Determination of number-average aggregation numbers of bile salts micelles with a special emphasis on their oxo derivatives - The effect of the steroid skeleton

Biochimica et Biophysica Acta - General Subjects

Volumn 1840, Issue 3, 2014, Pages 1072-1082

  Poša, Mihalj ^a   Sebenji, Ana ^a  

^a UNIVERSITY OF NOVI SAD   (Serbia)

Author keywords

aggregation number; conformational analysis; micelle of bile salt; spin lattice relaxation time; steroid skeleton

Indexed keywords

7 OXODEOXICHOLIC ACID; AMPHOPHILE; BILE SALT; HYODEOXICHOLIC ACID; MONOMER; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; HYDROGEN BOND; HYDROPHOBICITY; MAGNETIC FIELD; MICELLE; MICELLIZATION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RELAXATION TIME; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; THERMODYNAMICS;

AGGREGATION NUMBER; CONFORMATIONAL ANALYSIS; MICELLE OF BILE SALT; SPIN-LATTICE RELAXATION TIME; STEROID SKELETON;

BILE ACIDS AND SALTS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; MOLECULAR CONFORMATION; STEROIDS;

EID: 84890824117     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2013.11.008     Document Type: Article

References (61)

1. M. Poša QSPR study of the effect of steroidal hydroxy and oxo substituents on the critical micellar concentrations of bile acids Steroids 76 1-2 2011 85 93
2. M. Calabresi, P. Andreozzi, and C. La Mesa Supra-molecular association and polymorphic behaviour in systems containing bile acid salts Molecules 12 8 2007 1731 1754
3. A. Roda, A.F. Hofmann, and K.J. Mysels The influence of bile salt structure on self-association in aqueous solutions J. Biol. Chem. 258 1983 6362 6370 (Pubitemid 13106811)
4. D.M. Small The physical chemistry of cholanic acids P.P. Nair, D. Kritchevsky, The Bile Acids: Chemistry, Physiology and Metabolism vol. 1 1971 Plenum Press New York (Chapter 8)
5. D.M. Small Studies on the size and structure of bile salt micelles, influences of structure, concentration, counterion concentration, pH and temperature Adv. Chem. Ser. 84 1968 31 52
6. D. Madenci, and S.U. Egelhaaf Self-assembly in aqueous bile salts solution Curr. Opin. Colloid Interface Sci. 15 2010 109 115
7. A.F. Hofmann, and A. Roda Physicochemical properities of bile acids and their relationship to biological properties: an overview of the problem J. Lipid Res. 25 1984 1477 1489 (Pubitemid 15169464)
8. M. Mikov, and J.P. Fawcett Bile Acids 2007 Medishet Publisher Geneva
9. J.Y. Chiang Bile acid regulation of hepatic physiology III. Bile acids and nuclear receptors Am. J. Physiol. 284 2003 G349 G356
10. C. Thomas, R. Pellicciari, M. Pruzanski, J. Auwerx, and K. Schoonjans Targeting bile-acid signalling or metabolic diseases Nat. Rev. Drug Disc. 7 2008 678 693
11. H. Sato, A. Macchiarulo, C. Thomas, A. Gioiello, M. Une, A.F. Hofmann, R. Saladin, K. Schoonjans, R. Pellicciari, and J. Auwerx Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies J. Med. Chem. 51 2008 1831 1841 (Pubitemid 351438866)
12. C. Thomas, A. Gioiello, L. Noriega, A. Strehle, J. Oury, G. Rizzo, A. Macchiarulo, H. Yamamoto, C. Mataki, M. Pruzanski, R. Pellicciari, J. Auwerx, and K. Schoonjans TGR5-mediated bile acid sensing controls glucose homeostasis Cell Metab. 10 2009 167 177
13. P. Garidel, A. Hildebrand, K. Knauf, and A. Blume Membranolytic activity of bile salts: influence of biological membrane properities and composition Molecules 12 2007 2292 2326
14. C. Bowe, L. Mokhtarzadeh, P. Venkatesen, S. Babu, H. Axelrod, M.J. Sofia, R. Kakarla, T.Y. Chan, J.S. Kim, H.J. Lee, G.L. Amidon, S.Y. Choe, S. Walker, and D. Kahne Desing of compounds that increase the absorption of polar molecules Proc. Natl. Acad. Sci. U. S. A. 94 1997 12218 12223 (Pubitemid 27467869)
15. G.S. Gordon, A.C. Moses, R.D. Silver, J.R. Flier, and M.C. Carey Nasal absorption of insulin: enhancement by hydrophobic bile salts Proc. Natl. Acad. Sci. U. S. A. 82 1985 7419 7423 (Pubitemid 16196831)
16. M. Poša, and Z. Farkaš Cholesterol solubilization by oxo derivatives of selected bile acids and their osmotic resistance Collect. Czechoslov. Chem. Commun. 75 8 2010 767 784
17. M. Poša, and K. Kuhajda Hydrophobicity and haemolytic potential of oxo derivatives of cholic, deoxycholic and chenodeoxycholic acids Steroids 75 2010 424 431
18. M. Poša, J. Csanádi, E.K. Kövér, V. Guzsvány, and Gy. Batta Biophysico-chemical study of molecular interactions between selected sodium salts of bile acids and morphine hydrochloride Colloids Surf. B 94 2012 317 323
19. M. Poša, V. Guzsvány, J. Csanádi, S. Kevrešan, and K. Kuhajda Formation of hydrogen-bonded complexes between bile acids and lidocaine in the lidocaine transfer from an aqueous phase to chloroform Eur. J. Pharm. Sci. 34 2008 281 292
20. I. Kuhajda, M. Poša, V. Jakovljević, V. Ivetić, and M. Mikov Effect of 12-monoketocholic acid on modulation of the analgesic action of morphine and tramadol Eur. J. Drug Metab. Pharmacokinet. 34 2009 73 78
21. M. Poša, and K. Kuhajda Influence of bile acids on the adsorption of lidocaine and verapamil in an in vitro experimrnt J. Serb. Chem. Soc. 75 4 2010 433 440
22. M. Mikov, S. Kevresan, K. Kuhajda, V. Jakovljevic, and V. Vasovic 3α,7α-dihydoxy-12-oxo-5β-cholanate as blood-brain barrier permeator Pol. J. Pharmacol. 56 2004 367 371
23. L. Yang, H. Zhang, M. Mikov, and I.G. Tucker Physicochemical and biological characterization of monoketocholic acid, a novel permeability enhancer Mol. Pharm. 6 2 2009 448 456
24. H. Al-Salami, G. Butt, I.G. Tucker, and M. Mikov Influence of the semisynthetic bile acid MKC on the ileal permeation of gliclazide in vitro in healthy and diabetic rats treated with probiotics Methods Find. Exp. Clin. Pharmacol. 30 2 2008 107 113 (Pubitemid 351738270)
25. V. Vasović, S. Vukmirović, M. Poša, M. Mikov, A. Rašković, and V. Jakovljević Effect of rat pretreatment with aqueous solution of stevioside and bile acids on the action of certain cardioactive drugs Eur. J. Drug Metab. Pharmacokinet. 31 2006 311 314
26. A. Rašković, M. Mikov, R. Škrbić, V. Jakovljević, V. Vasović, M. Poša, K. Kuhajda, S. Kevrešan, Z. Tomić, and Dj. Siladji Effect of stevioside and sodium salt of monoketocholic acid on glycemia in normoglycemic and diabetic rats Eur. J. Drug Metab. Pharmacokinet. 33 2008 17 22 (Pubitemid 351629149)
27. M. Atanacković, M. Poša, H. Heinle, Lj. Gojković-Bukarica, and J. Cvejić Solubilization of resveratrol in micellar solutions of different bile acids Colloids Surf. B 72 2009 148 155
28. M. Poša, and V. Tepavčević Mixed micelles of 7,12-dioxolithocholic acid and selected hydrophobic bile acids: interaction parameter, partition coefficient of nitrazepam and mixed micelles haemolytic potential Colloids Surf. B 86 2011 285 291
29. S.T. Singh, and S. Mitra Fluorescence properties of trans-ethyl-p- (dimethylamino) cinnamate in presence of bile acid host J. Photochem. Photobiol. A Biol. 96 2009 193 200
30. M. Poša, A. Pilipović, M. Lalić, and J. Popović Determination and importance of temperature dependence of retention coefficient (RPHPLC) in QSAR model of nitrazepams' partition coefficient in bile acid micelles Talanta 83 2011 1634 1642
31. M. Poša, V. Guzsvány, M. Mikov, and J. Csanádi Effect 7-oxodeoxycholic and 3,7,12-trioxocholanoic acids on verapamil hydrochloride in biophysico-chemical model experiments J. Serb. Chem. Soc. 76 2 2011 189 199
32. R. Nagarajan Comments on interpreting fluorescence measurements: what does thermodynamics have to say about change in micellar aggregation number versus change in size distribution induced by increasing concentration of the surfactant in solution? Langmuir 10 1994 2028 2034
33. H. Sugioka, and Y. Moroi Micelle formation of sodium cholate and solubilization into the micelle Biochim. Biophys. Acta 1394 1998 99 110 (Pubitemid 28451581)
34. K. Matsuoka, and Y. Moroi Micelle formation of sodium deoxycholate and sodium ursodeoxycholate Biochim. Biophys. Acta 1580 2002 189 199 (Pubitemid 34203873)
35. S. Gouin, and X.X. Zhu Fluorescence and NMR studies of the effect of a bile acid dimer on the micellization of bile salts Langmuir 14 1998 4025 4029 (Pubitemid 128624862)
36. R. Shaw, W.H. Elliot, and B.G. Barisas Estimation of critical micelle concentrations of bile acids by reversed-phase high performance liquid chromatography Microchim. Acta 105 1991 137 145
37. B. Natalini, R. Sardella, E. Camaioni, A. Gioiello, and R. Pellicciari Correlation between CMC and chromatographic index: simple and effective evaluation of the hydrophobic/hydrophilic balance of bile acids Anal. Bioanal. Chem. 388 2007 1681 1688 (Pubitemid 47173087)
38. B. Natalini, R. Sardella, E. Camaioni, A. Macchiarulo, A. Gioiello, G. Carbone, and R. Pellicciari Derived chromatographic indices as effective tools to study the self-aggregation process of bile acids J. Pharm. Biomed. Anal. 50 2009 613 621
39. B. Natalini, R. Sardella, A. Gioiello, E. Rosatelli, F. Ianni, E. Camaioni, and R. Pellicciari Fast chromatographic determination of the bile salt critical micellar concentration Anal. Bioanal. Chem. 401 2011 267 274
40. B. Natalini, R. Sardella, A. Gioiello, F. Ianni, A. Michele, and M. Marinozzi Determination of bile salt critical micellization concentration on the road to drug discovery J. Pharm. Biomed. Anal. 2013 10.1016/j.jpba.2013.06.029
41. K. Valkó, C. Bevan, and D. Reynolds Chromatographic hydrophobicity index by fast-gradient RP-HPLC: a high-throughput alternative to log P/log D Anal. Chem. 69 1997 2022 2029 (Pubitemid 127698689)
42. Lj. Djaković Colloid Chemistry 2006 Zavod za udžbenike i nastavna sredstva Beograd
43. M. Poša Heuman indices of hydrophobicity of bile acids and their comparison with a newly developed and conventional molecular descriptors Biochimie 2013 10.1016/j.biochi.2013.09.010
44. D. Miljković, K. Kuhajda, and J. Hranisavljević Selective C-12 oxidation of cholic acid J. Chem. Res. S 1996 106 107 (Pubitemid 126458422)
45. B.F. Tullar, inventor. Hemi-diethylene glycol adduct of 3,12-dihydroxy-7-ketocjholanoicacid and preparation thereof. US patent 2,549,947 (1951).
46. L.F. Fieser, and S. Rajagopalan Oxidation of Steroids III. Selective oxidations and acylations in bile acid series J. Am. Chem. Soc. 72 1950 5530 5536
47. M. Poša, A. Pilipović, and M. Lalić The influence of NaCl on hydrophobicity of selected, pharmacologically active bile acids expressed with chromatographic retention index and critical micellar concentration Colloids Surf. B 81 2010 336 343
48. P.J. Hore Nuclear Magnetic Resonance 1995 Oxford University Press Oxford
49. J.K.M. Sanders, and B.K. Hunter Modern NMR spectroscopy 1995 Oxford University Press Oxford
50. H. Kawamura, Y. Murata, T. Yamaguchi, H. Igimi, M. Tanaka, G. Sugihara, and J.P. Kratohvil Spin label studies bile salt micelles J. Phys. Chem. 93 1989 3321 3326
51. K. Matsuoka, K. Takagi, and C. Honda Micelle formation of sodium hyodeoxycholate Chem. Phys. Lipids 172-173 2013 6 13
52. L.B. Pártai, P. Jedlovszky, and M. Sega Molecular aggregates in aqueous solutions of bile acid salts. Molecular dynamics simulation study J. Phys. Chem. B 111 2007 9886 9896 (Pubitemid 47387872)
53. L.B. Pártai, M. Sega, and P. Jedlovszky Counterion binding in the aqueous solutions of bile acid salts, as studied by computer simulation method Langmuir 24 2008 10729 10736
54. L.B. Pártai, M. Sega, and P. Jedlovszky Morphology of bile salts micelles as studied by computer simulation methods Langmuir 23 2007 12322 12328 (Pubitemid 350197409)
55. P. Venkatesan, Y. Cheng, and D. Kahne Hydrogen bonding in micelle formation J. Am. Chem. Soc. 116 1994 6955 6956 (Pubitemid 24981379)
56. N. Funasaki, M. Fukuba, T. Kitagawa, M. Nomura, S. Ishikawa, S. Hirota, and S. Neya Two-dimensional NMR study on the structures of micelles of sodium taurocholate J. Phys. Chem. B 108 2004 438 443
57. M. Otto Chemometrics second ed. 2007 Wiley-VCH Weinheim
58. M. Poša, A. Pilipović, M. Lalić, and J. Popović Hydrophobicity and retention coefficient of selected bile acid oxo derivatives Acta Chim. Slov. 57 2010 828 835
59. C. Onişor, M. Poša, S. Kevrešan, K. Kuhajda, and C. Sârbu Estimation of chromatographic lipophilicity of bile acids and their derivatives by reversed-phase thin layer chromatography J. Sep. Sci. 33 2010 3110 3118
60. P. Garidel, A. Hildebrand, A. Neubert, and A. Blume Thermodynamic characterization of bile salt aggregation as a function of temperature and ionic strength using isothermal titration calorimetry Langmuir 16 2000 5267 5275
61. M. Poša Hydrophobicity and self-association of bile acids with a special emphasis on oxo derivatives of 5-β-cholanic acid Curr. Org. Chem. 16 2012 1876 1904