Crystal structure of chenodeoxycholic acid, ursodeoxycholic acid and their two 3β,7α- and 3β,7β-dihydroxy epimers

Steroids

Volumn 72, Issue 6-7, 2007, Pages 535-544

  Alvarez, M ^a   Jover, A ^a   Carrazana, J ^a   Meijide, F ^a   Soto, V H ^a   Tato, J Vázquez ^a  

^a Universidad de Santiago da Compostela   (Spain)

Author keywords

Chenodeoxycholic acid; Chenodeoxycholic acid epimers; Crystal structure; Hydrogen bond network; Inclusion compounds; Ursodeoxycholic acid

Indexed keywords

3BETA, 7ALPHA DIHYDROXY EPIMER DERIVATIVE; 3BETA, 7BETA DIHYDROXY EPIMER DERIVATIVE; CHENODEOXYCHOLIC ACID; ISOCHENODEOXYCHOLIC ACID; ISOURSODEOXYCHOLIC ACID; UNCLASSIFIED DRUG; URSODEOXYCHOLIC ACID;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; DIHYDROXYLATION; DRUG CONFORMATION; DRUG STRUCTURE; EPIMER; HYDROGEN BOND; ISOMER; STOICHIOMETRY;

CHENODEOXYCHOLIC ACID; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; URSODEOXYCHOLIC ACID;

EID: 34248522808     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.03.007     Document Type: Article

References (62)

1. Carey M.C., and Small D.M. Micelle formation by bile salts. Physical-chemical and thermodynamic considerations. Arch Intern Med 130 (1972) 506-527
2. Coello A., Meijide F., Rodríguez Núñez E., and Vázquez Tato J. Aggregation behavior of bile salts in aqueous solution. J Pharm Sci 85 (1996) 9-15
3. Hofmann A.F. Bile Acids. In: Arias I.M., Boyer J.L., Fausto N., Jakoby W.B., Schacter D.A., and Shafritz D.A. (Eds). The liver: biology and pathobiology. 3rd ed. (1994), Raven Press Ltd, New York
4. Jirsa M., Klinot J., Klinotova E., Ubik K., and Kucera K. Classical bile acids in animals, β-phocaecholic acid in ducks. Comp. Biochem Physiol 92B (1989) 357-360
5. Hagey L.R., Crombie D.L., Espinosa E., Carey M.C., Igimi H., and Hofmann A.F. Ursodeoxycholic acid in the ursidae: biliary bile acids of bears, pandas, and related carnivores. J Lipid Res 34 (1993) 1911-1917
6. Makino I., and Tanaka H. From a choleretic to an immunomodulator: historical review of ursodeoxycholic acid as a medicament. J Gastroenterol. Hepatol. 13 (1998) 659-664
7. Giglio E. Inclusion compounds of deoxycholic acid. In: Atwood J.L., Davies J.E.D., and MacNicol D.D. (Eds). Inclusion compounds (1984), Academic Press, London 207-229
8. Miyata M., and Sada K. Deoxycholic acid and related hosts. In: MacNicol D.D., Toda F., and Bishop R. (Eds). Comprehensive supramolecular chemistry (1996), Elsevier, Oxford 147-176
9. Campanelli A.R., Candeloro de Sanctis S., Giglio E., Pavel N.V., and Quagliata C. From crystal to micelle: a new approach to the micellar structure. J Inclusion Phenom Macrocyclic Chem 7 (1989) 391-400
10. Miyata M., and Takemoto K. Radiation-induced polymerization of 2,3-disubstituted butadienes in deoxycholic acid inclusion compounds. J Polym Sci, Polym Lett Ed 13 (1975) 221-223
11. Miyata M., and Takemoto K. Functional monomers and polymers. 32. Radiation-induced polymerization of 2,3-dichlorobutadiene in deoxycholic acid canal complexes. Angew Makromol Chem 55 (1976) 191-202
12. Audisio G., and Silvani A. Inclusion asymmetric polymerization of penta-1,3-dienes in deoxycholic acid. J Chem Soc Chem Commun 12 (1976) 481-482
13. Miyata M., Morioka K., and Takemoto K. Functional monomers and polymers. XXXVIII. Postirradiation polymerization of 2,3-dimethylbutadiene in deoxycholic acid canal complexes. J Polym Sci Polym Chem Ed 15 (1977) 2987-2996
14. Miyata M., and Takemoto K. Functional monomers and polymers. XXXIX. Synthesis of optically active poly(trans-2-methylpentadiene) by asymmetric inclusion polymerization in deoxycholic acid. Polym J 9 (1977) 111-112
15. Takemoto K., and Miyata M. Polymerization of vinyl and diene monomers in canal complexes. J Macromol Sci Rev Macromol Chem C18 (1980) 83-107
16. Miyata M., Kitahara Y., Osaki Y., and Takemoto K. Inclusion polymerization of various diene monomers in apocholic acid canals. J Inclusion Phenom Macrocyclic Chem 2 (1984) 391-398
17. Miyata M., Noma F., Okanishi K., Tsutsumi H., and Takemoto K. Inclusion polymerization of diene and diacetylene monomers in deoxycholic acid and apocholic acid canals. J Inclusion Phenom Macrocyclic Chem 5 (1987) 249-252
18. Miyata M., Tsuzuki T., Noma F., Takemoto K., and Kamachi M. Functional monomers and polymers. 161. Inclusion polymerization in deoxycholic acid and apocholic acid canals: decisive role of a relative size between a canal and a monomer. Makromol Chem Rapid Commun 9 (1988) 45-50
19. Takemoto K., and Miyata M. Polymerization of diene and diyne monomers in deoxycholic and apocholic acid inclusion compounds. Mol Cryst Liq Cryst 186 (1990) 189-195
20. Goonewardena W., Miyata M., and Takemoto K. Relative size effect on the polymerization with methyl cholate inclusion compounds. Polym J 23 (1991) 1405-1408
21. Goonewardena W., Miyata M., and Takemoto K. One-dimensional inclusion polymerization of diene and vinyl monomers by using methyl cholate as a host. Polym J 25 (1993) 731-740
22. Chikada M., Sada K., and Miyata M. Intercalation and polymerization in chenodeoxycholic acid channels with retention of a crystalline state. Polym J 31 (1999) 1061-1064
23. Miyata M., Shibakami M., and Takemoto K. Optical resolution of lactones by an inclusion method using cholic acid as the host. J Chem Soc Chem Commun (1988) 655-656
24. Miki K., Kasai N., Shibakami M., Takemoto K., and Miyata M. New chiral recognition ability of a steroidal bile acid; direct evidence for efficient optical resolution of racemic lactones by cholic acid inclusion crystals. J Chem Soc Chem Commun (1991) 1757
25. Bortolini O., Fantin G., Fogagnolo M., Medici A., and Pedrini P. Optical resolution of sulfoxides by inclusion in host dehydrocholic acid. Chem Commun (2000) 365-366
26. Bortolini O., Fantin G., Fogagnolo M., Medici A., and Pedrini P. Resolution of unfunctionalized epoxides by cholic acid inclusion compounds. Chem Lett (2000) 1246-1247
27. Bortolini O., Fantin G., and Fogagnolo M. Bile acid derivatives as enantiodifferentiating host molecules in inclusion processes. Chirality 17 (2005) 121-130
28. Bortolini O., Fantin G., Fogagnolo M., and Maietti S. Resolution of organic racemates via host-guest enantioselective inclusion complexation in bile acid derivatives. Arkivoc (2006) 40-48
29. Froemming K.H., and Sandmann R. New preparative method for gastric juice-resistant forms at active substances. Arch Pharmaz 303 (1970) 371-378
30. Small D.M. Size and structure of bile salt micelles. Influence of structure, concentration, counterion concentration, pH, and temperature. Adv Chem Ser 84 (1968) 31-52
31. Nakano K., Sada K., Kurozumi Y., and Miyata M. Importance of packing coefficients of host cavities in the isomerization of open host frameworks: guest-size-dependent isomerization in cholic acid inclusion crystals with monosubstituted benzenes. Chem Eur J 7 (2001) 209-220
32. Nakano K., Mochizuki E., Yasui N., Morioka K., Yamauchi Y., Kanehisa N., et al. Mechanism of selective and unselective enclathration by a host compound possessing open, flexible host frameworks. Eur J Org Chem (2003) 2428-2436
33. Schmassmann A., Angellotti M.A., Clerici C., Hofmann A.F., Ton-Nu H.T., Schteingart C.D., et al. Transport, metabolism, and effect of chronic feeding of lagodeoxycholic acid: a new, natural bile acid. Gastroenterology 99 (1990) 1092-1104
34. Jover A., Meijide F., Rodríguez Núñez E., Vázquez Tato J., Castiñeiras A., Hofmann A.F., et al. Crystal structure of 3β,12α-dihydroxy-5β-cholan-24-oic acid (iso-deoxycholic acid). J Mol Struct 523 (2000) 299-307
35. Jover A., Meijide F., Soto Tellini V.H., Vázquez Tato J., Rodríguez Núñez E., Ton-Nu H.T., et al. Successful prediction of the hydrogen bond network of the 3-oxo-12β-hydroxy-5β-cholan-24-oic acid crystal from resolution of the crystal structure of deoxycholic acid and its three 3,12-dihydroxy epimers. Steroids 69 (2004) 379-388
36. Hofmann A.F., Sjövall J., Kurz G., Radominska A., Schteingart C.D., Tint G.S., et al. A proposed nomenclature for bile acids. J Lipid Res 33 (1992) 599-604
37. Lehn J.M. Supramolecular chemistry (1995), VCH, Weinheim
38. Jover A., Meijide F., Rodríguez Núñez E., and Vázquez Tato J. Aggregation behavior of bile salts. Recent Res Dev Phys Chem 3 (1999) 323-335
39. Cozzolino S., Galantini L., Giglio E., Hoffmann S., Leggio C., and Pavel N.V. Structure of sodium glycodeoxycholate micellar aggregates from small-angle X-ray scattering and light-scattering techniques. J Phys Chem B 110 (2006) 12351-12359
40. Jover A., Meijide F., Rodríguez Núńez E., Vázquez Tato J., Mosquera M., and Rodríguez Prieto F. Unusual pyrene excimer formation during sodium deoxycholate gelation. Langmuir 12 (1996) 1789-1793
41. Briganti G., D'Archivio A.A., Galantini L., and Giglio E. Structural study of the micellar aggregates of sodium and rubidium glyco- and taurodeoxycholate. Langmuir 12 (1996) 1180-1187
42. Jean B., Oss-Ronen L., Terech P., and Talmon Y. Monodisperse bile-salt nanotubes in water: kinetics of formation. Adv Mater 17 (2005) 728-731
43. Soto Tellini, VH, Jover A, Meijide F. Vázquez Tato J, Galantini L, Pavel NV., Supramolecular structures generated by a p-tert-butylphenyl-amide derivative of cholic acid. From vesicles to molecular tubes. Adv Mater, doi:10.1002/adma.200602581.
44. Soto Tellini V.H., Jover A., Galantini L., Pavel N.V., Meijide F., and Vázquez Tato J. New lamellar structure formed by an adamantyl derivative of cholic acid. J Phys Chem B 110 (2006) 13679-13681
45. Van der Sluis P., Schouten A., and Kanters J.A. Structure of chenodeoxycholic acid in chenodeoxycholic acid ethyl acetate solvate. Acta Crystallogr C46 (1990) 2165-2168
46. Rizkallah P.J., Harding M.M., Lindley P.F., Aigner A., and Bauer A. Structure of a low-temperature polymorph of chenodeoxycholic acid, C24H40O4, determined with synchrotron radiation. Acta Crystallogr B46 (1990) 262-266
47. Lindley P.F., Mahmoud M.M., Watson F.E., and Jones W.A. The structure of chenodeoxycholic acid, C24H40O4. Acta Crystallogr B36 (1980) 1893-1897
48. Giuseppetti G., and Paciotti M. Polymorphism of chenodeoxycholic acid. Farmaco Ed Sci 33 (1978) 64-72
49. Higuchi T., Kamitori S., Hirotsu K., and Takeda H. Structure of ursodeoxycholic acid. Yakugaku Zasshi 105 (1985) 1115-1121
50. Lindley P.F., and Carey M.C. Molecular packing of bile acids: structure of ursodeoxycholic acid. J Crystall Spect Res 17 (1987) 231-249
51. Fukami T., Yamaguchi K., Tozuka Y., Moribe K., Oguchi T., and Yamamoto K. Novel channel structure of bile acid-guest inclusion complex formed between ursodeoxycholic acid and phenanthrene. Chem Pharm Bull 51 (2003) 227-229
52. Miyake Y., Hirose J., Hasegawa Y., Sada K., and Miyata M. Novel channel-type inclusion compounds of 3-epiursodeoxycholic acid. Chem Commun (1998) 111-112
53. Thomas HG. Procedure for the preparation of isoursodeoxychloic acid. Patent 1996; DE 1994-4443377 A.
54. Altona C., Geise H.J., and Romers C. Conformation of nonaromatic ring compounds. XXV. Geometry and conformation of ring D in some steroids from X-ray structure determinations. Tetrahedron 24 (1968) 13-32
55. Coiro V.M., Mazza F., Pochetti G., Giglio E., and Pavel N.V. The structure of the 2/1 channel inclusion compound between deoxycholic acid and pinacolone, 2C24H40O4.C6H12O. Acta Crystallogr C41 (1985) 229-232
56. Miki K., Kasai N., Tsutsumi H., Miyata M., and Takemoto K. Structure of a 2:1 complex between deoxycholic acid and ferrocene. J Chem Soc Chem Commun (1987) 545-546
57. Padmanabhan K., Ramamurthy V., and Venkatesan K. Structure reactivity correlation in inclusion complexes: deoxycholic acid-thiocamphenilone. J Inclusion Phenom Macrocyclic Chem 5 (1987) 315-323
58. Cerrini S., Pochetti G., Gallese F., and Possagno E. The monoclinic phase of the 2/1 inclusion compound between deoxycholic acid and o-xylene. Acta Crystallogr C49 (1993) 1087-1092
59. Johnson P.L., and Schaefer J.P. Crystal and molecular structure of an addition compound of cholic acid and ethanol. Acta Crystallogr 28 (1972) 3083-3088
60. Jones E.L., and Nassimbeni L.R. Crystal and molecular structures of the inclusion compounds of cholic acid with methanol, ethanol and 1-propanol. Acta Crystallogr B46 (1990) 399-405
61. Limmatvapirat S., Yamaguchi K., Yonemochi E., Oguchi T., and Yamamoto K. A 1:1 deoxycholic acid-salicylic acid complex. Acta Crystallogr C53 (1997) 803-805
62. Giglio E., and Quagliata C. Side-chain and ring D conformation in cholanic acids. Acta Crystallogr B31 (1975) 743-746