5-Aminolaevulinic acid peptide prodrugs enhance photosensitization for photodynamic therapy

Molecular Cancer Therapeutics

Volumn 7, Issue 6, 2008, Pages 1720-1729

  Bourré, Ludovic ^a   Giuntini, Francesca ^c   Eggleston, Ian M ^c   Wilson, Michael ^b   MacRobert, Alexander J ^a  

^a ROYAL FREE AND UNIVERSITY COLLEGE MEDICAL SCHOOL   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL DEXTRO PHENYLALANYLAMINOLEVULINIC ACID METHYL ESTER; ACETYLPHENYLALANYLAMINOLEVULINIC ACID; ACETYLPHENYLALANYLAMINOLEVULINIC ACID METHYL ESTER; AMINOLEVULINIC ACID; AMINOLEVULINIC ACID METHYL ESTER; PROTOPORPHYRIN; UNCLASSIFIED DRUG; ESTERASE; FLUORESCEIN; PEPTIDE; PHOTOSENSITIZING AGENT; PRODRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG STABILITY; EXPLANT; KERATINOCYTE; MOUSE; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; PHOTOTOXICITY; PRIORITY JOURNAL; SKIN; ANIMAL; CELL DEATH; CELL LINE; CHEMISTRY; ENDOCYTOSIS; FEMALE; FLUORESCENCE; IN VITRO STUDY; KINETICS; METABOLISM; PATHOLOGY; PHOTOCHEMOTHERAPY; SWINE;

AMINOLEVULINIC ACID; ANIMALS; CELL DEATH; CELL LINE; ENDOCYTOSIS; ESTERASES; FEMALE; FLUORESCEIN; FLUORESCENCE; KINETICS; MICE; PEPTIDES; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PRODRUGS; PROTOPORPHYRINS; SKIN; SWINE;

EID: 49849091384     PISSN: 15357163     EISSN: None     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-08-0092     Document Type: Article

References (39)

1. Bonnett R. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem Soc Rev 1995;24:19-33.
2. Milgrom L, MacRobert S. Light years ahead. Chem Br 1998;34:45-50.
3. Peng Q, Warloe T, Berg K, et al. 5-Aminolevulinic acid-based photodynamic therapy-clinical research and future challenges. Cancer 1997;79:2282-308.
4. Casas A, Batlle A. Rational design of 5-aminolevulinic acid derivatives aimed at improving photodynamic therapy. Curr Med Chem Anticancer Agents 2002;2:465-75.
5. Lopez RF, 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;56:77-94.
6. Lang K, Lehmann P, Bolsen K, Ruzicka T, Fritsch C. Aminolevulinic acid: pharmacological profile and clinical indication. Expert Opin Investig Drugs 2001;10:1139-56.
7. Pech O, Gossner L, May A, et al. Long-term results of photodynamic therapy with 5-aminolevulinic acid for superficial Barrett's cancer and high-grade intraepithelial neoplasia. Gastrointest Endosc 2005;62:24-30.
8. Kloek J, Beijersbergen vH. Prodrugs of 5-aminolevulinic acid for photodynamic therapy. Photochem Photobiol 1996;64:994-1000.
9. 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;57:1481-6.
10. Uehlinger P, Zellweger M, Wagnieres G, et al. 5-Aminolevulinic acid and its derivatives: physical chemical properties and protoporphyrin IX formation in cultured cells. J Photochem Photobiol B 2000;54:72-80.
11. Berger Y, Greppi A, Siri O, Neier R, Juillerat-Jeanneret L. Ethylene glycol and amino acid derivatives of 5-aminolevulinic acid as new photosensitizing precursors of protoporphyrin IX in cells. J Med Chem 2000;43:4738-46.
12. Battah SH, Chee CE, Nakanishi H, et al. Synthesis and biological studies of 5-aminolevulinic acid-containing dendrimers for photodynamic therapy. Bioconjug Chem 2001;12:980-8.
13. Di Venosa GM, Casas AG, Battah S, et al. Investigation of a novel dendritic derivative of 5-aminolaevulinic acid for photodynamic therapy. Int J Biochem Cell Biol 2006;38:82-91.
14. Battah S, O'Neill S, Edwards C, et al. Enhanced porphyrin accumulation using dendritic derivatives of 5-aminolaevulinic acid for photodynamic therapy: an in vitro study. Int J Biochem Cell Biol 2006;38:1382-92.
15. Casas A, Perotti C, Saccoliti M, et al. ALA and ALA hexyl ester in free and liposomal formulations for the photosensitisation of tumour organ cultures. Br J Cancer 2002;86:837-42.
16. Casas A, Batlle A. Aminolevulinic acid derivatives and liposome delivery as strategies for improving 5-aminolevulinic acid-mediated photodynamic therapy. Curr Med Chem 2006;13:1157-68.
17. Webber J, Kessel D, Fromm D. Side effects and photosensitization of human tissues after aminolevulinic acid. J Surg Res 1997;68:31-7.
18. Casas A, Batlle AMD, Butler AR, et al. Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. Br J Cancer 1999;80:1525-32.
19. Berger Y, Ingrassia L, Neier R, Juillerat-Jeanneret L. Evaluation of dipeptide-derivatives of 5-aminolevulinic acid as precursors for photosensitizers in photodynamic therapy. Bioorg Med Chem 2003;11:1343-51.
20. Rogers LMA, McGivern PG, Butler AR, MacRobert AJ, Eggleston IM. An efficient synthesis of 5-aminolaevulinic acid (ALA)-containing peptides for use in photodynamic therapy. Tetrahedron 2005;61:6951-8.
21. Kloek J, Akkermans W, van Henegouwen GMJB. Derivatives of 5-aminolevulinic acid for photodynamic therapy: enzymatic conversion into protoporphyrin. Photochem Photobiol 1998;67:150-4.
22. Gederaas OA, Holroyd A, Brown SB, et al. 5-Aminolaevulinic acid methyl ester transport on amino acid carriers in a human colon adenocarcinoma cell line. Photochem Photobiol 2001;73:164-9.
23. Washbrook R, Riley PA. Comparison of δ-aminolaevulinic acid and its methyl ester as an inducer of porphyrin synthesis in cultured cells. Br J Cancer 1997;75:1417-20.
24. Smith PK, Krohn RI, Hermanson GT, et al. Measurement of protein using bicinchoninic acid. Anal Biochem 1985;150:76-85.
25. Bech O, Phillips D, Moan J, MacRobert AJ. A hydroxypyridinone (CP94) enhances protoporphyrin IX formation in 5-aminolaevulinic acid treated cells. J Photochem Photobiol B 1997;41:136-44.
26. Doring F, Walter J, Will J, et al. δ-Aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications. J Clin Invest 1998;101:2761-7.
27. Langer S, Abels C, Botzlar A, et al. Active and higher intracellular uptake of 5-aminolevulinic acid in tumors may be inhibited by glycine. J Invest Dermatol 1999;112:723-8.
28. Rud E, Gederaas O, Hogset A, Berg K. 5-Aminolevulinic acid, but not 5-aminolevulinic acid esters, is transported into adenocarcinoma cells by system BETA transporters. Photochem Photobiol 2000;71:640-7.
29. Irie M, Terada T, Sawada K, Saito H, Inui K. Recognition and transport characteristics of nonpeptidic compounds by basolateral peptide transporter in Caco-2 cells. J Pharmacol Exp Ther 2001;298:711-7.
30. Novotny A, Xiang J, Stummer W, et al. Mechanisms of 5-aminolevulinic acid uptake at the choroid plexus. J Neurochem 2000;75:321-8.
31. Perotti C, Casas A, Fukuda H, Sacca P, Batlle A. ALA and ALA hexyl ester induction of porphyrins after their systemic administration to tumour bearing mice. Br J Cancer 2002;87:790-5.
32. Battah S, Balaratnam S, Casas A, et al. Macromolecular delivery of 5-aminolaevulinic acid for photodynamic therapy using dendrimer conjugates. Mol Cancer Ther 2007;6:876-85.
33. Jevprasesphant R, Penny J, Attwood D, D'Emanuele A. Transport of dendrimer nanocarriers through epithelial cells via the transcellular route. J Control Release 2004;97:259-67.
34. El Sayed M, Rhodes CA, Ginski M, Ghandehari H. Transport mechanism(s) of poly (amidoamine) dendrimers across Caco-2 cell monolayers. Int J Pharm 2003;265:151-7.
35. Rodriguez L, Batlle A, Di VG, et al. Mechanisms of 5-aminolevulinic acid ester uptake in mammalian cells. Br J Pharmacol 2006;147:825-33.
36. Scaloni A, Jones WM, Barra D, et al. Acylpeptide hydrolase: inhibitors and some active site residues of the human enzyme. J Biol Chem 1992;267:3811-8.
37. Schoenberger OL, Schwobel H, Ebert W. N-acetylalanine aminopeptidase activity in normal and tumour cells. J Clin Chem Clin Biochem 1986;24:375-8.
38. Scaloni A, Jones W, Pospischil M, et al. Deficiency of acylpeptide hydrolase in small-cell lung carcinoma cell lines. J Lab Clin Med 1992;120:546-52.
39. Juillerat-Jeanneret L, Lohm S, Hamou MF, Pinet F. Regulation of aminopeptidase A in human brain tumor vasculature: evidence for a role of transforming growth factor-β. Lab Invest 2000;80:973-80.