Evaluation of RGD-targeted albumin carriers for specific delivery of auristatin E to tumor blood vessels

Bioconjugate Chemistry

Volumn 17, Issue 6, 2006, Pages 1385-1394

  Temming, Kai ^a,b   Meyer, Damon L ^c   Zabinski, Roger ^c   Dijkers, Eli C F ^a   Poelstra, Klaas ^a   Molema, Grietje ^a   Kok, Robbert J ^a,d  

^a UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

^b Kreatech Biotechnology BV   (Netherlands)

^c SEATTLE GENETICS INC   (United States)

^d UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BLOOD VESSELS; CELL DEATH; CONTROLLED DRUG DELIVERY; DRUG INTERACTIONS; ENDOTHELIAL CELLS; ENZYME INHIBITION; PEPTIDES; POLYETHYLENE GLYCOLS; TARGETED DRUG DELIVERY;

ATTRACTIVE STRATEGIES; BLOOD SUPPLY; CELL-BE; CELL/B.E; CELL/BE; DRUG-TARGETING; ENDOTHELIAL-CELLS; HUMAN SERUM ALBUMINS; INTEGRINS; SOLID TUMORS;

TUMORS;

ALBUMIN CONJUGATE; ANTIMITOTIC AGENT; ARGINYLGLYCYLASPARTIC ACID; CARRIER PROTEIN; CYCLOPEPTIDE; HUMAN SERUM ALBUMIN; LYSOSOME ENZYME; MACROGOL; MONOMETHYL AURISTATIN E; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR;

ANGIOGENESIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; C26 TUMOR; CANCER INHIBITION; COLON CARCINOMA; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOTOXICITY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; DRUG TRANSPORT; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; INTERNALIZATION; INTRACELLULAR TRANSPORT; MALE; MOUSE; NONHUMAN; PROTEIN ANALYSIS; PROTEIN EXPRESSION; PROTEIN MODIFICATION; PROTEIN PROTEIN INTERACTION; PROTEIN TRANSPORT; SOLID TUMOR; TUMOR VASCULARIZATION;

EID: 33845200360     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060087z     Document Type: Article

References (34)

1. Ferrara, N., and Kerbel, R. S. (2005) Angiogenesis as a therapeutic target. Nature (London) 438, 967-974.
2. Pettit, G. R. (1997) The dolastatins. Fortschr. Chem. Org. Naturst. 70, 1-79.
3. Doronina, S. O., Toki, B. E., Torgov, M. Y., Mendelsohn, B. A., Cerveny, C. G., Chace, D. F., DeBlanc, R. L., Gearing, R. P., Bovee, T. D., Siegall, C. B., Francisco, J. A., Wahl, A. F., Meyer, D. L., and Senter, P. D. (2003) Development of potent monoclonal antibody auristatin conjugates for cancer therapy. Nat. Biotechnol. 21, 778-784.
4. Law, C. L., Cerveny, C. G., Gordon, K. A., Klussman, K., Mixan, B. J., Chace, D. F., Meyer, D. L., Doronina, S. O., Siegall, C. B., Francisco, J. A., Senter, P. D., and Wahl, A. F. (2004) Efficient elimination of B-lineage lymphomas by anti-CD20-auristatin conjugates. Clin. Cancer Res. 10, 7842-7851.
5. Afar, D. E., Bhaskar, V., Ibsen, E., Breinberg, D., Henshall, S. M., Kench, J. G., Drobnjak, M., Powers, R., Wong, M., Evangelista, F., O'Hara, C., Powers, D., DuBridge, R. B., Caras, I., Winter, R., Anderson, T., Solvason, N., Stricker, P. D., Cordon-Cardo, C., Scher, H. I., Grygiel, J. J., Sutherland, R. L., Murray, R., Ramakrishnan, V., and Law, D. A. (2004) Preclinical validation of anti-TMEFF2-auristatin E-conjugated antibodies in the treatment of prostate cancer. Mol. Cancer Ther. 3, 921-932.
6. Bhaskar, V., Law, D. A., Ibsen, E., Breinberg, D., Cass, K. M., DuBridge, R. B., Evangelista, F., Henshall, S. M., Hevezi, P., Miller, J. C., Pong, M., Powers, R., Senter, P., Stockett, D., Sutherland, R. L., von Freeden-Jeffry, U., Willhite, D., Murray, R., Afar, D. E., and Ramakrishnan, V. (2003) E-selectin up-regulation allows for targeted drug delivery in prostate cancer. Cancer Res. 63, 6387-6394.
7. Sanderson, R. J., Hering, M. A., James, S. F., Sun, M. M., Doronina, S. O., Siadak, A. W., Senter, P. D., and Wahl, A. F. (2005) In vivo drug-linker stability of an anti-CD30 dipeptide-linked auristatin immunoconjugate. Clin. Cancer Res. 11, 843-852.
8. Dubowchik, G. M., Mosure, K., Knipe, J. O., and Firestone, R. A. (1998) Cathepsin B-sensitive dipeptide prodrugs. 2. Models of anticancer drugs paclitaxel (Taxol), mitomycin C and doxorubicin. Bioorg. Med. Chem. Lett. 8, 3347-3352.
9. Dubowchik, G. M., Firestone, R. A., Padilla, L., Willner, D., Hofstead, S. J., Mosure, K., Knipe, J. O., Lasch, S. J., and Trail, P. A. (2002) Cathepsin B-labile dipeptide linkers for lysosomal release of doxorubicin from internalizing immunoconjugates: model studies of enzymatic drug release and antigen-specific in vitro anticancer activity. Bioconjugate Chem. 13, 855-869.
10. Pierschbacher, M. D., and Ruoslahti, E. (1984) Cell attachment activity of fibronectin can be duplicated by small synthetic fragments of the molecule. Nature (London) 309, 30-33.
11. Temming, K., Schiffelers, R. M., Molema, G., and Kok, R. J. (2005) RGD-based strategies for selective delivery of therapeutics and imaging agents to the tumour vasculature. Drug Resist. Updates 8, 381-402.
12. Kok, R. J., Schraa, A. J., Bos, E. J., Moorlag, H. E., Asgeirsdottir, S. A., Everts, M., Meijer, D. K., and Molema, G. (2002) Preparation and functional evaluation of RGD-modified proteins as alpha(v)-beta(3) integrin directed therapeutics. Bioconjugate Chem. 13, 128-135.
13. Schraa, A. J., Kok, R. J., Berendsen, A. D., Moorlag, H. E., Bos, E. J., Meijer, D. K., de Leij, L. F., and Molema, G. (2002) Endothelial cells internalize and degrade RGD-modified proteins developed for tumor vasculature targeting. J. Controlled Release 83, 241-251.
14. Schraa, A. J., Kok, R. J., Botter, S. M., Withoff, S., Meijer, D. K., de Leij, L. F., and Molema, G. (2004) RGD-modified anti-CD3 antibodies redirect cytolytic capacity of cytotoxic T lymphocytes toward alphavbeta3-expressing endothelial cells. Int. J. Cancer. 112, 279-285.
15. Kumar, C. C., Nie, H., Rogers, C. P., Malkowski, M., Maxwell, E., Catino, J. J., and Armstrong, L. (1997) Biochemical characterization of the binding of echistatin to integrin alphavbeta3 receptor. J. Pharmacol. Exp. Ther. 283, 843-853.
16. Hunter, W. M., and Greenwood, F. C. (1962) Preparation of iodine-131 labelled human growth hormone of high specific activity. Nature (London) 194, 495-496.
17. Verel, I., Visser, G. W., Boellaard, R., Stigter-van, Walsum, M., Snow, G. B., and van Dongen, G. A. (2003) 89Zr immuno-PET: comprehensive procedures for the production of 89Zr-labeled monoclonal antibodies. J. Nucl. Med. 44, 1271-1281.
18. Alley, M. C., Scudiero, D. A., Monks, A., Hursey, M. L., Czerwinski, M. J., Fine, D. L., Abbott, B. J., Mayo, J. G., Shoemaker, R. H., and Boyd, M. R. (1988) Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res. 48, 589-601.
19. Schraa, A. J., Kok, R. J., Moorlag, H. E., Bos, E. J., Proost, J. H., Meijer, D. K., de Leij, L. F., and Molema, G. (2002) Targeting of RGD-modified proteins to tumor vasculature: a pharmacokinetic and cellular distribution study. Int. J. Cancer. 102, 469-475.
20. Thumshirn, G., Hersel, U., Goodman, S. L., and Kessler, H. (2003) Multimeric cyclic RGD peptides as potential tools for tumor targeting: solid-phase peptide synthesis and chemoselective oxime ligation. Chemistry 9, 2717-2725.
21. Verel, I., Visser, G. W., Boerman, O. C., van Eerd, J. E., Finn, R., Boellaard, R., Vosjan, M. J., Stigter-van, Walsum, M., Snow, G. B., and van Dongen, G. A. (2003) Long-lived positron emitters zirconium-89 and iodine-124 for scouting of therapeutic radioimmunoconjugates with PET. Cancer Biother. Radiopharm. 18, 655-661.
22. Perk, L. R., Visser, G. W., Vosjan, M. J., Stigter-van, Walsum, M., Tijink, B. M., Leemans, C. R., and van Dongen, G. A. (2005) (89)Zr as a PET surrogate radioisotope for scouting biodistribution of the therapeutic radiometals (90)Y and (177)Lu in tumor-bearing nude mice after coupling to the internalizing antibody cetuximab. J. Nucl. Med. 46, 1898-1906.
23. Wu, A. M., and Senter, P. D. (2005) Arming antibodies: prospects and challenges for immunoconjugates. Nat. Biotechnol. 23, 1137-1146.
24. Wester, H. J., and Kessler, H. (2005) Molecular targeting with peptides or peptide-polymer conjugates: just a question of size? J. Nucl. Med. 46, 1940-1945.
25. Temming, K., Lacombe, M., Schaapveld, R. Q. J., Orfi, L., Keri, G., Poelstra, K., Molema, G., and Kok, R. J. (2006) Rational Design of RGD-albumin conjugates for targeted delivery of the VEGF-R kinase inhibitor PTK787 to angiogenic endothelium. ChemMedChem 11, Epub ahead of print, DOI: 10.1002/cmdc.200600201.
26. Temming, K., Lacombe, M., van der Hoeven, P., Prakash, J., Gonzalo, T., Dijkers, E. C. F., Orfi, L., Keri, G., Poelstra, K., Molema, G., and Kok, R. J. (2006) Delivery of the p38 MAPkinase inhibitor SB202190 to angiogenic endothelial cells: development of novel RGD-equipped and pegylated drug-albumin conjugates using platinum(II) based drug linker technology. Bioconjugate Chem. Epub ahead of print.
27. Toublan, F. J., Boppart, S., and Suslick, K. S. (2006) Tumor targeting by surface-modified protein microspheres. J. Am. Chem. Soc. 128, 3472-3473.
28. Kim, W. J., Yockman, J. W., Jeong, J. H., Christensen, L. V., Lee, M., Kim, Y. H., and Kim, S. W. (2006) Anti-angiogenic inhibition of tumor growth by systemic delivery of PEI-g-PEG-RGD/pCMV-sFlt-1 complexes in tumor-bearing mice. J. Controlled Release 114, 381-388.
29. Shukla, R., Thomas, T. P., Peters, J., Kotlyar, A., Myc, A., and Baker, J. R., Jr. (2005) Tumor angiogenic vasculature targeting with PAMAM dendrimer-RGD conjugates. Chem. Commun. (Camb.) 5739-5741.
30. Tse, K. F., Jeffers, M., Pollack, V. A., McCabe, D. A., Shadish, M. L., Khramtsov, N. V., Hackett, C. S., Shenoy, S. G., Kuang, B., Boldog, F. L., MacDougall, J. R., Rastelli, L., Hermann, J., Gallo, M., Gazit-Bornstein, G., Senter, P. D., Meyer, D. L., Lichenstein, H. S., and LaRochelle, W. J. (2006) CR011, a fully human monoclonal antibody-auristatin E conjugate, for the treatment of melanoma. Clin. Cancer Res. 12, 1373-1382.
31. Francisco, J. A., Cerveny, C. G., Meyer, D. L., Mixan, B. J., Klussman, K., Chace, D. F., Rejniak, S. X., Gordon, K. A., DeBlanc, R., Toki, B. E., Law, C. L., Doronina, S. O., Siegall, C. B., Senter, P. D., and Wahl, A. F. (2003) cAC10-vcMMAE, an anti-CD30-monomethyl auristatin E conjugate with potent and selective antitumor activity. Blood 102, 1458-1465.
32. Tanaka, T., Shiramoto, S., Miyashita, M., Fujishima, Y., and Kaneo, Y. (2004) Tumor targeting based on the effect of enhanced permeability and retention (EPR) and the mechanism of receptor-mediated endocytosis (RME). Int. J. Pharm. 277, 39-61.
33. Caliceti, P., and Veronese, F. M. (2003) Pharmacokinetic and biodistribution properties of poly(ethylene glycol)-protein conjugates. Adv. Drug Delivery Rev. 55, 1261-1277.
34. Mitra, A., Mulholland, J., Nan, A., McNeill, E., Ghandehari, H., and Line, B. R. (2005) Targeting tumor angiogenic vasculature using polymer-RGD conjugates. J. Controlled Release 102, 191-201.