Photodiagnosis and Photodynamic Therapy
Volume 2, Issue 2 , Pages 129-134 , June 2005

Formation of protoporphyrin IX from carboxylic- and amino-derivatives of 5-aminolevulinic acid

  • Miron Kaliszewski, M.Sc.

      Affiliations

    • Department of Radiation Biology, Institute for Cancer Research, 0310 Montebello, Oslo, Norway
    • Institute of Optoelectronics, Military University of Technology, ul. Kaliskiego 2, 00-908 Warsaw, Poland
    • Corresponding Author InformationCo-corresponding author. Tel.: +48 22 683 70 17; fax: +48 22 666 89 50.
    • ,
  • Asta Juzeniene

      Affiliations

    • Department of Radiation Biology, Institute for Cancer Research, 0310 Montebello, Oslo, Norway
    • ,
  • Petras Juzenas, Ph.D.

      Affiliations

    • Department of Radiation Biology, Institute for Cancer Research, 0310 Montebello, Oslo, Norway
    • Corresponding Author InformationCorresponding author. Tel.: +47 22 93 51 13; fax: +47 22 93 42 70.
    • ,
  • Miroslaw Kwasny

      Affiliations

    • Institute of Optoelectronics, Military University of Technology, ul. Kaliskiego 2, 00-908 Warsaw, Poland
    • ,
  • Jaroslaw Kaminski

      Affiliations

    • Industrial Chemistry Research Institute, ul. Rydygiera 8, 01-793 Warsaw, Poland
    • ,
  • Zbigniew Dabrowski

      Affiliations

    • Industrial Chemistry Research Institute, ul. Rydygiera 8, 01-793 Warsaw, Poland
    • ,
  • Jerzy Golinski

      Affiliations

    • Industrial Chemistry Research Institute, ul. Rydygiera 8, 01-793 Warsaw, Poland
    • ,
  • Johan Moan

      Affiliations

    • Department of Radiation Biology, Institute for Cancer Research, 0310 Montebello, Oslo, Norway

References 

  1. Kloek J, Beijersbergen von Henegouwen GMJ. Prodrugs of 5-aminolevulinic acid for photodynamic therapy. Photochem Photobiol. 1996;64(6):994–1000
  2. Roy BN, Van Vugt DA, Weagle GE, Pottier RH, Reid RL. Effect of continuous and multiple doses of 5-aminolevulinic acid on protoporphyrin IX concentrations in the rat uterus. J Photochem Photobiol B: Biol. 1997;41:122–127
  3. Lopez RFV, Lange N, Guy R, Bentley MV. Photodynamic therapy of skin cancer: controlled drug delivery of 5-ALA and its esters. Adv Drug Deliv Rev. 2004;56(1):77–94
  4. De Rosa FS, Tedesco AC, Lopez RFV, et al. In vitro skin permeation and retention of 5-aminolevulinic acid ester derivatives for photodynamic therapy. J Controlled Release. 2003;89:261–269
  5. Tunstall RG, Barnett AA, Schofield J, et al. Porphyrin accumulation induced by 5-aminolevulinc acid esters in tumour cells growing in vitro and in vivo. Br J Cancer. 2002;87:246–250
  6. Gaullier JM, Berg K, Peng Q, et al. Use of 5-aminolevulinic aid esters to improve photodynamic therapy on cells in culture. Cancer Res. 1997;57:1481–1486
  7. Kaliszewski M, Kwasny M, Kaminski J, Dabrowski Z, Burdziakowska E. The stability of 5-aminolevulinic acid and its ester derivatives. Acta Pol Pharm Drug Res. 2004;61(1):15–19
  8. Bunke A, Zerbe O, Schmid H, Burmeister G, Merkle FTP, Gander B. Degradation mechanism and stability of 5-aminolevulinic acid. J Pharm Sci. 2000;89(10):1335–1341
  9. Dabrowski Z, Kwasny M, Kaminski J, et al. The synthesis and application of 5-aminolevulinic acid derivatives in photodynamic therapy and photodiagnosis. Acta Pol Pharm Drug Res. 2003;60(3):219–224
  10. Noguchi P, Wallace R, Johnson J, et al. Characterization of WiDr: a human colon carcinoma cell line. In Vitro. 1979;15:401–408
  11. Iinuma S, Farshi SS, Ortel B, Hasan TA. Mechanistic study of cellular photodestruction with 5-aminolaevulinic acid-induced porphyrin. Br J Cancer. 1994;70(1):21–28
  12. Cosserat-Gerardin I, Bezdetnaya L, Notter D, Vigneron C, Guillemin F. Biosynthesis and photodynamic efficacy of protoporphyrin IX (PPIX) generated by 5-aminolevulinic acid (ALA) or its hexylester (hALA) in rat bladder carcinoma cells. J Photochem Photobiol B: Biol. 2000;59:72–79
  13. Juzeniene A, Ma LW, Juzenas P, Iani V, Lange N, Moan J. Production of Protoporphyrin IX from 5-aminolevulinic acid and two of its esters in cells in vitro and tissue in vivo. Cell Mol Biol. 2002;48(8):911–916
  14. Casas A, Batlle AM, Butler AR, et al. Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. Br J Cancer. 1999;80(10):1525–1532
  15. Novo M, Hüttmann G, Diddens H. Chemical instability of 5-aminolevulinic acid used in the fluorescence diagnosis of bladder tumours. J Photochem Photobiol B: Biol. 2000;34:143–148
  16. Jarret C, Stauffer F, Henz ME, et al. Inhibition of Escherichia coli porphobilinogen synthase using analogs of postulated intermediates. Chem Biol. 2000;7(3):185–196
  17. Luond RM, Neier R. On the formation of the mixed pyrrole catalysed by porphobilinogen synthase from Rhodobacter spheroides. Biochim Biophys Acta. 1996;1289(1):83–86
  18. Frere F, Schubert WD, Stauffer F, et al. Structure of porphobilinogen synthase from Pseudomonas aeruginosa in complex with 5-fluorolevulinic acid suggests a double Schiff base mechanism. J Mol Biol. 2002;320(2):237–247
  19. Ninomiya Y, Itoh Y, Tajima S, Ishibashi A. In vitro and in vivo expression of protoporphyrin IX induced by lipophilic 5-aminolevulinic acid derivatives. J Dermatol Sci. 2001;27(2):114–120

PII: S1572-1000(05)00012-8

doi: 10.1016/S1572-1000(05)00012-8

Photodiagnosis and Photodynamic Therapy
Volume 2, Issue 2 , Pages 129-134 , June 2005

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