title: Synthesis, G-quadruplexes DNA binding, and photocytotoxicity of novel cationic expanded porphyrins.
abstract: Intensive reports allowed the conclusion that molecules with extended aromatic surfaces always do good jobs in the DNA interactions. Inspired by the previous successful researches, herein, we designed a series of cationic porphyrins with expanded planar substituents, and evaluated their binding behaviors to G-quadruplex DNA using the combination of surface-enhanced raman, circular dichroism, absorption spectroscopy and fluorescence resonance energy transfer melting assays. Asymmetrical tetracationic porphyrin with one phenyl-4-N-methyl-4-pyridyl group and three N-methyl-4-pyridyl groups exhibit the best G4-DNA binding affinities among all the designed compounds, suggesting that the bulk of the substituents should be matched to the width of the grooves they putatively lie in. Theoretical calculations applying the density functional theory have been carried out and explain the binding properties of these porphyrins reasonably. Meanwhile, these porphyrins were proved to be potential photochemotherapeutic agents since they have photocytotoxic activities against both myeloma cell (Ag8.653) and gliomas cell (U251) lines.
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Shu-fang
authors.initials: SF
authors.lastname: Jin
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China. Electronic address: zhaoping666@163.com.
authors.forename: Ping
authors.initials: P
authors.lastname: Zhao
authors.affiliation: School of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, PR China. Electronic address: miss_xulc@126.com.
authors.forename: Lian-cai
authors.initials: LC
authors.lastname: Xu
authors.affiliation: School of Basic, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Min
authors.initials: M
authors.lastname: Zheng
authors.affiliation: School of Pharmacy, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Jia-zheng
authors.initials: JZ
authors.lastname: Lu
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Peng-liang
authors.initials: PL
authors.lastname: Zhao
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Qiu-lan
authors.initials: QL
authors.lastname: Su
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Hui-xian
authors.initials: HX
authors.lastname: Chen
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Ding-tong
authors.initials: DT
authors.lastname: Tang
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Jiong
authors.initials: J
authors.lastname: Chen
authors.affiliation: School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, No. 280, Waihuandong Road, Education Mega Centre, Guangzhou 510006, PR China.
authors.forename: Jia-qi
authors.initials: JQ
authors.lastname: Lin
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002412:Cations / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D031541:Fluorescence Resonance Energy Transfer; D054856:G-Quadruplexes / Q000187:drug effects*; D006801:Humans; D008027:Light; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy / Q000378:metabolism; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013816:Thermodynamics; D014466:Ultraviolet Rays
chemical_list: D000970:Antineoplastic Agents; D002412:Cations; D017319:Photosensitizing Agents; D011166:Porphyrins; D004247:DNA
keywords: Expanded cationic porphyrins; G-quadruplex DNA; Photocytotoxic; Spectral method