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Chemical Compound Review

Chloroacetic     2-chloroethanoic acid

Synonyms: sJPhLQDIKTp@, LS-7, NSC-142, CHEMBL14090, NSC142, ...
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Disease relevance of Monochloroethanoic acid


High impact information on Monochloroethanoic acid


Chemical compound and disease context of Monochloroethanoic acid


Biological context of Monochloroethanoic acid

  • Evidence for a close similarity in the catalytic sites of papain and ficin in near-neutral media despite differences in acidic and alkaline media. Kinetics of the reactions of papain and ficin with chloroacetate [16].
  • 1. The pH-dependences of the second-order rate constants (k) for the alkylation by chloroacetate of the active-centre thiol groups of papain (EC and ficin (EC were determined over a wide range of pH at 25 degrees C at I 0 [16].
  • MEG-A2 cells showed positive phenotypes for periodic acid Schiff and alpha-naphthylbutyrate esterase reactions, but were negative for myeloperoxidase and naphthol ASD chloroacetate esterase reactions [17].
  • Cleavage of the chloroacetate followed by exhaustive hydrogenation completes the total synthesis of the targeted glycolipid 1 [18].
  • After 3 days, MHE226 cells displayed cytological, enzymatic (alpha-naphthyl acetate esterase and chloroacetate esterase), and functional (phagocytosis) characteristics of monocytic cells [19].

Anatomical context of Monochloroethanoic acid

  • Two of these isozymes were shown to have chloroacetate esterase activity characteristic of granulocytes [20].
  • IL-8 expression was observed in Hodgkin and Reed-Sternberg cells in 3 of 33 cases of classical HD and in reactive cells in 20 of 33 HD cases as evidenced by combined isotopic in situ hybridization and immunohistology for the demonstration of cell-type-characteristic antigens or enzyme histochemistry for chloroacetate esterase [21].
  • Mast cell progenitors (c-kit(+) CD13(+) cells with chloroacetate esterase activity) were purified from 4-week-old cultures of cord blood mononuclear cells maintained in stem cell factor, interleukin-6 (IL-6), and IL-10 using a CD14 depletion column [22].
  • The vast majority of typical and lacunar type H and SR cells contained the granulocyte-related antigens detected by monoclonal antibodies TU5, TU6, TU9 and 3C4, whereas other more or less specific granulopoietic cell markers (such as peroxidase, chloroacetate esterade, lysozyme, cationic leukocyte antigen and OKMI) were consistently absent [23].
  • Treatment of crude bovine RPE membranes with (3R)-3-[boc-lys(biotinyl)-O]-all-trans-retinol chloroacetate 1 in the low micromolar range led to the specific labeling of RPE65 and lecithin retinol acyltransferase (LRAT) [24].

Associations of Monochloroethanoic acid with other chemical compounds


Gene context of Monochloroethanoic acid


Analytical, diagnostic and therapeutic context of Monochloroethanoic acid


  1. Acute monocytic leukemia with chloroacetate esterase positivity: FAB M4 or M5? Miller-Canfield, P., Dubell, J., Schumacher, H.R. Am. J. Clin. Pathol. (1993) [Pubmed]
  2. Chloroacetate esterase positivity in acute lymphoblastic leukemia. Keifer, J., Abromowitch, M., Stass, S.A. Am. J. Clin. Pathol. (1985) [Pubmed]
  3. Microbial degradation of beta-chlorinated four-carbon aliphatic acids. Kohler-Staub, D., Kohler, H.P. J. Bacteriol. (1989) [Pubmed]
  4. Localized Leishmania lymphadenitis. Immunohistochemical studies. Azadeh, B., Sells, P.G., Ejeckam, G.C., Rampling, D. Am. J. Clin. Pathol. (1994) [Pubmed]
  5. The pathology of murine myelogenous leukemias. Perkins, A.S. Curr. Top. Microbiol. Immunol. (1989) [Pubmed]
  6. Eosinophilic differentiation of the human promyelocytic leukemia cell line, HL-60. Fischkoff, S.A., Pollak, A., Gleich, G.J., Testa, J.R., Misawa, S., Reber, T.J. J. Exp. Med. (1984) [Pubmed]
  7. Neutrophils deficient in PU.1 do not terminally differentiate or become functionally competent. Anderson, K.L., Smith, K.A., Pio, F., Torbett, B.E., Maki, R.A. Blood (1998) [Pubmed]
  8. Primary myelodysplastic syndromes: diagnostic and prognostic significance of immunohistochemical assessment of bone marrow biopsies. Mangi, M.H., Mufti, G.J. Blood (1992) [Pubmed]
  9. Differential expression of HLA-DR antigens in subsets of human CFU-GM. Griffin, J.D., Sabbath, K.D., Herrmann, F., Larcom, P., Nichols, K., Kornacki, M., Levine, H., Cannistra, S.A. Blood (1985) [Pubmed]
  10. Evidence for significant hematopoiesis in the human thymus. Taylor, C.R., Skinner, J.M. Blood (1976) [Pubmed]
  11. Acute myelomonocytic leukemia: an unusual variant with both granulocytic and monocytic esterases in the leukemic cells. Li, C.Y., Phyliky, R.L., Yam, L.T. Mayo Clin. Proc. (1986) [Pubmed]
  12. Protective action of diethyldithiocarbamate and carbon disulfide against acute toxicities induced by 1,1-dichloroethylene in mice. Masuda, Y., Nakayama, N. Toxicol. Appl. Pharmacol. (1983) [Pubmed]
  13. Bone marrow mastocytosis associated with an undifferentiated extramedullary tumor of hemopoietic origin. Horny, H.P., Kaiserling, E., Sillaber, C., Walchshofer, S., Valent, P. Arch. Pathol. Lab. Med. (1997) [Pubmed]
  14. Micronuclei induction and chromosomal aberrations in Rattus norvegicus by chloroacetic acid and chlorobenzene. Faisal Siddiqui, M., Ahmad, R., Ahmad, W., Hasnain, A.U. Ecotoxicol. Environ. Saf. (2006) [Pubmed]
  15. Preleukemic granulocytic sarcoma of cervix and vagina: initial manifestation by cytology. Spahr, J., Behm, F.G., Schneider, V. Acta Cytol. (1982) [Pubmed]
  16. Evidence for a close similarity in the catalytic sites of papain and ficin in near-neutral media despite differences in acidic and alkaline media. Kinetics of the reactions of papain and ficin with chloroacetate. Brocklehurst, K., Mushiri, S.M., Patel, G., Willenbrock, F. Biochem. J. (1982) [Pubmed]
  17. Establishment and characterization of an immature human megakaryoblastic cell line, MEG-A2. Abe, A., Emi, N., Kato, H., Adachi, K., Murate, T., Saga, S., Ogura, M., Kojima, T., Tanimoto, M., Morishita, N. Leukemia (1995) [Pubmed]
  18. Total synthesis of woodrosin I--part 2: final stages involving RCM and an orthoester rearrangement. Fürstner, A., Jeanjean, F., Razon, P., Wirtz, C., Mynott, R. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  19. Avian myeloblastic cell lines transformed by two nuclear oncoproteins, P135gag-myb-ets and p61/63myc: a model of retinoic acid-induced differentiation not abrogated by v-erbA. al Moustafa, A.E., Gautier, R., Saule, S., Dieterlen-Lièvre, F., Cormier, F. Cell Growth Differ. (1994) [Pubmed]
  20. Expression of multiple isozymes of granulocyte, monocyte, and macrophage esterases in polycythemic Friend erythroleukemia cells. Woytowicz, J.M., Daoust, P.R., André-Schwartz, J., Levy, S.B. Blood (1983) [Pubmed]
  21. Interleukin-8 in Hodgkin's disease. Preferential expression by reactive cells and association with neutrophil density. Foss, H.D., Herbst, H., Gottstein, S., Demel, G., Araujó, I., Stein, H. Am. J. Pathol. (1996) [Pubmed]
  22. Human Mast cell progenitors can be infected by macrophagetropic human immunodeficiency virus type 1 and retain virus with maturation in vitro. Bannert, N., Farzan, M., Friend, D.S., Ochi, H., Price, K.S., Sodroski, J., Boyce, J.A. J. Virol. (2001) [Pubmed]
  23. Identification of Hodgkin and Sternberg-reed cells as a unique cell type derived from a newly-detected small-cell population. Stein, H., Gerdes, J., Schwab, U., Lemke, H., Mason, D.Y., Ziegler, A., Schienle, W., Diehl, V. Int. J. Cancer (1982) [Pubmed]
  24. A cleavable affinity biotinylating agent reveals a retinoid binding role for RPE65. Jahng, W.J., David, C., Nesnas, N., Nakanishi, K., Rando, R.R. Biochemistry (2003) [Pubmed]
  25. IL-3-dependent growth of basophil-like cells and mastlike cells from human bone marrow. Kirshenbaum, A.S., Goff, J.P., Dreskin, S.C., Irani, A.M., Schwartz, L.B., Metcalfe, D.D. J. Immunol. (1989) [Pubmed]
  26. Hepatic involvement in systemic mast cell disease. Yam, L.T., Chan, C.H., Li, C.Y. Am. J. Med. (1986) [Pubmed]
  27. Acute promyelocytic leukemia: morphological aspects. Castoldi, G.L., Liso, V., Specchia, G., Tomasi, P. Leukemia (1994) [Pubmed]
  28. Establishment of a novel human acute myeloblastic leukemia cell line (YNH-1) with t(16;21), t(1;16) and 12q13 translocations. Yamamoto, K., Hamaguchi, H., Nagata, K., Kobayashi, M., Tanimoto, F., Taniwaki, M. Leukemia (1997) [Pubmed]
  29. A morphologic and cytochemical study of acute myelomonocytic leukemia with abnormal marrow eosinophils associated with inv(16)(p13q22). Bitter, M.A., Le Beau, M.M., Larson, R.A., Rosner, M.C., Golomb, H.M., Rowley, J.D., Vardiman, J.W. Am. J. Clin. Pathol. (1984) [Pubmed]
  30. Granulocytic sarcoma of the female genital tract: a clinicopathologic study of 11 cases. Oliva, E., Ferry, J.A., Young, R.H., Prat, J., Srigley, J.R., Scully, R.E. Am. J. Surg. Pathol. (1997) [Pubmed]
  31. Acute promyelocytic leukemia, hypogranular variant, with uncharacteristic staining with chloroacetate esterase. Dunphy, C.H., Polski, J.M., Johns, G., Evans, H.L., Gardner, L.J. Leuk. Lymphoma (2001) [Pubmed]
  32. Monochloroacetic acid inhibits liver gluconeogenesis by inactivating glyceraldehyde-3-phosphate dehydrogenase. Sakai, A., Shimizu, H., Kono, K., Furuya, E. Chem. Res. Toxicol. (2005) [Pubmed]
  33. Quantitative cytochemistry of blood neutrophils in acute myeloid leukaemia. Schofield, K.P., Stone, P.C., Stuart, J. Br. J. Haematol. (1983) [Pubmed]
  34. Multimarker immunohistochemical staining of calgranulins, chloroacetate esterase, and S100 for simultaneous demonstration of inflammatory cells on paraffin sections. Chilosi, M., Mombello, A., Montagna, L., Benedetti, A., Lestani, M., Semenzato, G., Menestrina, F. J. Histochem. Cytochem. (1990) [Pubmed]
  35. Erythroleukemic infiltration of a lymph node: use of hemoglobin immunohistochemical techniques in diagnosis. Keifer, J., Zaino, R., Ballard, J.O. Hum. Pathol. (1984) [Pubmed]
  36. Kinetics of monochloroacetic acid in adult male rats after intravenous injection of a subtoxic and a toxic dose. Saghir, S.A., Fried, K., Rozman, K.K. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  37. High-performance liquid chromatographic determination of N-[2(S)-(mercaptomethyl)-3-(2-methylphenyl)-1-oxopropyl]-L-methionine, the active plasma metabolite of a prodrug atriopeptidase inhibitor (SCH 42495), using a thiol selective (Au/Hg) amperometric detector. Alton, K.B., Hernandez, A., Alvarez, N., Patrick, J.E. J. Chromatogr. (1992) [Pubmed]
  38. Kinetics of monochloroacetic acid at subtoxic and toxic doses in rats after single oral and dermal administrations. Saghir, S.A., Rozman, K.K. Toxicol. Sci. (2003) [Pubmed]
  39. Identification and kinetics of leukocytes after severe ischaemia/reperfusion renal injury. Ysebaert, D.K., De Greef, K.E., Vercauteren, S.R., Ghielli, M., Verpooten, G.A., Eyskens, E.J., De Broe, M.E. Nephrol. Dial. Transplant. (2000) [Pubmed]
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