TY - JOUR
T1 - Design, synthesis and mode of action of novel 2-(4-aminophenyl)benzothiazole derivatives bearing semicarbazone and thiosemicarbazone moiety as potent antimicrobial agents
AU - Singh, Meenakshi
AU - Singh, Sudhir Kumar
AU - Gangwar, Mayank
AU - Nath, Gopal
AU - Singh, Sushil K.
N1 - Funding Information:
The authors are grateful to The Head, Department of Chemistry, Faculty of Science, Banaras Hindu University (BHU), Varanasi, India, for C NMR spectroscopy and SAIF, Central Drug Research Institute (CDRI), Lucknow for H NMR and Mass spectroscopy. One of the authors, Meenakshi Singh, gratefully acknowledges Indian Council of Medical Research (ICMR), New Delhi for the award of Senior Research Fellowship. 13 1
Publisher Copyright:
© 2015 Springer Science+Business Media New York.
PY - 2016/2/1
Y1 - 2016/2/1
N2 - A novel series of substituted benzothiazoles, bearing semicarbazone and thiosemicarbazone moieties, was designed, synthesized and evaluated for their antimicrobial activity and possible mode of action. Structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, IR and Mass spectral data. The results revealed that compounds SC06, SC09, TS05 and TS07 have potent antibacterial activity against both Gram-positive and Gram-negative strains. Compound TS05 displayed most potent activity with MIC values of 3.91, 7.81 and 1.56 μg/ml against S. aureus, E. coli and P. aeruginosa, respectively. The results from cytoplasmic membrane permeabilization assay, FACS study as well as DNA-binding assays, evaluated against clinically relevant pathogens S. aureus and E. coli, suggest membrane perturbing as well as intracellular mode of action of this class of compounds. In addition, hemolytic activity of the compounds was measured which indicated their low cytotoxicity.
AB - A novel series of substituted benzothiazoles, bearing semicarbazone and thiosemicarbazone moieties, was designed, synthesized and evaluated for their antimicrobial activity and possible mode of action. Structures of the synthesized compounds were elucidated by 1H NMR, 13C NMR, IR and Mass spectral data. The results revealed that compounds SC06, SC09, TS05 and TS07 have potent antibacterial activity against both Gram-positive and Gram-negative strains. Compound TS05 displayed most potent activity with MIC values of 3.91, 7.81 and 1.56 μg/ml against S. aureus, E. coli and P. aeruginosa, respectively. The results from cytoplasmic membrane permeabilization assay, FACS study as well as DNA-binding assays, evaluated against clinically relevant pathogens S. aureus and E. coli, suggest membrane perturbing as well as intracellular mode of action of this class of compounds. In addition, hemolytic activity of the compounds was measured which indicated their low cytotoxicity.
KW - Antimicrobials
KW - Benzothiazole
KW - DNA binding
KW - Membrane permeabilization
KW - Semicarbazone/thiosemicarbazone
UR - http://www.scopus.com/inward/record.url?scp=84954207191&partnerID=8YFLogxK
U2 - 10.1007/s00044-015-1479-5
DO - 10.1007/s00044-015-1479-5
M3 - Article
AN - SCOPUS:84954207191
VL - 25
SP - 263
EP - 282
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
SN - 1054-2523
IS - 2
ER -