Tetrapyrroles pp 128-148 | Cite as

Tetrapyrroles in Photodynamic Therapy

Part of the Molecular Biology Intelligence Unit book series (MBIU)


The destructive photosensitising ability of porphyrins in patients suffering from porphyria has been well documented. Patients with those porphyrias that accumulate high levels of porphyrins in the skin suffer from a range of light-activated skin manifestations, the type and severity of which depends on the nature of the porphyrin that accumulates. In all cases the effect of solar irradiation of the porphyrin in the skin is to damage the tissue surface layers and its underlying structures. In most of the porphyrias this tissue damage can be severe in those areas of skin that are repeatedly exposed to sunlight and this is one of the major manifestations of these diseases. This inherent photosensitising ability of porphyrins can however be turned to good therapeutic use. The treatment of tumours and other lesions by the combined action of porphyrins, light and molecular oxygen has been developed into an effective technique called photodynamic therapy (PDT). The aim of this article is to give a brief overview of the development of tetrapyrroles in clinical photodynamic therapy and to report on those tetrapyrroles currendy in clinical trials. There are several other classes of compounds being developed for PDT but this review will only highlight the tetrapyrrole based photosensitisers.


Photodynamic Therapy Actinic Keratosis Photodynamic Treatment Hematoporphyrin Derivative Haematoporphyrin Derivative 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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  1. 1.
    Lipson RL, Baldes EJ. The photodynamic properties of a particular hematoporphyrin derivative. Arch Dermatol 1960; 82:508–516.PubMedGoogle Scholar
  2. 2.
    Lipson RL, Baldes EJ, Olsen AM. Hematoporphyrin derivative: A new aid for endoscopic detection of malignant disease. J Thorac Cardiovasc Surg 1961; 42:623–629.PubMedGoogle Scholar
  3. 3.
    Kelly JF, Snell ME. Hematoporphyrin derivative: A possible aid in the diagnosis and therapy of carcinoma of the bladder. J Urol 1976; 115:150–151.PubMedGoogle Scholar
  4. 4.
    Bonnett R. Photodynamic therapy in historical perspective. Rev Contemp Pharmacother 1999; 10:1–17.Google Scholar
  5. 5.
    Ackroyd R, Kelty C, Brown N et al. The history of photodetection and photodynamic therapy. Photochem Photobiol 2001; 74:656–669.PubMedCrossRefGoogle Scholar
  6. 6.
    Moan J, Peng Q. An outline of the hundred-year history of PDT. Anticancer Res 2003; 23:3591–3600.PubMedGoogle Scholar
  7. 7.
    Dolmans DEJGJ, Fukumura D, Jain RK. Photodynamic therapy for cancer. Nat Rev Cancer 2003; 3:380–387.PubMedCrossRefGoogle Scholar
  8. 8.
    Niedre M, Patterson MS, Wilson BC. Direct near-infrared luminescence detection of singlet oxygen generated by photodynamic therapy in cells in vitro and tissues in vivo. Photochem Photobiol 2002; 75:382–391.PubMedCrossRefGoogle Scholar
  9. 9.
    Grossweiner LI, Patel AS, Grossweiner JB. Type I and type II mechanisms in the photosensitized lysis of phosphatidylcholine liposomes by hematoporphyrin. Photochem Photobiol 1982; 36:159–167.PubMedCrossRefGoogle Scholar
  10. 10.
    Moan J, Berg K. The photodegradation of porphyrins in cells can be used to estimate the lifetime of singlet oxygen. Photochem Photobiol 1991; 53:549–553.PubMedCrossRefGoogle Scholar
  11. 11.
    Dahle J, Angell-Petersen E, Steen HB et al. Bystander effects in cell death induced by photodynamic treatment UVA radiation and inhibitors of ATP synthesis. Photochem Photobiol 2001; 73:378–387.PubMedCrossRefGoogle Scholar
  12. 12.
    Tuite EM, Kelly JM. Photochemical interactions of methylene blue and analogues with DNA and other biological substrates. J Photochem Photobiol B 1993; 21:103–124.PubMedCrossRefGoogle Scholar
  13. 13.
    Dubbelman TMAR et al. Photodynamic therapy: Membrane and enzyme photobiology. Photodynamic Therapy: Basic Principles and Clinical Applications. New York: Marcel Dekker Inc., 1992:37–46.Google Scholar
  14. 14.
    Brancaleon L, Moseley H. Laser and nonlaser light sources for photodynamic therapy. Lasers Med Sci 2002; 17:173–186.PubMedCrossRefGoogle Scholar
  15. 15.
    Henderson BW, Dougherty TJ. How does photodynamic therapy work? Photochem Photobiol 1992; 55:145–157.PubMedCrossRefGoogle Scholar
  16. 16.
    Star WM, Marijnissen HP, van den Berg-Blok AE et al. Destruction of rat mammary tumor and normal tissue microcirculation by hematoporphyrin derivative photoradiation observed in vivo in sandwich observation chambers. Cancer Res 1986; 46:2532–2540.PubMedGoogle Scholar
  17. 17.
    Roberts DJH, Cairnduff F, Driver I et al. Tumor vascular shutdown following photodynamic therapy based on polyhematoporphyrin or 5-aminolevulinic acid. Int J Oncol 1994; 5:763–768.Google Scholar
  18. 18.
    Dolmans DE, Kadambi A, Hill JS et al. Vascular accumulation of a novel photosensitizer, MV6401, causes selective thrombosis in tumor vessels after photodynamic therapy. Cancer Res 2002; 62:2151–2156.PubMedGoogle Scholar
  19. 19.
    Krammer B. Vascular effects of photodynamic therapy. Anticancer Res 2001; 21:4271–4277.PubMedGoogle Scholar
  20. 20.
    Robinson DJ, de Bruijn HS, van d V et al. Protoporphyrin IX fluorescence photobleaching during ALA-mediated photodynamic therapy of UVB-induced tumors in hairless mouse skin. Photochem Photobiol 1999; 69:61–70.PubMedCrossRefGoogle Scholar
  21. 21.
    Kanduc D, Mittelman A, Serpico R et al. Cell death: Apoptosis versus necrosis (review). Int J Oncol 2002; 21:165–170.PubMedGoogle Scholar
  22. 22.
    Luo Y, Chang CK, Kessel D. Rapid initiation of apoptosis by photodynamic therapy. Photochem Photobiol 1996; 63:528–534.PubMedCrossRefGoogle Scholar
  23. 23.
    Kessel D, Luo Y, Deng Y et al. The role of subcellular localization in initiation of apoptosis by photodynamic therapy. Photochem Photobiol 1997; 65:422–426.PubMedCrossRefGoogle Scholar
  24. 24.
    Zaidi SI, Oleinick NL, Zaim MT et al. Apoptosis during photodynamic therapy-induced ablation of RIF-1 tumors in C3H mice: Electron microscopic, histopathologic and biochemical evidence. Photochem Photobiol 1993; 58:771–776.PubMedCrossRefGoogle Scholar
  25. 25.
    Petit PX, Susin SA, Zamzami N et al. Mitochondria and programmed cell death: Back to the future. FEBS Letters 1996; 396:7–13.PubMedCrossRefGoogle Scholar
  26. 26.
    Kessel D, Luo Y. Mitochondrial photodamage and PDT-induced apoptosis. J Photochem Photobiol B 1998; 42:89–95.PubMedCrossRefGoogle Scholar
  27. 27.
    Oleinick NL, 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.PubMedCrossRefGoogle Scholar
  28. 28.
    Dellinger M. Apoptosis or necrosis following Photofrin photosensitization: Influence of the incubation protocol. Photochem Photobiol 1996; 64:182–187.PubMedCrossRefGoogle Scholar
  29. 29.
    Blant SA, Ballini JP, van den Bergh H et al. Time-dependent biodistribution of tetra(m-hydroxyphenyl)chlorin and benzoporphyrin derivative monoacid ring A in the hamster model: Comparative fluorescence microscopy study. Photochem Photobiol 2000; 71:333–340.CrossRefGoogle Scholar
  30. 30.
    Holroyd JA. The pharmacokinetics of the photosensitising drug polyhaematoporphyrin. PhD Thesis. University of Leeds, 1995.Google Scholar
  31. 31.
    Marti A, Jichlinski P, Lange N et al. Comparison of aminolevulinic acid and hexylester aminolevulinate induced protoporphyrin IX distribution in human bladder cancer. J Urol 2003; 170:428–432.PubMedCrossRefGoogle Scholar
  32. 32.
    Kongshaug M. Distribution of tetrapyrrole photosensitizers among human plasma proteins. Int J Biochem 1992; 24:1239–1265.PubMedCrossRefGoogle Scholar
  33. 33.
    Allison BA, Pritchard PH, Richter AM et al. The plasma distribution of benzoporphyrin derivative and the effects of plasma lipoproteins on its biodistribution. Photochem Photobiol 1990; 52:501–507.PubMedCrossRefGoogle Scholar
  34. 34.
    Kessel D. Porphyrin-lipoprotein association as a factor in porphyrin localization. Cancer Lett 1986; 33:183–188.PubMedCrossRefGoogle Scholar
  35. 35.
    Candide C, Morliere P, Maziere JC et al. In vitro interaction of the photoactive anticancer porphyrin derivative photofrin II with low density lipoprotein, and its delivery to cultured human fibroblasts. FEBS Lett 1986; 207:133–138.PubMedCrossRefGoogle Scholar
  36. 36.
    Norata G, Canti G, Ricci L et al. In vivo assimilation of low density lipoproteins by a fibrosarcoma tumour line in mice. Cancer Lett 1984; 25:203–208.PubMedCrossRefGoogle Scholar
  37. 37.
    Korbelik M. Low density lipoprotein receptor pathway in the delivery of Photofrin: How much is it relevant for selective accumulation of the photosensitizer in tumors? J Photochem Photobiol B 1992; 12:107–109.PubMedCrossRefGoogle Scholar
  38. 38.
    Kessel D, Garbo GM, Hampton J. The role of lipoproteins in the distribution of tin etiopurpurin (SnET2) in the tumour-bearing rat. Photochem Photobiol 1993; 57:298–301.PubMedCrossRefGoogle Scholar
  39. 39.
    Kessel D, Whitcomb KL, Schulz V. Lipoprotein-mediated distribution of N-aspartyl chlorin-E6 in the mouse. Photochem Photobiol 1992; 56:51–56.PubMedCrossRefGoogle Scholar
  40. 40.
    Jori G. In vivo transport and pharmacokinetic behavior of tumour photosensitizers. Ciba Found Symp 1989; 146:78–86.PubMedGoogle Scholar
  41. 41.
    Lipson RL, Baldes EJ, Olsen AM. The use of a derivative of hematoporhyrin in tumor detection. J Natl Cancer Inst 1961; 26:1–11.PubMedGoogle Scholar
  42. 42.
    Bonnett R, Ridge RJ, Scourides PA et al. On the nature of hematoporphyrin derivative. J Chem Soc [Perkins 1] 1981; 3135–3140.Google Scholar
  43. 43.
    Kessel D, Cheng ML. Biological and biophysical properties of the tumor-localizing component of hematoporphyrin derivative. Cancer Res 1985; 45:3053–3057.PubMedGoogle Scholar
  44. 44.
    Berenbaum MC, Bonnett R, Scourides PA. In vivo biological activity of the components of haematoporphyrin derivative. Br J Cancer 1982; 45:571–581.PubMedGoogle Scholar
  45. 45.
    Byrne CJ, Marshallsay LV, Ward AD. The composition of Photofrin II. J Photochem Photobiol B 1990; 6:13–27.PubMedCrossRefGoogle Scholar
  46. 46.
    Dougherty TJ. An update on photodynamic therapy applications. J Clin Laser Med Surg 2002; 20:3–7.PubMedCrossRefGoogle Scholar
  47. 47.
    Dougherty TJ. Photodynamic therapy. Photochem Photobiol 1993; 58:895–900.PubMedCrossRefGoogle Scholar
  48. 48.
    Friedberg JS, Mick R, Stevenson JP et al. Phase II trial of pleural photodynamic therapy and surgery for patients with nonsmall-cell lung cancer with pleural spread. J Clin Oncol 2004; 22:2192–2201.PubMedCrossRefGoogle Scholar
  49. 49.
    Yamaguchi S, Tsuda H, Takemori M et al. Photodynamic therapy for cervical intraepithelial neoplasia. Oncology 2005; 69:110–116.PubMedCrossRefGoogle Scholar
  50. 50.
    Marks PV, Belchetz PE, Saxena A et al. Effect of photodynamic therapy on recurrent pituitary adenomas: Clinical phase I/II trial—an early report. Br J Neurosurg 2000; 14:317–325.PubMedCrossRefGoogle Scholar
  51. 51.
    Brown SB, Vernon DI, Holroyd JA et al. Pharmacokinetics of Photofrin in Man. Photodynamic Therapy and Biomedical Lasers. New York: Elsevier, 1992:475–479.Google Scholar
  52. 52.
    Bellnier DA, Dougherty TJ. A preliminary pharmacokinetic study of intravenous Photofrin in patients. J Clin Laser Med Surg 1996; 14:311–314.PubMedGoogle Scholar
  53. 53.
    Driver I, Lowdell CP, Ash DV. In vivo measurement of the optical interaction coefficients of human tumours at 630 nm. Phys Med Biol 1991; 36:805–813.PubMedCrossRefGoogle Scholar
  54. 54.
    Shackley DC, Whitehurst C, Moore JV et al. Light penetration in bladder tissue: Implications for the intravesical photodynamic therapy of bladder tumours. BJU Int 2000; 86:638–643.PubMedCrossRefGoogle Scholar
  55. 55.
    Wan S, Anderson RR, Parrish JA. Analytical modeling for the optical properties of the skin with in vitro and in vivo applications. Photochem Photobiol 1981; 34:493–499.PubMedGoogle Scholar
  56. 56.
    Sternberg ED, Dolphin D, Bruckner C. Porphyrin-based photosensitizers for use in photodynamic therapy. Tetrahedron 1998; 54:4151–4202.CrossRefGoogle Scholar
  57. 57.
    Berenbaum MC, Akande SL, Bonnett R et al. meso-Tetra(hydroxyphenyl)porphyrins, a new class of potent tumour photosensitisers with favourable selectivity. Br J Cancer 1986; 54:717–725.PubMedGoogle Scholar
  58. 58.
    Berenbaum MC, Bonnett R. Tetra(hydroxyphenyl)porphyrins. Photodynamic Therapy of Neoplastic Disease. Vol. 2. Boca Raton: CRC Press Inc., 1990:169–177.Google Scholar
  59. 59.
    Bonnett R, White RD, Winfield UJ et al. Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumour photosensitizers. Biochem J 1989; 261:277–280.PubMedGoogle Scholar
  60. 60.
    Post JG, te Poele JA, Schuitmaker JJ et al. A comparison of functional bladder damage after intravesical photodynamic therapy with three different photosensitizers. Photochem Photobiol 1996; 63:314–321.PubMedCrossRefGoogle Scholar
  61. 61.
    van Geel IP, Oppelaar H, Oussoren YG et al. Photosensitizing efficacy of MTHPC-PDT compared to photofrin-PDT in the RIF1 mouse tumour and normal skin. Int J Cancer 1995; 60:388–394.PubMedGoogle Scholar
  62. 62.
    Ball DJ, Vernon DI, Brown SB. The high photoactivity of m-THPC in photodynamic therapy. Unusually strong retention of m-THPC by RIF-1 cells in culture. Photochem Photobiol 1999; 69:360–363.PubMedCrossRefGoogle Scholar
  63. 63.
    Michael Titus AT, Whelpton R, Yaqub Z. Binding of temoporfin to the lipoprotein fractions of human serum. Br J Clin Pharmacol 1995; 40:594–597.PubMedGoogle Scholar
  64. 64.
    Hopkinson HJ, Vernon DI, Brown SB. Identification and partial characterization of an unusual distribution of the photosensitizer meta-tetrahydroxyphenyl chlorin (temoporfin) in human plasma. Photochem Photobiol 1999; 69:482–488.PubMedCrossRefGoogle Scholar
  65. 65.
    Copper MP, Tan IB, Oppelaar H et al. 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.PubMedCrossRefGoogle Scholar
  66. 66.
    Lovat LB, Jamieson NF, Novelli MR et al. Photodynamic therapy with m-tetrahydroxyphenyl chlorin for high-grade dysplasia and early cancer in Barrett’s columnar lined esophagus. Gastrointest Endosc 2005; 62:617–623.PubMedCrossRefGoogle Scholar
  67. 67.
    Hopper C, Kubier A, Lewis H et al. mTHPC-mediated photodynamic therapy for early oral squamous cell carcinoma. Int J Cancer 2004; 111:138–146.PubMedCrossRefGoogle Scholar
  68. 68.
    Lou PJ, Jager HR, Jones L et al. Interstitial photodynamic therapy as salvage treatment for recurrent head and neck cancer. Br J Cancer 2004; 91:441–446.PubMedCrossRefGoogle Scholar
  69. 69.
    Jones HJ, Vernon DI, Brown SB. Photodynamic therapy effect of m-THPC (Foscan) in vivo: Correlation with pharmacokinetics. Br J Cancer 2003; 89:398–404.PubMedCrossRefGoogle Scholar
  70. 70.
    Cramers P, Ruevekamp M, Oppelaar H et al. Foscan uptake and tissue distribution in relation to photodynamic efficacy. Br J Cancer 2003; 88:283–290.PubMedCrossRefGoogle Scholar
  71. 71.
    Rovers JP, de Jode ML, Rezzoug H et al. In vivo photodynamic characteristics of the near-infrared photosensitizer 5,10,15,20-tetrakis(M-hydroxyphenyl) bacteriochlorin. Photochem Photobiol 2000; 72:358–364.PubMedCrossRefGoogle Scholar
  72. 72.
    Bonnett R, Charlesworth P, Djelal BD et al. Photophysical properties of 5,10,15,20-tetrakis(mhydroxyphenyl)porphyrin-(m-THPP), 5,10,15,20-tetrakis(mhydroxyphenyl)chlorin (m-THPC) and 5,10,15,20-tetrakis(m-hydroxyphenyl)bacteriocrilorin (m-THPBC): A comparative study. J Chem Soc, Perkin Transactions 2 1999; 325–328.CrossRefGoogle Scholar
  73. 73.
    Rovers JP, de Jode ML, Grahn MF. Significantly increased lesion size by using the near-infrared photosensitizer 5,10,15,20-tetrakis (m-hydroxyphenyl)bacteriochlorin in interstitial photodynamic therapy of normal rat liver tissue. Lasers Surg Med 2000; 27:235–240.PubMedCrossRefGoogle Scholar
  74. 74.
    Engelmann K, Mack MG, Eichler K et al. Interstitial photodynamic laser therapy for liver metastases: First results of a clinical phase I-study. Rofo-Fortschritte Auf dem Gebiet der Rontgenstrahlen und der Bildgebenden Verfahren 2003; 175:682–687.CrossRefGoogle Scholar
  75. 75.
    van Duijnhoven FH, Rovers JP, Engelmann K et al. Photodynamic therapy with 5,10,15, 20-tetrakis(m-hydroxyphenyl) bacteriochlorin for colorectal liver metastases is safe and feasible: Results from a phase I study. Ann Surg Oncol 2005; 12:808–816.PubMedCrossRefGoogle Scholar
  76. 76.
    Richter AM, Kelly B, Chow J et al. Preliminary studies on a more effective phototoxic agent than hematoporphyrin. J Natl Cancer Inst 1987; 79:1327–1332.PubMedGoogle Scholar
  77. 77.
    Aveline B, Hasan T, Redmond RW. Photophysical and photosensitizing properties of benzoporphyrin derivative monoacid ring A (BPD-MA). Photochem Photobiol 1994; 59:328–335.PubMedCrossRefGoogle Scholar
  78. 78.
    Aveline BM, Hasan T, Redmond RW. The effects of aggregation, protein binding and cellular incorporation on the photophysical properties of benzoporphyrin derivative monoacid ring A (BPDMA). J Photochem Photobiol B 1995; 30:161–169.PubMedCrossRefGoogle Scholar
  79. 79.
    Allison BA, Pritchard PH, Levy JG. Evidence for low-density lipoprotein receptor-mediated uptake of benzoporphyrin derivative. Br J Cancer 1994; 69:833–839.PubMedGoogle Scholar
  80. 80.
    Fingar VH, Kik PK, Haydon PS et al. Analysis of acute vascular damage after photodynamic therapy using benzoporphyrin derivative (BPD). Br J Cancer 1999; 79:1702–1708.PubMedCrossRefGoogle Scholar
  81. 81.
    Richter AM, Jain AK, Canaan AJ et al. Photosensitizing efficiency of two regioisomers of the benzoporphyrin derivative monoacid ring A (BPD-MA). Biochem Pharmacol 1992; 43:2349–2358.PubMedCrossRefGoogle Scholar
  82. 82.
    Lui H, Hobbs L, Tope WD et al. Photodynamic therapy of multiple nonmelanoma skin cancers with verteporfin and red light-emitting diodes: Two-year results evaluating tumor response and cosmetic outcomes. Arch Dermatol 2004; 140:26–32.PubMedCrossRefGoogle Scholar
  83. 83.
    Brown SB, Mellish KJ. Verteporfin: A milestone in opthalmology and photodynamic therapy. Expert Opin Pharmacother 2001; 2:351–361.PubMedCrossRefGoogle Scholar
  84. 84.
    Michels S, Michels R, Simader C et al. Verteporfin therapy for choroidal hemangioma: A long-term follow-up. Retina 2005; 25:697–703.PubMedCrossRefGoogle Scholar
  85. 85.
    Pogue BW, Redmond RW, Trivedi N et al. Photophysical properties of tin ethyl etiopurpurin I (SnET2) and tin octaethylbenzochlorin (SnOEBC) in solution and bound to albumin. Photochem Photobiol 1998; 68:809–815.PubMedCrossRefGoogle Scholar
  86. 86.
    Mang TS, Allison R, Hewson G et al. A phase II/III clinical study of tin ethyl etiopurpurin (Purlytin)-induced photodynamic therapy for the treatment of recurrent cutaneous metastatic breast cancer. Cancer J Sci Am 1998; 4:378–384.PubMedGoogle Scholar
  87. 87.
    Wilson BD, Bernstein Z, Sommer C et al. Photodynamic therapy for kaposis-sarcoma using photofrin and tin ethyl-etiopurpurin (Snet2). J Invest Dermatol 1995; 104:693.CrossRefGoogle Scholar
  88. 88.
    Roberts WG, Shiau FY, Nelson JS et al. In vitro characterization of monoaspartyl chlorin e6 and diaspartyl chlorin e6 for photodynamic therapy. J Natl Cancer Inst 1988; 80:330–336.PubMedCrossRefGoogle Scholar
  89. 89.
    Taber SW, Fingar VH, Coots CT et al. Photodynamic therapy using mono-L-aspartyl chlorin e6 (Npe6) for the treatment of cutaneous disease: A Phase I clinical study. Clin Cancer Res 1998; 4:2741–2746.PubMedGoogle Scholar
  90. 90.
    Chan AL, Juarez M, Allen R et al. Pharmacokinetics and clinical effects of mono-L-aspartyl chlorin e6 (NPe6) photodynamic therapy in adult patients with primary or secondary cancer of the skin and mucosal surfaces. Photodermatol Photoimmunol Photomed 2005; 21:72–78.PubMedCrossRefGoogle Scholar
  91. 91.
    Kato H, Furukawa K, Sato M et al. Phase II clinical study of photodynamic therapy using mono-L-aspartyl chlorin e6 and diode laser for early superficial squamous cell carcinoma of the lung. Lung Cancer 2003; 42:103–111.PubMedCrossRefGoogle Scholar
  92. 92.
    Lustig RA, Vogl TJ, Fromm D et al. A multicentre phase I safety study of intratumoral photoactivation of Talaporfin Sodium in patients with refractory solid tumors. Cancer 2003; 98:1767–1771.PubMedCrossRefGoogle Scholar
  93. 93.
    Chen Q, Huang Z, Luck D et al. Preclinical studies in normal canine prostate of a novel palladium-bacteriopheophorbide (WST09) photosensitizer for photodynamic therapy of prostate cancers. Photochem Photobiol 2002; 76:438–445.PubMedCrossRefGoogle Scholar
  94. 94.
    Vakrat-Haglili Y, Weiner L, Brumfeld V et al. The microenvironment effect on the generation of reactive oxygen species by Pd-bacteriopheophorbide. J Am Chem Soc 2005; 127:6487–6497.PubMedCrossRefGoogle Scholar
  95. 95.
    Brun PH, DeGroot JL, Dickson EF et al. Determination of the in vivo pharmacokinetics of palladium-bacteriopheophorbide (WST09) in EMT6 tumour-bearing Balb/c mice using graphite furnace atomic absorption spectroscopy. Photochem Photobiol Sci 2004; 3:1006–1010.PubMedCrossRefGoogle Scholar
  96. 96.
    Borle F, Radu A, Monnier P et al. Evaluation of the photosensitizer Tookad for photodynamic therapy on the Syrian golden hamster cheek pouch model: Light dose, drug dose and drug-light interval effects. Photochem Photobiol 2003; 78:377–383.PubMedCrossRefGoogle Scholar
  97. 97.
    Koudinova NV, Pinthus JH, Brandis A et al. Photodynamic therapy with Pd-Bacteriopheophorbide (TOOKAD): Successful in vivo treatment of human prostatic small cell carcinoma xenografts. Int J Cancer 2003; 104:782–789.PubMedCrossRefGoogle Scholar
  98. 98.
    Weersink RA, Bogaards A, Gertner M et al. Techniques for delivery and monitoring of TOOKAD (WST09)-mediated photodynamic therapy of the prostate: Clinical experience and practicalities. J Photochem Photobiol B 2005; 79:211–222.PubMedCrossRefGoogle Scholar
  99. 99.
    Pandey RK, Bellnier DA, Smith KM et al. Chlorin and porphyrin derivatives as potential photosensitizers in photodynamic therapy. Photochem Photobiol 1991; 53:65–72.PubMedCrossRefGoogle Scholar
  100. 100.
    Pandey RK, Sumlin AB, Constantine S et al. Alkyl ether analogs of chlorophyll-a Derivatives: Part 1. Synthesis, photophysical properties and photodynamic efficacy. Photochem Photobiol 1996; 64:194–204.PubMedCrossRefGoogle Scholar
  101. 101.
    Bellnier DA, Henderson BW, Pandey RK et al. Murine pharmacokinetics and antitumour efficacy of the photodynamic sensitizer 2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a. J Photochem Photobiol B 1993; 20:55–61.PubMedCrossRefGoogle Scholar
  102. 102.
    Bellnier DA, Greco WR, Loewen GM et al. Population pharmacokinetics of the photodynamic therapy agent 2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a in cancer patients. Cancer Res 2003; 63:1806–1813.PubMedGoogle Scholar
  103. 103.
    Bellnier DA, Greco WR, Nava H et al. Mild skin photosensitivity in cancer patients following injection of Photochlor (2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a; HPPH) for photodynamic therapy. Cancer Chemother Pharmacol 2005; 1–6.Google Scholar
  104. 104.
    Sharman WM, Allen CM, van Lier JE. Photodynamic therapeutics: Basic principles and clinical applications. Drug Discov Today 1999; 4:507–517.PubMedCrossRefGoogle Scholar
  105. 105.
    Rosenthal I. Phthalocyanines as photodynamic sensitizers. Photochem Photobiol 1991; 53:859–870.PubMedGoogle Scholar
  106. 106.
    Chan WS, Marshall JF, Hart IR. Photodynamic therapy of a murine tumor following sensitisation with chloro aluminum sulfonated phthalocyanine. Photochem Photobiol 1987; 46:867–871.PubMedCrossRefGoogle Scholar
  107. 107.
    Allen CM, Sharman WM, van Lier JE. Current status of phthalocyanines in the photodynamic therapy of cancer. Journal of Porphyrins and Phthalocyanines 2001; 5:161–169.CrossRefGoogle Scholar
  108. 108.
    Dougherty TJ, Corner CJ, Henderson BW et al. Photodynamic therapy. J Natl Cancer Inst 1998; 90:889–905.PubMedCrossRefGoogle Scholar
  109. 109.
    Kereiakes DJ, Szyniszewski AM, Wahr D et al. Phase I drug and light dose-escalation trial of motexafin lutetium and far red light activation (phototherapy) in subjects with coronary artery disease undergoing percutaneous coronary intervention and stent deployment: Procedural and long-term results. Circulation 2003; 108:1310–1315.PubMedCrossRefGoogle Scholar
  110. 110.
    Kennedy JC, Pottier RH. Endogenous protoporphyrin IX, a clinically useful photosensitizer for photodynamic therapy. J Photochem Photobiol B 1992; 14:275–292.PubMedCrossRefGoogle Scholar
  111. 111.
    Batlle AM. Porphyrins, porphyrias, cancer and photodynamic therapy—a model for carcinogenesis. J Photochem Photobiol B 1993; 20:5–22.PubMedCrossRefGoogle Scholar
  112. 112.
    Hinnen P, de Rooij FWM, Edixhoven A et al. Porphyrin biosynthesis in human Barrett’s oesophagus and adenocarcinoma after ingestion of 5-aminolaevulinic acid. Br J Cancer 2000; 83:539–543.PubMedCrossRefGoogle Scholar
  113. 113.
    Rittenhouse-Diakun K, Van Leengoed H, Morgan J et al. The role of transferrin receptor (CD71) in photodynamic therapy of activated and malignant lymphocytes using the heme precursor delta-aminolevulinic acid (ALA). Photochem Photobiol 1995; 61:523–528.PubMedCrossRefGoogle Scholar
  114. 114.
    Van den Akker JTHM, Brown SB. Photodynamic Therapy based on 5-aminolevulinic acid: Applications in dermatology. Photobiology for the 21st Century. Overland Park: Valdenmar Publishing Company, 2002:165–181.Google Scholar
  115. 115.
    Kelty C, Brown NJ, Reed M et al. The use of 5-aminolaevulinic acid as a photosensitiser in photodynamic therapy and photodiagnosis. Photochem Photobiol Sci 2002; 1:158–168.PubMedCrossRefGoogle Scholar
  116. 116.
    Kennedy JC, Pottier RH, Pross DC. Photodynamic therapy with endogenous protoporphyrin IX: Basic principles and present clinical experience. J Photochem Photobiol B 1990; 6:143–148.PubMedCrossRefGoogle Scholar
  117. 117.
    Cairnduff F, Stringer MR, Hudson EJ et al. Superficial photodynamic therapy with topical 5-aminolaevulinic acid for superficial primary and secondary skin cancer. Br J Cancer 1994; 69:605–608.PubMedGoogle Scholar
  118. 118.
    Stables GI, Stringer MR, Robinson DJ et al. Large patches of Bowen’s disease treated by topical aminolaevulinic acid photodynamic therapy. Br J Dermatol 1997; 136:957–960.PubMedCrossRefGoogle Scholar
  119. 119.
    Svanberg K, Andersson T, Killander D et al. Photodynamic therapy of nonmelanoma malignant tumours of the skin using topical delta-amino levulinic acid sensitization and laser irradiation. Br J Dermatol 1994; 130:743–751.PubMedCrossRefGoogle Scholar
  120. 120.
    Morton CA, Whitehurst C, Moseley H et al. Comparison of photodynamic therapy with cryotherapy in the treatment of Bowen’s disease. Br J Dermatol 1996; 135:766–771.PubMedCrossRefGoogle Scholar
  121. 121.
    Robinson DJ, Collins P, Stringer MR et al. Improved response of plaque psoriasis after multiple treatments with topical 5-aminolaevulinic acid photodynamic therapy. Acta Derm Venereol 1999; 79:451–455.PubMedCrossRefGoogle Scholar
  122. 122.
    Collins P, Robinson DJ, Stringer MR et al. The variable response of plaque psoriasis after a single treatment with topical 5-aminolaevulinic acid photodynamic therapy. Br J Dermatol 1997; 137:743–749.PubMedCrossRefGoogle Scholar
  123. 123.
    Schick E, Ruck A, Boehncke WH et al. Topical photodynamic therapy using methylene blue and 5-aminolaevulinic acid in psoriasis. J Dermatolog Treat 1997; 8:17–19.CrossRefGoogle Scholar
  124. 124.
    Soler AM, Angell-Petersen E, Warloe T et al. Photodynamic therapy of superficial basal cell carcinoma with 5-aminolevulinic acid with dimethylsulfoxide and ethylendiaminetetraacetic acid: A comparison of two light sources. Photochem Photobiol 2000; 71:724–729.PubMedCrossRefGoogle Scholar
  125. 125.
    Fink-Puches R, Soyer-H, Hofer A et al. Long-term follow-up and histological changes of superficial nonmelanoma skin cancers treated with topical delta-aminolevulinic acid photodynamic therapy. Arch Dermatol 1998; 134:821–826.PubMedCrossRefGoogle Scholar
  126. 126.
    Harth Y, Hirshowitz B, Kaplan B. Modified topical photodynamic therapy of superficial skin tumors, utilizing aminolevulinic acid, penetration enhancers, red light, and hyperthermia. Dermatol Surg 1998; 24:723–726.PubMedCrossRefGoogle Scholar
  127. 127.
    Rhodes LE, Tsoukas MM, Anderson RR et al. Iontophoretic delivery of ALA provides a quantitative model for ALA pharmacokinetics and PpIX phototoxicity in human skin. J Invest Dermatol 1997; 108:87–91.PubMedCrossRefGoogle Scholar
  128. 128.
    Peng QA, Warloe T, Moan J et al. Distribution of 5-aminolevulinic acid-induced porphyrins in noduloulcerative basal-cell carcinoma. Photochem Photobiol 1995; 62:906–913.PubMedCrossRefGoogle Scholar
  129. 129.
    De Rosa FS, Marchetti JM, Thomazini JA et al. A vehicle for photodynamic therapy of skin cancer: Influence of dimethylsulphoxide on 5-aminolevulinic acid in vitro cutaneous permeation and in vivo protoporphyrin IX accumulation determined by confocal microscopy. J Control Release 2000; 65:359–366.PubMedCrossRefGoogle Scholar
  130. 130.
    Gannon MJ, Johnson N, Roberts DJ et al. Photosensitization of the endometrium with topical 5-aminolevulinic acid. Am J Obstet Gynecol 1995; 173:1826–1828.PubMedCrossRefGoogle Scholar
  131. 131.
    Wyss P, Caduff R, Tadir Y et al. Photodynamic endometrial ablation: Morphological study. Lasers Surg Med 2003; 32:305–309.PubMedCrossRefGoogle Scholar
  132. 132.
    Gossner L, Stolte M, Sroka R et al. Photodynamic ablation of high-grade dysplasia and early cancer in Barrett’s esophagus by means of 5-aminolevulinic acid. Gastroenterology 1998; 114:448–455.PubMedCrossRefGoogle Scholar
  133. 133.
    Ackroyd R, Brown NJ, Davis MF et al. Photodynamic therapy for dysplastic Barrett’s oesophagus: A prospective, double blind, randomised, placebo controlled trial. Gut 2000; 47:612–617.PubMedCrossRefGoogle Scholar
  134. 134.
    Kelty CJ, Ackroyd R, Brown NJ et al. Photodynamic therapy for dysplastic Barrett’s oesophagus: Longterm follow-up. Br J Surg 2001; 88:478.CrossRefGoogle Scholar
  135. 135.
    Gaullier JM, Berg K, Peng Q et al. Use of 5-aminolevulinic acid esters to improve photodynamic therapy on cells in culture. Cancer Res 1997; 57:1481–1486.PubMedGoogle Scholar
  136. 136.
    Peng Q, Soler AM, Warloe T et al. Selective distribution of porphyrins in skin thick basal cell carcinoma after topical application of methyl 5-aminolevulinate. J Photochem Photobiol B 2001; 62:140–145.PubMedCrossRefGoogle Scholar
  137. 137.
    Van den Akker JTHM, Holroyd JA, Vernon DI et al. Comparative in vitro percutaneous penetration of 5-aminolevulinic acid and two of its esters through excised hairless mouse skin. Lasers Surg Med 2003; 33:173–181.PubMedCrossRefGoogle Scholar
  138. 138.
    Freeman M, Vinciullo C, Francis D et al. A comparison of photodynamic therapy using topical methyl aminolevulinate (Metvix) with single cycle cryotherapy in patients with actinic keratosis: A prospective, randomized study. J Dermatolog Treat 2003; 14:99–106.PubMedCrossRefGoogle Scholar
  139. 139.
    Soler AM, Warloe T, Berner A et al. A follow-up study of recurrence and cosmesis in completely responding superficial and nodular basal cell carcinomas treated with methyl 5-aminolaevulinate-based photodynamic therapy alone and with prior curettage. Br J Dermatol 2001; 145:467–471.PubMedCrossRefGoogle Scholar
  140. 140.
    Tarstedt M, Rosdahl I, Berne B et al. A randomized multicenter study to compare two treatment regimens of topical methyl aminolevulinate (Metvix)-PDT in actinic keratosis of the face and scalp. Acta Derm Venereol 2005; 85:424–428.PubMedCrossRefGoogle Scholar
  141. 141.
    Zimmermann A, Ritsch-Marte M, Kostron H. mTHPC-mediated photodynamic diagnosis of malignant brain tumors. Photochem Photobiol 2001; 74:611–616.PubMedCrossRefGoogle Scholar
  142. 142.
    Kriegmair M, Zaak D, Stepp H et al. Transurethral resection and surveillance of bladder cancer supported by 5-aminolevulinic acid-induced fluorescence endoscopy. Eur Urol 1999; 36:386–392.PubMedCrossRefGoogle Scholar
  143. 143.
    Baumgartner R, Huber RM, Schulz H et al. Inhalation of 5-aminolevulinic acid: A new technique for fluorescence detection of early stage lung cancer. J Photochem Photobiol B 1996; 36:169–174.PubMedCrossRefGoogle Scholar
  144. 144.
    Hillemanns P, Weingandt H, Baumgartner R et al. Photodetection of cervical intraepithelial neoplasia using 5-aminolevulinic acid-induced porphyrin fluorescence. Cancer 2000; 88:2275–2282.PubMedCrossRefGoogle Scholar
  145. 145.
    Ladner DP, Steiner RA, Allemann J et al. Photodynamic diagnosis of breast tumours after oral application of aminolevulinic acid. Br J Cancer 2001; 84:33–37.PubMedCrossRefGoogle Scholar
  146. 146.
    Jichlinski P, Leisinger HJ. Photodynamic therapy in superficial bladder cancer: Past, present and future. Urol Res 2001; 29:396–405.PubMedCrossRefGoogle Scholar
  147. 147.
    Lange N, Jichlinski P, Zellweger M et al. Photodetection of early human bladder cancer based on the fluorescence of 5-aminolaevulinic acid hexylester-induced protoporphyrin IX: A pilot study. Br J Cancer 1999; 80:185–193.PubMedCrossRefGoogle Scholar
  148. 148.
    Jiang H, Granville DJ, North JR et al. Selective action of the photosensitizer QLT0074 on activated human T lymphocytes. Photochem Photobiol 2002; 76:224–231.PubMedCrossRefGoogle Scholar
  149. 149.
    Anderson CY, Freye K, Tubesing KA et al. A comparative analysis of silicon phthalocyanine photosensitizers for in vivo photodynamic therapy of RIF-1 tumors in C3H mice. Photochem Photobiol 1998; 67:332–336.PubMedCrossRefGoogle Scholar
  150. 150.
    Hill JS, Kahl SB, Stylli SS et al. Selective tumor kill of cerebral glioma by photodynamic therapy using a boronated porphyrin photosensitizer. Proc Natl Acad Sci USA 1995; 92:12126–12130.PubMedCrossRefGoogle Scholar
  151. 151.
    Chang SC, Buonaccorsi GA, MacRobert AJ et al. Interstitial photodynamic therapy in the canine prostate with disulfonated aluminum phthalocyanine and 5-aminolevulinic acid-induced protoporphyrin IX. Prostate 1997; 32:89–98.PubMedCrossRefGoogle Scholar

Copyright information

© Landes Bioscience and Springer Science+Business Media 2009

Authors and Affiliations

  1. 1.Institute of Molecular and Cell Biology, Department of Biological SciencesUniversity of LeedsLeedsUK

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