光动力治疗用酞菁类光敏剂的合成研究进展

doi:10.7517/j.issn.1674-0475.2003.02.138

摘要/Abstract

摘要： 本文介绍了光动力治疗原理、酞菁类光敏剂的合成方法及其近年来得到的研究进展,并介绍了酞菁在光动力治疗中的光化学生物过程和光漂白现象,还对其存在的缺点和今后的研究方向进行了讨论.

Abstract: The principle of photodynamic therapy(PDT) and the synthetic progress of phthalocyanine have been reviewed.The photobiochemical process of using phthalocyanines and photobleaching in PDT are also introduced.

Key words: photodynamic therapy(PDT), phthalocyanines, photobleaching

中图分类号:

俞开潮, 程红, 金玲. 光动力治疗用酞菁类光敏剂的合成研究进展[J]. 影像科学与光化学, 2003, 21(2): 138-146.

YU Kai-chao, CHENG Hong, JIN Ling. PROGRESS OF SYNTHESIZING PHTHALOCYANINES USED FOR PHOTODYNAMIC THERAPY[J]. Imaging Science and Photochemistry, 2003, 21(2): 138-146.

参考文献

[1] 黄金陵,陈耐生,黄剑东,刘尔生,薛金萍,杨素苓,黄自强,孙建成.用于光动力治疗的金属酞菁配合物——两亲性酞菁锌配合物ZnPcS2P2的制备、表征及抗癌活性[J].中国科学(B辑),2000,30:481-488.Huang J L,Chen N S,Huang J D,Liu E S,Xue J P,Yang S L,Huang Z Q,Sun J C.Metallic phthalocyanine complexes used in photodynamic therapy-the preparation,characterization and antitumour activity of an amphiphilic Zn phthalocyanine ZnPcS₂P₂[J].Science in China(Series B),2000,30:481-488.
[2] Hendersson B W,Dougherty T J.Photodynamic Therapy:Basic Principles and Clinical Applications[M].New York:Marcel Dekker INC,1992.63.
[3] 刘尔生,黄剑东,戴志飞,杨素苓,吴谊群,陈耐生,黄金陵,黄自强,孙建成,徐建华.磺酸基邻苯二甲酰亚氨甲基酞菁锌的合成及光动力抗肿瘤活性研究[J].无机化学学报,1997,13:411-415.Liu E S,Huang J D,Dai Z F,Yang S L,Wu Y Q,Chen N S,Huang J L,Huang Z Q,Sun J C,Xu I H.Study on the synthesis and photodynamic antitumour activity of sulfonated phthalimidomethyl phthalocyanine zinc[J].J.Inorg.Chem.,1997,13:411-415.
[4] Raymond B.Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy[J].Chemical Society Reviews,1995,24:19-33.
[5] Ochsmer M.New trends in photobiology(invited review) photophysical and photobiological processes in the photodynamic therapy of tumours[J].J.Photochem.Photobiol.,B:Biol.,1997,39:1-18.
[6] Rotomskis R,Streckyte G,Bagdonas S.Phototransformations of sensitizers 1.Significance of the nature of the sensitizer in the photobleaching process and photoproduct formation in aqueous solution[J].J.Photochem.Photobiol.,B:Biol.,1997,39:167-171.
[7] McCubbin Ⅰ,Phillips D.The photophysics and photostability of Zn(Ⅱ) and aluminum(Ⅲ) sulfonated naphthalocyanines[J].J.Photochem.,1986,34:187-195.
[8] Ruck A,Hildebrandt C,Kollner T,Schneckenburger H,Steiner R.Competition between photobleaching and fluorescence increase of photosensitizing porphyrins and tetrasulphonated chloroaluminiumphthalocyanine[J].J.Photochem.Photobiol.,B:Biol.,1990,5:311-319.
[9] Raymond B,Gabriel M.Photobleaching of sensitisers used in photodynamic therapy[J].Tetrahedron,2001,57:9513-9547.
[10] Spikes J D,van Lier J E,Bommer J C.A comparison of the photoproperties of zinc phthalocyanine and zinc naphthalocyanine tetrasulfonates:model sensitizers for the photodynamic therapy of tumors[J].J.Photochem.Photobiol.,A:Chem.,1995,91:193-198.
[11] 程铸生.精细化学品化学[M].编辑:朱承炎等.上海:华东理工大学出版社,1996.161-164.Cheng Z S.The Chemistry of Refined Chemical Products[M].Zhu C Y,et al eds.Shanghai:Huadong University of Science and Technology,1996.161-164.
[12] Maria P D F,Donata D,Lia F,Gabrio R.Synthesis of a new water-soluble octa-cationic phthalocyanine derivative for PDT[J].Tetrahedron Lett.,2000,41:9143-9147.
[13] Jori G.Tumor photosensitizers:approaches to enhance the selectivity and efficiency of photodynamic therapy[J].J.Photochem.Photobiol.,B:Biol.,1996,36:87-93.
[14] Yang Y C,Ward J R,Seiders R P.Dimerization of Cobalt(Ⅱ) tetrasulfonated phthalocyanine in water and aqueous alcoholic solutions[J].Inorganic Chemistry,1985,24(12):1765-1769.
[15] Ogawa K,Kinoshita S,Yonehara H,Nakahara H,Fukuda K.Highly ordered monolayer assemblies of phthalocyanine derivatives[J].J.Chem.Soc.,Chem.Commun.,1989,8:477-479.
[16] Kliesch H,Weitemeyer A,Muller S,Whrle D.Synthesis of phthalocyanines with one sulfonic acid,carboxylic acid,or amino group[J].Liebigs Ann.,1995,7:1269-1273.
[17] Boyle R W,van Lier J E.Phosphorylating agents:versatile tools for the synthesis of amphiphilic water-soluble photosensitizers[J].Int.Congr.Ser.-Excerpta Med.,1992,1011:845-849.
[18] Sharman W M,Kudrevich S V,van Lier J E.Novel water-soluble phthalocyanines substituted with phosphonate moieties on the benzo rings[J].Tetrahedron Lett.,1996,37(33):5831-5834.
[19] Leznoff C C,Vigh S,Svirskaya P I,Greenberg S,Drew D M,Ben-Hur E,Rosenthal I.Synthesis and photocytotoxicity of some new substituted phthtalocyanines[J].Photochem.Photobiol.,1989,49:279-284.
[20] Whrle D,Iskander N,Graschew G,Sinn H,Friedrich E A,Maier-Borst W,Stern J,Schlag P.Synthesis of positively charged phthalocyanines and their activity in the photodynamic therapy of cancer cells[J].Photochem.Photobiol.,1990,51:351-356.
[21] Daniel A F,Josefina A,Lelia E D.Synthesis and photophysical properties of a new cationic water-soluble Zn phthalocyanine[J].J.Photochem.Photobiol.,B:Biol.,1997,41:227-232.
[22] Murphy M P.Selective targeting of bioactive compunds to mitochondria[J].Trends Biotechnol.,1997,15(8):326-330.
[23] Daniel A F,Lelia E D,Josefina A.Synthesis and properties of two new N-alkyl substituted phthalocyanines[J].J.Hetercyclic Chem.,1995,32:519-522.
[24] Griffiths J,Schofield J,Wainwright M,Brown S B.Some observation on the synthesis of polysubstituted zinc phthalocyanine sensitisers for photodynamic therapy[J].Dyes and Pigments,1997,33:65-78.
[25] Cuomo V,Jori G,Rither B,Kenney M E,Rodgers M A J.Liposome-delivered Si(Ⅳ)-naphthalocyanine as a photodynamic sensitizer for experimental tumors:pharmacokinetic and phototherapeutic studies[J].Br.J.Cancer,1990,62:966-970.
[26] Ho X,Pandey R,Sumlin A,Missert J,Bellnier D,Dougherty T.Potential new photosensitizers for photodynamic therapy[J].Proc.Soc.Photo-Opt.Instrum.Eng.,1990,1203:293-300.
[27] Wilson B C,Jeeves W P.Photomedicine[M].E.Ben-Hur,I.Rosenthal,eds.Vol.2,CRC Press Boca Raton,FL,1987.127.
[28] Whrle D,Shopova M,Müller S,Milev A,Mantareva V,Krastev K.Lipsome-delivered Zn(Ⅱ)-2,3-naphthalocyanines as potential sensitizers for PDT:synthesis,photochemical,pharmacokinetic and phototherapeutic study[J].J.Photochem.Photobiol.,B:Biol.,1993,21:155-165.
[29] Shopova M,whrle D,Stoichkova N,Milev A,Mantareva V,Müller S,Georgiev K.Hydrophobic Zn(Ⅱ)-2,3-naphthalcyanines as photodynamic therapy agents for Lewis lung carcinoma[J].J.Photochem.Photobiol.,B:Biol.,1994,23:35-42.
[30] Müller S,Mantareva V,Stoichkova N,Kliesch H,Sobbi A,Whrle D,Shopova M.tetraamido-substituted 2.3-naphthalocyaine zinc(Ⅱ)complexes as phototherapeutic agents:synthesis,comparative photochemical and photobiological studies[J].J.Photochem.Photobiol.,B:Biol.,1996,35:167-174.
[31] Ilya B Z,Leu B Z,Maria J B.The mechanism of Zn-phthalocyanine photosensitizer lysis of human erythrocytes[J].J.Photochem.Photobiol.,B:Biol.,2002,67:1-10.
[32] Ben-Hur E,Orenstein A.The endothelium and red blood cells as a potential targets in PDT-induced vascular stasis[J].Int.J.Radiat.Biol.,1991,60(N 1/2):293-301.
[33] Deuticke B,Henseleit U,Haest C W M,Heller K B,Dubbelman T M A R.Enhancement of transbilayer mobility of a membrane lipid probe accompanies formation of membrane leaks during photodynamic treatment of erythrocytes[J].Biochim.Biophys.Acta,1989,982:53-61.
[34] Ben-Hur E,Freud A,Canfi A,et al.The role of glycolysis and univalent ions in phthalocyanine-sensitized photohaemolysis of human erythrocytes[J].Jnt.J.Radiat.Biol.,1991,59:797-806.
[35] Ben-Hur E,Rosenthal I.A new class of mammalian cells photosensitizers with a potential for cancer phototherapy[J].Int.J.Radiat.Biol.,1985,47:145-147.
[36] Cook J S,Blum H F.Does relationship and oxygen dependence in ultraviolet and photodynamic haemolysis[J].J.Cell.Comp.Physiol.,1959,53:41-60.