3-[(E)-(acridin-9'-ylmethylidene)amino]-1-substituted thioureas and their biological activity.
This paper describes the synthesis of a novel series of acridine thiosemicarbazones through a two-step reaction between various isothiocyanates and hydrazine followed by treatment with acridin-9-carbaldehyde. The properties of this series of seven new derivatives are studied using NMR and biochemical techniques, and the DNA-binding properties of the compounds are determined using spectrophotometric studies (UV-vis absorption, fluorescence, and circular/linear dichroism) and viscometry. The binding constants K are estimated as being in the range of 2.2 to 7.8×104M-1and the percentage of hypochromism was found to be 22.11-49.75% (from UV-vis spectral titration). Electrophoretic experiments prove that the novel compounds demonstrate moderate inhibitory effects against Topo I activity at a concentration of 60×10-6M.
Department of Organic Chemistry, Institute of Chemistry, Faculty of Science, P.J.Šafárik University, Moyzesova 11, Košice, Slovak Republic.
Michal
M
Bečka
Department of Organic Chemistry, Institute of Chemistry, Faculty of Science, P.J.Šafárik University, Moyzesova 11, Košice, Slovak Republic.
Mária
M
Vilková
Department of Biochemistry, Institute of Chemistry, Faculty of Science, P.J.Šafárik University, Moyzesova 11, Košice, Slovak Republic.
Othman
O
Salem
Department of Biophysics, Faculty of Science, Palacky University, Slechtitelu 27, 783 71 Olomouc, Czech Republic.
Jana
J
Kašpárková
Department of Biophysics, Faculty of Science, Palacky University, Slechtitelu 27, 783 71 Olomouc, Czech Republic.
Viktor
V
Brabec
Department of Biochemistry, Institute of Chemistry, Faculty of Science, P.J.Šafárik University, Moyzesova 11, Košice, Slovak Republic; Biomedical Research Center, University Hospital Hradec Kralove, Sokolovska 581, Hradec Kralove, Czech Republic. Electronic address: maria.kozurkova@upjs.sk.
Mária
M
Kožurková
D000166:Acridines / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D004264:DNA Topoisomerases, Type I; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013056:Spectrophotometry, Ultraviolet; D013882:Thiosemicarbazones / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D013890:Thiourea / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D059004:Topoisomerase I Inhibitors / Q000032:analysis / Q000737:chemistry / Q000378:metabolism
D000166:Acridines; D013882:Thiosemicarbazones; D059004:Topoisomerase I Inhibitors; D004247:DNA; D004264:DNA Topoisomerases, Type I; D013890:Thiourea
Acridine; DNA-binding; Spectroscopic study; Thiosemicarbazone; Topoisomerase I