cholates

Summary

Summary: Salts and esters of CHOLIC ACID.

Top Publications

  1. Shih A, Freddolino P, Sligar S, Schulten K. Disassembly of nanodiscs with cholate. Nano Lett. 2007;7:1692-6 pubmed
    ..For this purpose, small-angle X-ray scattering experiments and coarse-grained molecular dynamics simulations were performed and compared. The study offers a detailed view of nanodisc dynamics. ..
  2. Groen A, Kunne C, Paulusma C, Kramer W, Agellon L, Bull L, et al. Intestinal bile salt absorption in Atp8b1 deficient mice. J Hepatol. 2007;47:114-22 pubmed
    ..Despite these findings, we observed only mildly impaired canalicular BS transport. In the present report we tested the hypothesis that Atp8b1(G308V/G308V) mice hyperabsorb BS in the intestine during BS feeding...
  3. Groen A, Kunne C, Oude Elferink R. Increased serum concentrations of secondary bile salts during cholate feeding are due to coprophagy. A study with wild-type and Atp8b1-deficient mice. Mol Pharm. 2006;3:756-61 pubmed
    ..Whether housed in conventional cages or in metabolic cages, wild-type and Atp8b1-deficient mice had similar concentrations in portal blood, suggesting that intestinal bile salt absorption is not altered in Atp8b1-deficient mice. ..
  4. Bayburt T, Grinkova Y, Sligar S. Assembly of single bacteriorhodopsin trimers in bilayer nanodiscs. Arch Biochem Biophys. 2006;450:215-22 pubmed
    ..These nanoscale bilayers offer the opportunity to understand and control the assembly of oligomeric integral membrane proteins critical to macromolecular recognition and cellular signaling. ..
  5. Zhao Y, Zhong Z. Oligomeric cholates: amphiphilic foldamers with nanometer-sized hydrophilic cavities. J Am Chem Soc. 2005;127:17894-901 pubmed
    ..and the resulting amino-functionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in ..
  6. Holert J, Yücel O, Suvekbala V, Kulić Z, Möller H, Philipp B. Evidence of distinct pathways for bacterial degradation of the steroid compound cholate suggests the potential for metabolic interactions by interspecies cross-feeding. Environ Microbiol. 2014;16:1424-40 pubmed publisher
    ..These results indicate that bacteria with potentially different pathways for cholate degradation coexist in natural habitats and may interact via interspecies cross-feeding. ..
  7. Cerda Maira F, Ringelberg C, Taylor R. The bile response repressor BreR regulates expression of the Vibrio cholerae breAB efflux system operon. J Bacteriol. 2008;190:7441-52 pubmed publisher
    ..These results provide new insight into a transcriptional regulator and a transport system that likely play essential roles in the ability of V. cholerae to resist the action of bile in the host. ..
  8. Yuangklang C, Wensing T, Lankhorst A, Lemmens A, Fielmich Bouman X, Jittakhot S, et al. Cholate and deoxycholate counteract the calcium-induced lowering of fat digestion in rats. J Anim Physiol Anim Nutr (Berl). 2005;89:337-41 pubmed
    ..As a result, more cholate than deoxycholate would be available to support the process of fat digestion. Rats fed cholate had higher liver and serum cholesterol concentrations than did the rats fed deoxycholate. ..
  9. Naso F, Gandaglia A, Formato M, Cigliano A, Lepedda A, Gerosa G, et al. Differential distribution of structural components and hydration in aortic and pulmonary heart valve conduits: Impact of detergent-based cell removal. Acta Biomater. 2010;6:4675-88 pubmed publisher
    ..Future insights into the distribution of load-bearing components in human conduits are likely to provide indications important to optimize the surgical positioning of valvular grafts. ..

More Information

Publications62

  1. Wehner F, Tinel H. Uptake of bromosulfophthalein via SO2-4/OH- exchange increases the K+ conductance of rat hepatocytes. Am J Physiol. 1999;276:G1380-90 pubmed
    ..It is concluded that K+ channel activation by BSP (as well as by DIDS and indocyanine green) may reflect a physiological mechanism linking the sinusoidal uptake of certain anions to their electrogenic canalicular secretion. ..
  2. Naruhashi K, Kurahashi Y, Fujita Y, Kawakita E, Yamasaki Y, Hattori K, et al. Comparison of the expression and function of ATP binding cassette transporters in Caco-2 and T84 cells on stimulation by selected endogenous compounds and xenobiotics. Drug Metab Pharmacokinet. 2011;26:145-53 pubmed
    ..These results suggest that Caco-2 cells are more suitable for identifying whether MDR1 mediates drug transport, while T84 cells are more useful for assessing the induction capacity of compounds. ..
  3. De Jong M, Huskens J, Reinhoudt D. Influencing the binding selectivity of self-assembled cyclodextrin monolayers on gold through their architecture. Chemistry. 2001;7:4164-70 pubmed
    ..The mixed monolayers of 2, in which the cyclodextrin is less substituted and has more flexibility, bind steroidal guests (6a-6e) with the same selectivity as beta-cyclodextrin in solution. ..
  4. Xie J, Yang Z, Yu B, Zhang L, Sun Y, Weng S, et al. [Study on calcium-cholate-phosphate ternary complexes by FTIR spectroscopy]. Guang Pu Xue Yu Guang Pu Fen Xi. 2001;21:111-2 pubmed
    ..5:1 in reaction. The FTIR spectroscopic results demonstrated that in the ternary complexes Ca2+ was coordinated with O in both COO- and PO(4)3- groups. ..
  5. Deeg M. Dietary cholate is required for antiatherogenic effects of ethanol in mouse models. Alcohol Clin Exp Res. 2003;27:1499-506 pubmed
    ..Dietary cholate increased and ethanol reduced NF-kappaB binding activity in the aorta. These results suggest that ethanol inhibits atherosclerosis in the presence of dietary cholate, which may occur via an anti-inflammatory mechanism. ..
  6. Widanapathirana L, Zhao Y. Aromatically functionalized cyclic tricholate macrocycles: aggregation, transmembrane pore formation, flexibility, and cooperativity. J Org Chem. 2012;77:4679-87 pubmed publisher
    ..The acceptor-acceptor interactions among naphthalenediimide (NDI) groups were more effective than the pyrene-NDI donor-acceptor interactions in promoting the transmembrane pore formation of the oligocholate macrocycles. ..
  7. Reed J, Kelley R, Backes W. An evaluation of methods for the reconstitution of cytochromes P450 and NADPH P450 reductase into lipid vesicles. Drug Metab Dispos. 2006;34:660-6 pubmed
    ..Both cholate methods resulted in the loss of a proportion of spectrally detectable carbon monoxyferrous P450, resulting from incubation of the proteins with detergent. ..
  8. Ravnikar M, Irman A, Radic N, Lunder M, Strukelj B. Chemoporation using saponins or cholates: an alternative method for transformation of bacterial cells. Biotechnol Lett. 2009;31:1943-6 pubmed publisher
    ..New data about interactions between cholates and biomembranes is revealed that may contribute to better understanding of bacterial transformation.
  9. Simões S, Marques C, Cruz M, Cevc G, Martins M. The effect of cholate on solubilisation and permeability of simple and protein-loaded phosphatidylcholine/sodium cholate mixed aggregates designed to mediate transdermal delivery of macromolecules. Eur J Pharm Biopharm. 2004;58:509-19 pubmed
    ..Calcein efflux from such vesicles was compared with SPC/NaChol/SOD mixed aggregates. Our results should contribute to the future design of vesicle mediated transdermal delivery of antioxidant enzymes. ..
  10. Birkenmaier A, Möller H, Philipp B. Identification of a thiolase gene essential for ?-oxidation of the acyl side chain of the steroid compound cholate in Pseudomonas sp. strain Chol1. FEMS Microbiol Lett. 2011;318:123-30 pubmed publisher
    ..Sequence comparisons revealed that other steroid-degrading bacteria such as Comamonas testosteroni contain genes encoding proteins very similar to Skt, suggesting a widespread role of this enzyme in bacterial steroid degradation. ..
  11. Pan X, Zhao Y. Efficient construction of oligocholate foldamers via "click" chemistry and their tolerance of structural heterogeneity. Org Lett. 2009;11:69-72 pubmed publisher
    ..Despite large structural perturbations, the clicked oligocholates folded similarly as the parent foldamers, demonstrating the robustness of the solvophobically driven folding mechanism. ..
  12. Ren C, Gong T, Sun X, Zhang Z, Zhang Y. Alpha-Asarone incorporated in mixed micelles suitable for intravenous administration: formulation, in-vivo distribution and anaphylaxis study. Pharmazie. 2011;66:875-80 pubmed
    ..In conclusion, ARE-SPC-DC-MMs could be an excellent substitute for commercially available CA-AREs for intravenous administration. ..
  13. Yu L, Gupta S, Xu F, Liverman A, Moschetta A, Mangelsdorf D, et al. Expression of ABCG5 and ABCG8 is required for regulation of biliary cholesterol secretion. J Biol Chem. 2005;280:8742-7 pubmed
    ..Thus G5 and G8 are required to modulate biliary cholesterol secretion in response to cholate and diosgenin, but the choleretic effects of these two steroids are mediated by different mechanisms requiring FXR and PXR, respectively...
  14. Leclerc M, Grondin G, Gendron F, Sevigny J, Beaudoin A. Identification, characterization, and immunolocalization of a nucleoside triphosphate diphosphohydrolase in pig liver. Arch Biochem Biophys. 2000;377:372-8 pubmed
    ..In general, those located in the perilobular zone were more reactive than those located in the central zone and in the periphery of the centrolobular vein. ..
  15. Price C, Reid S, Driessen A, Abratt V. The Bifidobacterium longum NCIMB 702259T ctr gene codes for a novel cholate transporter. Appl Environ Microbiol. 2006;72:923-6 pubmed publisher
    ..longum ctr gene, encoding a cholate efflux transporter, was transformed into the efflux-negative mutant Escherichia coli KAM3, conferring resistance to bile salts and other antimicrobial compounds and causing the efflux of [14C]cholate...
  16. Hulzebos C, Voshol P, Wolters H, Kruit J, Ottenhof R, Groen A, et al. Bile duct proliferation associated with bile salt-induced hypercholeresis in Mdr2 P-glycoprotein-deficient mice. Liver Int. 2005;25:604-12 pubmed
    ..Bile duct proliferation in Mdr2(-/-) mice enhances cholehepatic shunting of bile salts, which is associated with a disproportionally high bile flow but does not affect bile salt synthesis. ..
  17. Zhao Y. Spacer-dependent folding and aggregation of oligocholates in SDS micelles. J Org Chem. 2009;74:7470-80 pubmed publisher
    ..Folding was favored both below and above the CMC of SDS and was enhanced by an increase in the chain length. ..
  18. Qiao Y, Lin Y, Yang Z, Chen H, Zhang S, Yan Y, et al. Unique temperature-dependent supramolecular self-assembly: from hierarchical 1D nanostructures to super hydrogel. J Phys Chem B. 2010;114:11725-30 pubmed publisher
    ..The driving forces of self-assembled complex nanostructures and the unique role of temperature are also discussed. ..
  19. Elsayed M, Cevc G. The vesicle-to-micelle transformation of phospholipid-cholate mixed aggregates: a state of the art analysis including membrane curvature effects. Biochim Biophys Acta. 2011;1808:140-53 pubmed publisher
    ..The smallest tested vesicles (2r(v)=45nm), with the highest bilayer curvature, require ~30% less cholate for complete solubilisation than the largest tested vesicles (2r(v)=120nm). ..
  20. Tripisciano C, Kozynchenko O, Linsberger I, Phillips G, Howell C, Sandeman S, et al. Activation-dependent adsorption of cytokines and toxins related to liver failure to carbon beads. Biomacromolecules. 2011;12:3733-40 pubmed publisher
    ..These structural changes went hand in hand with enhanced adsorption of small adsorbates, such as IL-6 and cholic acid and, to a lesser extent, also of large molecules, such as TNF-?. ..
  21. Krueger S, Henderson M, Siddens L, Vandyke J, Benninghoff A, Karplus P, et al. Characterization of sulfoxygenation and structural implications of human flavin-containing monooxygenase isoform 2 (FMO2.1) variants S195L and N413K. Drug Metab Dispos. 2009;37:1785-91 pubmed publisher
    ..Although these allelic variants are expected to occur infrequently as mutations to the FMO2*1 allele, they contribute to our overall understanding of mammalian FMO structure and function. ..
  22. Bina X, Philippart J, Bina J. Effect of the efflux inhibitors 1-(1-naphthylmethyl)-piperazine and phenyl-arginine-beta-naphthylamide on antimicrobial susceptibility and virulence factor production in Vibrio cholerae. J Antimicrob Chemother. 2009;63:103-8 pubmed publisher
    ..RND efflux inhibitors represent potential novel therapeutics for the treatment of cholera. ..
  23. Shimono K, Goto M, Kikukawa T, Miyauchi S, Shirouzu M, Kamo N, et al. Production of functional bacteriorhodopsin by an Escherichia coli cell-free protein synthesis system supplemented with steroid detergent and lipid. Protein Sci. 2009;18:2160-71 pubmed publisher
    ..This approach might be useful for the high yield production of functional membrane proteins. ..
  24. Holert J, Kulić Z, Yücel O, Suvekbala V, Suter M, Möller H, et al. Degradation of the acyl side chain of the steroid compound cholate in Pseudomonas sp. strain Chol1 proceeds via an aldehyde intermediate. J Bacteriol. 2013;195:585-95 pubmed publisher
    ..The reaction leading to the aldehyde is presumably catalyzed by an aldolase encoded by the gene skt, which was previously predicted to be a ?-ketothiolase. ..
  25. Houbiers M, Spruijt R, Wolfs C, Hemminga M. Conformational and aggregational properties of the gene 9 minor coat protein of bacteriophage M13 in membrane-mimicking systems. Biochemistry. 1999;38:1128-35 pubmed
    ..On the basis of our results, we propose that the principal conformational state of membrane-bound gene 9 protein in vivo is alpha-helical. ..
  26. Gui X, Carraway R. Enhancement of jejunal absorption of conjugated bile acid by neurotensin in rats. Gastroenterology. 2001;120:151-60 pubmed
    ..This effect of NT may involve increases in paracellular absorption and carrier-mediated transport by mechanisms not yet identified. ..
  27. van Aardt M, Duncan S, Bourne D, Marcy J, Long T, Hackney C, et al. Flavor threshold for acetaldehyde in milk, chocolate milk, and spring water using solid phase microextraction gas chromatography for quantification. J Agric Food Chem. 2001;49:1377-81 pubmed
  28. Tran P, Hiou Tim F, Frosst P, Lussier Cacan S, Bagley P, Selhub J, et al. The curly-tail (ct) mouse, an animal model of neural tube defects, displays altered homocysteine metabolism without folate responsiveness or a defect in Mthfr. Mol Genet Metab. 2002;76:297-304 pubmed
  29. Hwang E, Cheong H, Kim S, Kwon O, Blain K, Choe S, et al. Crystal structure of the EnvZ periplasmic domain with CHAPS. FEBS Lett. 2017;591:1419-1428 pubmed publisher
    ..Together with ?-galactosidase assay, these results suggest that bile salts may affect the EnvZ structure and function in Escherichia coli. ..
  30. Holert J, Jagmann N, Philipp B. The essential function of genes for a hydratase and an aldehyde dehydrogenase for growth of Pseudomonas sp. strain Chol1 with the steroid compound cholate indicates an aldolytic reaction step for deacetylation of the side chain. J Bacteriol. 2013;195:3371-80 pubmed publisher
    ..Based on these results and on sequence alignments with predicted aldolases from other bacteria, we conclude that the enzyme encoded by sal catalyzes this aldolytic cleavage. ..
  31. DiVittorio K, Lambert T, Smith B. Steroid-derived phospholipid scramblases induce exposure of phosphatidylserine on the surface of red blood cells. Bioorg Med Chem. 2005;13:4485-90 pubmed
    ..phospholipids across vesicle membranes, which supports the hypothesis that cholate-induced exposure of endogenous PS on the erythrocyte surface is due to the ability of the cationic cholates to promote anionic phospholipid flip-flop.
  32. Van Eck M, Bos I, Hildebrand R, Van Rij B, Van Berkel T. Dual role for scavenger receptor class B, type I on bone marrow-derived cells in atherosclerotic lesion development. Am J Pathol. 2004;165:785-94 pubmed
    ..It thus appears that, depending on the stage of atherosclerotic lesion development, SR-BI in bone marrow-derived cells is either pro-atherogenic or anti-atherogenic, indicating a unique dual role in the pathogenesis of atherosclerosis. ..
  33. Al Aboudi A, Mohammad M, Haddad S, Al Far R, Choudhary M, Atta Ur Rahman -. Biotransformation of methyl cholate by Aspergillus niger. Steroids. 2009;74:483-6 pubmed publisher
    ..The structure elucidation of the new compound was achieved using 1D and 2D NMR, MS and X-ray diffraction. ..
  34. Wang T, Widanapathirana L, Zhao Y, Hong M. Aggregation and dynamics of oligocholate transporters in phospholipid bilayers revealed by solid-state NMR spectroscopy. Langmuir. 2012;28:17071-8 pubmed publisher
    ..The study also shows a strong preference of the linear trimer for the membrane surface, consistent with its lack of transport activity in earlier liposome leakage assays. ..
  35. Thakur R, Das A, Chakraborty A. Photophysical and photodynamical study of ellipticine: an anticancer drug molecule in bile salt modulated in vitro created liposome. Phys Chem Chem Phys. 2012;14:15369-78 pubmed publisher
    ..Entrapment of ellipticine in the interfacial region was also supported by an increase in the rotational relaxation time with addition of bile salt. ..
  36. Zhang S, Zhao Y. Flexible oligocholate foldamers as membrane transporters and their guest-dependent transport mechanism. Org Biomol Chem. 2012;10:260-6 pubmed publisher
    ..Different selectivity was observed in the oligocholate transporters depending on the guest involved. ..
  37. Sorg J, Sonenshein A. Bile salts and glycine as cogerminants for Clostridium difficile spores. J Bacteriol. 2008;190:2505-12 pubmed publisher
    ..difficile spores but prevented the growth of vegetative C. difficile. A model of resistance to C. difficile colonization mediated by the normal bacterial flora is proposed...
  38. Kuo C, Sun S. Separation of bisbenzylisoquinoline alkaloids by micellar electrokinetic chromatography. Phytochem Anal. 2002;13:63-8 pubmed
    ..The elution order of the bisbenzylisoquinoline alkaloids was related to their lipophilicity. The resolution, run time and detection limits of the MEKC method were compared with those of an HPLC method developed previously. ..
  39. Schwarz M, Russell D, Dietschy J, Turley S. Marked reduction in bile acid synthesis in cholesterol 7alpha-hydroxylase-deficient mice does not lead to diminished tissue cholesterol turnover or to hypercholesterolemia. J Lipid Res. 1998;39:1833-43 pubmed
  40. Vergnes L, Phan J, Strauss M, Tafuri S, Reue K. Cholesterol and cholate components of an atherogenic diet induce distinct stages of hepatic inflammatory gene expression. J Biol Chem. 2003;278:42774-84 pubmed
  41. Connelly P, Maguire G, Draganov D. Separation and quantitative recovery of mouse serum arylesterase and carboxylesterase activity. J Lipid Res. 2004;45:561-6 pubmed
    ..The contribution of serum carboxylesterase to the total esterase activity significantly confounds the interpretation of total arylesterase activity in mouse serum. ..
  42. Raskovic A, Jakovljevic V, Mikov M, Gavrilovic M. Joint effect of commercial preparations of Stevia rebaudiana Bertoni and sodium monoketocholate on glycemia in mice. Eur J Drug Metab Pharmacokinet. 2004;29:83-6 pubmed
    ..33:10.54). As for the interaction of mkc and stevia it was found that the combined pretreatment yielded lower values of glycemia compared with that measured after treatment with stevia alone (6.40:7.82). ..
  43. Sorg J, Sonenshein A. Chenodeoxycholate is an inhibitor of Clostridium difficile spore germination. J Bacteriol. 2009;191:1115-7 pubmed publisher
    ..Here we show that chenodeoxycholate inhibits the germination of C. difficile spores in response to cholate and taurocholate...
  44. Rösch V, Denger K, Schleheck D, Smits T, Cook A. Different bacterial strategies to degrade taurocholate. Arch Microbiol. 2008;190:11-8 pubmed publisher
    ..Pseudomonas spp., e.g. strain TAC-K3 and Rhodococcus equi TAC-A1 grew with the cholate moiety and released taurine quantitatively. Delftia acidovorans SPH-1 utilized the taurine moiety and released cholate. ..
  45. Dias J, Pascal R, Morrill J, Holder A, Gao H, Barnes C. Remarkable structures of cyclotri(deoxycholate) and cyclotetra(24-norcholate) acetate esters. J Am Chem Soc. 2002;124:4647-52 pubmed
    ..The latter cyclotetramer is one of the largest open macrocycles ever subjected to crystallography. ..
  46. Wang Y. The function of OmpA in Escherichia coli. Biochem Biophys Res Commun. 2002;292:396-401 pubmed
  47. Baumgartner U, Baier P, Mappes H, Farthmann E. Pericentral hepatocytes translocate hydrophilic bile acids more rapidly than hydrophobic ones. Dig Dis Sci. 2001;46:2098-103 pubmed
    ..Therefore, different or additional translocation pathways for bile acids may be involved in periportal versus pericentral cells. ..
  48. Srivastava R, Averna M, Srivastava N, Pape M. Dietary cholate increases plasma levels of apolipoprotein B in mice by posttranscriptional mechanisms. Int J Biochem Cell Biol. 2001;33:1215-26 pubmed
    ..Thus, dietary cholate modulates plasma levels of apoB primarily by posttranscriptional mechanisms. ..
  49. Mohn W, Wilbrink M, Casabon I, Stewart G, Liu J, van der Geize R, et al. Gene cluster encoding cholate catabolism in Rhodococcus spp. J Bacteriol. 2012;194:6712-9 pubmed publisher
    ..Our results demonstrate that the above-mentioned gene cluster encodes cholate catabolism and is distinct from a more widely occurring gene cluster encoding cholesterol catabolism. ..
  50. Remington K, Trejo S, Buczynski G, Li H, Osheroff W, Brown J, et al. Inactivation of West Nile virus, vaccinia virus and viral surrogates for relevant and emergent viral pathogens in plasma-derived products. Vox Sang. 2004;87:10-8 pubmed
    ..In addition, the data support the use of model viruses to predict the inactivation of similar emergent viral pathogens. ..
  51. Giordano B, Copper C, Collins G. Micellar electrokinetic chromatography and capillary electrochromatography of nitroaromatic explosives in seawater. Electrophoresis. 2006;27:778-86 pubmed
    ..Electrokinetic injections of 8 min at high voltage allow for detection limits of explosives below 100 microg/L. ..
  52. Bhat S, Leikin Gobbi D, Konikoff F, Maitra U. Use of novel cationic bile salts in cholesterol crystallization and solubilization in vitro. Biochim Biophys Acta. 2006;1760:1489-96 pubmed
    ..These findings suggest that cationic bile salts have physico-chemical properties analogous to those of natural anionic bile salts, and thus may have therapeutic potential. ..
  53. Milona A, Owen B, van Mil S, Dormann D, Mataki C, Boudjelal M, et al. The normal mechanisms of pregnancy-induced liver growth are not maintained in mice lacking the bile acid sensor Fxr. Am J Physiol Gastrointest Liver Physiol. 2010;298:G151-8 pubmed publisher
    ..Understanding pregnancy-induced hepatocyte hypertrophy in mice could suggest mechanisms for safely increasing functional liver capacity in women during increased metabolic demand. ..