Doxorubicin-formaldehyde conjugates targeting αvβ 3 integrin

Molecular Cancer Therapeutics

Volumn 3, Issue 12, 2004, Pages 1593-1604

  Burkhart, David J ^a   Kalet, Brian T ^a   Coleman, Michael P ^a   Post, Glen C ^a   Koch, Tad H ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CILENGITIDE; DEXTRO PHENYLALANINE; DOXORUBICIN; DOXSALIFORM; FORMALDEHYDE; FUNCTIONAL GROUP; HYDROXYLAMINE; PHENYLALANINE DERIVATIVE; SALICYLAMIDE; UNCLASSIFIED DRUG; VITRONECTIN; VITRONECTIN RECEPTOR; WATER;

ARTICLE; BINDING AFFINITY; BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; CELL ADHESION; CELL ASSAY; CELL MEMBRANE; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; PROTEIN TARGETING; SOLUBILITY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ANTINEOPLASTIC COMBINED CHEMOTHERAPY PROTOCOLS; BREAST NEOPLASMS; CELL ADHESION; CELL MEMBRANE; CELL PROLIFERATION; DOXORUBICIN; DRUG DESIGN; FEMALE; FORMALDEHYDE; HUMANS; INHIBITORY CONCENTRATION 50; INTEGRIN ALPHAVBETA3; PEPTIDE FRAGMENTS; PRODRUGS; RECEPTORS, VITRONECTIN; TUMOR CELLS, CULTURED; VITRONECTIN;

EID: 12344253955     PISSN: 15357163     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. Sweatman TW, Israel M. Anthracyclines. In: Teicher BA, editor. Cancer therapeutics, experimental and clinical agents. Totowa (NJ): Humana Press; 1997. p. 113-35.
2. Wang AHJ, Gao YG, Liaw YC, Li YK. Formaldehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray diffraction studies. Biochemistry 1991;30:3812-5.
3. Cullinane C, van Rosmalen A, Phillips DR. Does Adriamycin induce interstrand cross-links in DNA? Biochemistry 1994;33:4632-8.
4. Taatjes DJ, Gaudiano G, Resing K, Koch TH. A redox pathway leading to the alkylation of DNA by the anthracycline, anti-tumor drugs, Adriamycin and daunomycin. J Med Chem 1997;40:1276-86.
5. Zeman SM, Phillips DR, Crothers DM. Characterization of covalent Adriamycin-DNA adducts. Proc Natl Aced Sci U S A 1998;95:11561-5.
6. Kato S, Burke PJ, Fenick DJ, Taatjes DJ, Bierbaum VM, Koch TH. Mass spectrometric measurement of formaldehyde generated in breast cancer cells upon treatment with anthracycline antitumor drugs. Chem Res Toxicol 2000;13:509-16.
7. Taatjes DJ, Gaudiano G, Koch TH. Production of formaldehyde and DNA-Adriamycin or -daunomycin adducts, initiated through redox chemistry of DTT/iron, xanthine oxidase/NADH/iron, or glutathione/iron. Chem Res Toxicol 1997;10:953-61.
8. Fenick DJ, Taatjes DJ, Koch TH. Doxoform and Daunoform: anthracycline-formaldehyde conjugates toxic to resistant tumor cells. J Med Chem 1997;40:2452-61.
9. Cogan PS, Fowler CR, Post GC, Koch TH. Doxsaliform: a novel N-Mannich base prodrug of a doxorubicin formaldehyde conjugate. Lett Drug Design Dis 2004;1:247-55.
10. Sinha BK, Mimnaugh EG. Free radicals and anticancer drug resistance: oxygen free radicals in the mechanisms of drug cytotoxicity and resistance by certain tumors. Free Radic Biol Med 1990;8:567-81.
11. Lampidis TJ, Kolonias D, Podona T, et al. Circumvention of P-GP MDR as a function of anthracycline lipophilicity and charge. Biochemistry 1997;36:2679-85.
12. Cogan PS, Koch TH. Rational design and synthesis of androgen receptor targeted non-steroidal anti-androgen ligands for the tumor specific delivery of a doxorubicin-formaldehyde conjugate. J Med Chem 2003;46:5258-70.
13. Burke PJ, Koch TH. Design, synthesis, and biological evaluation of doxorubicin-formaldehyde conjugates targeted to breast cancer cells. J Med Chem 2004;47:1193-206.
14. Hellmann K, Franks CR. Reduction of doxorubicin-induced cardiotoxicity by dexrazoxane. Contrib Oncol 1995;48:40-7.
15. Albelda SM, Mette SA, Elder DE, et al. Integrin distribution in malignant melanoma: association of the β 3 subunit with tumor progression. Cancer Res 1990;50:6757-64.
16. Pignatelli M, Cardillo MR, Hanby A, Stamp GW. Integrins and their accessory adhesion molecules in mammary carcinomas: loss of polarization in poorly differentiated tumors. Hum Pathol 1992;23: 1159-66.
17. Gringas MC, Roussel E, Bruner JM, Branch CD, Moser RP. Comparison of cell adhesion molecule expression between glioblastoma multiforme and autologous normal brain tissue. J Neuroimmunol 1995; 57:143-53.
18. 3 integrin and intracellular adhesion molecule-1 expression in cutaneous malignant melanoma lesions. Cancer Res 1997;57:1554-60.
19. Altieri DC. Regulation of leukocyte-endothelium interaction by fibrinogen. Thromb Haemost 1999;82:781-6.
20. 3 on vascular cells controls recognition of prothrombin. J Cell Biol 1998; 143:2081-92.
21. 3 regulates cell adhesion and migration to bone sialoprotein. Exp Cell Res 2000;254:299-308.
22. Humphries MJ. Insights into integrin-ligand binding and activation from the first crystal structure. Arthritis Res 2002;4 Suppl 3:S69-78.
23. Felding-Habermann B, O'Toole TE, Smith JF, et al. Integrin activation controls metastasis in human breast cancer. Proc Natl Aced Sci U S A 2001; 98:1853-8.
24. 3 to support tumor cell arrest under dynamic flow conditions. J Biol Chem 2002;277:21930-8.
25. Liekens S, De Clercq E, Neyts J. Angiogenesis regulators and clinical applications. Biochem Pharmacol 2001;61:253-70.
26. 3 integrin antagonists. J Med Chem 1999;42:3033-40.
27. 3 integrin inhibitor cyclo(-RGDfV-) and its retro-inverso peptide. J Am Chem Soc 1997;119:1328-35.
28. Arap W, Oasqualini R, Ruoslahti E. Cancer treatment by targeted drug delivery to tumor vasculature in a mouse model. Science 1998;279: 377-80.
29. Wonhee S, Han S-O, Yu L, Kim SW. An angiogenic, endothelial-cell-targeted polymeric gene carrier. Mol Ther 2002;6:664-72.
30. Hart SL, Knight AM, Harbottle RP, et al. Cell binding and internalization by filamentous phage displaying a cyclic Arg-Gly-Asp-containing peptide. J Biol Chem 1994;269:12468-74.
31. de Groot FMH, Broxterman HJ, Adams HPHM, et al. Design, synthesis, and biological evaluation of a dual tumor-specific motive containing integrin-targeted plasmin-cleavable doxorubicin prodrug. Mol Cancer Ther 2002;1:901-11.
32. Devy L, de Groot FHM, Blacher S, et al. Plasmin-activated doxorubicin prodrug containing a spacer reduce tumor growth and angiogenesis without systemic toxicity. FASEB J 2004;18:565-7.
33. 3 integrin binding peptides in a nude mouse model. Cancer Res 2002;62:6146-51.
34. Calileau R, Olive M, Cruciger QV. Long-term human breast carcinoma cell lines of metastatic origin: preliminary characterization. In Vitro 1978;14:911-5.
35. Durand RE, Olive PL. Flow cytometry studies of intracellular Adriamycin in single cells in vitro. Cancer Res 1981;41:3489-94.
36. Taatjes DJ, Koch TH. Growth inhibition, nuclear uptake, and retention of anthracycline-formaldehyde conjugates in prostate cancer cells relative to clinical anthracyclines. Anticancer Res 1999;19:1201-8.
37. Assa-Munt N, Jia X, Laakkonen P, Ruoslahti E. Solution structures and integrin binding activities of an RGD peptide with two isomers. Biochemistry 2001;40:2373-8.
38. 3 in complex with an Arg-Gly-Asp ligand. Science 2002;296:151-5.
39. Bartsch JE, Staren ED, Appert HE. Adhesion and migration of extracellular matrix-stimulated breast cancer. J Surg Res 2003;110:287-94.
40. de Groot FMH, Broxterman HJ, Adams HPHM, et al. Design, synthesis, and biological evaluation of a dual tumor-specific motive containing integrin-targeted plasmin-cleavable doxorubicin prodrug. Mol Cancer Therap 2002;1:901-11.
41. de Groot FMH, de Bart ACW, Verheijen JH, Scheeren HW. Synthesis and biological evaluation of novel prodrugs of anthracyclines for selective activation by the tumor-associated protease plasmin. J Med Chem 1999;42:5277-83.
42. Czerwinski G, Tarasova NI, Michejda CJ. Cytotoxic agents directed to peptide hormone receptors: defining the requirements for a successful drug. Proc Natl Aced Sci U S A 1998;95:11520-5.
43. Skladanowski A, Konopa J. Adriamycin and daunomycin induce programmed cell death (apoptosis) in tumour cells. Biochem Pharmacol 1993;46:375-82.
44. Skladanowski A, Konopa J. Relevance of interstrand DNA cross-linking induced by anthracyclines for their biological activity. Biochem Pharmacol 1994;47:2279-87.
45. Burke PJ, Koch TH. Doxorubicin-formaldehyde conjugate, Doxoform: induction of apoptosis relative to doxorubicin. Anticancer Res 2001;21: 2753-60.