47676-48-2Relevant academic research and scientific papers
METHODS FOR PREPARING BILE ACIDS
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, (2019/02/15)
The present disclosure provides methods of preparing cholic acid, deoxycholic acid, or chenodeoxycholic acid, an ester thereof, or a pharmaceutically or cosmetically acceptable salt thereof, and novel and useful synthetic intermediates, for example, as described for methods 1, 1A, 1B, 2, 3, 3A, and 4. The method can start with a plant derived steroid as a starting material, such as dehydroepiandrosterone (DHEA) or Acetyl-dehydroepiandrosterone (Ac-DHEA). Also provided are pharmaceutical or cosmetic compositions and uses thereof, which comprise one or more of cholic acid, deoxycholic acid, or chenodeoxycholic acid, an ester thereof, or a pharmaceutically or cosmetically acceptable salt thereof, which is of high purity, for example, free of animal derived impurities.
Oral Delivery of Cholic Acid-Derived Amphiphile Helps in Combating Salmonella-Mediated Gut Infection and Inflammation
Yadav, Kavita,Yavvari, Prabhu Srinivas,Pal, Sanjay,Kumar, Sandeep,Mishra, Deepakkumar,Gupta, Siddhi,Mitra, Madhurima,Soni, Vijay,Khare, Neha,Sharma, Priyanka,Srikanth, Chittur V.,Kapil, Arti,Singh, Archana,Nandicoori, Vinay Kumar,Bajaj, Avinash
, p. 721 - 732 (2019/02/19)
A major impediment to developing effective antimicrobials against Gram-negative bacteria like Salmonella is the ability of the bacteria to develop resistance against existing antibiotics and the inability of the antimicrobials to clear the intracellular bacteria residing in the gastrointestinal tract. As the critical balance of charge and hydrophobicity is required for effective membrane-targeting antimicrobials without causing any toxicity to mammalian cells, herein we report the synthesis and antibacterial properties of cholic acid-derived amphiphiles conjugated with alkyl chains of varied hydrophobicity. Relative to other hydrophobic counterparts, a compound with hexyl chain (6) acted as an effective antimicrobial against different Gram-negative bacteria. Apart from its ability to permeate the outer and inner membranes of bacteria; compound 6 can cross the cellular and lysosomal barriers of epithelial cells and macrophages and kill the facultative intracellular bacteria without disrupting the mammalian cell membranes. Oral delivery of compound 6 was able to clear the Salmonella-mediated gut infection and inflammation, and was able to combat persistent, stationary, and multi-drug-resistant clinical strains. Therefore, our study reveals the ability of cholic acid-derived amphiphiles to clear intracellular bacteria and Salmonella-mediated gut infection and inflammation.
New cholic acid derivatives: Biocatalytic synthesis and molecular docking study
Zígolo, M. Antonela,García Li?ares, Guadalupe,Baldessari, Alicia
, p. 10 - 19 (2016/03/04)
A series of cholic acid derivatives was synthesized by enzyme catalysis. Eleven acetyl and ester derivatives of cholic acid, eight of them new compounds, were obtained through regioselective lipase-catalyzed reactions in very good to excellent yield. The influence of various reaction parameters in the enzymatic esterification, acetylation and alcoholysis reactions, such as enzyme source, alcohol or acylating agent: substrate ratio, enzyme: substrate ratio, solvent and temperature, was studied. Moreover, in order to shed light to cholic acid behavior in the enzymatic reactions, molecular docking of the lipase with cholic acid and some derivatives was carried out.
Synthesis and antimicrobial activity of cholic acid hydrazone analogues
Rasras, Anas J.M.,Al-Tel, Taleb H.,Al-Aboudi, Amal F.,Al-Qawasmeh, Raed A.
experimental part, p. 2307 - 2313 (2010/06/19)
Synthesis and antimicrobial activity of cholic acid analogues 4a-t are reported. The synthesis of 4a-t was accomplished from ethylcholate 2. The hydrazone moiety was introduced via coupling of the cholic acide hydrazide (3) with appropriately functionalized aldehyde utilizing acetic acid as a catalyst. Quiet of interest in relation to the synthesized hydrazones is the formation of two rotamers s-cis.E and s-trans.E. Most compounds showed stronger antimicrobial activity against Gram-positive bacteria than Cefaclor and Cefixime. Compounds 4d, 4i and 4j indicated 15-fold stronger antimicrobial activities against Enterobacter faecalis compared to Cefaclor and Cefixime. Some of the synthesized compounds (e.g. 4a, 4c, 4d, 4i, and 4l) reflected twofolds less activity against Escherichia coli relative to Cefixime.
Regio- and stereoselective reductions of dehydrocholic acid
Cravotto, Giancarlo,Binello, Arianna,Boffa, Luisa,Rosati, Ornelio,Boccalini, Marco,Chimichi, Stefano
, p. 469 - 475 (2007/10/03)
Dehydrocholic acid (DHCA), an unnatural bile acid, is manufactured by oxidation of cholic acid. Its biotransformation by two basidiomycetes (Trametes hirsuta and Collybia velutipes) is reported. These mycelia showed different affinities for the substrate and selectivities of attack: T. hirsuta in particular regio- and stereoselectively reduced the 3-keto group to yield 3α-hydroxy-7,12-diketo-5β-cholan-24-oic acid (7,12-diketolithocolic acid) as the main product. A number of different chemical reductions were carried out on DHCA; among them hydrogenation with Raney Nickel in water under high-intensity ultrasound proved highly regio- and stereoselective, yielding 7,12-diketolithocolic acid exclusively. 1H and 13C resonances were assigned in details thanks to a series of 1D and 2D NMR runs including DEPT, NOESY, H-H COSY, gHSQC and gHMBC.
Chemical modifications of bile acids under high-intensity ultrasound or microwave irradiation
Cravotto, Giancarlo,Boffa, Luisa,Turello, Marta,Parenti, Massimo,Barge, Alessandro
, p. 77 - 83 (2007/10/03)
High-intensity ultrasound (HIU) and microwave (MW) irradiation, having emerged as effective promoters of organic reactions, were exploited for the synthesis of bile acids derivatives. Esterification, amidation, hydrolysis, oxidation, and reduction were investigated. Compared to conventional methods, both techniques proved much more efficient, increasing product yields and dramatically cutting down reaction times. Scaled-up studies are now under way.
