title: Mono- and tetra-substituted zinc(II) phthalocyanines containing morpholinyl moieties: Synthesis, antifungal photodynamic activities, and structure-activity relationships.
abstract: A series of zinc(II) phthalocyanines (ZnPcs) mono-substituted and tetra-substituted with morpholinyl moieties and their quaternized derivatives have been synthesized and evaluated for their antifungal photodynamic activities toward Candida albicans. The α-substituted, quaternized, and mono-substituted ZnPcs are found to have higher antifungal photoactivity than β-substituted, neutral, and tetra-substituted counterparts. The cationic α-mono-substituted ZnPc (6a) exhibits the highest photocytotoxicity. Moreover, it is more potent than axially di-substituted analogue. The different photocytotoxicities of these compounds have also been rationalized by investigating their spectroscopic and photochemical properties, aggregation trend, partition coefficients, and cellular uptake. The IC90 value of 6a against C. albicans cells is as low as 3.3 μM with a light dose of 27 J cm(-2), meaning that 6a is a promising candidate as the antifungal photosensitizer for future investigations.
authors.affiliation: College of Chemistry, Fuzhou University, Fuzhou 350116, China.
authors.forename: Bi-Yuan
authors.initials: BY
authors.lastname: Zheng
authors.affiliation: College of Chemistry, Fuzhou University, Fuzhou 350116, China.
authors.forename: Mei-Rong
authors.initials: MR
authors.lastname: Ke
authors.affiliation: College of Chemistry, Fuzhou University, Fuzhou 350116, China.
authors.forename: Wen-Liang
authors.initials: WL
authors.lastname: Lan
authors.affiliation: College of Chemistry, Fuzhou University, Fuzhou 350116, China.
authors.forename: Lu
authors.initials: L
authors.lastname: Hou
authors.affiliation: College of Chemistry, Fuzhou University, Fuzhou 350116, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Guo
authors.affiliation: College of Chemistry, Fuzhou University, Fuzhou 350116, China.
authors.forename: Dong-Hua
authors.initials: DH
authors.lastname: Wan
authors.affiliation: Department of Engineering, Aarhus University, Denmark.
authors.forename: Ling-Zhi
authors.initials: LZ
authors.lastname: Cheong
authors.affiliation: College of Chemistry, Fuzhou University, Fuzhou 350116, China. Electronic address: jdhuang@fzu.edu.cn.
authors.forename: Jian-Dong
authors.initials: JD
authors.lastname: Huang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000166:cytology / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology*; D054833:Isoindoles; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D015032:Zinc / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; D015032:Zinc; C013647:phthalocyanine
keywords: Antifungal; C. albicans; Morpholine; Photodynamic inactivation; Photosensitizer; Zinc(II) phthalocyanine