47676-48-2Relevant articles and documents
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.
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.
