α,β-Acetylenic amino thiolester inhibitors of aldehyde dehydrogenases 1&3: Suppressors of apoptogenic aldehyde oxidation and activators of apoptosis

Current Medicinal Chemistry

Volumn 20, Issue 4, 2013, Pages 527-533

  Fournet, G ^c   Martin, G ^b   Quash, G ^a,b  

^a INSERM   (France)

^b Advanced BioDesign   (France)

^c UNIVERSITÉ LYON 1   (France)

Author keywords

Aldehyde dehydrogenases; ALDH inhibitors; Apoptogenic aldehydes; Bcl2; Cancer

Indexed keywords

4 HYDROXYNONENAL; ALDEHYDE; ALDEHYDE DEHYDROGENASE; CARBOXYLIC ACID; ENZYME INHIBITOR; ESTER DERIVATIVE; GLUTATHIONE; METHIONAL; NUCLEOPHILE; PROTEIN BCL 2; REACTIVE OXYGEN METABOLITE; THIOESTER; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER CELL; CELL CULTURE; CELL LINE; CELL PROTECTION; DECARBOXYLATION; DRUG CYTOTOXICITY; ELECTRON TRANSPORT; ENZYME ACTIVITY; EPITHELIUM CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPID PEROXIDATION; LYMPHOID CELL; MITOCHONDRION; NONHUMAN; NUCLEOPHILICITY; OXIDATION; SUBSTITUTION REACTION;

EID: 84878002115     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986713804910148     Document Type: Article

References (81)

1. Weiner, H. Aldehyde dehydrogenase Enzymology of Carbonyl Metabolism: aldehyde dehydrogenase and aldo/keto reductase. Progress in Clinical and Biological Research, 1982, 114, 1-9.
2. Yoshida, A.; Rzhetsky, A.; Hsu, L.C.; Chang, C. Human aldehyde dehydrogenase gene family. Eur. J. Biochem., 1998, 251, 549-557. (Pubitemid 28108946)
3. Sladek, N.E. Human aldehyde dehydrogenases: potential pathological, pharmacological and toxicological impact. J. Biochem. Mol. Toxicol., 2003, 17, 7-23. (Pubitemid 36416554)
4. Vasilou, V.; Pappa, A.; Estey, T. Role of human aldehyde dehydrogenases in endobiotic and xenobiotic metabolism. Drug Metab. Rev., 2004, 36, 279-299. (Pubitemid 38807313)
5. Lindahl, R. Aldehyde dehydrogenases and their role in carcinogenesis. Critical Rev. Biochem. Mol. Biol., 1992, 27, 283-335.
6. Ferro, M.; Bassi, A.M.; Penco, S.; Muzio, G.; Canuto, R.A. Susceptibility of hepatoma cells to lipid peroxidation and adaptation of ALDH3C activity to iron-induced oxidative stress. Advances in Exp. Med. Biol., 1999, 463, 171-179.
7. Storms, R.W.; Trujillo, A.; Springer, J.B.; Shah, I.; Colvin, O.M.; Ludeman, S.M.; Smith, C. Isolation of primitive human hematopoietic progenitors on the basis of aldehyde dehydrogenase activity. Proc Natl Acad Sci USA, 1999, 96, 9118-9123. (Pubitemid 29374717)
8. Hess, D.A.; Meyerrose, T.; Wirthlin, I.; Craft, T.; Herrbrich, P.E.; Creer, M.H.; Nolta, J.A. Functional characterization of highly purified human hematopoietic repopulating cells according to aldehyde dehydrogenase activity. Blood, 2004, 104, 1648-1655. (Pubitemid 39202270)
9. Al-Hajj, M.; Wicha, M.S.; Benito-Hernandez, A.; Morrison, S.J.; Clarke, M.F. Prospective identification of tumorigenic breast cancer cells. Proc. Natl. Acad. Sci. USA, 2003, 100, 3983-3988. (Pubitemid 36418143)
10. Singh, S.K.; Hawkin, C.; Clarke, I.D.; Squire, J.; Bayani, J.; Hide, T.; Henkelman, R.M.; Cusimano, M.D.; Dirks P.B. Identification of human brain tumour initiating cells. Nature, 2004, 432, 396-401. (Pubitemid 39551674)
11. Reya, T.; Morrison, S.J.; Clarke, M.F.; Weissman, I.L. Stem cells, cancer, and cancer stem cells. Nature, 2001, 414, 105-111. (Pubitemid 33041634)
12. Ma, I.; Allan A.L. The role of human aldehyde dehydrogenase in normal and cancer stem cells. Stem Cell Rev. and Rep., 2011, 7, 292-306.
13. Moreb, J.S. Aldehyde dehydrogenase as a marker for stem cells. Curr. Stem Cell Res. Ther., 2008, 3, 237-246
14. Ginestier, C.; Hur, M.H.; Charafe-Jauffret, E.; Monville, F.; Dutcher, J.; Brown, M.; Jacquemier, J.; Viens, P.; Kleer, C.; Liu, S.; Shott, A.; Hayes, D.; Birnbaum, D.; Wicha, M.S.; Dontu, G. ALDH1 is a marker of normal and malignant human mammary stem cells and a predictor of poor clinical outcome. Cell Stem Cell, 2007, 1, 555-567. (Pubitemid 350056407)
15. Summerfield, F.W.; Tappel, A.L. Cross-linking of DNA in liver and testes of rats fed 1,3-propanediol. Chem. Biol. Interact., 1984, 50, 87-96. (Pubitemid 14124175)
16. Kerr, J.F.; Wyllie, A.H.; Currie, A.R. Apoptosis: a basic biological phenomenon with wide-ranging implications in tissues kinetics. Br. J. Cancer, 1972, 26, 239-257.
17. Portt, L.; Norman,G.; Clapp,C.; Greenwood, M.; Greenwood, M. Antiapoptosis and cell survival: A review. Biochim. Biophys. Acta, 2011, 1813, 238-259.
18. Orrenius,S.; Nicotera, P.; Zhivotovsky,B. Cell death mechanisms and their implications in toxicology. Tox. Sci., 2011, 119(1), 3-19.
19. Quash, G.; Roch, A.M.; Chantepie, J.; Michal, Y.; Fournet, G.; Dumontet, C. Methional derived from 4-methylthio-2-oxobutanoate is a cellular mediator of apoptosis in BAF3 lymphoid cells. Biochem. J., 1995, 305, 1017-1025.
20. Roch, A.M.; Panaye, G.; Michal, Y.; Quash, G.; Methional a cellular metabolite induces apoptosis preferentially in G2/M-synchronized BAF3 murine lymphoid cells. Cytometry, 1998, 31, 10-19. (Pubitemid 28050058)
21. Tang, B.; Kadariya, Y.; Murphy, M.E.; Kruger, W.D. The methionine salvage pathway compound 4-methylthio-2-oxobutanoate causes apoptosis independent of down-regulation of ornithine decarboxylase. Biochem. Pharmacol., 2006, 72, 806-815 (Pubitemid 44301049)
22. Li, L.; Hamilton, R.F.; Kirichenko, A.; Holian, A. 4-Hydroxy nonenalinduced cell death in murine alveolar macrophages. Toxicol. Appl. Pharmacol., 1996, 139, 135-143. (Pubitemid 26247071)
23. Backlund, P.S.; Chang, C.P.; Smith, R.A. Identification of 2-keto-4-methylthiobutyrate as an intermediate compound in methionine synthesis from 5'-methylthioadenosine. J. Biol. Chem., 1982, 257, 4196-4202. (Pubitemid 12080141)
24. Costeas, P.A.; Chinsky, J.M. Glucocorticoid regulation of branched-chain -ketoacid dehydrogenase E2 subunit gene expression. Biochem. J., 2000, 347, 449-457. (Pubitemid 30229392)
25. Eden, A.; Benvenisty, N. Involvement of branched-chain amino acid aminotransferase (Bcat1/Eca39) in apoptosis. FEBS Lett., 1999, 457, 255-261. (Pubitemid 29401939)
26. Jones, S.M.; Yeaman, S.J. Oxidative decarboxylation of 4-methylthio-2-oxobutyrate by branched-chain 2-oxo acid dehydrogenase complex. Biochem. J., 1986, 237, 621-623. (Pubitemid 16043726)
27. Scislowski, P.; Hokland, B.; Davis-van Thienen, W.; Bremer, J.; Davis E.J.; Methionine metabolism by rat muscle and other tissues. Occurrence of a new carnitine intermediate. Biochem. J., 1987, 247, 35-40.
28. Quash, G.; Fournet G. Methionine-derived metabolites in apoptosis: therapeutic opportunities for inhibitors of their metabolism in chemoresistant cancer cells. Curr. Med. Chem., 2009, 16, 3686-3700.
29. Summerfield, F.W.; Tappel, A.L. Determination of malondialdehye-DNA cross-links by fluorescence and incorporation of tritium. Anal. Biochem., 1981, 111, 77-82.
30. Nair, V.; Cooper, C.S.; Vietti, D.E.; Turner, G.A. The chemistry of lipid peroxidation metabolites: crosslinking reactions of malondiaaldehyde. Lipids, 1986, 21, 6-10. (Pubitemid 16167930)
31. Roch, A.M.; Quash, G.; Michal, Y.; Chantepie, J.; Chantegrel, B.; Deshayes, C.; Doutheau, A.; Marvel, J. Altered methional homoeostasis is associated with decreased apoptosis in BAF3 bcl2 murine lymphoid cells. Biochem. J., 1996, 313, 973-981. (Pubitemid 26050836)
32. Quash, G.; Fournet, G.; Chantepie, J.; Ardiet, C.; Ardail, D.; Michal, Y.; Goré, J.; Reichert, U. Novel competitive irreversible inhibitors of aldehyde dehydrogenase (ALDH1): restoration of chemosensitivity of L1210 cells overexpressing ALDH1 and induction of apoptosis in BAF3 cells overexpressing bcl2. Biochem. Pharmacol., 2002, 64, 1279-1292. (Pubitemid 35264613)
33. Quash, G.; Fournet, G.; Raffin, C.; Chantepie, J.; Michal, Y.; Goré, J.; Reichert, U. A thioester analogue of an amino acetylenic aldehyde is a suicide inhibitor of aldehyde dehydrogenase and an inducer of apoptosis in mouse lymphoid cells overexpressing the bcl2 gene. Adv. Exp. Med. Biol., 1999, 7, 97-106.
34. Esterbauer, H.; Schaur, R.J.; Zollner, H. Chemistry and biochemistry of 4-hydroxynonenal malondialdehyde and related aldehydes. J. Biol. Chem., 1991, 11, 81-128. (Pubitemid 121003917)
35. Benedetti, A.; Comporti, H.; Esterbauer, H.; Identificationof 4-hydroxynonenal as a cytotoxic product originating from the peroxidation of liver microsomal lipids. Biochim. Biophys. Acta, 1980, 620, 281-296. (Pubitemid 11216247)
36. Murphy, M. How mitochondria produce reactive oxygen species. Biochem. J., 2009, 417, 1-13.
37. Seyfried, T.N.; Shelton, L.M. Cancer as a metabolic disease. Nutr. Metab. (Lond), 2010, 7, 7, doi:10.1186/1743-7075-7-7.
38. Muzio, G.; Salvo, R.A.; Trombetta, A.; Autelli, R.; Maggiora, M.; Terreno, M.; Dianzani, M.U.; Canuto, R.A. Dose-dependent inhibition of cell proliferation induced by lipid peroxidation products in rat hepatoma cells after enrichment with arachidonic acid. Lipids, 1999, 34, 705-711. (Pubitemid 29381839)
39. Kruman, I.; Bruce-Keller, A.J.; Bredesen, D.; Waeg, G.; Mattson, M.P. Evidence that 4-hydroxynonenal mediates oxidative stress-induced neuronal apoptosis. J. Neurosci., 1997, 17, 5089-5100. (Pubitemid 27263822)
40. Sunjic, S.B.; Cipak, A, Rabuzin F, Wildburger, R, Zarkovic, N. The influence of 4-hydroxy-2-nonenal on proliferation differentiation and apoptosis of human osteosarcoma cells. Biofactors 2005; 24:141-148. (Pubitemid 41750537)
41. Cadenas, E.; Muller, A.; Brigelius, R.; Esterbauer, H.; Sies, H. Effects of hydroxynonenal on isolated hepatocytes. Studies on chemiluminescence response, alkane production and glutathione status. Biochem. J., 1983, 214, 479-487. (Pubitemid 13035530)
42. Franco, R.; Cidlowski, J.A. Apoptosis and glutathione: beyond an antioxidant, Cell Death Differ. 2009, 16, 1303-1314.
43. Gendron, M.C.; Schrantz, N.; Métivier, D.; Kroemer, G.; Maciorowska, Z.; Sureau, F.; Koester, S.; Petit, P.X. Oxidation of pyridine nucleotides during Fas-And ceramide-induced apoptosis in Jurkat cells: correlation with changes in mitochondria glutathione depletion intracellular acidification and caspase 3 activation. Biochem. J., 2001, 353, 357-367. (Pubitemid 32096946)
44. Petit, P.X. Mitochondrial implication in cell death, In: Mitochondria in Pathogenesis Lemasters and Nieminen (Ed); Kluwer Academic/Plenum Publishers; New York 2001 pp. 215-240.
45. Liu, X.; Kim, C.M.; Yang, J.; Jemmerson, R.; Wang, X.; Induction of apoptotic program in cell-free extracts: requirement for dATP and cytochromeC. Cell, 1996, 86, 147-157. (Pubitemid 26256586)
46. Townsend, A.J.; Leone-Kabler, S.; Haynes, R.L.; Wu, Y. Selective protection by stable transfected human ALDH3A1 (but not human ALDH1A1) against toxicity of aliphatic aldehydes in V79 cells. Chem. Biol. Interact., 2001, 130-132, 261-273. (Pubitemid 32295821)
47. Trombetta, A.; Maggiora, M.; Canuto, R.A.; Martinasso, G.; Muzio, G.; Class 3 aldehyde dehydrogenase and cell proliferation. Curr. Topics Biochem. Res., 2001, 4, 103-115.
48. Lindhal, R.; Petersen D.R. Lipid aldehyde oxidation as a physiological role for class 3 aldehyde dehydrogenases. Biochem. Pharmacol., 1991, 41, 1583-1587.
49. Pappa, A.; Estey, T.; Manzer, R.; Brown, D.; Vasiliou, V.; Human aldehyde dehydrogenase 3A1 (ALDH3A1): biochemical characterization and immunohistochemical localization in the cornea. Biochem. J., 2003, 376, 615-623. (Pubitemid 38063115)
50. Haynes, R.L.; Szweda, L.; Pickin, K.; Welker, M.E.; Townsend, A.J. Structure-Activity relationships for growth inhibition and induction of apoptosis by 4-hydroxynonenal in Raw 264.7 cells. Mol.. Pharmacol., 2000, 58, 788-794.
51. Sladek, N.E.; Rekha, G.; Lee, M.J.C.; Nagasawa H.T. Inhibition of ALDH 3 A1-catalysed oxidation by chlorpropamide analogues. Chem. Biol. Interact., 2001, 130-132, 135-149. (Pubitemid 32295809)
52. Marnett, L.J.; Buck, J.; Tuttle, M.; Basu, A.K.; Bull, A.W. Distribution and oxidation of malondialdehyde in mice. Prostaglandins, 1985, 30, 241-254. (Pubitemid 16245431)
53. Scholem, RD, Brown, GK, Metabolism of malonic semialdehyde in man. Biochem. J., 1983, 216, 81-85. (Pubitemid 13019337)
54. Steinmetz, C.G.; Xie, P.; Weiner, H. Structure of mitochondrial aldehyde dehydrogenase: the genetic component of alcohol aversion. Structure, 1997, 5, 701-711. (Pubitemid 27236268)
55. Kitson, T.M.; Studies on the interaction between disulfiram and sheep liver cytoplasmic aldehyde dehydrogenase. Biochem. J., 1978, 175, 83-90. (Pubitemid 9057116)
56. Lipsky, J.J.; Shen, M.L.; Naylor, S. Overview-In vitro inhibition of aldehyde dehydrogenase by disulfiram and metabolites. Chem. Biol. Interact., 2001, 130-132, 81-91. (Pubitemid 32295805)
57. Chen, D.; Cui, Q.C.; Yang, H.; Ping Dou, Q. Disulfuram a clinically used anti-Alcoholism drug and copper-binding agent induces apoptotic cell death in breast cancer cultures and xenografts via inhibition of the proteasome activity. Cancer Res., 2006, 66, 10425-10433. (Pubitemid 44799763)
58. Wattenberg, L.W. Inhibition of Dimethylhydrazine-induced neoplasia of the large intestine by disulfiram. J. Natl. Cancer Inst., 1975, 54, 1005-1006.
59. Furuya, Y.; Krajewski, S.; Epstein, J.I.; Reed, J.C. Expression of bcl-2 and the progression of human and rodent prostate cancers. Clin Cancer Res, 1996, 2, 389-398. (Pubitemid 26075642)
60. Quash, G.; Fournet, G.; Courvoisier, C.; Martinez, M.; Chantepie, J.; Paret, M.J.; Pharaboz, J.; Joly-Pharaboz, M.O.; Goré, J.; André, J.; Reichert, U.; Aldehyde dehydrogenase inhibitors: alpha, beta-Acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture. Eur. J. Med. Chem., 2008, 43, 906-916. (Pubitemid 351615229)
61. Canuto, R.A.; Muzio, G.; Salvo, R.A.; Maggiora, M.; Trombetta, A.; Chantepie, J.; Fournet, G.; Reichert, U.; Quash, G. The effect of a novel inhibitor of aldehyde dehydrogenases 1 and 3 on tumour cell growth and death. Chem. Biol. Interact., 2001, 130-132, 209-218. (Pubitemid 32295816)
62. Abeles, R.H. Enzyme-Activated Irreversible Inhibitors, Seiler N.; Jung M.J.; Kock-Weser J, (Eds). Elsevier/North-Holland 1978 pp 1-12.
63. Silverman, R.B.; Hoffman, S.J. The organic chemistry of mechanism-based enzyme inhibition: a chemical approach to drug design. Med. Res. Rev., 1984, 3, 415-447. (Pubitemid 14073190)
64. Hurley, T.D.; Weiner, H. Evaluation of the roles of the conserved residues of aldehyde dehydrogenase. Adv. Exp. Med. Biol., 1999, 463, 45-52.
65. Mukerjee, N.; Pietruszko, R. Human mitochondrial aldehyde dehydrogenase substrate specificity: comparison of esterase with dehydrogenase reaction. Arch. Biochem. Biophys., 1992, 299, 23-29.
66. Kitson, T.M.; Kitson, K.E. Studies of the esterase activity of cytosolic aldehyde dehydrogenase with resorufin acetate as substrate. Biochem. J., 1997, 322, 701-708. (Pubitemid 27135614)
67. DeMaster, E.G.; Nagasawa H.T. Inhibition of aldehyde dehydrogenase by propiolaldehyde a possible metabolite of pargyline. Res. Comm. Chem. Pathol. Pharmacol., 1978, 21, 497-505. (Pubitemid 9022936)
68. Blatter, E.E.; Tasayco, M.L.; Prestwich, G.; Pietruszko, R. Chemical modification of aldehyde dehydrogenase by a vinyl ketone analogue of an insect pheromone. Biochem. J., 1990, 272, 351-358.
69. Quemener, V.; Quash, G.; Moulinoux, J.P.; Penlap, V.; Ripol,l H.; Havouis, R.; Doutheau, A.; Goré, J. In vivo antitumor activity of 4-Amino 4-methyl 2-pentyne 1-Al, an inhibitor of aldehyde dehydrogenase. In Vivo, 1989, 3, 325-330. (Pubitemid 20057609)
70. Pietruszko, R.; Abriol,a D.P.; Izaguirre, G.; Kikonyogo, A.; Dryjanski, M.; Ambroziak, W. Aldehyde inhibitors of aldehyde dehydrogenases. Adv. Exp. Med. Biol., 1999, 463, 79-87.
71. Kitson, T.; Kitson, K.; King, G.J. Covalent modification of sheep liver cytosolic aldehyde dehydrogenase by the oxidative addition of coloured phenoxazine, phenothiazine and phenazine derivatives. Adv. Exp. Med. Biol., 1999, 463, 89-96.
72. Helander, A.; Cronholm, T.; Tottmat, O. Inhibition of aldehyde dehydrogenase by methylene blue. Biochem. Pharmacol., 1993, 46, 2135-2138.
73. Muzio, G.; Canuto, R.A.; Trombetta, A.; Maggiora, M. Inhibition of cytosolic class 3 aldehyde dehydrogenase by antisense oligonucleotides in rat hepatoma cells. Chem. Biol. Interact., 2001, 130-132, 219-225. (Pubitemid 32295817)
74. Sladek, N.E.; Kollander, R.; Sreerama, L.; Kiang, D.T. Cellular levels of aldehyde dehydrogenases (ALDH1A1 and ALDH3A1) as predictors of therapeutic responses to cyclophosphamide-based chemotherapy of breast cancer: a retrospective study. Rational individualization of oxazaphosphorine-based cancer chemotherapeutic regimens. Cancer Chemother. Pharmacol., 2002; 49, 309-321. (Pubitemid 34253270)
75. Koppaka, V.; Thompson, D.C.; Chen, Y.; Ellerman, M.; Nicolaou, K.C.; Juvonen, R.O.; Petersen, D.; Deitrich, R.A.; Hurley, T.D.; Vasiliou, V. Aldehyde dehydrogenase inhibitors: a comprehensive review of the pharmacology, mechanism of action, substrate specificity, and clinical application. Pharmacol. Revs., 2012, 64, 520-539.
76. Croker, A.K.; Allan, A.L. Inhibition of aldehyde dehydrogenase (ALDH) activity reduces chemotherapy and radiation resistance of stem-cell ALDHhi CD44+ human breast cancer cells. Breast Cancer Res. Treat., 2011, 133, 75-87.
77. Khanna, M.; Chen, C.H.; Kimble-Hill, A.; Parajuli, B.; Perez-Miller, S.; Baskaram, S.; Kim, J.; Dria, K.; Vasilou, V.; Mochly-Rosen, D.; Hurley, T.D. Discovery of a novel class of covalent inhibitor for aldehyde dehydrogenase. J. Biol. Chem., 2011, 286, 43486-43494.
78. Parajuli, B.; Kimble-Hill, A.C.; Khanna, M.; Ivanova, Y.; Meroueh, S.; Hurley, T.D. Discovery of novel modulators of Aldehyde Dehydrogenase. Chem. Biol. Interact., 2011, 191, (1-3) 153-158.
79. Cooper, A.J. Glutamine aminotransferases and -Amidases. in: Glutamine and glutamate in mammals, Vol.1, E. Kvamme (Ed), CRC Press, Inc. Boca Raton, Florida, 1988, pp 33-52.
80. Cooper, A.J.; Meister, A. Isolation and properties of highly purified glutamine transaminase. Biochemistry, 1972, 11, 661-671.
81. Tangerman, A.; Wilcken, B.; Levy, H.L.; Boers, G.H.; Mudd, S.H. Methionine transamination in patients with homocystinuria due to cystathionine beta-synthase deficiency. Metabolism, 2000, 49, 1071-1077. (Pubitemid 30641447)