Enzymatic synthesis of bile acid derivatives and biological evaluation against Trypanosoma cruzi

Liñares, Guadalupe Eugenia Garcia; Zígolo, María Antonela; Simonetti, Leandro; Longhi, Silvia Andrea; Baldessari, Alicia

doi:10.1016/j.bmc.2015.05.035

Cited by 24 publications

(31 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From the obtained results, it can be seen that 100% conversion was achieved even at E/S = 0.5 after 72 hs of reaction. LIP showed a superb efficiency for this reaction, since this value of E/S is very low in comparison with previous work [36,37]. Considering the results schematized in the figure 2, E/S = 0.5 was the ratio of choice.…”

Section: Enzymatic Esterificationmentioning

confidence: 53%

“…It is interesting to note that towards biocatalytic esterification, HDCA behaves differently in comparison to other dihydroxylated bile acids previously studied, whereas its reactivity is similar to cholic acid (CA) [36,37]. In the case of chenodeoxycholic acid (CDCA) and deoxycholic acid (DCA), CAL B was the best biocatalyst and the conditions involved E/S: 10, Nu/S: 5, hexane as solvent and a temperature of 55 °C.…”

Section: Enzymatic Esterificationmentioning

confidence: 98%

“…Usually, the potential application of bile acids depends on their amphiphilic properties, therefore we have recently studied and reported the synthesis of derivatives of many bile acids searching for an increase in its lipophilicity [28,36,37]. We described the application of lipases to the esterification, acetylation and alcoholysis of CDCA, DCA, LCA and CA.…”

Section: Scheme 1 Structure Of Important Bile Acidsmentioning

confidence: 99%

“…In addition, the reaction using ethanol both as nucleophile and solvent was also performed. Taking into account the optimal reaction conditions for similar transformations, the reactions were carried out at 55 °C using E/S: 10 and nucleophile:substrate ratio Nu/S: 10 [36,37].…”

Section: Enzymatic Esterificationmentioning

confidence: 99%

“…Recently, we have reported the synthesis of 3-acetyl derivatives of chenodeoxycholic and deoxycholic acid using CAL B as biocatalyst. Under the same reaction conditions, with lithocholic acid as substrate, the lipase catalyzed both the acetylation and esterification reactions affording ethyl lithocholate 3-acetate as the only product in one pot-two steps [36]. In addition, it was not possible to acetylate cholic acid in a regioselective way, chemically or enzymatically.…”

Section: Enzymatic Acetylationmentioning

confidence: 99%

See 4 more Smart Citations

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

et al. 2018

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Enzymatic Esterificationmentioning

confidence: 53%

Section: Enzymatic Esterificationmentioning

confidence: 98%

Section: Scheme 1 Structure Of Important Bile Acidsmentioning

confidence: 99%

Section: Enzymatic Esterificationmentioning

confidence: 99%

Section: Enzymatic Acetylationmentioning

confidence: 99%

See 3 more Smart Citations

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

The Applications of Acetone and Ethyl Acetate

Wan

2017

Solvents as Reagents in Organic Synthesis

View full text Add to dashboard Cite

Improving Retinoic Acid Efficacy: Lipase‐Catalyzed Synthesis of Derivatives with Antiviral Activity

Bravo,

Montalbetti,

Freije García

et al. 2024

ChemBioChem

View full text Add to dashboard Cite

An efficient enzymatic approach was applied to the synthesis of new derivatives of retinoic acid. Nine derivatives, four of them new compounds, were obtained through lipase‐catalysis with excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile:substrate ratio, enzyme:substrate ratio, solvent and temperature was studied. The excellent results obtained by lipase catalysis made the procedure very efficient considering their advantages such as mild reaction conditions and low environmental impact. In addition, several synthesized compounds exhibited lower cytotoxicity than the retinoic acid in Vero cells and a remarkably higher antiviral activity against Herpes simplex virus type 1 (HSV‐1) and Herpes simplex virus type 2 (HSV‐2).

show abstract

Enzymatic synthesis of bile acid derivatives and biological evaluation against Trypanosoma cruzi

Cited by 24 publications

References 45 publications

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

Bile acids: Lipase-catalyzed synthesis of new hyodeoxycholic acid derivatives

The Applications of Acetone and Ethyl Acetate

Improving Retinoic Acid Efficacy: Lipase‐Catalyzed Synthesis of Derivatives with Antiviral Activity

Contact Info

Product

Resources

About