Use of novel cationic bile salts in cholesterol crystallization and solubilization in vitro

Biochimica et Biophysica Acta - General Subjects

Volumn 1760, Issue 10, 2006, Pages 1489-1496

  Bhat, Shreedhar ^a   Leikin Gobbi, Diana ^b   Konikoff, Fred M ^b   Maitra, Uday ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b TEL AVIV SOURASKY MEDICAL CENTER   (Israel)

Author keywords

Cationic bile salt; Cationic micelle; Cholesterol crystallization; Cholesterol dissolution; log P value; Pyrene probe

Indexed keywords

BILE SALT; CATION; CHOLESTEROL; CHOLIC ACID; DEOXYCHOLIC ACID; PYRENE; TAUROCHENODEOXYCHOLIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; CRYSTALLIZATION; DISSOLUTION; FLUORESCENCE; MICELLE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SOLUBILITY; SOLUBILIZATION;

BILE ACIDS AND SALTS; CATIONS; CHOLATES; CHOLESTEROL; CRYSTALLIZATION; HYDROGEN-ION CONCENTRATION; MICELLES; SOLUBILITY; TAUROCHOLIC ACID;

EID: 33748939460     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2006.06.013     Document Type: Article

References (61)

1. Igimi H., and Carey M.C. Cholesterol gallstone dissolution in bile: dissolution kinetics of crystalline (anhydrate and monohydrate) cholesterol with chenodeoxycholate, ursodeoxycholate, and their glycine and taurine conjugates. J. Lipid Res. 22 (1981) 254-270
2. Carey M.C., Montet M., Philips J.C., Armstrong M.J., and Mazer N.A. Thermodynamic and molecular basis for dissimilar cholesterol-solubilizing capacities by micellar solutions of bile salts: cases of sodium chenodeoxycholate and sodium ursodeoxycholate and their glycine and taurine conjugates. Biochemistry 20 (1981) 3637
3. Reynier M.O., Montet J.C., Marteau C., and Gerolami A. Intestinal cholesterol uptake from mixed micelles. In vitro effects of taurocholate, taurochenodeoxycholate and tauroursodeoxycholate. Biochim. Biophys. Acta 664 (1981) 616
4. Reynier M.O., Montet J.C., Gerolami A., Marteau C., Crotte C., Montet M., and Mathieu S. Comparative effects of cholic acid, chenodeoxycholic and ursodeoxycholic acids on micellar solubilization and intestinal absorption of cholesterol. J. Lipid Res. 22 (1981) 467
5. Konikoff F.M. Gallstones-approach to medical management, Medscape general medicine. Gastroenterology 5 (2003) 1-9
6. Salvioli G., Igimi H., and Carey M.C. Cholesterol gallstone dissolution in bile. Dissolution kinetics of crystalline cholesterol monohydrate by conjugated chenodeoxycholate-lecithin and conjugated ursodeoxycholate-lecithin mixtures: dissimilar phase equilibria and dissolution mechanism. J. Lipid Res. 24 (1983) 701
7. Ikeda I., Tanabe Y., and Sugano M. Effect of sitosterol and sitostanol on micellar solubility of cholesterol. J. Nutr. Sci. Vitaminol. 35 (1989) 361
8. Montet J.C. Ursodeoxycholic acid. Physical and hepatoprotective activity. Pathol. Biol. 39 (1991) 621
9. Mitra S., and Dungan S.R. Cholesterol solubilization in aqueous micellar solutions of Quillaja Saponin, bile salts, or nonionic surfactants. J. Agric. Food Chem. 49 (2001) 384
10. Zhang Z.-H., Janout V., Renner J.L., Urgami M., and Regan S.L. Enhancing the "stickiness" of bile acids to cross linked polymers. A bioconjugate approach to design of bile acid sequestrants. Bioconjugate Chem. 11 (2000) 397-400
11. Fears R., Brown R., Ferres H., Grenier F., and Tyrrell A.W. Effect of bile salt on cholesterol metabolism in rats and guinea-pigs. Biochem. Pharmacol. 40 (1990) 2029-2037
12. Firpi A., Walker J.T., and Lack L. Interactions of cationic bile salt derivatives with the ileal bile salt transport system. J. Lipid Res. 16 (1975) 379
13. Bernheim F., and Lack L. The effect of quaternary ammonium derivatives of bile acids on the rate of swelling of Pseudomonas aeruginosa in solutions of sodium and potassium salts. Can. J. Microbiol. 17 (1971) 323-327
14. Fini A., Roda A., Bellini A.M., Mencini E., and Guarneri M. Quantitative structure-antimicrobial activity relationship in 5b-cholanyl-24-benzylamine derivatives. J. Pharm. Sci. 79 (1990) 603-605
15. Bellini A.M., Mencini E., Quaglio M.P., Guarneri M., and Fini A. Antimicrobial activity of basic cholane derivatives. Arch. Pharm. (Weinheim, Germ.) 323 (1990) 201-205
16. Bellini A.M., Quaglio M.P., Mencini E., Guarneri M., Cavazzini G., and Fini A. Antimicrobial activity of basic cholane derivatives. VIII. Arch. Pharm. (Weinheim, Germ.) 322 (1989) 879-883
17. Kwan K.H., Higuchi W.I., Molokhia A., and Hofmann A.F. Cholesterol gallstone dissolution rate accelerators I: exploratory investigations. J. Pharm. Sci. 66 (1977) 1105-1108
18. Walker S., Sofia M.J., Kakarla R., Kogan N.A., Wierichs L., Longley C.B., Bruker K., Axelrod H.R., Midha S., Babu S., and Kahne D. Cationic facial amphiphiles: a promising class of transfection agents. Proc. Natl. Acad. Sci. 93 (1996) 1585-1590
19. Walker S., Sofia M.J., and Axelrod H.R. Chemistry and cellular aspects of cationic facial amphiphiles. Adv. Drug Delivery Rev. 30 (1998) 61-71
20. Araki Y.-I., Lee A., Sugihara G., Furuichi M., Yamashita S., and Ohseto F. New cationic surfactants derived from bile acids: synthesis and thermodynamic and biophysicochemical properties such as membrane perturbation and protein solubilizing abilities. Colloids Surf., B 8 (1996) 81
21. 13C-NMR relaxation enhancement measurements of the interactions of bile acids with synthetic cationic bile acid derivatives, and with spin labeled fatty acids. Chem. Phys. Lipids 60 (1991) 143-151
22. Borgstrom B. The action of bile salts and other detergents on pancreatic lipase and the interaction with colipase. Biochim. Biophys. Acta 488 (1977) 381-391
23. Bandyopadhyay P., Janout V., Zhang L.-H., Sawko J.A., and Regan S.L. An ion conductor derived from spermine and cholic acid. J. Am. Chem. Soc. 122 (2000) 12888-12889
24. Maitra U., Mukhopadhyay S., Sarkar A., Rao P., and Indi S.S. Hydrophobic pockets in a nonpolymeric aqueous gel: observation of such a gelation process by color change. Angew. Chem., Int. Ed. 40 (2001) 2281-2283
25. 2O: C-66.74, H-10.80, and N-2.78. Found: C-66.29, H-10.43, and N-3.25.
26. Richmond W. Preparation and properties of a cholesterol oxidase from Nocardia sp. and its application to the enzymatic assay of total cholesterol in serum. Clin. Chem. 19 (1973) 1350
27. Tarbutton P.N., and Gunter C.R. Enzymatic determination of total cholesterol in serum. Clin. Chem. 20 (1974) 724-725
28. Allain C.C., Poon L.S., Chain C.S.G., Richmond W., and Fu P.C. Enzymatic determination of total serum cholesterol. Clin. Chem. 20 (1974) 470
29. Mizoguchi T., Edano T., and Koshi T.A. Method of direct measurement for the enzymatic determination of cholesteryl esters. J. Lipid Res. 45 (2004) 396-401
30. Ringel Y., Somjen G.J., Konikoff F.M., Rosenberg R., Michowitz M., and Gilat T. The effects of phospholipid molecular species on cholesterol crystallization in model biles: the influence of phospholipid head groups. J. Hepatol. 28 (1998) 1008-1014
31. Levy P.F., Smith B.F., and LaMont J.T. Human gallbladder mucin accelerates nucleation of cholesterol in artificial bile. Gastroenterology 87 (1984) 270-275
32. Aggregation of compound 5, 7, and 8 are pH dependant at very low pH values (strongly acidic medium).
33. Kalyansundaram K., and Thomas J.K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 99 (1977) 2039-2044
34. The experiments were repeated at least thrice.
35. Matsuzaki K., Yokoyama I., Komatsu H., Handa T., and Miyajima K.A. Fluorescent probing study on microenvironments in bile salt micelles and bile salt/phospatidylcholine mixtures in the absence or presence of cholesterol. Biochim. Biophys. Acta 980 (1989) 371-376
36. Meyerhoffer S.M., and McGown L.B. Microenvironments of fluorescence probes in sodium taorocholate and taurodeoxycholate bile salt media. Anal. Chem. 63 (1991) 2082-2086
37. Hisadome T. Role of sodium ion on the cholesterol solubilization in bile in relation to cholesterol gallstone. Fukuoka Igaku Zasshi 72 (1981) 53-70
38. Weican Z., Ganzuo L., Jianhai M., Qiang1 S., Liqiang Z., Haojun L., and Chi W. Effect of KBr on the micellar properties of CTAB. Chin. Sci. Bull. 45 (2000) 1854-1857
39. Aggregation numbers were determined by fluorescence quenching method. Reciprocal of micelle concentration has been calculated from Stern-Volmer type of plot that yields a straight line. Measured slopes were equal to (from Fig. 6) 0.132 for compound 5, 0.113 - compound 6, and 0.106-compound 7 respectively (R>0.99). The slope (100 - CMC) was taken as an average aggregation number of a given bile salt. Calculated aggregation numbers are 13, 11 and 10 for compounds 5, 6 and 7 respectively (within 10 % error-limit).
40. The comparison was made with the bile acid conjugates rather than the bile acid. This is because of their higher resemblance of the micellar properties with the cationic bile salts.
41. Tamesue N., Inoue T., and Juniper K. Solubility of cholesterol in bile salt-lecithin model systems. Dig. Dis. 18 (1973) 670-678
42. Carey M.C., and Small D.M. The physical chemistry of cholesterol solubility in bile. J. Clin. Invest. 61 (1977) 998-1026
43. Anwer M.S., O"maille E.R.L., Hofmann A.F., Dipietro R.A., and Michelotti E. Influence of side-chain charge on hepatic transport of bile acids and bile acid analogues. Am. J. Physiol. 249 (1985) G479-G488
44. Goldsmith M.A., Huling S., and Jones A.L. Hepatic handling of bile salts and protein in the rat during intrahepatic cholestasis. Gastroenterology 84 (1983) 978-986
45. Grandjean E.M., Karlganis G., Noelpp U., Huegli H., Roesler H., and Paumgartner G. Hepatic handling of a gamma emiting bile salt derivative, 123 I-cholylglycylhistamine, in the dog. Scand. J. Gastroenterol. 14 (1979) 955-960
46. Spenney J.G., Tobin M.M., Mihas A.A., Gibson R.G., Hirschowitz B.I., Johnson B.J., and Tauxe W.N. Utilization of a radioiodinated bile salts for kinetic studies and hepatic scintigraphy. Gastroenterology 76 (1979) 272-278 (19)
47. Hofmann A.F., Higuchi W.I., Kwan K.H., Prakongpan S., Thistle J.L., and Molokhia A. Factors influencing the dissolution rate of model gallstone in bile acid solutions. In: Paumgartner G., Stiehl A., and Gerok W. (Eds). Biological Effects of Bile Acids (1979), MTP, Lancaster, UK 79-89
48. Han S.K., and Kim N.H. Yakhak Hoechi 21 (1977) 135-140
49. Matasuoka K., Kuranaga Y., and Moroi Y. Solubilization of cholesterol and polycyclic aromatic compounds into sodium bile salt micelle (Part 2). Biochim. Biophys. Acta 1580 (2002) 200-214
50. Renshaw P.F., Janoff A.S., and Miller K.W. J. Lipid Res. 24 (1983) 47-51
51. Saad H., Higuchi, et al. J. Pharm. Sci. 54 (1965) 1205-1206
52. Roda A., Minutello A., Angellotti M.A., and Fini A. Bile acid structure-activity relationship: evaluation of bile acid liphophilicity using 1-Octanol/water partition coefficient and reverse phase HPLC. J. Lipid Res. 31 (1990) 1433-1443
53. Armstrong M.J., and Carey M.C. The hydrophilic-hydrophobic balance of bile salts. Inverse co-relation between reverse-phase high performance liquid chromatographic mobilities and micellar cholesterol-solubilizing capacities. J. Lipid Res. 23 (1982) 70-80
54. Nagadome S., Yamauchi A., Miyashita K., Igimi H., and Sugihara G. Transport behavior of four bile salt micelles and cholesterol solubilized by their micelles across porous membrane. Colloid Polym. Sci. 276 (1998) 59-65
55. Liu C.-L., and Higuchi W.I. Cholesterol crystallite nucleation in supersaturated model biles from a thermodynamic standpoint. Biochim. Biophys. Acta 1588 (2002) 15-25
56. Abbreviations used: Ch: Cholesterol, PC: Egg Yolk Phosphatidylcholine, TC: Taurocholic acid sodium salt.
57. Jungst D., Lang T., Huber P., Lange V., and Paumgartner G. Effect of phospholipids and bile acids on cholesterol nucleation time and vesicular/micellar cholesterol in gallbladder bile of patients with cholesterol stones. J. Lipid Res. 34 (1993) 1457-1464
58. Su C.C., Park J.Y., Higuchi W.I., et al. Mesophase formation during In vitro cholesterol gallstone dissolution: a specific effect of ursodeoxycholic acid. J. Pharm. Sci. 70 (1981) 713-715
59. Park Y.-H., Igimi H., and Carey M.C. Dissolution of human cholesterol gallstone in simulated chenodeoxycholate-rich and ursodeoxycholate-rich biles. An in vitro study of dissolution rates and mechanisms. Gastroenterology 87 (1984) 150-158
60. Matsuoka K., Maeda M., and Moroi Y. Micelle formation of sodium glyco- and taurocholates and sodium glyco- and taurodeoxycholates and solubilization of cholesterol into their micelles. Colloids Surf., B Biointerfaces 32 (2003) 87-95
61. Suglhara G., Yamakawa K., Murala Y., and Tanaka M. Effects of pH, pNa, and temperature on micelle formation and solubilization of cholesterol in aqueous solutions of bile salts. J. Phys. Chem. 86 (1982) 2784-2788