Urokinase-plasminogen-activator sensitive polymeric photosensitizer prodrugs: Design, synthesis and in vitro evaluation

Journal of Drug Delivery Science and Technology

Volumn 19, Issue 1, 2009, Pages 15-24

  Gabriel, D ^a   Zuluaga, M F ^a   Martinez, M N ^a   Campo, M A ^a   Lange, Norbert ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Photodynamic therapy; Protease sensitive prodrugs; Urokinase plasminogen activator

Indexed keywords

PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG; UROKINASE PLASMINOGEN ACTIVATOR POLYMERIC PHOTOSENSITIZER PRODRUG;

ARTICLE; CELL ACTIVATION; CELL CULTURE; CELL FATE; CELL LINE; CELL SCREENING; CELL SURVIVAL; CELL TRANSPORT; CELLULAR DISTRIBUTION; DARK TOXICITY; DRUG ACTIVATION; DRUG DESIGN; DRUG SYNTHESIS; ENERGY TRANSFER; ENZYME ACTIVATION; ENZYME DEGRADATION; ENZYME LOCALIZATION; HUMAN; HUMAN CELL; IN VITRO STUDY; INTERMETHOD COMPARISON; MALE; PHOTOCHEMICAL QUENCHING; PHOTODYNAMIC THERAPY; PHOTOTOXICITY; SUBSTITUTION LINE; UPREGULATION;

EID: 59849128473     PISSN: 17732247     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1773-2247(09)50002-0     Document Type: Article

References (51)

1. Ringsdorf H. - Structure and properties of pharmacologically active polymers. - Journal of Polymer Science, Polymer Symposia, 51, 135-153, 2004.
2. Duncan R. - Polymer conjugates as anticancer nanomedicines. - Nat. Rev Cancer, 6, 688-701, 2006.
3. Vicent M.J., Duncan R. - Polymer conjugates: nanosized medicines for treating cancer. - Trends Biotechnol., 24, 39-47, 2006.
4. Maeda H., Wu J., Sawa T., Matsumura Y., Hori K. - Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. - J. Control Release, 65, 271-284, 2000.
5. Vasey P.A., Kaye S.B., Morrison R., Twelves C., Wilson P., Duncan R., Thomson A.H., Murray L.S., Hilditch T.E., Murray T., Burtles S., Fraier D., Frigerio E., Cassidy J. - Phase I clinical and pharmacokinetic study of PK1 [N-(2-hydroxypropyl)methacrylamide copolymer doxorubicin]: first member of a new class of chemotherapeutic agents-drug-polymer conjugates. Cancer Research Campaign Phase I/II Committee. - Clin. Cancer Res., 5, 83-94, 1999.
6. Dolmans D.E., Fukumura D., Jain R.K. - Photodynamic therapy for cancer. - Nat. Rev. Cancer, 3, 380-387, 2003.
7. Hopper C. - Photodynamic therapy: a clinical reality in the treatment of cancer. - Lancet Oncol., 1, 212-219, 2000.
8. Campo M.A., Gabriel D., Kucera P., Gurny R., Lange N. - Polymeric photosensitizer prodrugs for photodynamic therapy. - Photochem Photobiol., 83, 958-965, 2007.
9. Choi Y., Weissleder R., Tung C.H. - Selective antitumor effect of novel protease-mediated photodynamic agent. - Cancer Res., 66, 7225-7229, 2006.
10. Choi Y., Weissleder R., Tung C.H. - Protease-mediated phototoxicity of a polylysine-chlorin(E6) conjugate. - ChemMedChem., 1, 698-701, 2006.
11. Gabriel D., Campo M.A., Gurny R., Lange N. - Tailoring protease-sensitive photodynamic agents to specific disease-associated enzymes. - Bioconjug. Chem, 18, 1070-1077, 2007.
12. Shiah J.-G., Konak C., Spikes J.D., Kopecek J. - Solution and Photoproperties of N-(2-Hydroxypropyl)methacrylamide Copolymer-Meso-chlorin e6 Conjugates. - Journal of Physical Chemistry B, 101, 6803-6809, 2006.
13. van Kempen L.C., de Visser K.E., Coussens L.M. - Inflammation, proteases and cancer. - Eur. J. Cancer, 42, 728-734, 2006.
14. Berdowska I. - Cysteine proteases as disease markers. - Clin. Chim. Acta, 342, 41-69, 2004.
15. Andreasen P.A., Kjoller L., Christensen L., Duffy M.J. - The urokinase-type plasminogen activator system in cancer metastasis: a review. - Int. J. Cancer, 72, 1-22, 1997.
16. Han B., Nakamura M., Mori I., Nakamura Y., Kakudo K. - Urokinase-type plasminogen activator system and breast cancer (Review). - Oncol. Rep., 14, 105-112, 2005.
17. Harbeck N., Kates R.E., Gauger K., Willems A., Kiechle M., Magdolen V., Schmitt M. - Urokinase-type plasminogen activator (uPA) and its inhibitor PAI-I: novel tumor-derived factors with a high prognostic and predictive impact in breast cancer. - Thromb. Haemost., 91, 450-456, 2004.
18. Kim T.D., Song K.S., Li G., Choi H., Park H.D., Lim K., Hwang B.D., Yoon W.H. - Activity and expression of urokinase-type plasminogen activator and matrix metalloproteinases in human colorectal cancer. - BMC Cancer, 6, 211, 2006.
19. Cozzi P.J., Wang J., Delprado W., Madigan M.C., Fairy S., Russell P.J., Li Y. - Evaluation of urokinase plasminogen activator and its receptor in different grades of human prostate cancer. - Hum. Pathol., 37, 1442-1451, 2006.
20. van der Burg M.E., Henzen-Logmans S.C., Berns E.M., van Putten W.L., Klijn J.G., Foekens J.A. - Expression of urokinase-type plasminogen activator (uPA) and its inhibitor PAI-1 in benign, borderline, malignant primary and metastatic ovarian tumors. - Int. J. Cancer, 69, 475-479, 1996.
21. Kuhn W., Schmalteldt B., Reuning U., Pache L., Berger U., Ulm K., Harbeck N., Spathe K., Dettmar P., Hofler H., Janicke F., Schmitt M., Graeff H. - Prognostic significance of urokinase (uPA) and its inhibitor PAI-1 for survival in advanced ovarian carcinoma stage FIGO IIIc. - Br. J. Cancer, 79, 1746-1751, 1999.
22. Konecny G., Untch M., Pihan A., Kimmig R., Gropp M., Stieber P., Hepp H., Slamon D., Pegram M. - Association of urokinase-type plasminogen activator and its inhibitor with disease progression and prognosis in ovarian cancer. - Clin. Cancer Res., 7, 1743-1749, 2001.
23. Daneri-Navarro A., Macias-Lopez G., Oceguera-Villanueva A., Toro-Arreola S., Bravo-Cuellar A., Perez-Montfort R., Orbach-Arbouys S. - Urokinase-type plasminogen activator and plasminogen activator inhibitors (PAI-1 and PAI-2) in extracts of invasive cervical carcinoma and precursor lesions. - Eur. J. Cancer, 34, 566-569, 1998.
24. Daneri-Navarro A., Toro-Arreola S., Bravo-Cuellar A., Cabrera N., Orbach-Arbouys S., Perez-Montfort R. - Proteolytic activity in extracts of invasive cervical carcinoma and precursor lesions. - Biomed. Pharmacother., 49, 304-310, 1995.
25. Stutchbury T.K., Al Ejeh F., Stillfried G.E., Croucher D.R., Andrews J., Irving D., Links M., Ranson M. - Preclinical evaluation of 213Bi-labeled plasminogen activator inhibitor type 2 in an orthotopic murine xenogenic model of human breast carcinoma. - Mol. Cancer Ther., 6, 203-212, 2007.
26. Schweinitz A., Steinmetzer T., Banke I.J., Arlt M.J., Sturzebecher A., Schuster O., Geissler A., Giersiefen H., Zeslawska E., Jacob U., Kruger A., Sturzebecher J. - Design of novel and selective inhibitors of urokinase-type plasminogen activator with improved pharmacokinetic properties for use as antimetastatic agents. - J. Biol. Chem, 279, 33613-33622, 2004.
27. Chung D.E., Kratz F. - Development of a novel albumin-binding prodrug that is cleaved by urokinase-type-plasminogen activator (uPA). - Bioorg. Med. Chem Lett., 16, 5157-5163, 2006.
28. Graeser R., Chung D.E., Esser N., Moor S., Schachtele C., Unger C., Kratz F. - Synthesis and biological evaluation of an albumin-binding prodrug of doxorubicin that is cleaved by prostate-specific antigen (PSA) in a PSA-positive orthotopic prostate carcinoma model (LNCaP). - Int. J. Cancer, 122, 1145-1154, 2008.
29. Gerspach J., Nemeth J., Munkel S., Wajant H., Pfizenmaier K. - Target-selective activation of a TNF prodrug by urokinase-type plasminogen activator (uPA) mediated proteolytic processing at the cell surface. - Cancer Immunol. Immunother., 55, 1590-1600, 2006.
30. Abi-Habib R.J., Singh R., Liu S., Bugge T.H., Leppla S.H., Frankel A.E. - A urokinase-activated recombinant anthrax toxin is selectively cytotoxic to many human tumor cell types. - Mol. Cancer Thor., 5, 2556-2562, 2006.
31. Janssen S., Jakobsen C.M., Rosen D.M., Ricklis R.M., Reineke U., Christensen S.B., Lilja H., Denmeade S.R. - Screening a combinatorial peptide library to develop a human glandular kallikrein 2-activated prodrug as targeted therapy for prostate cancer. - Mol. Cancer Ther., 3, 1439-1450, 2004.
32. Janssen S., Rosen D.M., Ricklis R.M., Dionne C.A., Lilja H., Christensen S.B., Isaacs J.T., Denmeade S.R. - Pharmacokinetics, biodistribution, and antitumor efficacy of a human glandular kallikrein 2 (hK2)-activated thapsigargin prodrug. - Prostate, 66, 358-368, 2006.
33. Denmeade S.R., Jakobsen C.M., Janssen S., Khan S.R., Garrett E.S., Lilja H., Christensen S.B., Isaacs J.T. - Prostate-specific antigen-activated thapsigargin prodrug as targeted therapy for prostate cancer. - J. Natl. Cancer Inst., 95, 990-1000, 2003.
34. Chau Y., Tan F.E., Langer R. - Synthesis and characterization of dextran-peptide-methotrexate conjugates for tumor targeting via mediation by matrix metalloproteinase II and matrix metalloproteinase IX. - Bioconjug. Chem, 15, 931-941, 2004.
35. Chau Y., Padera R.F., Dang N.M., Langer R. - Antitumor efficacy of a novel polymer-peptide-drug conjugate in human tumor xenograft models. - Int. J. Cancer, 118, 1519-1526, 2006.
36. Devy L., de Groot F.M., Blacher S., Hajitou A., Beusker PH., Scheeren H.W., Foidart J.M., Noel A. - Plasmin-activated doxorubicin prodrugs containing a spacer reduce tumor growth and angiogenesis without systemic toxicity. - FASEB J., 18, 565-567, 2004.
37. de Groot FM., Broxterman H.J., Adams H.P., van Vliet A., Tesser G.I., Elderkamp Y.W., Schraa A.J., Kok R.J., Molema G., Pinedo H.M., Scheeren H.W. - Design, synthesis, and biological evaluation of a dual tumor-specific motive containing integrin-targeted plasmin-cleavable doxorubicin prodrug. - Mol. Cancer Ther., 1, 901-911, 2002.
38. de Groot F.M., Busscher G.F., Aben R.W., Scheeren H.W. - Novel 20-carbonate linked prodrugs of camptothecin and 9-amino-camptothecin designed for activation by tumor-associated plasmin. - Bioorg. Med. Chem Lett., 12, 2371-2376, 2002.
39. Rizzi S.C., Hubbell J.A. - Recombinant protein-co-PEG networks as cell-adhesive and proteolytically degradable hydrogel matrixes. Part I: Developmentand physicochemical characteristics. - Biomacromolecules., 6, 1226-1238, 2005.
40. Rizzi S.C., Ehrbar M., Halstenberg S., Raeber G.P., Schmoekel H.G., Hagenmuller H., Muller R., Weber F.E., Hubbell J.A. - Recombinant protein-co-PEG networks as cell-adhesive and proteolytically degradable hydrogel matrixes. Part II: biofunctional characteristics. - Biomacromolecules., 7, 3019-3029, 2006.
41. Ke S.H., Coombs G.S., Tachias K., Navre M., Corey D.R., Madison E.L. - Distinguishing the specificities of closely related proteases. Role of P3 in substrate and inhibitor discrimination between tissue-type plasminogen activator and urokinase. - J. Biol. Chem, 272, 16603-16609, 1997.
42. Coombs G.S., Bergstrom R.C., Madison E.L., Corey D.R. - Directing sequence-specific proteolysis to new targets. The influence of loop size and target sequence on selective proteolysis by tissue-type plasminogen activator and urokinase-type plasminogen activator. - J. Biol. Chem, 273, 4323-4328, 1998.
43. Putnam D., Gentry C.A., Pack D.W., Langer R. - Polymer-based gene delivery with low cytotoxicity by a unique balance of side-chain termini. - Proc. Natl. Acad. Sci. USA, 98, 1200-1205, 2001.
44. Mosinger J., Mosinger B. - Photodynamic sensitizers assay: rapid and sensitive iodometric measurement. - Experientia, 51, 106-109, 1995.
45. Hackbarth S., Horneffer V., Hillenkamp F., Wiehe A., Roeder B. - Photophysical properties of pheophorbide a-substituted diaminobutane poly-propylene-imine dendrimer. - Chemical Physics, 269, 339-346, 2001.
46. Hackbarth S., Ermilov E.A., Roder B. - Interaction of Pheophorbide a molecules covalently linked to DAB dendrimers. - Optics Communications, 248, 295-306, 2005.
47. Spraggon G., Phillips C., Nowak U.K., Ponting C.P., Saunders D., Dobson C.M., Stuart D.I., Jones E.Y. -The crystal structure of the catalytic domain of human urokinase-type plasminogen activator. - Structure., 3, 681-691, 1995.
48. Hong S., Leroueil P.R., Janus E.K., Peters J.L., Kober M.M., Islam M.T., Orr B.G., Baker J.R. Jr., Banaszak Holl M.M. - Interaction of polycationic polymers with supported lipid bilayers and cells: nanoscale hole formation and enhanced membrane permeability. - Bioconjug. Chem, 17, 728-734, 2006.
49. Friedrich B., Jung K., Lein M., Turk I., Rudolph B., Hampel G., Schnorr D., Loening S.A. - Cathepsins B, H, L and cysteine protease inhibitors in malignant prostate cell lines, primary cultured prostatic cells and prostatic tissue. - Eur. J. Cancer, 35, 138-144, 1999.
50. Kobayashi H., Moniwa N., Sugimura M., Shinohara H., Ohi H., Terao T. - Effects of membrane-associated cathelpsin B on the activation of receptor-bound prourokinase and subsequent invasion of reconstituted basement membranes. - Biochim. Biophys. Acta, 1178, 55-62, 1993.
51. Basbaum C.B., Werb Z. - Focalized proteolysis: spatial and temporal regulation of extracellular matrix degradation at the cell surface. - Curr. Opin. Cell Biol., 8, 731-738, 1996.