Photocytotoxicity of mTHPC (temoporfin) loaded polymeric micelles mediated by lipase catalyzed degradation

Pharmaceutical Research

Volumn 25, Issue 9, 2008, Pages 2065-2073

  Hofman, Jan Willem ^a   Carstens, Myrra G ^a,b   Van Zeeland, Femke ^a   Helwig, Conny ^a   Flesch, Frits M ^a   Hennink, Wim E ^a   Van Nostrum, Cornelus F ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Drug release; Enzymatic degradation; Meta tetra(hydroxyphenyl)chlorin (mTHPC); Photodynamic therapy (PDT); Polymeric micelles

Indexed keywords

EPSILON CAPROLACTONE; FOSLIP; FOSPEG; LACTONE DERIVATIVE; PHOTOFRIN; POLYMER; PORPHYRIN; TEMOPORFIN; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CYTOTOXICITY; DRUG RELEASE; DRUG STRUCTURE; ENZYMATIC DEGRADATION; HUMAN; HUMAN CELL; MICELLE; PHOTODYNAMIC THERAPY; PHOTOTOXICITY; POLYMERIZATION; PRIORITY JOURNAL;

CARCINOMA, SQUAMOUS CELL; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; DOSE-RESPONSE RELATIONSHIP, DRUG; HEAD AND NECK NEOPLASMS; HEXANOIC ACIDS; HUMANS; LACTONES; LIPASE; LIPOSOMES; MESOPORPHYRINS; MICELLES; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; POLYETHYLENE GLYCOLS; TECHNOLOGY, PHARMACEUTICAL;

EID: 49549089042     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-008-9590-7     Document Type: Article

References (48)

1. T. J. Dougherty C. J. Gomer B. W. Henderson G. Jori D. Kessel M. Korbelik J. Moan Q. Peng 1998 Photodynamic therapy J. Natl. Cancer Inst 90 889 905
2. D. E. Dolmans D. Fukumura R. K. Jain 2003 Photodynamic therapy for cancer Nat. Rev. Cancer 3 380 387
3. R. Bonnett 1995 Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy Chem. Soc. Rev 24 19 33
4. C. M. Moore T. R. Nathan W. R. Lees C. A. Mosse A. Freeman M. Emberton S. G. Bown 2006 Photodynamic therapy using meso tetra hydroxy phenyl chlorin (mTHPC) in early prostate cancer Lasers Surg. Med 38 356 363
5. C. Hopper A. Kubler H. Lewis I. B. Tan G. Putnam 2004 mTHPC-mediated photodynamic therapy for early oral squamous cell carcinoma Int. J. Cancer 111 138 146
6. J. S. Friedberg R. Mick J. Stevenson J. Metz T. Zhu J. Buyske D. H. Sterman H. I. Pass E. Glatstein S. M. Hahn 2003 A phase I study of Foscan-mediated photodynamic therapy and surgery in patients with mesothelioma Ann. Thorac. Surg 75 952 959
7. L. Ma J. Moan K. Berg 1994 Evaluation of a new photosensitizer, meso-tetra-hydroxyphenyl-chlorin, for use in photodynamic therapy: a comparison of its photobiological properties with those of two other photosensitizers Int. J. Cancer 57 883 888
8. T. Kiesslich J. Berlanda K. Plaetzer B. Krammer F. Berr 2007 Comparative characterization of the efficiency and cellular pharmacokinetics of Foscan- and Foslip-based photodynamic treatment in human biliary tract cancer cell lines Photochem. Photobiol. Sci 6 619 627
9. S. Sasnouski V. Zorin I. Khludeyev M. A. D'Hallewin F. Guillemin L. Bezdetnaya 2005 Investigation of FoscanÒ interactions with plasma proteins Biochim. Biophys. Acta 1725 394 402
10. Biolitec Pharma Ltd. Foscan, summary of product characteristics.
11. T. Krueger H. J. Altermatt D. Mettler B. Scholl L. Magnusson H. B. Ris 2003 Experimental photodynamic therapy for malignant pleural mesothelioma with pegylated mTHPC Lasers Surg. Med 32 61 68
12. T. Reuther A. C. Kubler U. Zillmann C. Flechtenmacher H. Sinn 2001 Comparison of the in vivo efficiency of photofrin II-, mTHPC-, mTHPC-PEG- and mTHPCnPEG-mediated PDT in a human xenografted head and neck carcinoma Lasers Surg. Med 29 314 322
13. M. F. Grahn A. Giger A. McGuinness M. L. de Jode J. C. M. Stewart H. B. Ris H. J. Altermatt N. S. Williams 1999 mTHPC polymer conjugates: the in vivo photodynamic activity of four candidate compounds Lasers Med. Sci 14 40 46
14. J. Buchholz B. Kaser-Hotz T. Khan C. Rohrer Bley K. Melzer R. A. Schwendener M. Roos H. Walt 2005 Optimizing photodynamic therapy: in vivo pharmacokinetics of liposomal meta-(tetrahydroxyphenyl)chlorin in feline squamous cell carcinoma Clin. Cancer Res 11 7538 7544
15. B. Pegaz E. Debefve J. P. Ballini G. Wagnieres S. Spaniol V. Albrecht D. V. Scheglmann N. E. Nifantiev H. van den Bergh Y. N. Konan-Kouakou 2006 Photothrombic activity of m-THPC-loaded liposomal formulations: pre-clinical assessment on chick chorioallantoic membrane model Eur. J. Pharm. Sci 28 134 140
16. V. P. Torchilin 2001 Structure and design of polymeric surfactant-based drug delivery systems J. Control. Release 73 137 172
17. G. Gaucher M. H. Dufresne V. P. Sant N. Kang D. Maysinger J. C. Leroux 2005 Block copolymer micelles: preparation, characterization and application in drug delivery J. Control. Release 109 169 188
18. G. S. Kwon T. Okano 1996 Polymeric micelles as new drug carriers Adv. Drug Deliv. Rev 21 107 116
19. M.-C. Jones J.-C. Leroux 1999 Polymeric micelles-a new generation of colloidal drug carriers Eur. J. Pharm. Biopharm 48 101 111
20. G. S. Kwon 2003 Polymeric micelles for delivery of poorly water-soluble compounds Crit. Rev. Ther. Drug Carrier Syst 20 357 403
21. V. P. Torchilin 2007 Micellar nanocarriers: pharmaceutical perspectives Pharm. Res 24 1 16
22. C. F. van Nostrum 2004 Polymeric micelles to deliver photosensitizers for photodynamic therapy Adv. Drug Deliv. Rev 56 9 16
23. N. Rapoport 2007 Physical stimuli-responsive polymeric micelles for anti-cancer drug delivery Prog. Polym. Sci 32 962 990
24. Z. Sezgin N. Yuksel T. Baykara 2006 Preparation and characterization of polymeric micelles for solubilization of poorly soluble anticancer drugs Eur. J. Pharm. Biopharm 64 261 268
25. J. Taillefer M. C. Jones N. Brasseur J. E. van Lier J. C. Leroux 2000 Preparation and characterization of pH-responsive polymeric micelles for the delivery of photosensitizing anticancer drugs J. Pharm. Sci 89 52 62
26. D. Le Garrec J. Taillefer J. E. Van Lier V. Lenaerts J.-C. Leroux 2002 Optimizing pH-responsive polymeric micelles for drug delivery in a cancer photodynamic therapy model J. Drug Target 10 429 437
27. C. J. F. Rijcken J.-W. Hofman F. van Zeeland C. F. van Nostrum W. E. Hennink 2007 Photosensitiser-loaded biodegradable polymeric micelles: preparation, characterisation and in vitro PDT efficacy J. Control. Release 124 144 153
28. Y. Kakizawa A. Harada K. Kataoka 1999 Environment-sensitive stabilization of core-shell structured polyion complex micelle by reversible cross-linking of the core through disulfide bond [13] J. Am. Chem. Soc 121 11247 11248
29. Y. Katayama T. Sonoda M. Maeda 2001 A polymer micelle responding to the protein kinase a signal Macromolecules 34 8569 8573
30. C. J. F. Rijcken O. Soga W. E. Hennink C. F. van Nostrum 2007 Triggered destabilisation of polymeric micelles and vesicles by changing polymers polarity: an attractive tool for drug delivery J. Control. Release 120 131 148
31. M. G. Carstens J. J. L. Bevernage C. F. van Nostrum M. J. van Steenbergen F. M. Flesch R. Verrijk L. G. J. de Leede D. J. A. Crommelin W. E. Hennink 2007 Small oligomeric micelles based on end group modified mPEG-oligocaprolactone with monodisperse hydrophobic blocks Macromolecules 40 116 122
32. V. Weissig K. R. Whiteman V. P. Torchilin 1998 Accumulation of protein-loaded long-circulating micelles and liposomes in subcutaneous Lewis lung carcinoma in mice Pharm. Res 15 1552 1556
33. A. Vonarbourg C. Passirani P. Saulnier J. P. Benoit 2006 Parameters influencing the stealthiness of colloidal drug delivery systems Biomaterials 27 4356 4373
34. X. Sun R. Rossin J. L. Turner M. L. Becker M. J. Joralemon M. J. Welch K. L. Wooley 2005 An assessment of the effects of shell cross-linked nanoparticle size, core composition, and surface PEGylation on in vivo biodistribution Biomacromolecules 6 2541 2554
35. J. Liu Y. Xiao C. Allen 2004 Polymer-drug compatibility: a guide to the development of delivery systems for the anticancer agent, ellipticine J. Pharm. Sci 93 132 143
36. M. Yokoyama P. Opanasopit T. Okano K. Kawano Y. Maitani 2004 Polymer design and incorporation methods for polymeric micelle carrier system containing water-insoluble anti-cancer agent camptothecin J. Drug Target 12 373 384
37. M. Watanabe K. Kawano M. Yokoyama P. Opanasopit T. Okano Y. Maitani 2006 Preparation of camptothecin-loaded polymeric micelles and evaluation of their incorporation and circulation stability Int. J. Pharm 308 183 189
38. M. L. Forrest A. Zhao C. Y. Won A. W. Malick G. S. Kwon 2006 Lipophilic prodrugs of Hsp90 inhibitor geldanamycin for nanoencapsulation in poly(ethylene glycol)-b-poly(epsilon-caprolactone) micelles J. Control. Release 116 139 149
39. A. Lavasanifar J. Samuel G. S. Kwon 2002 The effect of fatty acid substitution on the in vitro release of amphotericin B from micelles composed of poly(ethylene oxide)-block-poly(N-hexyl stearate-aspartamide) J. Control. Release 79 165 172
40. D. A. Scudiero R. H. Shoemaker K. D. Paull A. Monks S. Tierney T. H. Nofziger M. J. Currens D. Seniff M. R. Boyd 1988 Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines Cancer Res 48 4827 4833
41. M. G. Carstens C. F. van Nostrum R. Verrijk L. G. J. de Leede D. J. A. Crommelin W. E. Hennink 2008 A mechanistic study of the chemical and enzymatic degradation of PEG-oligo(e-caprolactone) micelles J. Pharm. Sci 97 506 518
42. P. K. Smith R. I. Krohn G. T. Hermanson 1985 Measurement of protein using bicinchoninic acid Anal. Biochem 150 76 85
43. M. G. Carstens P. H. J. L. F. de Jong C. F. Van Nostrum J. Kemmink R. Verrijk L. G. J. De Leede D. J. A. Crommelin W. E. Hennink 2008 The effect of core composition in biodegradable oligomeric micelles as taxane formulations Eur. J. Pharm. Biopharm 68 596 606
44. S. Hirohara M. Obata S. Ogata K. Kajiwara C. Ohtsuki M. Tanihara S. Yano 2006 Sugar-dependent aggregation of glycoconjugated chlorins and its effect on photocytotoxicity in HeLa cells J. Photochem. Photobiol., B Biol 84 56 63
45. K. Lang J. Mosinger D. M. Wagnerova 2004 Photophysical properties of porphyrinoid sensitizers non-covalently bound to host molecules; models for photodynamic therapy Coord. Chem. Rev 248 321 350
46. W. J. Lin L. W. Juang C. C. Lin 2003 Stability and release performance of a series of pegylated copolymeric micelles Pharm. Res 20 668 673
47. M. P. Thompson J. E. Koons E. T. H. Tan M. R. Grigor 1981 Modified lipoprotein lipase activities, rates of lipogenesis, and lipolysis as factors leading to lipid depletion in C57BL mice bearing the preputial gland tumor, ESR-586 Cancer Res 41 3228 3232
48. D. Cerne E. Melkic Z. Trost M. Sok J. Marc 2007 Lipoprotein lipase activity and gene expression in lung cancer and in adjacent noncancer lung tissue Exp. Lung Res 33 217 225