title: Synthesis of 2-morpholinetetraphenylporphyrins and their photodynamic activities.
abstract: A series of 2-morpholinetetraphenylporphyrins functionalized with various substituents (Cl, Me, MeO group) at 4-phenyl position were prepared via nucleophilic substitution of 2-nitroporphyrin copper derivatives with morpholine by refluxing under a nitrogen atmosphere and then demetalization. Their basic photophysical properties, intracellular localization, cytotoxicities in vitro and in vivo were also investigated. All synthesized photosensitizers exhibited longer maxima absorption wavelengths than Hematoporphyrin monomethyl ether (HMME). They showed low dark cytotoxicity compared with that of HMME and were more phototoxic than HMME against Eca-109 cells in vitro. M3 also exhibited better photodynamic antitumor efficacy on BALB/c nude mice at a lower concentration. Therefore, M3 is a promising antitumor photosensitizer in photodynamic therapy application.
authors.affiliation: Department of Pharmaceutical Science & Technology, College of Chemistry and Biology, Donghua University, Shanghai 201620, PR China.
authors.forename: Ping-Yong
authors.initials: PY
authors.lastname: Liao
authors.affiliation: Department of Pharmaceutical Science & Technology, College of Chemistry and Biology, Donghua University, Shanghai 201620, PR China.
authors.forename: Xin-Rong
authors.initials: XR
authors.lastname: Wang
authors.affiliation: Eastern Hepatobiliary Surgery Hospital, Second Military Medical University, Shanghai 200433, China.
authors.forename: Xiang-Hua
authors.initials: XH
authors.lastname: Zhang
authors.affiliation: Shanghai Xianhui Pharmaceutical Co. Ltd., Shanghai 200433, China.
authors.forename: Tai-Shan
authors.initials: TS
authors.lastname: Hu
authors.affiliation: Shanghai Xianhui Pharmaceutical Co. Ltd., Shanghai 200433, China.
authors.forename: Mei-Zhen
authors.initials: MZ
authors.lastname: Zheng
authors.affiliation: Department of Pharmaceutical Science & Technology, College of Chemistry and Biology, Donghua University, Shanghai 201620, PR China.
authors.forename: Ying-Hua
authors.initials: YH
authors.lastname: Gao
authors.affiliation: Shanghai Xianhui Pharmaceutical Co. Ltd., Shanghai 200433, China.
authors.forename: Yi-Jia
authors.initials: YJ
authors.lastname: Yan
authors.affiliation: Department of Pharmaceutical Science & Technology, College of Chemistry and Biology, Donghua University, Shanghai 201620, PR China. Electronic address: zlchen1967@qq.com.
authors.forename: Zhi-Long
authors.initials: ZL
authors.lastname: Chen
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005260:Female; D006415:Hematoporphyrins / Q000494:pharmacology; D006801:Humans; D008807:Mice, Inbred BALB C; D008819:Mice, Nude; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use*; D009369:Neoplasms / Q000188:drug therapy*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use*
chemical_list: C509964:5,10,15,20-tetraphenylporphyrin; D006415:Hematoporphyrins; D009025:Morpholines; D017319:Photosensitizing Agents; D011166:Porphyrins; C494379:hematoporphyrin monomethyl ether
keywords: Antitumor; Photodynamic therapy; Photosensitizer; Porphyrin