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Chemical Compound Review

acivicin     (2S)-2-amino-2-[(5S)-3- chloro-4,5-dihydro...

Synonyms: Acivicine, Acivicino, Acivicinum, ACIA, SureCN4159, ...
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Disease relevance of acivicin


Psychiatry related information on acivicin


High impact information on acivicin

  • The pig enzyme, which has Ala-523 in place of Thr-523, is inhibited by acivicin with esterification at Ser-405 [5].
  • Basal CD14 and CD11b expression were slightly reduced by DEX and PTX, but neither drug modified the acivicin-induced increases [6].
  • Thus, DEX and PTX effectively block the acivicin-induced expression of TNF-alpha and IL-1 beta, but they have little influence on the acivicin-induced differentiation process.(ABSTRACT TRUNCATED AT 250 WORDS)[6]
  • DEX and PTX did not alter cell growth, and did not block the acivicin-induced block in growth [6].
  • DEX and PTX reduced the acivicin-induced increases in TNF-alpha and IL-1 beta mRNA expression, but they had little or no effect on the acivicin-induced decreases in expression of mRNA for c-myc and c-myb [6].

Chemical compound and disease context of acivicin


Biological context of acivicin

  • In ECV304 cells and human umbilical venous endothelial cells, acivicin favored Hcy plus Cu2+-induced apoptosis whereas dexamethasone counteracted the apoptotic process [12].
  • Acivicin pharmacokinetics were studied in Phase I patients receiving i.v. treatment on single-dose or daily x5 (daily times five doses) regimens repeated every 3 weeks [13].
  • Acivicin kinetics appeared to be dose-independent over the range of 8.5-150 mg/m2/day [13].
  • Based on previous reports of the biochemical mechanisms of Acivicin actions, several additives to the tissue culture medium were tested for their ability to protect MiaPaCa-2 cells from inhibition of cell cycle progression [14].
  • This study was designed to determine the effects of acivicin on the levels of HL-60 cell mRNA transcripts of several cytokines, growth factors, and protooncogenes implicated in the control of hematopoietic cell proliferation and differentiation [15].

Anatomical context of acivicin


Associations of acivicin with other chemical compounds


Gene context of acivicin

  • Acivicin treatment also caused the cells to have diminished steady-state expression of messenger RNA (mRNA) for c-myc and c-myb, and increased expression of mRNA for TNF-alpha and IL-1 beta [6].
  • Acivicin, which inhibits GSH breakdown by gamma-glutamyl transpeptidase (GGT), had no effect on the enhanced uptake seen during the respiratory burst [18].
  • The activity is membrane-bound and is inhibited by acivicin, a known inhibitor of GGT [19].
  • Acivicin inhibits GMP synthetase irreversibly by covalent modification [20].
  • Furthermore, we report on the detailed characterization of the inhibition of the glutaminase domain, and thus PLP synthesis, by the glutamine analog acivicin [21].

Analytical, diagnostic and therapeutic context of acivicin


  1. Monocytoid differentiation of freshly isolated human myeloid leukemia cells and HL-60 cells induced by the glutamine antagonist acivicin. Nichols, K.E., Chitneni, S.R., Moore, J.O., Weinberg, J.B. Blood (1989) [Pubmed]
  2. Prevention of central nervous system toxicity of the antitumor antibiotic acivicin by concomitant infusion of an amino acid mixture. Williams, M.G., Earhart, R.H., Bailey, H., McGovren, J.P. Cancer Res. (1990) [Pubmed]
  3. Effects of acivicin and dipyridamole on hepatoma 3924A cells. Zhen, Y.S., Lui, M.S., Weber, G. Cancer Res. (1983) [Pubmed]
  4. Mechanism of resistance of a variant of P388 leukemia to L-(alpha S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (acivicin). Jayaram, H.N., Ardalan, B., Deas, M., Johnson, R.K. Cancer Res. (1985) [Pubmed]
  5. Different sites of acivicin binding and inactivation of gamma-glutamyl transpeptidases. Smith, T.K., Ikeda, Y., Fujii, J., Taniguchi, N., Meister, A. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  6. Inhibition of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta) messenger RNA (mRNA) expression in HL-60 leukemia cells by pentoxifylline and dexamethasone: dissociation of acivicin-induced TNF-alpha and IL-1 beta mRNA expression from acivicin-induced monocytoid differentiation. Weinberg, J.B., Mason, S.N., Wortham, T.S. Blood (1992) [Pubmed]
  7. Enhancement of the sensitivity of human colon cancer cells to growth inhibition by acivicin achieved through inhibition of nucleic acid precursor salvage by dipyridamole. Fischer, P.H., Pamukcu, R., Bittner, G., Willson, J.K. Cancer Res. (1984) [Pubmed]
  8. Inhibition of gamma-glutamyl transpeptidase activity by acivicin in vivo protects the kidney from cisplatin-induced toxicity. Hanigan, M.H., Gallagher, B.C., Taylor, P.T., Large, M.K. Cancer Res. (1994) [Pubmed]
  9. Collateral sensitivity to N-(phosphonacetyl)-L-aspartic acid in a line of P388 leukemia cells selected for resistance to L-(alpha S, 5S)-alpha-amino-3- chloro-4,5-dihydro-5-isoxazoleacetic acid (acivicin). Ardalan, B., Jayaram, H.N., Johnson, R.K. Cancer Res. (1983) [Pubmed]
  10. Cytotoxicity and cell-proliferation induced by the nephrocarcinogen hydroquinone and its nephrotoxic metabolite 2,3,5-(tris-glutathion-S-yl)hydroquinone. Peters, M.M., Jones, T.W., Monks, T.J., Lau, S.S. Carcinogenesis (1997) [Pubmed]
  11. Phase II trials of 5-day vinblastine infusion (NSC 49842), L-alanosine (NSC 153353), acivicin (NSC 163501), and aminothiadiazole (NSC 4728) in patients with recurrent or metastatic renal cell carcinoma. Elson, P.J., Kvols, L.K., Vogl, S.E., Glover, D.J., Hahn, R.G., Trump, D.L., Carbone, P.P., Earle, J.D., Davis, T.E. Investigational new drugs. (1988) [Pubmed]
  12. Efficiency of homocysteine plus copper in inducing apoptosis is inversely proportional to gamma-glutamyl transpeptidase activity. Bessede, G., Miguet, C., Gambert, P., Neel, D., Lizard, G. FASEB J. (2001) [Pubmed]
  13. Pharmacokinetic and biochemical studies on acivicin in phase I clinical trials. McGovren, J.P., Pratt, E.A., Belt, R.J., Taylor, S.A., Benjamin, R.S., Ardalan, B., Ohnuma, T. Cancer Res. (1985) [Pubmed]
  14. Inhibition of cell cycle progression of human pancreatic carcinoma cells in vitro by L-(alpha S, 5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid, Acivicin (NSC 163501). Meck, R.A., Clubb, K.J., Allen, L.M., Yunis, A.A. Cancer Res. (1981) [Pubmed]
  15. Relationship of acivicin-induced monocytoid differentiation of human myeloid leukemia cells to acivicin-induced modulation of growth factor, cytokine, and protooncogene mRNA expression. Weinberg, J.B., Mason, S.N. Cancer Res. (1991) [Pubmed]
  16. Enhancement of antitumor activity of glutamine antagonists 6-diazo-5-oxo-L-norleucine and acivicin in cell culture by glutaminase-asparaginase. Rosenfeld, H., Roberts, J. Cancer Res. (1981) [Pubmed]
  17. Phase I clinical trial of a combination of dipyridamole and acivicin based upon inhibition of nucleoside salvage. Willson, J.K., Fischer, P.H., Tutsch, K., Alberti, D., Simon, K., Hamilton, R.D., Bruggink, J., Koeller, J.M., Tormey, D.C., Earhart, R.H. Cancer Res. (1988) [Pubmed]
  18. The phagocytosis-associated respiratory burst in human monocytes is associated with increased uptake of glutathione. Seres, T., Knickelbein, R.G., Warshaw, J.B., Johnston, R.B. J. Immunol. (2000) [Pubmed]
  19. Metabolism of leukotriene C4 in gamma-glutamyl transpeptidase-deficient mice. Carter, B.Z., Wiseman, A.L., Orkiszewski, R., Ballard, K.D., Ou, C.N., Lieberman, M.W. J. Biol. Chem. (1997) [Pubmed]
  20. The glutamine hydrolysis function of human GMP synthetase. Identification of an essential active site cysteine. Nakamura, J., Straub, K., Wu, J., Lou, L. J. Biol. Chem. (1995) [Pubmed]
  21. On the two components of pyridoxal 5'-phosphate synthase from Bacillus subtilis. Raschle, T., Amrhein, N., Fitzpatrick, T.B. J. Biol. Chem. (2005) [Pubmed]
  22. Biochemical assessment of the effects of acivicin and dipyridamole given as a continuous 72-hour intravenous infusion. Fischer, P.H., Willson, J.K., Risueno, C., Tutsch, K., Bruggink, J., Ranhosky, A., Trump, D.L. Cancer Res. (1988) [Pubmed]
  23. Luminal and basolateral membrane transport of glutathione in isolated perfused S(1), S(2), and S(3) segments of the rabbit proximal tubule. Parks, L.D., Zalups, R.K., Barfuss, D.W. J. Am. Soc. Nephrol. (2000) [Pubmed]
  24. Direct evidence of intercellular sharing of glutathione via metabolic cooperation. Kavanagh, T.J., Martin, G.M., Livesey, J.C., Rabinovitch, P.S. J. Cell. Physiol. (1988) [Pubmed]
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