RRC ID 67719
Author Sirajuddin M, Ali S, McKee V, Ullah H.
Title Synthesis, spectroscopic characterization and in vitro antimicrobial, anticancer and antileishmanial activities as well interaction with Salmon sperm DNA of newly synthesized carboxylic acid derivative, 4-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid.
Journal Spectrochim Acta A Mol Biomol Spectrosc
Abstract This paper stresses on the synthesis, characterization of novel carboxylic acid derivative and its application in pharmaceutics. Carboxylic acid derivatives have a growing importance in medicine, particularly in oncology. A novel carboxylic acid, 4-(4-methoxy-2-nitrophenylamino)-4-oxobutanoic acid, was synthesized and characterized by elemental analysis, FT-IR, NMR ((1)H, and (13)C), mass spectrometry and single crystal X-ray structural analysis. The structure of the title compound, C11H12N2O6, shows the molecules dimerised by short intramolecular OH⋯O hydrogen bonds. The compound was screened for in vitro antimicrobial, anticancer, and antileishmanial activities as well as interaction with SS-DNA. The compound was also checked for in vitro anticancer activity against BHK-21, H-157 and HCEC cell lines, and showed significant anticancer activity. The compound was almost non-toxic towards human corneal epithelial cells (HCEC) and did not show more than 7.4% antiproliferative activity when used at the 2.0μg/mL end concentration. It was also tested for antileishmanial activity against the promastigote form of leishmania major and obtained attractive result. DNA interaction study exposes that the binding mode of the compound with SS-DNA is an intercalative as it results in hypochromism along with minor red shift. A new and efficient strategy to identify pharmacophores sites in carboxylic acid derivative for antibacterial/antifungal activity using Petra, Osiris and Molinspiration (POM) analyses was also carried out.
Volume 138
Pages 569-78
Published 2015-3-5
DOI 10.1016/j.saa.2014.11.061
PII S1386-1425(14)01720-X
PMID 25536453
MeSH Anilides / chemical synthesis* Anilides / metabolism Anilides / pharmacology* Animals Anti-Infective Agents / chemical synthesis Anti-Infective Agents / pharmacology* Antineoplastic Agents / chemical synthesis Antineoplastic Agents / pharmacology* Antiprotozoal Agents / chemical synthesis Antiprotozoal Agents / pharmacology* Bacteria / drug effects Carbon-13 Magnetic Resonance Spectroscopy Carboxylic Acids / chemical synthesis* Carboxylic Acids / metabolism Carboxylic Acids / pharmacology* Crystallography, X-Ray DNA / metabolism* Fungi / drug effects Humans Hydrogen Bonding Male Mass Spectrometry Microbial Sensitivity Tests Molecular Conformation Proton Magnetic Resonance Spectroscopy Salmon Spectrophotometry, Ultraviolet Spectroscopy, Fourier Transform Infrared Spermatozoa / metabolism* Succinates / chemical synthesis* Succinates / metabolism Succinates / pharmacology*
IF 2.931
Human and Animal Cells HCE-T(RCB2280)