PMID- 18304723 OWN - NLM STAT- MEDLINE DCOM- 20080507 LR - 20131121 IS - 0301-4622 (Print) IS - 0301-4622 (Linking) VI - 134 IP - 1-2 DP - 2008 Apr TI - DNA binding and photocleavage properties of a novel cationic porphyrin-anthraquinone hybrid. PG - 72-83 LID - 10.1016/j.bpc.2008.01.009 [doi] AB - A novel cationic porphyrin-anthraquinone (Por-AQ) hybrid has been synthesized and characterized. Using the combination of absorption titration, fluorescence spectra, circular dichroism (CD) as well as viscosity measurements, the binding properties of the hybrid to calf thymus (CT) DNA have been investigated compared with its parent porphyrin. The experimental results show that at low [Por]/[DNA] ratios, the parent porphyrin binds to DNA in an intercalative mode while the hybrid binds in a combined mode of outside binding (for porphyrin moiety) and partial intercalation (for anthraquinone). Ethidium bromide (EB) competition experiment determined the binding affinity constants (K(app)) of the compounds for CT DNA. Theoretical calculational results applying the density functional theory (DFT) can explain the different DNA binding behaviors reasonably. (1)O(2) was suggested to be the reactive species responsible for the DNA photocleavage of porphyrin moieties in both two compounds. The wavelength-depending cleavage activities of the compounds were also investigated. FAU - Zhao, Ping AU - Zhao P AD - MOE Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, PR China. FAU - Xu, Lian-Cai AU - Xu LC FAU - Huang, Jin-Wang AU - Huang JW FAU - Zheng, Kang-Cheng AU - Zheng KC FAU - Liu, Jie AU - Liu J FAU - Yu, Han-Cheng AU - Yu HC FAU - Ji, Liang-Nian AU - Ji LN LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20080209 PL - Netherlands TA - Biophys Chem JT - Biophysical chemistry JID - 0403171 RN - 0 (Anthraquinones) RN - 0 (Intercalating Agents) RN - 0 (Porphyrins) RN - 9007-49-2 (DNA) RN - EN464416SI (Ethidium) SB - IM MH - Absorption MH - Animals MH - Anthraquinones/chemistry/*pharmacology MH - Binding, Competitive MH - Cattle MH - Circular Dichroism MH - DNA/genetics/*metabolism MH - DNA Cleavage/*drug effects/radiation effects MH - Drug Design MH - Ethidium/chemistry/pharmacology MH - Intercalating Agents/chemistry/pharmacology MH - Models, Chemical MH - Photolysis MH - Porphyrins/chemistry/*pharmacology MH - Spectrometry, Fluorescence MH - Titrimetry MH - Viscosity EDAT- 2008/02/29 09:00 MHDA- 2008/05/08 09:00 CRDT- 2008/02/29 09:00 PHST- 2007/11/09 00:00 [received] PHST- 2008/01/19 00:00 [revised] PHST- 2008/01/19 00:00 [accepted] PHST- 2008/02/29 09:00 [pubmed] PHST- 2008/05/08 09:00 [medline] PHST- 2008/02/29 09:00 [entrez] AID - S0301-4622(08)00022-7 [pii] AID - 10.1016/j.bpc.2008.01.009 [doi] PST - ppublish SO - Biophys Chem. 2008 Apr;134(1-2):72-83. doi: 10.1016/j.bpc.2008.01.009. Epub 2008 Feb 9.