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Chemical Compound Review

AC1L9RXY     [(1R,2S,5R)-2-(6-aminopurin- 9-yl)-5...

Synonyms: (-)-BCA
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Disease relevance of AIDS-005315

  • All these data are in favor of the use of mAb BCA 227 as an immunodiagnostic tool for breast cancer [1].
  • A new tumor-associated antigen expressed on breast carcinomas, defined by monoclonal antibody BCA 227 [1].
  • The present study has analysed a series of 23 formalin-fixed, paraffin wax-embedded tissue samples of Barrett's adenocarcinoma (BCA, n = 18) and non-neoplastic squamous oesophageal (n = 2) and gastric cardia mucosa (n = 3) by aCGH [2].
  • BCA exhibited a wide safety margin, showing no evidence of causing retinal toxicity, even at the 600- micro M concentration [3].
  • PURPOSE: To investigate whether 2'-benzoyl-oxycinnamaldehyde (BCA) induces apoptosis in human retinal pigment epithelial (hRPE) cells and has an antiproliferative effect in a proliferative vitreoretinopathy (PVR) model in the rabbit [3].

High impact information on AIDS-005315

  • After immunization of mice with the human breast carcinoma cell line MCF-7, we produced monoclonal antibody (mAb) BCA 227, which allowed us to characterize a new tumor-associated antigen [1].
  • In addition, BCA-induced activation of caspase-3 and degradation of poly(ADP-ribose) polymerase were abolished by pretreatment of cells with the anti-oxidants [4].
  • These results suggest that reactive oxygen species are major regulator of BCA-induced apoptosis [4].
  • As a derivative of HCA, BCA (2'-benzoyl-oxycinnamaldehyde) was synthesized by replacing hydroxyl group with benzoyl-oxyl group [4].
  • HCA or BCA-induced accumulation of reactive oxygen species was detected by using DCF-DA, an intracellular probe of oxidative stress [4].

Chemical compound and disease context of AIDS-005315


Biological context of AIDS-005315


Anatomical context of AIDS-005315

  • SMA reacting with rabbit liver (bile canaliculus antibodies, BCA) and with rat glomeruli (glomerulus antibodies) were of anti-actin specificity and were more common in CAH than in PBC [7].
  • Lymph node metastasis is one of the strongest negative prognostic factors for patients with Barrett's adenocarcinoma (BCA) [8].
  • The three-dimensional structure of bovine carbonic anhydrase III (BCA III) from red skeletal muscle cells has been determined by molecular replacement methods [9].
  • No changes were detected in BCA-associated intestinal metaplasia and squamous epithelium [10].
  • Data suggest that the delayed hepatic tumor development observed with BCA could be mediated by a long-term immunostimulating effect on T cells [5].

Associations of AIDS-005315 with other chemical compounds

  • Protoporphyrine IX inhibited EPO in BCA and PCA and abolished L-NG nitroarginine-resistant relaxation of BCA not PCA [11].
  • Subjects were randomized to receive single doses of treatment A (2 loratadine 5-mg tablets + ambroxol 30-mg tablets), B (2 ambroxol 30-mg tablets), or C (1 loratadine 10-mg tablet) in 1 of 3 sequences (ABC, BCA, or CAB) per period [12].
  • In contrast, the ability of IFN beta and IFN gamma to enhance the synthesis, expression and shedding of BCA 225, as well as to enhance HLA class II antigens, c-erbB-2 and ICAM-1 expression, was either unchanged or modestly reduced by simultaneous exposure to H-7 [13].
  • Cyclic AMP and cGMP concentrations were measured by radioimmunoassay and the results expressed per microgram of protein, which was determined by the Pierce Micro BCA protein assay [14].
  • Adhesion, the initial step of platelet activation, was estimated by the colorimetric method with BCA (bicinchoninic acid) solution in 96-well Fg-coated microtiter dishes [15].

Gene context of AIDS-005315

  • There was a correlation between GRB7 and ERBB2 in BCA at the DNA level (r(s) = 0.76, p < 0.001) and the mRNA level (r(s) = 0.89, p < 0.001) [16].
  • BCA II has a C-terminal knot structure similar to that observed in human CA II [17].
  • Shedding of BCA 225 from T47D cells was induced by TPA, mezerein, IFN beta and IFN gamma, whereas ADMB did not display this activity [13].
  • All three agents increased the surface expression of the tumor-associated antigen BCA 225 and various cellular antigens, including HLA class II antigens, intercellular adhesion molecule 1 (ICAM-1) and c-erbB-2 [13].
  • A dose of I microM of HCA and BCA inhibited the Con A-stimulated proliferation by 69% and 60%, and the LPS-induced proliferation by 29% and 21%, respectively [18].

Analytical, diagnostic and therapeutic context of AIDS-005315


  1. A new tumor-associated antigen expressed on breast carcinomas, defined by monoclonal antibody BCA 227. Blottière, H.M., Pelhate, S., Aubry, J., Kremer, M., Thedrez, P., Sai-Maurel, C., Douillard, J.Y., Chatal, J.F. Cancer Res. (1991) [Pubmed]
  2. Array-based comparative genomic hybridization for the detection of DNA sequence copy number changes in Barrett's adenocarcinoma. Albrecht, B., Hausmann, M., Zitzelsberger, H., Stein, H., Siewert, J.R., Hopt, U., Langer, R., Höfler, H., Werner, M., Walch, A. J. Pathol. (2004) [Pubmed]
  3. Effect of 2'-benzoyl-oxycinnamaldehyde on RPE cells in vitro and in an experimental proliferative vitreoretinopathy model. Lee, J.J., Park, J.K., Kim, Y.T., Kwon, B.M., Kang, S.G., Yoo, Y.D., Yu, Y.S., Chung, H. Invest. Ophthalmol. Vis. Sci. (2002) [Pubmed]
  4. 2'-benzoyloxycinnamaldehyde induces apoptosis in human carcinoma via reactive oxygen species. Han, D.C., Lee, M.Y., Shin, K.D., Jeon, S.B., Kim, J.M., Son, K.H., Kim, H.C., Kim, H.M., Kwon, B.M. J. Biol. Chem. (2004) [Pubmed]
  5. Delayed occurrence of H-ras12V-induced hepatocellular carcinoma with long-term treatment with cinnamaldehydes. Moon, E.Y., Lee, M.R., Wang, A.G., Lee, J.H., Kim, H.C., Kim, H.M., Kim, J.M., Kwon, B.M., Yu, D.Y. Eur. J. Pharmacol. (2006) [Pubmed]
  6. Eliminating positively charged lysine epsilon-NH3+ groups on the surface of carbonic anhydrase has no significant influence on its folding from sodium dodecyl sulfate. Gudiksen, K.L., Gitlin, I., Yang, J., Urbach, A.R., Moustakas, D.T., Whitesides, G.M. J. Am. Chem. Soc. (2005) [Pubmed]
  7. Different types of smooth muscle antibodies in chronic active hepatitis and primary biliary cirrhosis: their diagnostic and prognostic significance. Kurki, P., Miettinen, A., Linder, E., Pikkarainen, P., Vuoristo, M., Salaspuro, M.P. Gut (1980) [Pubmed]
  8. Molecular genetic changes in metastatic primary Barrett's adenocarcinoma and related lymph node metastases: comparison with nonmetastatic Barrett's adenocarcinoma. Walch, A.K., Zitzelsberger, H.F., Bink, K., Hutzler, P., Bruch, J., Braselmann, H., Aubele, M.M., Mueller, J., Stein, H., Siewert, J.R., Höfler, H., Werner, M. Mod. Pathol. (2000) [Pubmed]
  9. Refined structure of bovine carbonic anhydrase III at 2.0 A resolution. Eriksson, A.E., Liljas, A. Proteins (1993) [Pubmed]
  10. Her-2/neu gene amplification, elevated mRNA expression, and protein overexpression in the metaplasia-dysplasia-adenocarcinoma sequence of Barrett's esophagus. Walch, A., Specht, K., Bink, K., Zitzelsberger, H., Braselmann, H., Bauer, M., Aubele, M., Stein, H., Siewert, J.R., Höfler, H., Werner, M. Lab. Invest. (2001) [Pubmed]
  11. Mechanisms of L-NG nitroarginine/indomethacin-resistant relaxation in bovine and porcine coronary arteries. Graier, W.F., Holzmann, S., Hoebel, B.G., Kukovetz, W.R., Kostner, G.M. Br. J. Pharmacol. (1996) [Pubmed]
  12. Pharmacokinetic properties of single-dose loratadine and ambroxol alone and combined in tablet formulations in healthy men. Villacampa, J., Alcántar, F., Rodríguez, J.M., Morales, J.M., Herrera, J., Rosete, R. Clinical therapeutics. (2003) [Pubmed]
  13. Modulation of the antigenic phenotype of human breast carcinoma cells by modifiers of protein kinase C activity and recombinant human interferons. Leon, J.A., Gutierrez, M.C., Jiang, H., Estabrook, A., Waxman, S., Fisher, P.B. Cancer Immunol. Immunother. (1992) [Pubmed]
  14. Cyclic AMP and cyclic GMP concentrations in, and efflux from, preimplantation cattle embryos. Grealy, M., Glynn, M.A., Sreenan, J.M. Anim. Reprod. Sci. (1997) [Pubmed]
  15. Antioxidants with carcinostatic activity (resveratrol, vitamin E and selenium) in modulation of blood platelet adhesion. Zbikowska, H.M., Olas, B. J. Physiol. Pharmacol. (2000) [Pubmed]
  16. Coamplification and coexpression of GRB7 and ERBB2 is found in high grade intraepithelial neoplasia and in invasive Barrett's carcinoma. Walch, A., Specht, K., Braselmann, H., Stein, H., Siewert, J.R., Hopt, U., Höfler, H., Werner, M. Int. J. Cancer (2004) [Pubmed]
  17. Structure of bovine carbonic anhydrase II at 1.95 A resolution. Saito, R., Sato, T., Ikai, A., Tanaka, N. Acta Crystallogr. D Biol. Crystallogr. (2004) [Pubmed]
  18. Cinnamaldehyde inhibits lymphocyte proliferation and modulates T-cell differentiation. Koh, W.S., Yoon, S.Y., Kwon, B.M., Jeong, T.C., Nam, K.S., Han, M.Y. Int. J. Immunopharmacol. (1998) [Pubmed]
  19. Augmented gastric inhibitory polypeptide and insulin responses to a meal after an increase in carbohydrate (sucrose) intake. Mazzaferri, E.L., Starich, G.H., St Jeor, S.T. J. Clin. Endocrinol. Metab. (1984) [Pubmed]
  20. Influence of the Zn(II) cofactor on the refolding of bovine carbonic anhydrase after denaturation with sodium dodecyl sulfate. Gudiksen, K.L., Urbach, A.R., Gitlin, I., Yang, J., Vazquez, J.A., Costello, C.E., Whitesides, G.M. Anal. Chem. (2004) [Pubmed]
  21. Purification of supercoiled plasmid DNA using chromatographic processes. Ferreira, G.N., Cabral, J.M., Prazeres, D.M. J. Mol. Recognit. (1998) [Pubmed]
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