Design, synthesis and reactivity of C2-symmetric azobenzene-based amino acid-bis(propargyl sulfones).
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.
Mitra
Debarati
D
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Banerjee
Deb Ranjan
DR
Das
Amit Kumar
AK
Basak
Amit
A
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
D000480:Alkynes; D000596:Amino Acids; D001391:Azo Compounds; C116442:propargylic sulfone; D007510:Isatin; C009850:azobenzene