Successful prediction of the hydrogen bond network of the 3-oxo-12α-hydroxy-5β-cholan-24-oic acid crystal from resolution of the crystal structure of deoxycholic acid and its three 3,12-dihydroxy epimers

Steroids

Volumn 69, Issue 6, 2004, Pages 379-388

  Jover, A ^a   Meijide, F ^a   Soto, Victor H ^a   Vazquez Tato J ^a   Rodriguez Nunez E ^a   Ton Nu, H T ^b   Hofmann, A F ^b  

^a Facultade de Ciencias   (Spain)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

3 Oxo,12 hydroxy 5 cholan 24 oic acid; Crystal structure of deoxycholic acid; Crystal structure of deoxycholic acid epimers; Deoxycholic acid epimers; Hydrogen bond network; Inclusion compounds

Indexed keywords

3 OXO 12ALPHA HYDROXY 5BETA CHOLAN 24 OIC ACID; DEOXYCHOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; MICELLE; PREDICTION; STOICHIOMETRY; SYNTHESIS;

CHOLIC ACIDS; CRYSTALLOGRAPHY, X-RAY; DEOXYCHOLIC ACID; HYDROGEN BONDING; ISOMERISM; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 3042554286     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2004.03.007     Document Type: Article

References (51)

1. Hofmann AF. Bile acids. In: Arias IM, Boyer JL, Fausto N, Jakoby WB, Schacter DA, Shafritz DA, editors. The liver: biology and pathobiology. 3rd ed. New York: Raven Press Ltd.; 1994.
2. Carey M.C., Small D.M. Micelle formation by bile salts. Physical-chemical and thermodynamic considerations. Arch. Int. Med. 130:1972;506-527
3. Coello A., Meijide F., Rodríguez Núñez E., Vázquez Tato J. Aggregation behavior of bile salts in aqueous solution. J. Pharm. Sci. 85:1996;9-15
4. 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
5. Campanelli A.R., De Sanctis S.C., Giglio E., Pavel N.V., Quagliata C. From crystal to micelle: a new approach to the micellar structure. J. Inclusion Phenom. Mol. Recognit. Chem. 7:1989;391-400
6. 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
7. Gallese F., Guarino A., Possagno E. Isomerization processes in inclusion compounds: xylenes in deoxycholic acid. J. Inclusion Phenom. Mol. Recognit. Chem. 14:1992;55-64
8. Bottari E., D'Archivio A.A., Festa M.R., Galantini L., Giglio E. Structure and composition of sodium taurocholate micellar aggregates. Langmuir. 15:1999;2996-2998
9. Kawamura H., Murata Y., Yamaguchi T., Igimi H., Tanaka M., Sugihara G., et al. Spin-label studies of bile salt micelles. J. Phys. Chem. 93:1989;3321-3326
10. Cerrini S., Pochetti G., Gallese F., Possagno E. The monoclinic phase of the 2/1 inclusion compound between deoxycholic acid and o-xylene. Acta Crystallogr. C49:1993;1087-1092
11. Bonamico M, Giacomello G. Structural researches on a new choleic compound. Gazz Chim Ital 1962;647-50.
12. Schaefer J.P., Reed L.L. Structure of deoxycholic acid p-bromoanilide. Acta Crystallogr. B28:1972;1743-1748
13. De Sanctis S.C., Giglio E., Pavel V., Quagliata C. Crystal packing of the 2:1 and 3:1 canal complexes between deoxycholic acid and p-diiodobenzene and phenanthrene. Acta Crystallogr. B28:1972;3656-3661
14. De Sanctis S.C., Coiro V.M., Giglio E., Pagliuca S., Pavel N.V., Quagliata C. The hexagonal phase of the 3:2:1 canal complex between deoxycholic acid, ethanol and water: an inclusion compound with hydrophilic channels. Acta Crystallogr. B34:1978;1928-1933
15. De Sanctis S.C., Giglio E., Petri F., Quagliata C. The 2:1:1 canal complex between deoxycholic acid, dimethyl sulfoxide and water. Acta Crystallogr. B35:1979;226-228
16. Coiro V.M., D'Andrea A., Giglio E. The tetragonal phase of the 2:1:1 canal complex between deoxycholic acid, ethanol and water. Acta Crystallogr. B35:1979;2941-2944
17. Popovitz-Biro R., Tang C.P., Chang H.C., Lahav M., Leiserowitz L. Solid-state photochemistry of guest aliphatic ketones inside the channels of host deoxycholic and apocholic acids. J. Am. Chem. Soc. 107:1985;4043-4058
18. Padmanabhan K., Venkatesan K., Ramamurthy V. Structure-reactivity correlation in inclusion complexes: deoxycholic acid-di-tert-butyl thioketone. Can. J. Chem. 62:1984;2025-2028
19. De Sanctis S.C., Coiro V.M., Mazza F., Pochetti G. The inclusion compound of deoxycholic acid with (-)-camphor: a structural and energetic study. Acta Crystallogr. B51:1995;81-89
20. Jones J.G., Schwarzbaum S., Lessinger L., Low B.W. The structure of the 2:1 complex between the bile acid deoxycholic acid and (+)-camphor. Acta Crystallogr. B38:1982;1207-1215
21. Craven BM, DeTitta GT. Crystal structure determination of the 1:1 complex of deoxycholic acid and acetic acid. J Chem Soc, Chem Commun 1972:530-1.
22. Giglio E. Inclusion compounds of deoxycholic acid. In: Atwood Jl, Davies JED, MacNicol DD. editors. Inclusion compounds. London: Academic Press; 1984. p. 207-29.
23. Miyata M, Sada K. Deoxycholic acid and related hosts. In: MacNicol DD, Toda F, Bishop R, editors. Comprehensive supramolecular chemistry. Oxford: Elsevier; 1996. p. 147-76.
24. 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
25. Roda A., Hofmann A.F., Mysels K.J. The influence of bile salt structure on self-association in aqueous solutions. J. Biol. Chem. 258:1983;6362-6370
26. Iida T., Chang F.C. Potential bile acid metabolites. 8. 7, 12-Dihydroxy- and 7β-hydroxy-5β-cholanic acids. J. Org. Chem. 48:1983;1194-1197
27. Chang F.C., Wood N.F., Holton W.G. 3β, 12β-Dihydroxycholanic acid. J. Org. Chem. 30:1965;1718-1723
28. Gouin S., Zhu X.X. Synthesis of 3α-, 3β-dimers from selected bile acids. Steroids. 61:1996;664-669
29. Jones AS, Webb M, Smith F. Basic derivatives of steroids. 3-Amino-7, 12-dihydroxy- and 3-amino-12-hydroxycholanic acid. J Chem Soc 1949;2164-8.
30. Spek AL. HELENA. A program for data reduction of CAD4 data. University of Utrech; 1997.
31. North A.C.T., Phillips D.C., Mathews F.S. Acta Crystallogr. A24:1968;351-359
32. SADABS. Area-detector absorption correction. Madison, WI: Siemens Industrial Automation Inc.; 1996.
33. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., et al. J. Appl. Crystallogr. 32:1999;115-119
34. Sheldrick GM. SHELXL97. Programs for crystal structure analysis (Release 97-2). Germany: University of Göttingen; 1997.
35. Herbst-Irmer R., Sheldrick G.M. Refinement of twinned structures with SHELXL97. Acta Crystallogr. B54:1998;443-449
36. International tables for X-ray crystallography. Dordrecht: Kluwer; 1995.
37. Farrugia L.J. ORTEP3 for Windows. J. Appl. Crystallogr. 30:1997;565
38. Sada K, Sugahara M, Nakahata Y, Yasuda Y, Nishio A, Miyata M. First columnar monolayer structure of bile acids inclusion crystal. Inclusion compounds of 23-nordeoxycholic acid. Chem Lett 1998;31-2.
39. Sugahara M, Sada K, Miyata M. A robust structural motif in inclusion crystals of nor-bile acids. Chem Commun 1999;293-4.
40. Miki K., Masui A., Kasai N., Miyata M., Goonewardena W., Shibakami M., et al. Structure of a 2:1 addition compound of methyl deoxycholate with methanol. Acta Crystallogr. C45:1989;79-83
41. Sada K, Kitamura T, Miyata M. Inclusion phenomena of glycine-conjugated bile acids and the crystal structure of 1:1 complex of glycodeoxycholic acid and tetrahydrofuran. J Chem Soc, Chem Commun 1994;905-7.
42. Sada K, Hishikawa Y, Kondo T, Miyata M. Specific inclusion of water by N-methyldeoxycholanamide revealed by the crystal structure of the hemihydrate. Chem Lett 1994;2113-6.
43. Hishikawa Y, Sada K, Miyata M. Water-participation in the formation of a triangular pillar-like assembly in deoxycholamide inclusion crystals. J Chem Res (S) 1998;738-9.
44. Arora S.K., Germain G., Declercq J.P. The crystal and molecular structure of lithocholic acid. Acta Crystallogr. B32:1976;415-419
45. Hall S.R., Maslen E.N., Cooper A. Crystal and molecular structure of 3α, 6α-dihydroxy-5β-cholan-24 oic acid. Acta Crystallogr. B30:1974;1441-1447
46. Miyake Y, Matsuura Y, Sada K, Miyata M. Inclusion compounds of hyodeoxycholic acid and the crystal structure of a 1:1 complex between the acid and pyridine. Chem Lett 1997;1263-4.
47. Rizkallah P.J., Harding M.M., Lindley P.F., Aigner A., Bauer A. Structure of a low-temperature polymorph of chenodeoxycholic acid, C24H40O4, determined with synchrotron radiation. Acta Crystallogr. B46:1990;262-266
48. Lindley P.F., Mahmoud M.M., Watson F.E., Jones W.A. The structure of chenodeoxycholic acid, C24H40O4. Acta Crystallogr. B36:1980;1893-1897
49. Miki K., Kasai N., Shibakami M., Chirachanchai S., Takemoto K., Miyata M. Crystal structure of cholic acid with no guest molecules. Acta Crystallogr. C46:1990;2442-2445
50. Lehn JM. Supramolecular chemistry. Weinheim: VCH; 1995.
51. Bonar-Law R.P., Sanders J.K.M. Self-associating cyclocholates. Tetrahedron Lett. 34:1993;1677-1680