Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

A semisynthetic β-glucosidase inhibitor was identified from a chemically engineered extract prepared by reaction with benzenesulfonyl chloride. The structure includes a natural histamine portion and a benzenesulfonyl portion introduced during the diversification step. © 2011 Springer Science+Business Media B.V.

Registro:

Documento: Artículo
Título:Discovery of a β-glucosidase inhibitor from a chemically engineered extract prepared through sulfonylation
Autor:Salazar, M.O.; Micheloni, O.; Escalante, A.M.; Furlan, R.L.E.
Filiación:Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario 2000, Argentina
Departamento de Química, Escuela de Ciencias Agrarias, Naturales y Ambientales, Universidad Nacional Del Noroeste de la Provincia de Buenos Aires, Monteagudo 2772, Pergamino 2700, Argentina
Palabras clave:Biomolecular properties; Chemically engineered extract; Sulfonylation; benzene; beta glucosidase; chloride; article; chemical engineering; chemical reaction; chemical structure; priority journal; synthesis; beta-Glucosidase; Chemical Engineering; Enzyme Inhibitors; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Extracts; Sulfones; Urticaceae
Año:2011
Volumen:15
Número:3
Página de inicio:713
Página de fin:719
DOI: http://dx.doi.org/10.1007/s11030-010-9301-2
Título revista:Molecular Diversity
Título revista abreviado:Mol. Diversity
ISSN:13811991
CODEN:MODIF
CAS:benzene, 71-43-2; beta glucosidase, 51683-43-3, 9001-22-3; chloride, 16887-00-6; Enzyme Inhibitors; Plant Extracts; Sulfones; benzenesulfonyl chloride, 98-09-9; beta-Glucosidase, 3.2.1.21
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811991_v15_n3_p713_Salazar

Referencias:

  • Lopez, S.N., Ramallo, I.A., Sierra, M.G., Zacchino, S.A., Furlan, R.L.E., Chemically engineered extracts as an alternative source of bioactive natural product-like compounds (2007) Proceedings of the National Academy of Sciences of the United States of America, 104 (2), pp. 441-444. , DOI 10.1073/pnas.0608438104
  • Di Liberto, M., Svetaz, L., Furlan, R.L.E., Zacchino, S.A., Delporte, C., Novoa, M.A., Asencio, M., Cassels, B.K., Antifungal activity of saponin-rich extracts of Phytolacca dioica and of the sapogenins obtained through hydrolysis (2010) Nat Prod Commun, 5, pp. 1013-1018. , 20734930 1:CAS:528:DC%2BC3cXps12qsr8%3D
  • Mendez, L., Salazar, M.O., Ramallo, I.A., Rle, F., Brominated extracts as source of bioactive compounds (2011) ACS Comb Sci, , (in press). doi: 10.1021/co100073k
  • Salazar, M.O., Ramallo, I.A., Micheloni, O., Gonzalez Sierra, M., Furlan, R.L.E., Chemically engineered extracts: Bioactivity alteration through sulphonylation (2009) Bioorg Med Chem Lett, 19, pp. 5067-5070. , 10.1016/j.bmcl.2009.07.038 19635668 10.1016/j.bmcl.2009.07.038 1:CAS:528:DC%2BD1MXhtVSlsrzN
  • Lillelund, V.H., Jensen, H.H., Liang, X., Bols, M., Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin (2002) Chemical Reviews, 102 (2), pp. 515-553. , DOI 10.1021/cr000433k
  • Wagman, A.S., Nuss, J.M., Current therapies and emerging targets for the treatment of diabetes (2001) Current Pharmaceutical Design, 7 (6), pp. 417-450. , DOI 10.2174/1381612013397915
  • Asano, N., Kato, A., Watson, A.A., Therapeutic applications of sugar-mimicking glycosidase inhibitors (2001) Mini Rev Med Chem, 1, pp. 145-154. , 10.2174/1389557013407052 12374106 10.2174/1389557013407052 1:CAS:528:DC%2BD3MXks1Cltbs%3D
  • Wen, Y.-M., Lin, X., MaCurrent, Z.M., Exploiting new potential targets for anti-hepatitis B virus drugs (2003) Current Drug Targets - Infectious Disorders, 3 (3), pp. 241-246. , DOI 10.2174/1568005033481141
  • Robina, I., Moreno-Vargas, A.J., Carmona, A.T., Vogel, P., Glycosidase inhibitors as potential HIV entry inhibitors? (2004) Current Drug Metabolism, 5 (4), pp. 329-361. , DOI 10.2174/1389200043335513
  • Asano, N., Kizu, H., Oseki, K., Tomioka, E., Matsui, K., Okamoto, M., Babat, M., N-alkylated nitrogen-in-the-ring sugars: Conformational basis of inhibition of glycosidases and HW-1 replication (1995) J Med Chem, 38, pp. 2349-2356. , 10.1021/jm00013a012 7608901 10.1021/jm00013a012 1:CAS:528: DyaK2MXmtVyhtrw%3D
  • Marston, A., Kissling, J., Hostettmann, K., A rapid TLC bioautographic method for the detection of acetylcholinesterase and butyrylcholinesterase inhibitors in plants (2002) Phytochemical Analysis, 13 (1), pp. 51-54. , DOI 10.1002/pca.623
  • Ramallo, I.A., Zacchino, S.A., Furlan, R.L.E., A rapid TLC autographic method for the detection of xanthine oxidase inhibitors and superoxide scavengers (2006) Phytochemical Analysis, 17 (1), pp. 15-19. , DOI 10.1002/pca.874
  • Salazar, M.O., Furlan, R.L.E., A rapid TLC autographic method for the detection of glucosidase inhibitors (2007) Phytochemical Analysis, 18 (3), pp. 209-212. , DOI 10.1002/pca.971
  • Emmelin, N., Feldberg, W., The mechanism of the sting of the common nettle (Urtica urens) (1947) J Physiol, 106, pp. 440-455. , 1:CAS:528:DyaH1cXht1WgsQ%3D%3D
  • Field, R.A., Haines, A.H., Chrystal, E.J.T., Luszniak, M.C., Histidines, histamines and imidazoles as glycosidase inhibitors (1991) Biochem J, 274, pp. 885-889. , 2012615 1:CAS:528:DyaK3MXisVegsb0%3D
  • Magdolen, P., Vasella, A., Monocyclic, substituted imidazoles as glycosidase inhibitors (2005) Helvetica Chimica Acta, 88 (9), pp. 2454-2469. , DOI 10.1002/hlca.200590182
  • Li, Y.-K., Hsu, H.-S., Chang, L.-F., Chen, G., New imidazoles as probes of the active site topology and potent inhibitors of β-glucosidase (1998) Journal of Biochemistry, 123 (3), pp. 416-422
  • Wrodnigg, T.M., Diness, F., Gruber, C., Hausler, H., Lundt, I., Rupitz, K., Steiner, A.J., Wolfler, H., Probing the aglycon binding site of a β-glucosidase: A collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors (2004) Bioorganic and Medicinal Chemistry, 12 (13), pp. 3485-3495. , DOI 10.1016/j.bmc.2004.04.037, PII S0968089604003402
  • Viant, M.R., Improved methods for the acquisition and interpretation of NMR metabolomic data (2003) Biochemical and Biophysical Research Communications, 310 (3), pp. 943-948. , DOI 10.1016/j.bbrc.2003.09.092
  • Daszykowski, M., Serneels, S., Kaczmarek, K., Van Espen, P., Croux, C., Walczak, B., TOMCAT: A MATLAB toolbox for multivariate calibration techniques (2007) Chemometrics and Intelligent Laboratory Systems, 85 (2), pp. 269-277. , DOI 10.1016/j.chemolab.2006.03.006, PII S0169743906000724

Citas:

---------- APA ----------
Salazar, M.O., Micheloni, O., Escalante, A.M. & Furlan, R.L.E. (2011) . Discovery of a β-glucosidase inhibitor from a chemically engineered extract prepared through sulfonylation. Molecular Diversity, 15(3), 713-719.
http://dx.doi.org/10.1007/s11030-010-9301-2
---------- CHICAGO ----------
Salazar, M.O., Micheloni, O., Escalante, A.M., Furlan, R.L.E. "Discovery of a β-glucosidase inhibitor from a chemically engineered extract prepared through sulfonylation" . Molecular Diversity 15, no. 3 (2011) : 713-719.
http://dx.doi.org/10.1007/s11030-010-9301-2
---------- MLA ----------
Salazar, M.O., Micheloni, O., Escalante, A.M., Furlan, R.L.E. "Discovery of a β-glucosidase inhibitor from a chemically engineered extract prepared through sulfonylation" . Molecular Diversity, vol. 15, no. 3, 2011, pp. 713-719.
http://dx.doi.org/10.1007/s11030-010-9301-2
---------- VANCOUVER ----------
Salazar, M.O., Micheloni, O., Escalante, A.M., Furlan, R.L.E. Discovery of a β-glucosidase inhibitor from a chemically engineered extract prepared through sulfonylation. Mol. Diversity. 2011;15(3):713-719.
http://dx.doi.org/10.1007/s11030-010-9301-2