title: Design, synthesis and reactivity of C2-symmetric azobenzene-based amino acid-bis(propargyl sulfones).
abstract: C(2)-symmetric azobenzene-amino acid linked bis(propargyl sulfones) 1 and 2 containing stable E azo moiety have been synthesized. Upon irradiation with long wavelength UV these compounds isomerized to the Z-form, whose thermal reisomerization to the E-isomer slowed down considerably Under basic pH, the compounds showed DNA cleavage in μmolar concentrations with the Z-isomers showing better cleaving efficiency. The difference in cleaving efficiency between the Z and the E-isomer is more than the corresponding pair of sulfones without amino acid linker.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
authors.forename: Debarati
authors.initials: D
authors.lastname: Mitra
authors.forename: Deb Ranjan
authors.initials: DR
authors.lastname: Banerjee
authors.forename: Amit Kumar
authors.initials: AK
authors.lastname: Das
authors.forename: Amit
authors.initials: A
authors.lastname: Basak
mesh_terms: D000480:Alkynes / Q000737:chemistry / Q000494:pharmacology*; D000596:Amino Acids / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D015195:Drug Design; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000480:Alkynes; D000596:Amino Acids; D001391:Azo Compounds; C116442:propargylic sulfone; D007510:Isatin; C009850:azobenzene