, Masayoshi

AU - Abuo-Rahma, Gamal El Din A.A.

PY - 2019/10/1

Y1 - 2019/10/1

N2 - Abstract: Herein we report the synthesis of new N-4-piperazinyl thiadiazole and oxadiazole ciprofloxacin derivatives and their antibacterial and antimycobacterial activities. Although thiadiazole ciprofloxacin derivatives compound showed broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative organisms, the oxadiazole derivatives exhibited weaker antibacterial and antimycobacterial activities than thiadiazole derivatives against most of the tested strains compared with the reference ciprofloxacin. Moreover, the antimycobacterial screening revealed that compounds which containing thiadiazole scaffold potently inhibited Mycobacterium smegmatis at MIC of 1.56 and 3.13, respectively, and modestly inhibited the drug-resistant strains. DNA cleavage assay revealed that thiadiazole ciprofloxacin derivatives inhibited supercoil relaxation, albeit to a lesser extent than ciprofloxacin, and it also increased the amount of nicked substrate produced. Graphic abstract: [Figure not available: see fulltext.].

AB - Abstract: Herein we report the synthesis of new N-4-piperazinyl thiadiazole and oxadiazole ciprofloxacin derivatives and their antibacterial and antimycobacterial activities. Although thiadiazole ciprofloxacin derivatives compound showed broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative organisms, the oxadiazole derivatives exhibited weaker antibacterial and antimycobacterial activities than thiadiazole derivatives against most of the tested strains compared with the reference ciprofloxacin. Moreover, the antimycobacterial screening revealed that compounds which containing thiadiazole scaffold potently inhibited Mycobacterium smegmatis at MIC of 1.56 and 3.13, respectively, and modestly inhibited the drug-resistant strains. DNA cleavage assay revealed that thiadiazole ciprofloxacin derivatives inhibited supercoil relaxation, albeit to a lesser extent than ciprofloxacin, and it also increased the amount of nicked substrate produced. Graphic abstract: [Figure not available: see fulltext.].

KW - Antibacterial

KW - Antimycobacterial

KW - Ciprofloxacin

KW - DNA cleavage assay

KW - Oxadiazole

KW - Thiadiazole

UR - http://www.scopus.com/inward/record.url?scp=85074212274&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85074212274&partnerID=8YFLogxK

U2 - 10.1007/s00706-019-02478-4

DO - 10.1007/s00706-019-02478-4

M3 - Article

AN - SCOPUS:85074212274

VL - 150

SP - 1809

EP - 1824

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

SN - 0026-9247

IS - 10

ER -