title: Design, synthesis, and in vitro photodynamic activities of benzochloroporphyrin derivatives as tumor photosensitizers.
abstract: Novel benzochloroporphyrin derivatives (BCPDs) were designed, synthesized, and characterized. In vitro dark cytotoxicity and photodynamic efficacy of BCPDs were evaluated by MTT assay on human hepatoma BEL-7402 cells. The experimental results showed that BCPDs 15, 16, 17, and 18 have strong long wavelength absorptions around 670 nm and exhibit significantly lower dark cytotoxicity than BPDMA and possess potent photocytotoxicity, IC50 values 1.32 microg/mL for 15, 0.26 microg/mL for 16, 0.47 microg/mL for 17 of 0.27 microg/mL for 18, and 0.23 microg/mL for BPDMA. Among them, BCPDs 16 and 18 are more effective and promising PDT photosensitizers based on the studies with BEL-7402 cells and show nearly the same photodynamic efficacy as BPDMA. MG-P staining qualitative analysis also indicated that PDT with BCPDs 16 can induce apoptosis in BEL7402 cells.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China.
authors.forename: Jianzhong
authors.initials: J
authors.lastname: Yao
authors.forename: Wannian
authors.initials: W
authors.lastname: Zhang
authors.forename: Chunquan
authors.initials: C
authors.lastname: Sheng
authors.forename: Zhenyuan
authors.initials: Z
authors.lastname: Miao
authors.forename: Feng
authors.initials: F
authors.lastname: Yang
authors.forename: Jianxin
authors.initials: J
authors.lastname: Yu
authors.forename: Ling
authors.initials: L
authors.lastname: Zhang
authors.forename: Yunlong
authors.initials: Y
authors.lastname: Song
authors.forename: Ting
authors.initials: T
authors.lastname: Zhou
authors.forename: Youjun
authors.initials: Y
authors.lastname: Zhou
mesh_terms: D006528:Carcinoma, Hepatocellular / Q000188:drug therapy; D045744:Cell Line, Tumor; D002735:Chlorophyllides; D015195:Drug Design; D006801:Humans; D008113:Liver Neoplasms / Q000188:drug therapy; D010778:Photochemotherapy / Q000379:methods*; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011524:Protoporphyrins / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
chemical_list: D002735:Chlorophyllides; D017319:Photosensitizing Agents; D011166:Porphyrins; D011524:Protoporphyrins; C072905:chlorin p6; C475446:chlorin e4; C062985:phytochlorin; C041104:dimethyl protoporphyrin IX