A point mutation produced a class 3 aldehyde dehydrogenase with increased protective ability against the killing effect of cyclophosphamide

Biochemical Pharmacology

Volumn 76, Issue 5, 2008, Pages 690-696

  Ho, Kwok Ki ^a   Mukhopadhyay, Abhijit ^a   Li, Yi Feng ^a   Mukhopadhyay, Soma ^a   Weiner, Henry ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Aldehyde dehydrogenase; Aldophosphamide; Benzaldehyde; Cyclophosphamide; HeLa cell protection

Indexed keywords

ALDEHYDE DEHYDROGENASE; BENZALDEHYDE DERIVATIVE; CYCLOPHOSPHAMIDE; MAFOSFAMIDE; METHYL GROUP; THREONINE;

ARTICLE; CELL KILLING; CELL PROTECTION; ENZYME BINDING; ENZYME SUBSTRATE; GENETIC TRANSFECTION; HELA CELL; MOLECULAR CLONING; MOLECULAR MODEL; POINT MUTATION; PRIORITY JOURNAL;

ALDEHYDE DEHYDROGENASE; ALDEHYDES; ANTINEOPLASTIC AGENTS, ALKYLATING; BLOTTING, WESTERN; BONE MARROW CELLS; CLONING, MOLECULAR; CYCLOPHOSPHAMIDE; CYTOPROTECTION; HELA CELLS; HUMANS; PHOSPHORAMIDE MUSTARDS; POINT MUTATION; PRODRUGS; STOMACH; TRANSFECTION;

EID: 49149096532     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.06.018     Document Type: Article

References (44)

1. Fried W., Hussein S., Gregory S., Knospe W.H., and Trobaugh H. Effect of cyclophosphamide on the hematopoietic micro-environmental factors which influence hematopoietic stem cell proliferation. Cell Tissue Kinet 6 (1973) 155-163
2. Fried W., Kedo A., and Barone J. Effects of cyclophosphamide and of bisulphan on spleen-colony forming units and on hematopoietic stroma. Cancer Res 37 (1977) 1205-1209
3. Fried W., and Barone J. Residual marrow damage following therapy with cyclophosphamide. Exp Hematol 8 (1980) 610-614
4. Sladek N.E. Metabolism and pharmacokinetic behavior of cyclophosphamide and related oxazaphorines. In: Powes G. (Ed). Anticancer drugs: reactive metabolism and drug interactions (1994), Pergamon Press, UK 79-156
5. Hilton J. Deoxyribonucleic acid crosslinking by 4-hydroperoxycyclophosphamide in cyclophosphamide-sensitive and resistant L1210 cells. Biochem Pharmacol 33 (1984) 1867-1872
6. Sladek N.E. Metabolism of oxazaphosphorines. Pharmacol Ther 37 (1988) 301-355
7. Brookes P., and Lawley P.D. The reaction of mono- and di-functional alkylating agents with nucleic acids. Biochem J 80 (1961) 496-503
8. Dong Q., Barsky D., Colvin M.E., Melius C.F., Ludeman S.M., Moravek J.F., et al. A structural basis for a phosphoramide mustard-induced DNA interstrand cross-link at 5′-d(GAC). Proc Natl Acad Sci 92 (1995) 12170-12174
9. Friedman H.S., Colvin O.M., Kaufmann S.H., Ludeman S.M., Bullock N., Bigner D.D., et al. Cyclophosphamide resistance in medulloblastoma. Cancer Res 52 (1992) 5373-5378
10. Yoshida A., Dave V., Han H., and Scanlon K.J. Enhanced transcription of the cytosolic ALDH gene in cyclophosphamide resistant human carcinoma cells. Adv Exp Med Biol 328 (1993) 63-72
11. Sreerama L., and Sladek N.E. Identification of a methylcholanthrene-induced aldehyde dehydrogenase in a human breast adenocarcinoma cell line exhibiting oxazaphosphorine-specific acquired resistance. Cancer Res 54 (1994) 2176-2185
12. Rekha G.K., Sreerama L., and Sladek N.E. Intrinsic cellular resistance to oxazaphosphorines exhibited by a human colon carcinoma cell line expressing relatively large amounts of a class-3 dehydrogenase. Biochem Pharmacol 48 (1994) 1943-1952
13. Bunting K.D., and Townsend A.J. Protection by transfected rat or human class 3 aldehyde dehydrogenase against the cytotoxic effect of oxazaphosphorine alkylating agents in hamster V79 cell lines. J Biol Chem 271 (1996) 11891-11896
14. Sreerama L., and Sladek N.E. Identification of the class-3 aldehyde dehydrogenases present in human MCF-7/0 breast adenocarcinoma cells and normal human breasttissue. Biochem Pharmacol 48 (1994) 617-620
15. Moreb J., Schweder M., Suresh A., and Zucali J.R. Overexpression of the human aldehyde dehydrogenase class I results in increased resistance to 4-hydroperoxycyclophosphamide. Cancer Gene Ther 3 (1996) 24-30
16. Bunting K.D., and Townsend A.J. De novo expression of transfected human class 1 aldehyde dehydrogenase (ALDH) causes resistance to oxazaphosphorine anti-cancer alkylating agents in hamster V79 cell lines. J Biol Chem 271 (1996) 11884-11890
17. Sreerama L., and Sladek N.E. Identification and characterization of a novel class 3 aldehyde dehydrogenase overexpressed in a human breast adenocarcinoma cell line exhibiting oxazaphosphorine-specific acquired resistance. Biochem Pharmacol 45 (1993) 2487-2505
18. Vasiliou V., and Nebert D.W. Analysis and update of the human aldehyde dehydrogenase (ALDH) gene family. Hum Genomics 2 (2005) 138-143
19. Sladek N.E., Dockham P.A., and Lee M.O. Human and mouse hepatic aldehyde dehydrogenases important in the biotransformation of cyclophosphamide and the retinoids. Adv Exp Med Biol 284 (1990) 97-104
20. von Eitzen U., Meier-Tackmann D., Agarwal D.P., and Goedde H.W. Detoxification of cyclophosphamide by human aldehyde dehydrogenase isozymes. Cancer Lett 6 (1994) 45-49
21. Rekha G.K., and Sladek N.E. Inhibition of human class 3 aldehyde dehydrogenase, and sensitization of tumor cells that express significant amounts of this enzyme to oxazaphosphorines, by the naturally occurring compound gossypol. Adv Exp Med Biol 414 (1997) 133-146
22. Moreb J.S., Maccow C., Schweder M., and Hecomovich J. Expression of antisense RNA to aldehyde dehydrogenase class-1 sensitizes tumor cells to 4-hydroperoxycyclophosphamide in vitro. J Pharmacol Exp Ther 293 (2000) 390-396
23. Moreb J.S., Muhoczy D., Ostmark B., and Zucali J. RNAi-mediated knockdown of aldehyde dehydrogenase class-1A1 and class-3A1 is specific and reveals that each contributes equally to the resistance against 4 hydroperoxycyclophosphamide. Cancer Chemother Pharmacol 59 (2007) 127-136
24. Magni M., Shammah S., Schiro R., Mellado W., Dalla-Favera R., and Gianni A.M. Induction of cyclophosphamide-resistance by aldehyde-dehydrogenase gene transfer. Blood 87 (1996) 1097-1103
25. Moreb J., Schweder Suresh M.A., and Zucali J.R. Overexpression of the human aldehyde dehydrogenase class I results in increased resistance to 4-hydroperoxycyclophosphamide. Cancer Gene Ther 3 (1996) 24-30
26. Moreb J.S., Schweder M., Gray B., Zucali J., and Zori R. In vitro selection for K562 cells with higher retrovirally mediated copy number of aldehyde dehydrogenase class-1 and higher resistance to 4-hydroperoxycyclophosphamide. Hum Gene Ther 9 (1998) 611-619
27. Sorrentino B.P., and Nienhuis A.W. The hematopoietic system as a target for gene therapy. In: Friedmann T. (Ed). The development of gene therapy (1999), Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY 351-426
28. Giorgianni F., Bridson P.K., Sorrentino B.P., Pohl J., and Blakley R.L. Inactivation of aldophosphamide by human aldehyde dehydrogenase isozyme 3. Biochem Pharmacol 60 (2000) 325-338
29. Sladek N.E. Leukemic cell insensitivity to cyclophosphamide and other oxazaphosphorines mediated by aldehyde dehydrogenases. In: Andersson B., and Murray D. (Eds). Clinically revalent resistance in cancer chemotherapy (2002), Springer, Heidelberg 161-166
30. Dockham P.A., Lee M.O., and Sladek N.E. Identification of human liver aldehyde dehydrogenases that catalyze the oxidation of aldophosphamide and retinaldehyde. Biochem Pharmacol 43 (1992) 2453-2469
31. Mann C.J., and Weiner H. Differences in the roles of conserved glutamic acid residues in the active site of human class 3 and class 2 aldehyde dehydrogenases. Protein Sci 8 (1999) 1922-1929
32. Mukhopadhyay A., Ni L., and Weiner H. A co-translational model to explain the in vivo import of proteins into HeLa cell mitochondria. Biochem J 382 (2004) 385-392
33. Glover DM. DNA Cloning, vol. I. A Practical Approach. Oxford: IRL Press; 1985.
34. 2+ ions on the individual kinetic steps of human cytosolic and mitochondrial aldehyde dehydrogenases. Biochemistry 44 (2005) 8022-8029
35. Laemmli U.K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227 (1970) 680-685
36. Patel M., Sleep S.E.H., Lewis W.S., Spencer H.T., Mareya S.M., Sorrentino B.P., et al. Comparison of the protection of cells from antifolates by transduced human dihydrofolate reductase mutants. Hum Gene Ther 8 (1997) 2069-2077
37. Towbin H., Staehelin T., and Gordon J. Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc Natl Acad Sci 76 (1979) 4350-4354
38. Mierendorf R.C., Percy C., and Young R.A. Gene isolation screening lambda-gt11 libraries with antibodies. Methods Enzymol 152 (1987) 458-469
39. Combet C., Jambon M., Deleage G., and Geourjon C. Geno3D: automatic comparative molecular modelling of protein. Bioinformatics 18 (2002) 213-214
40. Schuttelkopf A.W., and van Aalten D.M. PRODRG: a tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr D Biol Crystallogr 60 (2004) 1355-1363
41. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., et al. UCSF Chimera-a visualization system for exploratory research and analysis. J Comput Chem 25 (2004) 1605-1612
42. Schmidt-Dannert C., and Arnold F.H. Directed evolution of industrial enzymes. Trends Biotechnol 17 (1999) 135-136
43. Ho K.K., Hurley T.D., and Weiner H. Selective alteration of the rate-limiting step in cytosolic aldehyde dehydrogenase through random mutagenesis. Biochemistry 45 (2007) 9445-9453
44. Wroczyński P., and Wierzchowski J. Aromatic aldehydes as fluorogenic indicators for human aldehyde dehydrogenases and oxidases: substrate and isozyme specificity. Analyst 125 (2000) 511-516