title: Molecular aspects on the interaction of isatin-3-isonicotinylhydrazone to deoxyribonucleic acid: model for intercalative drug-DNA binding.
abstract: Isatin-3-isonicotinylhydrazone was synthesized and characterized. The interaction of native calf thymus DNA with isatin-3-isonicotinylhydrazone (IINH) in 10 mM Tris-HCl aqueous solutions at neutral pH 7.4 has been investigated by spectrophotometric, circular dichroism (CD), melting temperature (T                         (                            m                         )), spectrofluorimetric, and viscometric techniques. It is found that IINH molecules could intercalate between base pairs of DNA as are evidenced by: hypochromism in UV absorption band of IINH, induced CD spectral changes, sharp increase in specific viscosity of DNA, and increase in the fluorescence of methylene blue (MB)-DNA solutions in the presence of increasing amounts of IINH, which indicates that it is able to release the intercalated MB completely. The binding constants of IINH-DNA complex at four different temperatures (277, 288, 298, and 310 K) were calculated to be 4.7 × 10(4), 2.2 × 10(4), 1.75 × 10(4) and 1.1 × 10(4) M(-1), respectively. Furthermore, the enthalpy and entropy of the reaction between IINH and CT-DNA showed that the reaction is enthalpy-favored and entropy- disfavored (∆H = -30.187 kJ mol(-1); ∆S = -20.46 J mol(-1)K(-1)) which are other evidences to indicate the IINH is able to be intercalated in the DNA base pairs.
authors.affiliation: Department of Chemistry, Faculty of Science, Sensor and Biosensor Research Center (SBRC) and Nanoscience and Nanotechnology Research Center (NNRC), Razi University, 67149, Kermanshah, Iran. kashanian_s@yahoo.com
authors.forename: Soheila
authors.initials: S
authors.lastname: Kashanian
authors.forename: Mohammad Mehdi
authors.initials: MM
authors.lastname: Khodaei
authors.forename: Parvaneh
authors.initials: P
authors.lastname: Pakravan
authors.forename: Hadi
authors.initials: H
authors.lastname: Adibi
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D002417:Cattle; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D006835:Hydrazones / Q000737:chemistry* / Q000378:metabolism*; D007364:Intercalating Agents / Q000737:chemistry* / Q000378:metabolism*; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism*; D007700:Kinetics; D008751:Methylene Blue / Q000378:metabolism; D008958:Models, Molecular; D009691:Nucleic Acid Denaturation; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature; D014783:Viscosity
chemical_list: D006835:Hydrazones; D007364:Intercalating Agents; C573075:isatin-3-isonicotinylhydrazone; D007510:Isatin; D004247:DNA; C427203:calf thymus DNA; D008751:Methylene Blue