Synthesis and investigation on the interaction with calf thymus deoxyribonucleic acid of a novel fluorescent probe 7-oxobenzo[b][1,10]phenanthroline-12(7H)-sulfonic acid.
In this paper, the synthetic route of a potential antitumor reagent, benzo[b][1,10] phenanthrolin-7(12H)-one (BPO), was improved. A sulfonic group was introduced to BPO to form a new compound, 7-oxobenzo[b][1,10]phenan-throline-12(7H)-sulfonic acid (OPSA), in order to enhance its water-solubility. The molecular structure of OPSA has been confirmed by IR, UV, MS, (1)H NMR and elements analysis. It was proved in our experiments that DNA could quench the fluorescence of OPSA and the maximum quenched intensity appeared at 408 nm (lambda(ex)=284 nm). The quenched fluorescence intensity was proportional to the concentration of DNA. Based on this phenomenon, OPSA had been used as the fluorescent probe for detection of calf thymus DNA (ct-DNA) and the corresponding linear response range was from 1.0 to 150.0 microg mL(-1) and the limit of detection (LOD) was 3.8 ng mL(-1). Its interaction with ct-DNA was investigated by fluorescence, absorption and viscosity measurements. When binding to ct-DNA, OPSA showed obvious fluorescence quenching and the quenched intensity was stable with the presence and absence of NaCl. The absorption spectra of OPSA had no evidence of increasing or decreasing when ct-DNA was added. The viscosity of OPSA and ct-DNA mixture showed no obvious change comparing with the viscosity of ct-DNA along. The results suggested that the interaction between OPSA and ct-DNA was groove binding in nature. Scatchard plots constructed from fluorescence titration data gave a binding constant of 8.9 x 10(5) L mol(-1) and a binding site size of 0.35 base pairs per bound drug molecule.
Guo
Longhua
L
Ministry of Education Key Laboratory of Analysis and Detection Technology for Food Safety, Department of Chemistry, Fuzhou University, Fuzhou 350002, China.
Qiu
Bin
B
Chen
Guonan
G
D000818:Animals; D000970:Antineoplastic Agents / Q000494:pharmacology; D002417:Cattle; D004247:DNA / Q000032:analysis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000494:pharmacology*; D007454:Iodides / Q000737:chemistry; D007477:Ions; D008956:Models, Chemical; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013050:Spectrometry, Fluorescence / Q000379:methods; D013451:Sulfonic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013950:Thymus Gland / Q000378:metabolism*
C519826:7-oxobenzo(b)(1,10)phenanthroline-12(7H)-sulfonic acid; D000970:Antineoplastic Agents; D005456:Fluorescent Dyes; D007454:Iodides; D007477:Ions; D010618:Phenanthrolines; D013451:Sulfonic Acids; D004247:DNA