Photodiagnosis and Photodynamic Therapy
Volume 6, Issue 1 , Pages 62-70 , March 2009

Biodistribution and phototherapeutic properties of Zinc (II) 2,9,16,23-tetrakis (methoxy) phthalocyanine in vivo

  • E. Inés Yslas, PhD

      Affiliations

    • Departamento de Biología Molecular, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina
    • Departamento de Química, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina
    • Corresponding Author InformationCorresponding author at: Departamento de Biología Molecular, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina.
  • ,
  • César Prucca

      Affiliations

    • Departamento de Biología Molecular, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina
  • ,
  • Silvia Romanini

      Affiliations

    • Departamento de Biología Molecular, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina
  • ,
  • Edgardo N. Durantini

      Affiliations

    • Departamento de Química, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina
  • ,
  • Mabel Bertuzzi

      Affiliations

    • Departamento de Biología Molecular, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina
  • ,
  • Viviana Rivarola

      Affiliations

    • Departamento de Biología Molecular, Universidad Nacional de Río Cuarto, Agencia Postal Nro 3, X580BYA Río Cuarto, Argentina

References 

  1. Dougherty TJ, Gomer CJ, Henderson BW, et al. Photodynamic therapy (review). J Natl Cancer Inst. 1998;90:889–905
  2. Dolmans DE, Fukumura D, Jain RK. Photodynamic therapy for cancer. Natl Rev Cancer. 2003;3:380–387
  3. Levy JG, Obochi M. New applications in photodynamic therapy. Introduction. Photochem Photobiol. 1996;64:737–739
  4. Dougherty TJ. An update on photodynamic therapy applications. J Clin Laser Med Surg. 2002;20:3–7
  5. Hasan T, Moor ACE, Ortel B. In:  Holland JF,  Frei EI,  Bast RCJ,  Kufe DW,  Morton DL,  Weichselbaum RR editor. Photodynamic therapy of cancer. Cancer medicine. 5th edition. Hamilton, Ontario: B.C. Decker; 2000;p. 489–502
  6. Copper MP, Tan IB, Oppelaar H, Ruevekamp MC, Stewart FA. Meta-tetra(hydroxyphenyl)chlorin photodynamic therapy in early-stage squamous cell carcinoma of the head and neck. Arch Otolaryngol Head Neck Surg. 2003;129:709–711
  7. Calzavara-Pinton PG, Venturini M, Sala R. A comprehensive overview of photodynamic therapy in the treatment of superficial fungal infections of the skin. Review. J Photochem Photobiol B: Biol. 2005;78:1–6
  8. Oleinick N, Morris RL, Belichenko I. The role of apoptosis in response to photodynamic therapy: what, where, why, and how. Photochem Photobiol Sci. 2002;1:1–21
  9. Katrin K, Nihal A, Tracy C, David B, Hasan M. Up-regulation of clusterin during phthalocyanine 4 photodynamic therapy-mediated apoptosis of tumor cells and ablation of mouse skin tumors. Cancer Res. 2000;60(21):5984–5987
  10. Röder B. In:  Meyers RA editors. Encyclopedia analytical chemistry. Chichester: Wiley; 2000;p. 302
  11. Rosenthal I. Phthalocyanines as photodynamic sensitizers. Photochem Photobiol. 1991;53:859–887
  12. Moser JD. Photodynamic tumor therapy 2nd and 3rd generation photosensitizer. New Delhi: Harwood Academic Publishers; 1998;
  13. Chen B, Roskams T, Xu Y, et al. Photodynamic therapy with hypericin induces vascular damage and apoptosis in the RIF-1 mouse tumor model. Int J Cancer. 2002;98:284–290
  14. Bellnier DA, Henderson BW. In:  Henderson BW,  Dougherty TJ editor. Determinants for PDT tissue destruction, in photodynamic therapy. New York: Marcel Dekker; 1992;p. 117–127
  15. Yslas EI, Rivarola V, Durantini EN. Synthesis and photodynamic activity of zinc(II) phthalocyanine derivatives bearing methoxy and trifluoromethylbenzyloxy substituents in homogeneous and biological media. Bioorg Med Chem. 2005;13(1):39–46
  16. Kremer JMH, Van der Esker MWJ, Pathmanoharan C, Wiersema PH. Vesicles of variable diameter prepared by a modified injection method. Biochemistry. 1977;16:3932–3935
  17. Whitacre CM, Feyes DK, Satoh T, et al. Photodynamic therapy with the phthalocyanine photosensitizer Pc 4 of SW480 human colon cancer xenografts in athymic mice. Clin Cancer Res. 2000;6:2021–2027
  18. Whitacre CM, Zborowska E, Willson JKV, Berger NA. Detection of poly (ADP-ribose) polymerase cleavage in response to treatment with topoisomerase I inhibitors: a potential surrogate end point to assess treatment effectiveness. Clin Cancer Res. 1999;5:665–672
  19. Hsu SM, Raine L, Fanger H. Use of avidin–biotin–peroxidase complex (ABC) in immunoperoxidase techniques. A comparison between ABC and unlabeled antibody (PAP) procedures. J Histochem Cytochem. 1981;29:577–580
  20. Sim HG, Lau WK, Olivo M, Tan PH, Cheng CW. Is photodynamic diagnosis using hypericin better than white-light cystoscopy for detecting superficial bladder carcinoma?. BJU Int. 2005;9:1215–1218
  21. Allen CM, Sharman WM, Van Lier JE. Current status of phthalocyanines in the photodynamic therapy of cancer. J Porphyr Phthalocya. 2001;5:161–169
  22. Damoiseau X, Schuitmaker HJ, Lagerberg JWM, Hoebeke M. Increase of the photosensitizing efficiency of bacteriochlorin a by liposome-incorporation. J Photochem Photobiol B: Biol. 2001;60:50–60
  23. Isele U, Schieweck K, Kessler R, Hoogevest PV, Capraro H. Pharmacokinetics and body distribution of liposomal zinc phthalocyanine in tumor-bearing mice: influence of aggregation state, particle size, and composition. J Pharm Sci. 1995;84:166–173
  24. Frank MM. The reticuloendothelial system and bloodstream clearance. J Lab Clin Med. 1993;122:487–488
  25. Romberg B, Oussoren C, Snel CJ, Hennink WE, Storm G. Effect of liposome characteristics and dose on the pharmacokinetics of liposomes coated with poly(amino acid)s. Pharm Res. 2007;24(12):2394–2401
  26. Ginevra F, Biffanti S, Pagnan A, Biolo R, Reddi E, Jori G. Delivery of the tumour photosensitizer zinc(II)-phthalocyanine to serum proteins by different liposomes: studies in vitro and in vivo. Cancer Lett. 1990;49(1):59–65
  27. Jori G, Reddi E. The role of lipoproteins in the delivery of tumour-targeting photosensitizers. Int J Biochem. 1993;25:1369–1375
  28. Love WG, Havenaar EC, Lowe PJ, Taylor PW. Uptake of zinc(II)-phthalocyanine by HepG2 cells expressing the low density lipoprotein receptor: studies with the liposomal formulation CGP55847. SPIE Proc. 1994;2078:381–388
  29. Baguley BC, Hicks KO, Wilson WR. In:  Baguley B,  Kerr D editor. Anticancer drug development. Tumor cell cultures in drug development. San Diego CA: Academic press; 2002;p. 269–284Chapter 15
  30. Dougherty TJ, Gomer CJ, Henderson BW, et al. Photodynamic therapy. J Nat Cancer Inst. 1998;90:889–905
  31. Yslas EI, Durantini EN, Rivarola VA. Zinc-(II) 2,9,16,23-tetrakis (methoxy) phthalocyanine: potential photosensitizer for use in photodynamic therapy in vitro. Bioorg Med Chem. 2007;15:4651–4660
  32. Polo L, Valduga G, Jori G, Reddi E. Low-density lipoprotein receptors in the uptake of tumour photosensitizers by human and rat transformed fibroblasts. Int J Biochem Cell Biol. 2002;34(1):10–23
  33. Josefsen LB, Boyle RW. Photodynamic therapy: novel third-generation photosensitizers one step closer?. Br J Pharmacol. 2008;154:1–3
  34. Castano AP, Demidova TN, Hamblin MR. Mechanisms in photodynamic therapy. Part three. Photosensitizer pharmacokinetics, biodistribution, tumor localization and modes of tumor destruction REVIEW. Photodiag Photodyn Ther. 2005;2:91–106
  35. Ismail MS, Dressler C, Koeppe P, et al. Pharmacokinetic analysis of octa-alpha-butyloxy-zinc phthalocyanine in mice bearing Lewis lung carcinoma. J Clin Laser Med Surg. 1997;15:157–161
  36. Zuk MM, Rihter BD, Kenney ME, Rodgers MA, Kreimer-Birnbaum M. Pharmacokinetic and tissue distribution studies of the photosensitizer bis(di-isobutyl octadecylsiloxy) silicon 2,3-naphthalocyanine (isoBOSINC) in normal and tumor-bearing rats. Photochem Photobiol. 1994;59:66–72
  37. Boyle RW, Leznoff CC, Van Lier JE. Biological activities of phthalocyanines. XVI. Tetrahydroxy- and tetraalkylhydroxy zinc phthalocyanines. Effect of alkyl chain length on in vitro and in vivo photodynamic activities. Br J Cancer. 1993;67:1177–1181

PII: S1572-1000(09)00028-3

doi: 10.1016/j.pdpdt.2009.03.001

Photodiagnosis and Photodynamic Therapy
Volume 6, Issue 1 , Pages 62-70 , March 2009