Novel bile acid derivatives (BANBs) with cytostatic activity obtained by conjugation of their side chain with nitrogenated bases

Biochemical Pharmacology

Volumn 73, Issue 9, 2007, Pages 1394-1404

  Vallejo, Marta ^a   Castro, Maria A ^a   Medarde, Manuel ^a   Macias, Rocio I R ^a   Romero, Marta R ^a   El Mir, Mohamad Y ^a   Monte, Maria J ^a   Briz, Oscar ^a   Serrano, Maria A ^a   Marin, Jose J G ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Cancer; Chemotherapy; Colon; Gut; Intestine; Liver; Resistance; Tumor

Indexed keywords

BILE ACID CONJUGATE; CISPLATIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER GRAFT; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CHO CELL; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LIVER CELL CARCINOMA; MALE; MOUSE; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANIMALS; ANTINEOPLASTIC AGENTS; BILE ACIDS AND SALTS; CARCINOMA, HEPATOCELLULAR; CELL SURVIVAL; DISEASE MODELS, ANIMAL; DRUG DELIVERY SYSTEMS; HUMANS; LIVER NEOPLASMS, EXPERIMENTAL; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; RATS; TUMOR CELLS, CULTURED; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 33947507423     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2006.12.027     Document Type: Article

References (36)

1. Marin J.J.G., Macias R.I.R., Monte M.J., El-Mir M.Y., and Serrano M.A. Liver targeting of cisplatin-derived cytostatic drugs (Bamets) by coupling to bile acids health. In: van Berge Henegouwen G.P., Keppler D., Leuschner U., Paumgartner G., and Stiehl A. (Eds). Biology of bile acids in health and disease (2001), Kluwer Academic Publishers, Dordrecht 271-277
2. Briz O., Serrano M.A., Rebollo N., Hagenbuch B., Meier P.J., Koepsell H., et al. Carriers involved in targeting the cytostatic bile acid-cisplatin derivatives cis-diammine-chloro-cholylglycinate-platinum(II) and cis-diammine-bisursodeoxycholate-platinum(II) toward liver cells. Mol Pharmacol 61 (2002) 853-860
3. Larena M.G., Martinez-Diez M.C., Monte M.J., Dominguez M.F., Pascual M.J., and Marin J.J.G. Liver organotropism and biotransformation of a novel platinum-ursodeoxycholate derivative, Bamet-UD2, with enhanced antitumour activity. J Drug Target 9 (2001) 185-200
4. Macias R.I.R., Monte M.J., El-Mir M.Y., Villanueva G.R., and Marin J.J.G. Transport and biotransformation of the new cytostatic complex cis-diammineplatinum(II)-chlorocholylglycinate (Bamet-R2) by the rat liver. J Lipid Res 39 (1998) 1792-1798
5. Dominguez M.F., Macias R.I.R., Izco-Basurko I., de la Fuente A., Pascual M.J., Criado J.M., et al. Low in vivo toxicity of a novel cisplatin-ursodeoxycholic derivative (Bamet-UD2) with enhanced cytostatic activity versus liver tumors. J Pharmacol Exp Ther 297 (2001) 1106-1112
6. Monte M.J., Ballestero M.R., Briz O., Perez M.J., and Marin J.J.G. Proapoptotic effect on normal and tumor intestinal cells of cytostatic drugs with enterohepatic organotropism. J Pharmacol Exp Ther 315 (2005) 24-35
7. Ballestero M.R., Monte M.J., Briz O., Jimenez F., Gonzalez-San Martin F., and Marin J.J.G. Expression of transporters potentially involved in the targeting of cytostatic bile acid derivatives to colon cancer and polyps. Biochem Pharmacol 72 (2006) 729-738
8. Canon J.L., Humblet Y., and Symann M. Resistance to cisplatin. How to deal with the problem?. Eur J Cancer 26 (1990) 1-3
9. Naito S., Koga H., Yokomizo A., Sakamoto N., Kotoh S., Nakashima M., et al. Molecular analysis of mechanisms regulating drug sensitivity and the development of new chemotherapy strategies for genitourinary carcinomas. World J Surg 24 (2000) 1183-1186
10. Briz O., Serrano M.A., Macias R.I.R., and Marin J.J.G. Overcoming cisplatin resistance in vitro by a free and liposome-encapsulated bile acid derivative: BAMET-R2. Int J Cancer 88 (2000) 287-292
11. Briz O., Macias R.I.R., Vallejo M., Silva A., Serrano M.A., and Marin J.J.G. Usefulness of liposome-encapsulated cytostatic bile acid derivatives to circumvent chemotherapy resistance of enterohepatic tumors. Mol Pharmacol 63 (2003) 742-750
12. Cui Y., Konig J., Nies A.T., Pfannschmidt M., Hergt M., Franke W.W., et al. Detection of the human organic anion transporters SLC21A6 (OATP2) and SLC21A8 (OATP8) in liver and hepatocellular carcinoma. Lab Invest 83 (2003) 527-538
13. Zollner G., Wagner M., Fickert P., Silbert D., Fuchsbichler A., Zatloukal K., et al. Hepatobiliary transporter expression in human hepatocellular carcinoma. Liver Int 25 (2005) 367-379
14. Kullak-Ublick G.A., Glasa J., Böker C., Oswald M., Grützner U., Hagenbuch B., et al. Chlorambucil-taurocholate is transported by bile acid carriers expressed in human hepatocellular carcinomas. Gastroenterology 113 (1997) 1295-1305
15. Monte M.J., Dominguez S., Palomero M.F., Macias R.I.R., and Marin J.J.G. Further evidence of the usefulness of bile acids as molecules for shuttling cytostatic drugs toward liver tumors. J Hepatol 31 (1999) 521-528
16. Zhang J.G., and Lindup W.E. Cisplatin nephrotoxicity. Decreases in mitochondrial protein, sulphydryl concentration and calcium uptake by mitochondria from rat renal cortical slices. Biochem Pharmacol 47 (1994) 1127-1135
17. Ellison R.R., Carey R.W., and Holland J.F. Continuous infusions of arabinosyl cytosine in patients with neoplastic disease. Clin Pharmacol Ther 8 (1967) 800-809
18. Galmarini C.M., Mackey J.R., and Dumontet C. Nucleoside analogues and nucleobases in cancer treatment. Lancet Oncol 3 (2002) 415-424
19. Damaraju V.L., Damaraju S., Young J.D., Baldwin S.A., Mackey J., Sawyer M.B., et al. Nucleoside anticancer drugs: the role of nucleoside transporters in resistance to cancer chemotherapy. Oncogene 22 (2003) 7524-7536
20. Alter P., Herzum M., Soufi M., Schaefer J.R., and Maisch B. Cardiotoxicity of 5-fluorouracil. Cardiovasc Hematol Agents Med Chem 4 (2006) 1-5
21. Tserng K.Y., Hachey D.L., and Klein P.D. An improved procedure for the synthesis of glycine and taurine conjugates of bile acids. J Lipid Res 18 (1977) 404-407
22. Huijghebaert S.M., and Hofmann A.F. Pancreatic carboxypeptidase hydrolysis of bile acid-amino conjugates: selective resistance of glycine and taurine amidates. Gastroenterology 90 (1986) 306-315
23. Bellau B., and Malek G.A. New convenient reagent for peptide synthesis. J Am Chem Soc 90 (1968) 1651-1652
24. Dyer E., Reitz J.M., and Farris Jr. R.E. Carbamates derived from aminopurines. J Med Chem 55 (1963) 289-291
25. Chheda G.E., and Hong C.I. Synthesis of naturally occurring 6-ureidopurines and their nucleosides. J Med Chem 14 (1971) 748-753
26. Ray P. Complex compounds of biguanides and guanylureas with metallic elements. Chem Rev 61 (1961) 313-359
27. Meier P.J., and Stieger B. Bile salt transporters. Annu Rev Physiol 64 (2002) 635-661
28. Marin J.J.G., Romero M.R., Vallejo M., and Monte M.J. Targeting of cytostatic bile acid derivatives toward tumours of the enterohepatic circuit. Cancer Ther 3 (2005) 57-64
29. Ho N.F.H. Utilizing bile acid carrier mechanisms to enhance liver and small intestine absorption. Ann N Y Acad Sci 507 (1987) 315-329
30. Kramer W., Wess G., Schubert G., Bickel M., Gribig F., Gutjahr U., et al. Liver-specific drug targeting by coupling to bile acids. J Biol Chem 267 (1992) 18598-18604
31. Marin J.J.G., Herrera M.C., Palomero M.F., Macias R.I.R., Monte M.J., El-Mir M.Y., et al. Rat liver transport and biotransformation of a cytostatic complex of bis-cholylglycinate and platinum(II). J Hepatol 28 (1998) 417-425
32. Wess G., Kramer W., and Han X.B. Synthesis and biological activity of bile acid-derived HMG-CoA reductase inhibitors. The role of 21 methyl in recognition of HMG-CoA reductase and the ileal bile acid transport system. J Med Chem 37 (1994) 3240-3246
33. Chung H., Jung J.Y., Cho S.D., Hong K.A., Kim H.J., Shin D.H., et al. The antitumor effect of LJ-529, a novel agonist to A3 adenosine receptor, in both estrogen receptor-positive and estrogen receptor-negative human breast cancers. Mol Cancer Ther 5 (2006) 685-692
34. Jarnagin W.R., Ruo L., Little S.A., Klimstra D., D'Angelica M., DeMatteo R.P., et al. Patterns of initial disease recurrence after resection of gallbladder carcinoma and hilar cholangiocarcinoma: implications for adjuvant therapeutic strategies. Cancer 98 (2003) 1689-1700
35. O'Connell J.B., Maggard M.A., Liu J.H., Etzioni D.A., Livingston E.H., and Ko C.Y. Rates of colon and rectal cancers are increasing in young adults. Am Surg 69 (2003) 866-872
36. Si M.S., Amersi F., Golish S.R., Ortiz J.A., Zaky J., Finklestein D., et al. Prevalence of metastases in hepatocellular carcinoma: risk factors and impact on survival. Am Surg 69 (2003) 879-885