In vitro and in vivo evaluation of a paclitaxel conjugate with the divalent peptide E-[c(RGDfK)2] that targets integrin αvβ3

International Journal of Pharmaceutics

Volumn 368, Issue 1-2, 2009, Pages 89-97

  Ryppa, Claudia ^a   Mann Steinberg, Hagit ^b   Biniossek, Martin L ^c   Satchi Fainaro, Ronit ^b   Kratz, Felix ^a  

^a TUMOR BIOLOGY CENTER   (Germany)

^b TEL AVIV UNIVERSITY   (Israel)

^c Zentrum fur Biochemie und Molekulare Zellforschung   (Germany)

Author keywords

Integrins; Paclitaxel; Prodrugs; RGD peptides; Vascular targeting

Indexed keywords

ARGINYLGLYCYLASPARTIC ACID; CYCLOPEPTIDE; HYDROXYL GROUP; PACLITAXEL; PACLITAXEL DERIVATIVE; VITRONECTIN RECEPTOR;

AMINO ACID SEQUENCE; ANGIOGENESIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CAPILLARY; CELL ADHESION; CELL MIGRATION; CELL PROLIFERATION; CHEMICAL BOND; CONJUGATE; CONTROLLED STUDY; DRUG EFFICACY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG TARGETING; ENDOCYTOSIS; ENDOTHELIUM CELL; FEMALE; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; HYDROPHOBICITY; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PRIORITY JOURNAL; TUMOR XENOGRAFT;

AMINO ACID SEQUENCE; ANIMALS; CELL LINE, TUMOR; CELL PROLIFERATION; ENDOTHELIAL CELLS; FEMALE; HUMANS; INTEGRIN ALPHAVBETA3; MICE; OLIGOPEPTIDES; PACLITAXEL; PRODRUGS;

EID: 58949095768     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2008.09.055     Document Type: Article

References (22)

1. Aumailley M., Gurrath M., Müller G., Calvete J., Timpl R., and Kessler H. Arg-Gly-Asp constrained within cyclic pentapeptides. Strong and selective inhibitors of cell adhesion to vitronectin and laminin fragment P1. FEBS Lett. 291 (1991) 50-54
2. Buerkle M.A., Pahernik S.A., Sutter A., Jonczyk A., Messmer K., and Dellian M. Inhibition of the alpha-nu integrins with a cyclic RGD peptide impairs angiogenesis, growth and metastasis of solid tumours in vivo. Br. J. Cancer 86 (2002) 788-795
3. 3 integrin. Mol. Cancer Ther. 3 (2004) 1593-1604
4. Cao Q., Li Z.B., Chen K., Wu Z., He L., Neamati N., and Chen X. Evaluation of biodistribution and anti-tumor effect of a dimeric RGD peptide-paclitaxel conjugate in mice with breast cancer. Eur. J. Nucl. Med. Mol. Imag. (2008) EPub
5. Chen X., Plasencia C., Hou Y., and Neamati N. Synthesis and biological evaluation of dimeric RGD peptide-paclitaxel conjugate as a model for integrin-targeted drug delivery. J. Med. Chem. 48 (2005) 1098-1106
6. Dechantsreiter M.A., Planker E., Matha B., Lohof E., Holzemann G., Jonczyk A., Goodman S.L., and Kessler H. N-Methylated cyclic RGD peptides as highly active and selective alpha(V)beta(3) integrin antagonists. J. Med. Chem. 42 (1999) 3033-3040
7. Deutsch H.M., Glinski J.A., Hernandez M., Haugwitz R.D., Narayanan V.L., Suffness M., and Zalkow L.H. Synthesis of congeners and prodrugs. 3.1 Water-soluble prodrugs of taxol with potent antitumor activity. J. Med. Chem. 32 (1989) 788-792
8. Dosio F., Brusa P., Crosasso P., Arpicco S., and Cattel L. Preparation, characterization and properties in vitro and in vivo of a paclitaxel-albumin conjugate. J. Control. Release 47 (1997) 293-304
9. Friess H., Langrehr J.M., Oettle H., Raedle J., Niedergethmann M., Dittrich C., Hossfeld D.K., Stöger H., Neyns B., Herzog P., Piedbois P., Dobrowolski F., Scheithauer W., Hawkins R., Katz F., Balcke P., Vermorken J., van Belle S., Davidson N., Esteve A.A., Castellano D., Kleeff J., Tempia-Caliera A.A., Kovar A., and Nippgen J. A randomized multi-center phase II trial of the angiogenesis inhibitor Cilengitide (EMD 121974) and gemcitabine compared with gemcitabine alone in advanced unresectable pancreatic cancer. BMC Cancer 6 (2006) 285
10. 3 antagonists. J. Am. Chem. Soc. 118 (1996) 7461-7472
11. Janssen M., Oyen W.J., Massuger L.F., Frielink C., Dijkgraaf I., Edwards D.S., Radjopadhye M., Corstens F.H., and Boerman O.C. Comparison of a monomeric and dimeric radiolabeled RGD-peptide for tumor targeting. Cancer Biother. Radiopharm. 17 (2002) 641-646
12. 3 integrin binding peptides in a nude mouse model. Cancer Res. 62 (2002) 6146-6151
13. Janssen M., Frielink C., Dijkgraaf I., Oyen W., Edwards D.S., Liu S., Rajopadhye M., Massuger L., Corstens F., and Boerman O. Improved tumor targeting of radiolabeled RGD peptides using rapid dose fractionation. Cancer Biother. Radiopharm. 19 (2004) 399-404
14. Kratz F., Müller I.A., Ryppa C., and Warnecke A. Prodrug strategies in anticancer chemotherapy. ChemMedChem 3 (2008) 20-53
15. Kussmann M., Lässing U., Stürmer C.A., Przybylski M., and Roepstorff P. Matrix-assisted laser desorption/ionization mass spectrometric peptide mapping of the neural cell adhesion protein neurolin purified by sodium dodecyl sulfate polyacrylamide gel electrophoresis or acidic precipitation. J. Mass Spectrom. 32 (1997) 483-493
16. Luo Y., and Prestwich G.D. Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate. Bioconjugate Chem. 10 (1999) 755-763
17. MacDonald T.J., Taga T., Shimada H., Tabrizi P., Zlokovic B.V., Cheresh D.A., and Laug W.E. Preferential susceptibility of brain tumors to the antiangiogenic effects of an alpha(v) integrin antagonist. Neurosurgery 48 (2001) 151-157
18. Nabors L.B., Mikkelsen T., Rosenfeld S.S., Hochberg F., Akella N.S., Fisher J.D., Cloud G.A., Zhang Y., Carson K., Wittemer S.M., Colevas A.D., and Grossman S.A. Phase I and correlative biology study of cilengitide in patients with recurrent malignant glioma. J. Clin. Oncol. 25 (2007) 1651-1657
19. 1 integrins. J. Biol. Chem. 269 (1994) 20233-20238
20. Temming K., Schiffelers R.M., Molema G., and Kok R.J. RGD-based strategies for selective delivery of therapeutics and imaging agents to the tumour vasculature. Drug Resist. Update 8 (2005) 381-402
21. Tucker G.C. Integrins: molecular targets in cancer therapy. Curr. Oncol. Rep. 8 (2006) 96-103
22. Wu A.W., and Senter P.D. Arming antibodies. Nat. Biotechnol. 23 (2005) 1137-1146