Comparation of liposomal formulations of ALA Undecanoyl ester for its use in photodynamic therapy

Journal of Photochemistry and Photobiology B: Biology

Volumn 96, Issue 2, 2009, Pages 152-158

  Venosa, Gabriela Di ^a   Hermida, Laura ^b   Fukuda, Haydée ^a,c   Defain, María Victoria ^b   Rodriguez, Lorena ^a   Mamone, Leandro ^a   MacRobert, Alexander ^d   Casas, Adriana ^a   Batlle, Alcira ^a  

^a HOSPITAL DE CLÍNICAS JOSÉ DE SAN MARTÍN   (Argentina)

^b INSTITUTO NACIONAL DE TECNOLOGÍA INDUSTRIAL   (Argentina)

^c UNIVERSIDAD DE BUENOS AIRES   (Argentina)

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

Author keywords

ALA; ALA esters; Aminolevulinic acid; Liposomes; PDT; Photodynamic therapy

Indexed keywords

AMINOLEVULINIC ACID; AMINOLEVULINIC ACID UNDECANOYL ESTER; LIPOSOME; PHOSPHATIDIC ACID; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLGLYCEROL; POLYMER; PORPHYRIN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BREAST TUMOR; CELL MEMBRANE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; ENDOCYTOSIS; HYDROPHILICITY; LIPOPHILICITY; MALE; MEMBRANE BINDING; MOUSE; NONHUMAN; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL; SKIN TUMOR; TUMOR CELL;

ADMINISTRATION, TOPICAL; AMINOLEVULINIC ACID; ANIMALS; CELL LINE, TUMOR; ETHERS; INJECTIONS, SUBCUTANEOUS; LIPOSOMES; MALE; MICE; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHYRINS;

MUS;

EID: 67649670104     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2009.06.001     Document Type: Article

References (39)

1. Martin D. Porphyrins. In: Martin D., Mayes P., and Rodwel V. (Eds). Harpeŕs Review of Biochemistry (1983), Los Altos, CA, Lange Medical Publications 317-333
2. Van Steveninck J., Tijssen K., Boegheim J., Van Der Zee J., and Dubbleman T. Photodynamic generation of hydroxyl radicals by haematoporphyrin derivative and light. Photochem. Photobiol. 44 (1986) 711-716
3. Kennedy J., and Pottier R. Endogenous protoporphyrin IX, a clinically useful photosensitizer for photodynamic therapy. J. Photochem. Photobiol. B 14 (1992) 275-292
4. Marti A., Lange N., van den Bergh H., Sedmera D., Jichlinski P., and Kucera P. Optimisation of the formation and distribution of protoporphyrin IX in the urothelium: an in vitro approach. J. Urol. 162 (1999) 546-552
5. Lange N., Jichinlinski P., Zellweger M., Forrer M., Marti A., Guillou L., Kuchera P., Wagnieres G., and van den Bergh H. Photodetection of early human bladder cancer based on the fluorescence of 5-aminolevulinic acid hexylester-induced protoporhyrin IX: a pilot study. Br. J. Cancer 80 (1999) 185-193
6. Kloek J., Beijersbergen G., and Henegouwen v. Prodrugs of 5-aminolevulinic acid for photodynamic therapy. Photochem. Photobiol. 64 (1996) 994-1000
7. Kloek J., Akkermans W., Beijersbergen G., and Henegouwen v. Derivatives of 5-Aminolevulinic acid for Photodynamic therapy: enzymatic conversion into protoporphyrin. Photochem. Photobiol. 67 (1998) 150-154
8. Gaullier J., Berg K., Peng Q., Anholt H., Selbo P., Ma L., and Moan J. Use of 5-aminolevulinic acid esters to improve photodynamic therapy on cells in culture. Cancer Res. 57 (1997) 1481-1486
9. Berger Y., Greppi A., Siri O., Neier R., and Jullierat-Jeanneret L. Ethylene glycol and amino acid derivatives of 5-aminolevulinic acid as new photosensitizing precursors of Protoporphyrin IX. J. Med. Chem. 43 (2000) 4738-4746
10. Uehlinger P., Zellweger M., Wagnières G., and Juillerat-Jeanneret L. H. van den Bergh, N. Lange, 5-Aminolevulinic acid and its derivatives: physical chemical properties and protoporphyrin IX formation in cultured cells. J. Photochem. Photobiol. B Biol. 54 (2000) 72-80
11. Casas A., Fukuda H., and Di Venosa G. A battle photosensitisation and mechanism of cytotoxicity induced by the use of ALA derivatives in photodynamic therapy. Br. J. Cancer 85 (2001) 279-284
12. Casas A., and Batlle A. Aminolevulinic acid derivatives and liposome delivery as strategies for improving 5-aminolevulinic acid-mediated photodynamic therapy. Curr. Med. Chem. 13 (2006) 1157-1168
13. Di Venosa G., Batlle A., Fukuda H., Macrobert A., and Casas A. Distribution of 5-aminolevulinic acid derivatives and induced porphyrin kinetics in mice tissues. Cancer Chemother. Pharmacol. 58 (2006) 478-486
14. Rodriguez L., Batlle A., Di Venosa G., Battah S., Dobbin P., Macrobert A., and Casas A. Mechanisms of 5-aminolevulinic acid ester uptake in mammalian cells. Br. J. Pharmacol. 147 (2006) 823-825
15. Perotti C., Fukuda H., Di Venosa G., MacRobert A., and Batlle A. A Casas A Porphyrins synthesis from ALA derivatives for photodynamic therapy In vitro and in vivo studies. Br. J. Cancer 90 (2004) 1660-1665
16. Pass H. Photodynamic therapy in oncology: mechanisms and clinical use. J. Natl. Cancer Inst. 85 (1993) 443-456
17. Derycke A.S., and Witte P.A. Liposomes for photodynamic therapy. Adv. Drug Deliv. Rev. 56 (2004) 17-30
18. Konan Y.N., Gurny R., and Allemann E. State of the art in the delivery of photosensitizers for photodynamic therapy. J. Photochem. Photobiol. B. 66 (2002) 89-106
19. Reddi E. Role of delivery vehicles for photosensitizers in the photodynamic therapy of tumours. J. Photochem. Photobiol. B. 37 (1997) 189-195
20. Fukuda H., Paredes S., and Batlle A.M. Tumor-localizing properties of porphyrins. In vitro studies using the porphyrin precursor, aminolevulinic acid, in free and liposome encapsulated forms. Drug Des. Deliv. 5 (1989) 133-139
21. Casas A., Perotti C., Saccoliti M., Sacca P., Fukuda H., and Batlle A.M. ALA and ALA hexyl ester in free and liposomal formulations for the photosensitisation of tumour organ cultures. Br. J. Cancer 86 (2002) 837-842
22. Fukuda H., Paredes S., and Batlle A.M. Tumour-localizing properties of porphyrins. In vivo studies using free and liposome encapsulated aminolevulinic acid. Comp. Biochem. Physiol. B. 102 (1992) 433-436
23. Casas A., Fukuda H., Di Venosa G., and Batlle A.M. The influence of the vehicle on the synthesis of porphyrins after topical application of 5-aminolaevulinic acid Implications in cutaneous photodynamic sensitization. Br. J. Dermatol. 143 (2000) 564-572
24. Pierre M.B., Tedesco A.C., Marchetti J.M., and Bentley M.V. Stratum corneum lipids liposomes for the topical delivery of 5-aminolevulinic acid in photodynamic therapy of skin cancer: preparation and in vitro permeation study. BMC Dermatol. 1 (2001) 5
25. Kosobe T., Moriyama E., Tokuoka Y., and Kawashima N. Size and surface charge effect of 5-aminolevulinic Acid-containing liposomes on photodynamic therapy for cultivated cancer cells. Drug Dev. Ind. Pharm. 31 (2005) 623-629
26. Han I., Jun M., Kim S., Kim M., and Kim J. Expression and intensity of protoporphyrin IX induced by liposomal 5-aminolevulinic acid in rat pilosebaceous unit throughout hair cycle. Arch. Dermatol. Res. 297 (2005) 210-217
27. Di Venosa G., Hermida L., Batlle A., Fukuda H., Defain M.V., Mamone L., Rodriguez L., and Casas A. Characterisation of liposomes containing aminolevulinic acid and derived esters. J. Photochem. Photobiol. B Biol. 92 (2008) 1-9
28. Takeya H. Preparation of 5-aminolevulinic acid alkyl ethers as herbicides. Chem. Abs. 116 (1992) 189633 m
29. Fry D., White C., and Goldman D. Rapid separation of low molecular weight solutes from liposomes without dilution. Anal. Biochem. 90 (1978) 809-815
30. Stewart J. Colorimetric determination of phospholipids with ammonium ferrothiocyanate. Anal. Biochem. 10 (1959) 10-14
31. Werbajh S., Urtereger A.J., Puricelli L.I., de Lustig E.S., Bal de Kier Joffe E., and Kornblihtt A.R. Downregulation of fibronectin transcription in highly metastatic adenocarcinoma cells. FEBS Lett. 440 (1998) 277-281
32. Denizot F., and Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 89 (1986) 271-277
33. Workman P., Balmain A., and Hickman J. United Kingdom Co-ordinating Committee on Cancer Research (UKCCCR) guidelines for the welfare of animals in experimental neoplasia. Br. J. Cancer 77 (1998) 1-10 (second Edition)
34. Van den Akker J., Iani V., Star W., Sterenborg H., and Moan J. Topical application of 5-aminolevulinic acid hexyl ester and 5-aminolevulinic acid to normal nude mouse skin: differences in Protoporphyrin IX fluorescence kinetics and the role of the stratum corneum. Photochem. Photobiol. 72 (2000) 681-689
35. Casas A., Batlle A.M., Butler A.R., Robertson D., Brown E.H., MacRobert A., and Riley P.A. Comparative effect of ALA derivatives on protoporphyrin IX production in human and rat skin organ cultures. Br. J. Cancer 80 (1999) 1525-1532
36. Di Venosa G., Fukuda H., Perotti C., Batlle A., and Casas A. A simple method for separating ALA from ALA derivatives using ionic exchange chromatography. J. Photochem. Photobiol. B 75 (2004) 157-163
37. Mauzerall M., and Granick S. The occurrence and determination of 5-aminolevulinic acid and porphobilinogen in urine. J. Biol. Chem. 219 (1956) 435-437
38. El Maghraby G., Barry B., and Williams A. Liposomes and skin: from drug delivery to model membranes. Eur. J. Pharm. Sci. 34 (2008) 203-222
39. Har-el Y., and Kato Y. Intracellular delivery of nanocarriers for cancer therapy. Curr. Nanosci. 3 (2007) 329-338