锌酞菁水溶性衍生物的合成与光动力学性能研究进展
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摘要
锌酞菁(ZnPc)是高效的第二代光敏剂,在光动力疗法中对恶性肿瘤细胞具有显著的光生物活性和强烈的细胞毒性。然而,由于共轭分子间的π-π作用力,ZnPc溶解性差、结晶趋势强,阻碍了其临床研究。因此,改善ZnPc水溶性和分散性的研究一直在进行。对近五年ZnPc水溶性衍生物(离子型与非离子型)的合成与光动力学性能的相关研究进行综述。
Zinc phthalocyanine is a highly efficient second-generation photosensitizer with significant photobioactivity and strong cytotoxicity against malignant cells in photodynamic therapy.However,due to the π-π interaction between conjugated molecules,Zn Pc has poor solubility and strong crystallization tendency,which hinders its clinical research.Therefore,how to improve the water solubility and dispersibility of Zn Pc have been investigated.This work aims to review the progress on the synthesis and photodynamic properties of Zn Pc water-soluble derivatives(ionic and nonionic) in the past five years.
Zinc phthalocyanine is a highly efficient second-generation photosensitizer with significant photobioactivity and strong cytotoxicity against malignant cells in photodynamic therapy.However,due to the π-π interaction between conjugated molecules,Zn Pc has poor solubility and strong crystallization tendency,which hinders its clinical research.Therefore,how to improve the water solubility and dispersibility of Zn Pc have been investigated.This work aims to review the progress on the synthesis and photodynamic properties of Zn Pc water-soluble derivatives(ionic and nonionic) in the past five years.
引文
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[24]LI X S,KE M R,ZHANG M F,et al.A non-aggregatedand tumour-associated macrophage-targeted photosensi-tiser for photodynamic therapy:a novel zinc(Ⅱ)phthal-ocyanine containing octa-sulphonates[J]. Chem. Com-mun.,2015,51(22):4 704-4 707.
[25]VENKATRAMAIAH N,PEREIRA P M,ALMEIDA P FA,et al. Dual functionality of phosphonic-acid-appendedphthalocyanines:inhibitors of urokinase plasminogen ac-tivator and anticancer photodynamic agents[J]. Chem.Commun.,2015,51(85):15 550-15 553.
[26]FRANCESCA S,RUBEN R G,SANTI N,et al. Synthe-sis,photophysical studies and1O2,generation of carbox-ylate-terminated zinc phthalocyanine dendrimers[J]. J.Inorg.Biochem.,2014,136:170-176.
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[28]MAKHSEED S,MACHACEK M,ALFADLY W,et al.Water-soluble non-aggregating zinc phthalocyanine andin vitro studies for photodynamic therapy[J]. Chem.Commun.,2013,49(95):11 149-11 151.
[29]RIEGA S D E,CHIARANTE N,VALLI F,et al. Novelhydro-and lipo-philic selenium zinc(Ⅱ)phthalocya-nines:synthesis,photophysical properties and photody-namic effects on CT26 colon carcinoma cells[J]. DyesPigments,2018,156:133-139.
[30]ATSAY A,GUL A,KOCAK M B,et al.A new hexadecasubstituted non-aggregating zinc phthalocyanine[J].Dyes Pigments,2014,100(1):177-183.
[31]YILDIZ S Z,COLAK S,TUNA M,et al. Non-ionic pe-ripherally substituted soluble phthalocyanines:synthesischaracterization and investigation of their solution prop-erties[J].J.Mol.Liq.,2014,195(195):22-29.
[32]COLAK S,DURMUS M,YILDIZ S Z,et al. The water-soluble zwitterionic and cationic tetra-substituted zinc(Ⅱ)phthalocyanines:synthesis,photophysical,photo-chemical and protein binding properties[J].Polyhedron,2016,113:115-122.
[33]LI G,ZHANG Q Q,WANG Y,et al.Zwitterionic phthal-ocyanine zinc(Ⅱ)synthesis,and photodynamic activitycomparison with nonionic and cationic phthalocyanine[J].Inorg.Chem.Commun.,2017,75:1-4.
[34]DINCER H,MERT H,CALISKAN E,et al. Synthesisand photophysicochemical studies of poly(ethylene gly-col)conjugated symmetrical and asymmetrical zincphthalocyanines[J]. J. Mol. Struct.,2015,1 102:190-196.
[35]SEN B N,MERT H,DINCER H,et al. Synthesis andcharacterization of terminalalkynyl-substituted unsym-metrical zinc phthalocyanine conjugated with well-de-fined polymers[J]. Dyes Pigments,2014,100(100):1-10.
[36]WANG A,LI G,LU S,et al.Tumor microenvironment-re-sponsive charge reversal zinc phthalocyanines based onamino acids for photodynamic therapy[J]. Dyes Pig-ments,2016,126:239-250.
[37]ALIOSMAN M,GOKSEL M,MANTAREVA V,et al.Tyrosine conjugated zinc(Ⅱ)phthalocyanine for photo-dynamic therapy:synthesis and photophysicochemicalproperties[J]. J. Photoch. Photobio. A,2017,334:101-106.
[38]BASEREN S C,ERDOGMUS A,GUL A,et al.Synthesisand boron interaction of new amino acid containingphthalocyanines and the precursor[J]. J. Organomet.Chem.,2018,866:105-111.
[39]MATLOU G G,KOBAYASHI N,KIMURA M,et al.Physicochemical properties of water soluble unsymmetri-cal phthalocyanine-folic acid conjugates[J]. Dyes Pig-ments,2018,149:393-398.
[40]GOKSEL M,DURMUS M,ATILLA D,et al. Synthesisand photophysicochemical properties of a set of asym-metrical peptide conjugated Zinc(Ⅱ)phthalocyaninesbearing different fluorophore units[J].Inorg.Chim.Acta,2016,456:95-104.
[41]MORI S,YOSHIYAMA H,TOKUNAGA E,et al. De-sign,synthesis,spectral investigations and biological ac-tivity of fluorinated phthalocyanine conjugated with ga-lactose and comparison to its non-fluorinated counterpart[J].J.Fluorine Chem.,2015,174:137-141.
[42]LAFONT D,ZORLU Y,SAVOIE H,et al. Monogly co-conjugated phthalocyanines:effect of sugar and linkageon photodynamic activity[J]. Photodiagn. Photodyn.,2013,10(3):252-259.
[2]LI X S,ZHENG B D,PENG X H,et al.Phthalocyaninesas medicinal photosensitizers:developments in the lastfive years[J].Coordin.Chem.Rev.,2019,379:147-160.
[3]PERVAIZ S,OLIVO M.Art and science of photodynamictherapy[J].Clin.Exp.Pharmacol.P.,2006,33(5/6):551-556.
[4]LI X S,KIM J,YOON J,et al.Cancer-associated,stimuli-driven,turn on theranostics for multimodality imaging andtherapy[J].Adv.Mater.,2017,29(23):1 606 857.
[5]MCCAW D L,BRYAN J N. Chapter 17-photodynamictherapy[J].Cancer Manag.Small Anim.Pract.,2010,163-166.
[6]BROWN S B,BROWN E A,WALKER I,et al.The pres-ent and future role of photodynamic therapy in cancertreatment[J].Lancet Oncol.,2004,5(8):497-508.
[7]GRUNER M,SIOZIOS V,HAGENHOFF B,et al. Struc-tural and photosensitizing features of phthalocyanine-zeo-lite hybrid nanomaterials[J]. Photochem. Photobiol.,2013,89(6):1 406-1 412.
[8]CAN O S,KAYA E N,DURMUS M,et al.High photosen-sitized singlet oxygen generating zinc(Ⅱ)and indium(Ⅲ)acetate phthalocyanines containing 6,8-di-tert-bu-tyl-3-(p-oxyphenyl)coumarin groups[J]. J. Photoch. Pho-tobio.A,2016,317:56-67.
[9]PERVAIZ S,OLIVO M.Art and science of photodynamictherapy[J].Clin.Exp.Pharmacol.P.,2006,33(5/6):551-556.
[10]VUMMIDI B R,NOREEN F,ALZEER J,et al.Photody-namic agents with anti-metastatic activities[J]. ACSChem.Biol.,2013,8(8):1 737.
[11]STERNBERG E D,DOLPHIN D.Porphyrin-based photo-sensitizers for use in photodynamic therapy[J]. Tetra-hedron,1998,54(17):4 151-4 202.
[12]JOSEFSEN L B,BOYLE R W. Unique diagnostic andtherapeutic roles of porphyrins and phthalocyanines inphotodynamic therapy,imaging and theranostics[J].Theranostics,2012,2(9):916-966.
[13]NYMAN E S,HYNNINEN P H. Research advances inthe use of tetrapyrrolic photosensitizers for photodynamictherapy[J].J.Photoch.Photobio.B,2004,73(1):1-28.
[14]ZHANG J,JIANG C S,LONGO J P F,et al.An updatedoverview on the development of new photosensitizers foranticancer photodynamic therapy[J].Acta Pharm.Sin.B,2018,8(2):137-146.
[15]HUANG Z. Photodynamic therapy in China:over 25years of unique clinical experience part one-history anddomestic photosensitizers[J]. Photodiagn. Photodyn.,2006,3(1):3-10.
[16]DAVIES K S,LINDER M K,KRYMAN M W,et al.Ex-tended rhodamine photosensitizers for photodynamictherapy of cancer cells[J]. Bioorg. Med. Chem.,2016,24(17):3 908-3 917.
[17]CAKIR D,CAKIR V,BIYIKLIOULU Z,et al.New watersoluble cationic zinc phthalocyanines as potential forphotodynamic therapy of cancer[J]. J. Organomet.Chem.,2013,745/746(22):423-431.
[18]AGIRTAS M,CELEBI M,GUMUS S,et al. New watersoluble phenoxy phenyl diazenyl benzoic acid substitutedphthalocyanine derivatives:synthesis,antioxidant activi-ties,atypical aggregation behavior and electronic proper-ties[J].Dyes Pigments,2013,99(2):423-431.
[19]ERDOUMUS A,NYOKONG T.Synthesis of zinc phthalo-cyanine derivatives with improved photophysicochemicalproperties in aqueous media[J]. J. Mol. Struct.,2010,977(1/3):26-38.
[20]WINCKEL E V D,SCHNEIDER R J,ESCOSURA A DL,et al. Multifunctional logic in a photosensitizer withtriple-mode fluorescent and photodynamic activity[J].Chemistry,2015,21(51):18 551-18 556.
[21]AVSAR G,SARI F A,YUZER A C,et al. Intracellularuptake and fluorescence imaging potential in tumor cellof zinc phthalocyanine[J].Int.J.Pharmaceut.,2016,505(1/2):369-375.
[22]LAN W L,LIU F R,KE M R,et al.The effects of formu-lation and serum albumin on the in vitro photodynamicactivity of zinc(Ⅱ)phthalocyanines substituted withsulfonated quinolineoxy groups[J]. Dyes Pigments,2016,128:215-225.
[23]IKEUCHI T,MACK J,NYOKONG T A,et al.Aggrega-tion control of robust water-soluble zinc(Ⅱ)phthalocy-anine-based photosensitizers[J]. Langmuir,2016,32(45):11 980-11 985.
[24]LI X S,KE M R,ZHANG M F,et al.A non-aggregatedand tumour-associated macrophage-targeted photosensi-tiser for photodynamic therapy:a novel zinc(Ⅱ)phthal-ocyanine containing octa-sulphonates[J]. Chem. Com-mun.,2015,51(22):4 704-4 707.
[25]VENKATRAMAIAH N,PEREIRA P M,ALMEIDA P FA,et al. Dual functionality of phosphonic-acid-appendedphthalocyanines:inhibitors of urokinase plasminogen ac-tivator and anticancer photodynamic agents[J]. Chem.Commun.,2015,51(85):15 550-15 553.
[26]FRANCESCA S,RUBEN R G,SANTI N,et al. Synthe-sis,photophysical studies and1O2,generation of carbox-ylate-terminated zinc phthalocyanine dendrimers[J]. J.Inorg.Biochem.,2014,136:170-176.
[27]YANIK H,AI-RAQA S Y,AIJUHANI A,et al.The syn-thesis of novel directly conjugated zinc(Ⅱ)phthalocya-nine via,palladium-catalyzed Suzuki-Miyaura cross-cou-pling reaction and its quaternized water-soluble deriva-tive:investigation of photophysical and photochemicalproperties[J].Dyes Pigments,2016,134:531-540.
[28]MAKHSEED S,MACHACEK M,ALFADLY W,et al.Water-soluble non-aggregating zinc phthalocyanine andin vitro studies for photodynamic therapy[J]. Chem.Commun.,2013,49(95):11 149-11 151.
[29]RIEGA S D E,CHIARANTE N,VALLI F,et al. Novelhydro-and lipo-philic selenium zinc(Ⅱ)phthalocya-nines:synthesis,photophysical properties and photody-namic effects on CT26 colon carcinoma cells[J]. DyesPigments,2018,156:133-139.
[30]ATSAY A,GUL A,KOCAK M B,et al.A new hexadecasubstituted non-aggregating zinc phthalocyanine[J].Dyes Pigments,2014,100(1):177-183.
[31]YILDIZ S Z,COLAK S,TUNA M,et al. Non-ionic pe-ripherally substituted soluble phthalocyanines:synthesischaracterization and investigation of their solution prop-erties[J].J.Mol.Liq.,2014,195(195):22-29.
[32]COLAK S,DURMUS M,YILDIZ S Z,et al. The water-soluble zwitterionic and cationic tetra-substituted zinc(Ⅱ)phthalocyanines:synthesis,photophysical,photo-chemical and protein binding properties[J].Polyhedron,2016,113:115-122.
[33]LI G,ZHANG Q Q,WANG Y,et al.Zwitterionic phthal-ocyanine zinc(Ⅱ)synthesis,and photodynamic activitycomparison with nonionic and cationic phthalocyanine[J].Inorg.Chem.Commun.,2017,75:1-4.
[34]DINCER H,MERT H,CALISKAN E,et al. Synthesisand photophysicochemical studies of poly(ethylene gly-col)conjugated symmetrical and asymmetrical zincphthalocyanines[J]. J. Mol. Struct.,2015,1 102:190-196.
[35]SEN B N,MERT H,DINCER H,et al. Synthesis andcharacterization of terminalalkynyl-substituted unsym-metrical zinc phthalocyanine conjugated with well-de-fined polymers[J]. Dyes Pigments,2014,100(100):1-10.
[36]WANG A,LI G,LU S,et al.Tumor microenvironment-re-sponsive charge reversal zinc phthalocyanines based onamino acids for photodynamic therapy[J]. Dyes Pig-ments,2016,126:239-250.
[37]ALIOSMAN M,GOKSEL M,MANTAREVA V,et al.Tyrosine conjugated zinc(Ⅱ)phthalocyanine for photo-dynamic therapy:synthesis and photophysicochemicalproperties[J]. J. Photoch. Photobio. A,2017,334:101-106.
[38]BASEREN S C,ERDOGMUS A,GUL A,et al.Synthesisand boron interaction of new amino acid containingphthalocyanines and the precursor[J]. J. Organomet.Chem.,2018,866:105-111.
[39]MATLOU G G,KOBAYASHI N,KIMURA M,et al.Physicochemical properties of water soluble unsymmetri-cal phthalocyanine-folic acid conjugates[J]. Dyes Pig-ments,2018,149:393-398.
[40]GOKSEL M,DURMUS M,ATILLA D,et al. Synthesisand photophysicochemical properties of a set of asym-metrical peptide conjugated Zinc(Ⅱ)phthalocyaninesbearing different fluorophore units[J].Inorg.Chim.Acta,2016,456:95-104.
[41]MORI S,YOSHIYAMA H,TOKUNAGA E,et al. De-sign,synthesis,spectral investigations and biological ac-tivity of fluorinated phthalocyanine conjugated with ga-lactose and comparison to its non-fluorinated counterpart[J].J.Fluorine Chem.,2015,174:137-141.
[42]LAFONT D,ZORLU Y,SAVOIE H,et al. Monogly co-conjugated phthalocyanines:effect of sugar and linkageon photodynamic activity[J]. Photodiagn. Photodyn.,2013,10(3):252-259.