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Abstract:

In this work we present an efficient, environmentally friendly approach to the synthesis of a series of hyodeoxycholic acid derivatives applying Biocatalysis. Fifteen acetyl and ester derivatives, twelve of them new, were obtained through an enzymatic strategy in a fully regioselective way and in very good to excellent yield. In order to find the optimal reaction conditions, the influence of several parameters such as enzyme source, alcohol or acylating agent:substrate ratio, enzyme:substrate ratio, temperature and reaction solvent was considered. The excellent results obtained made this procedure very efficient, particularly considering the low amount of enzyme required. In addition, this methodology uses mild reaction conditions and has reduced environmental impact, making biocatalysis a suitable way to obtaining these bile acids derivatives. © 2018 Elsevier Inc.

Registro:

Documento: Artículo
Título:Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives
Autor:Chanquia, S.N.; Ripani, E.; Baldessari, A.; García Liñares, G.
Filiación:Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, piso 3, Buenos Aires, C1428EGA, Argentina
Palabras clave:Bile acid; Biocatalysis; Hyodeoxycholic acid; Lipases; acetic acid derivative; alcohol; bile acid; ester derivative; hyodeoxycholic acid; solvent; triacylglycerol lipase; Article; biocatalysis; regioselectivity; synthesis
Año:2018
Volumen:140
Página de inicio:45
Página de fin:51
DOI: http://dx.doi.org/10.1016/j.steroids.2018.09.004
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:alcohol, 64-17-5; hyodeoxycholic acid, 83-49-8; triacylglycerol lipase, 9001-62-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v140_n_p45_Chanquia

Referencias:

  • Setchell, K.D., Kritchevsky, D., Nair, P.P., The Bile Acids: Chemistry, Physiology, and Metabolism: Volume 4: Methods and Applications (2012), Springer Science & Business Media; Karpen, H.E., Karpen, S.J., Bile Acid Metabolism During Development, Fetal and Neonatal Physiology (2017), pp. 913-929. , fifth ed. Elsevier; Hofmann, A.F., Hagey, L.R., Key discoveries in bile acid chemistry and biology and their clinical applications: history of the last eight decades (2014) J. Lipid Res., 55 (8), pp. 1553-1595
  • Feher, J.J., Quantitative Human Physiology: An Introduction (2017), Academic Press; Yu, D., Mattern, D.L., Forman, B.M., An improved synthesis of 6α-ethylchenodeoxycholic acid (6ECDCA), a potent and selective agonist for the Farnesoid X Receptor (FXR) (2012) Steroids, 77 (13), pp. 1335-1338
  • Bansal, S., Singh, M., Kidwai, S., Bhargava, P., Singh, A., Sreekanth, V., Singh, R., Bajaj, A., Bile acid amphiphiles with tunable head groups as highly selective antitubercular agents (2014) MedChemComm, 5 (11), pp. 1761-1768
  • Brossard, D., El Kihel, L., Clément, M., Sebbahi, W., Khalid, M., Roussakis, C., Rault, S., Synthesis of bile acid derivatives and in vitro cytotoxic activity with pro-apoptotic process on multiple myeloma (KMS-11), glioblastoma multiforme (GBM), and colonic carcinoma (HCT-116) human cell lines (2010) Eur. J. Med. Chem., 45 (7), pp. 2912-2918
  • Gadaleta, R.M., Garcia-Irigoyen, O., Moschetta, A., Bile acids and colon cancer: Is FXR the solution of the conundrum? (2017) Mol. Aspects Med., 56, pp. 66-74
  • Li, T., Chiang, J.Y., Bile acids as metabolic regulators (2015) Curr. Opinion Gastroenterol., 31 (2), p. 159
  • Hassan, N., Ahad, A., Ali, M., Ali, J., Chemical permeation enhancers for transbuccal drug delivery (2010) Expert Opinion Drug Deliv., 7 (1), pp. 97-112
  • Stojančević, M., Pavlović, N., Goločorbin-Kon, S., Mikov, M., Application of bile acids in drug formulation and delivery (2013) Front. Life Sci., 7 (3-4), pp. 112-122
  • Jampilek, J., Brychtova, K., Azone analogues: classification, design, and transdermal penetration principles (2012) Med. Res. Rev., 32 (5), pp. 907-947
  • Cirri, M., Maestrelli, F., Mennini, N., Mura, P., Combined use of bile acids and aminoacids to improve permeation properties of acyclovir (2015) Int. J. Pharm., 490 (1), pp. 351-359
  • Yang, L., Fawcett, J.P., Østergaard, J., Zhang, H., Tucker, I.G., Mechanistic studies of the effect of bile salts on rhodamine 123 uptake into RBE4 cells (2011) Mol. Pharm., 9 (1), pp. 29-36
  • Yang, L., Zhang, H., Fawcett, J.P., Mikov, M., Tucker, I.G., Effect of bile salts on the transport of morphine-6-glucuronide in rat brain endothelial cells (2011) J. Pharm. Sci., 100 (4), pp. 1516-1524
  • Shih, D.M., Shaposhnik, Z., Meng, Y., Rosales, M., Wang, X., Wu, J., Ratiner, B., Lusis, A.J., Hyodeoxycholic acid improves HDL function and inhibits atherosclerotic lesion formation in LDLR-knockout mice (2013) FASEB J., 27 (9), pp. 3805-3817
  • Buchholz, K., Kasche, V., Bornscheuer, U.T., Biocatalysts and enzyme Technology (2012), John Wiley & Sons; Faber, K., Biotransformations in Organic Chemistry: A Textbook (2011), Springer Science & Business Media; Whitthall, J., Sutton, P., Practical Methods for Biocatalysis and Biotransformations 2 (2012), John Wiley & Sons Ltd. New York; Tao, J.A., Lin, G.-Q., Liese, A., Biocatalysis for the Pharmaceutical Industry: Discovery, Development, and Manufacturing (2009), John Wiley & Sons; Carrea, G., Riva, S., Organic Synthesis with Enzymes in Non-aqueous Media (2008), John Wiley & Sons; Baldessari, A., Iglesias, L.E., Lipases in green chemistry: acylation and alcoholysis on steroids and nucleosides, Lipases and Phospholipases (2012) Methods Protocols, pp. 457-469
  • Hall, M., Kroutil, W., Faber, K., (2013), pp. 221-231. , The evolving role of biocatalysis in asymmetric synthesis, Asymmetric Synthesis II: More Methods and Applications; Gotor, V., Alfonso, I., García-Urdiales, E., Asymmetric Organic Synthesis with Enzymes (2008), John Wiley & Sons; Monsalve, L.N., Petroselli, G., Erra-Ballsells, R., Vázquez, A., Baldessari, A., Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films (2014) Polym. Int., 63 (8), pp. 1523-1530
  • Monsalve, L.N., Machado Rada, M.Y., Ghini, A.A., Baldessari, A., An efficient enzymatic preparation of 20-pregnane succinates: chemoenzymatic synthesis of 20β-hemisuccinyloxy-5αH-pregnan-3-one (2008) Tetrahedron, 64 (8), pp. 1721-1730
  • Quintana, P.G., Baldessari, A., Lipase-catalyzed regioselective preparation of fatty acid esters of hydrocortisone (2009) Steroids, 74 (13), pp. 1007-1014
  • Quintana, P.G., Canet, A., Marciello, M., Valero, F., Palomo, J.M., Baldessari, A., Enzyme-catalyzed preparation of chenodeoxycholic esters by an immobilized heterologous Rhizopus oryzae lipase (2015) J. Mol. Catal. B Enzym., 118, pp. 36-42
  • Quintana, P.G., García Liñares, G., Chanquia, S.N., Gorojod, R.M., Kotler, M.L., Baldessari, A., Improved enzymatic procedure for the synthesis of anandamide and N-fatty acylalkanolamine analogues: a combination strategy to antitumor activity (2016) Eur. J. Org. Chem., 2016 (3), pp. 518-528
  • Quintana, P.G., Guillén, M., Marciello, M., Valero, F., Palomo, J.M., Baldessari, A., Immobilized heterologous Rhizopus oryzae lipase as an efficient catalyst in the acetylation of cortexolone (2012) Eur. J. Org. Chem., 2012 (23), pp. 4306-4312
  • Rustoy, E.M., Baldessari, A., An efficient chemoenzymatic synthesis of the bactericide lapyrium chloride (2005) Eur. J. Org. Chem., 2005 (21), pp. 4628-4632
  • Rustoy, E.M., Sato, Y., Nonami, H., Erra-Balsells, R., Baldessari, A., Lipase-catalyzed synthesis and characterization of copolymers from ethyl acrylate as the only monomer starting material (2007) Polymer, 48 (6), pp. 1517-1525
  • García Liñares, G., Arroyo Mañez, P., Baldessari, A., Lipase-catalyzed synthesis of substituted phenylacetamides: Hammett analysis and computational study of the enzymatic aminolysis (2014) Eur. J. Org. Chem., 2014 (29), pp. 6439-6450
  • García Liñares, G., Parraud, G., Labriola, C., Baldessari, A., Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana (2012) Bioorg. Med. Chem., 20 (15), pp. 4614-4624
  • Chanquia, S.N., Boscaro, N., Alche, L., Baldessari, A., Liñares, G.G., An efficient lipase-catalyzed synthesis of fatty acid derivatives of vanillylamine with antiherpetic activity in acyclovir-resistant strains (2017) ChemistrySelect, 2 (4), pp. 1537-1543
  • García Liñares, G., Antonela Zígolo, M., Simonetti, L., Longhi, S.A., Baldessari, A., Enzymatic synthesis of bile acid derivatives and biological evaluation against Trypanosoma cruzi (2015) Bioorg. Med. Chem., 23 (15), pp. 4804-4814
  • Zígolo, M.A., García Liñares, G., Baldessari, A., New cholic acid derivatives: Biocatalytic synthesis and molecular docking study (2016) Steroids, 107, pp. 10-19
  • Tecelão, C., Rivera, I., Sandoval, G., Ferreira-Dias, S., Carica papaya latex: a low-cost biocatalyst for human milk fat substitutes production (2012) Eur. J. Lipid Sci. Technol., 114 (3), pp. 266-276
  • Haslewood, G., Comparative studies ofbile salts’. 7. Bile acids of the coypu, Myocastor coypus (1954) Biochem. J., 56 (4), p. 581
  • Haslewood, G., Comparative studies ofbile salts’. 9. The isolation and chemistry of hyocholic acid (1956) Biochem. J., 62 (4), p. 637
  • Baldessari, A., Lipases as catalysts in synthesis of fine chemicals, lipases and phospholipases (2012) Methods Protocols, pp. 445-456
  • Baldessari, A., Bruttomesso, A.C., Gros, E.G., Lipase-catalysed regioselective deacetylation of androstane derivatives (1996) Helv. Chim. Acta, 79 (4), pp. 999-1004

Citas:

---------- APA ----------
Chanquia, S.N., Ripani, E., Baldessari, A. & García Liñares, G. (2018) . Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives. Steroids, 140, 45-51.
http://dx.doi.org/10.1016/j.steroids.2018.09.004
---------- CHICAGO ----------
Chanquia, S.N., Ripani, E., Baldessari, A., García Liñares, G. "Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives" . Steroids 140 (2018) : 45-51.
http://dx.doi.org/10.1016/j.steroids.2018.09.004
---------- MLA ----------
Chanquia, S.N., Ripani, E., Baldessari, A., García Liñares, G. "Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives" . Steroids, vol. 140, 2018, pp. 45-51.
http://dx.doi.org/10.1016/j.steroids.2018.09.004
---------- VANCOUVER ----------
Chanquia, S.N., Ripani, E., Baldessari, A., García Liñares, G. Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives. Steroids. 2018;140:45-51.
http://dx.doi.org/10.1016/j.steroids.2018.09.004