Characterization of the hydrochlorothiazide: β-cyclodextrin inclusion complex. Experimental and theoretical methods

Journal of Physical Chemistry B

Volumn 117, Issue 1, 2013, Pages 206-217

  Onnainty, Renée ^a   Schenfeld, Esteban M ^a   Quevedo, Mario A ^a   Fernández, Mariana A ^b   Longhi, Marcela R ^a   Granero, Gladys E ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

^b DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; ENTHALPY; HYDROGEN BONDS; IONIZATION; MOLECULAR MODELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY; THREE DIMENSIONAL;

AFFINITY CONSTANTS; ANTIHYPERTENSIVE DRUGS; ASSOCIATION ENTHALPY; ASSOCIATION PROCESS; BINDING CONSTANT; BINDING MODES; CALORIMETRIC MEASUREMENTS; CD COMPLEX; COMPLEX ARCHITECTURES; ENERGETIC DECOMPOSITION; HYDROCHLOROTHIAZIDE; HYDROGEN BOND INTERACTION; HYDROXYL GROUPS; INCLUSION COMPLEX; IONIZATION STATE; ISOTHERMAL TITRATION; MOLECULAR ASPECTS; PH VALUE; PHASE SOLUBILITY; PROTON NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVATION ENERGY; STABILITY CONSTANTS; TEMPERATURE DEPENDENCE; THEORETICAL TECHNIQUE; THERMODYNAMIC PARAMETER;

TEMPERATURE;

EID: 84872344092     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp311274c     Document Type: Article

References (55)

1. Loftsson, T.; Brewster, M. E. J. Pharm. Sci. 2012, 101 (9) 3019-3032
2. Serno, T.; Geidobler, R.; Winter, G. Adv. Drug Delivery Rev. 2011, 63 (13) 1086-1106
3. Laza-Knoerr, A. L.; Gref, R.; Couvreur, P. J. Drug Target. 2010, 18 (9) 645-656
4. Carrier, R. L.; Miller, L. A.; Ahmed, I. J. Controlled Release 2007, 123 (2) 78-99
5. Loftsson, T.; Ducheîne, D. Int. J. Pharm. 2007, 329 (1-2) 1-11
6. Villalonga, R.; Cao, R.; Fragoso, A. Chem. Rev. 2007, 107, 3088-3116
7. Astray, G.; Gonzalez-Barreiro, C.; Mejuto, J. C.; Rial-Otero, R.; Simal-Gándara, J. Food Hydrocolloids 2009, 23 (7) 1631-1640
8. Cravotto, G.; Binello, A.; Baranelli, E.; Carraro, P.; Trotta, F. Curr. Nutr. Food Sci. 2006, 2 (4) 343-350
9. Maeztu, R.; Tardajos, G.; Gonzalez-Gaitano, G. J. Phys. Chem. B 2010, 114, 2798-2806
10. Centini, M.; Maggiore, M.; Casolaro, M.; Andreassi, M.; Maffei Facino, R.; Anselmi, C. J. Inclusion Phenom. Macrocyclic Chem. 2007, 57 (1-4) 109-112
11. Fakayode, S. O.; Lowry, M.; Fletcher, K. A.; Huang, X.; Powe, A. M.; Warner, I. M. Curr. Anal. Chem. 2007, 3 (3) 171-181
12. Liu, L.; Guo, Q. X. J. Inclusion Phenom. 2002, 42 (1-2) 1-14
13. Zhang, H.; Tan, T.; Feng, W.; Van Der Spoel, D. J. Phys. Chem. B 2012, 116, 12684-12693
14. Chen, Y.; Li, F.; Liu, B. W.; Jiang, B. P.; Zhang, H. Y.; Wang, L. H.; Liu, Y. J. Phys. Chem. B 2010, 114, 16147-16155
15. Jana, M.; Bandyopadhyay, S. J. Phys. Chem. B 2011, 115, 6347-6357
16. Harries, D.; Rau, D. C.; Parsegian, V. A. J. Am. Chem. Soc. 2005, 127, 2184-2190
17. Asandei, A.; Mereuta, L.; Luchian, T. J. Phys. Chem. B 2011, 115, 10173-10181
18. Challa, R.; Ahuja, A.; Ali, J.; Khar, R. K. AAPS PharmSciTech [electronic resource] 2005, 6 (2) E329-357
19. Khalil, S. K. H.; El-Feky, G. S.; El-Banna, S. T.; Khalil, W. A. Carbohydr. Polym. 2012, 90 (3) 1244-1253
20. Jug, M.; Kosalec, I.; Maestrelli, F.; Mura, P. Carbohydr. Polym. 2012, 90 (4) 1794-1803
21. Finger, S.; Wiegand, C.; Buschmann, H. J.; Hipler, U. C. Int. J. Pharm. 2012, 436 (1-2) 851-856
22. Nguyen, T. A.; Liu, B.; Zhao, J.; Thomas, D. S.; Hook, J. M. Food Chem. 2013, 136 (1) 186-192
23. Martins, M. H.; Calderini, A.; Pessine, F. B. T. J. Inclusion Phenom. Macrocyclic Chem. 2012, 74 (1-4) 109-116
24. Jug, M.; Maestrelli, F.; Mura, P. J. Inclusion Phenom. Macrocyclic Chem. 2012, 74 (1-4) 87-97
25. Messerli, F. H.; Bangalore, S. Am. J. Med. 2011, 124 (10) 896-899
26. Chen, M. L.; Amidon, G. L.; Benet, L. Z.; Lennernas, H.; Yu, L. X. Pharm. Res. 2011, 28 (7) 1774-1778
27. Trivedi, R. V.; Admane, P. S.; Taksande, J. B.; Mahore, J. G.; Umekar, M. J. Pharm. Lett. 2011, 3 (6) 8-17
28. Veena, G.; Saritha, M. J. Chem. Pharm. Res. 2011, 3 (4) 150-158
29. Denadai, A. M. L.; Santoro, M. M.; Silva, L. H. D.; Viana, A. T.; Santos, R. A. S.; Sinisterra, R. D. J. Inclusion Phenom. 2006, 55 (1-2) 41-49
30. Hansen, L. D.; Fellingham, G. W.; Russell, D. J. Anal. Biochem. 2011, 409 (2) 220-229
31. Zoppi, A.; Quevedo, M. A.; Delrivo, A.; Longhi, M. R. J. Pharm. Sci. 2010, 99 (7) 3166-3176
32. Zoppi, A.; Quevedo, M. A.; Longhi, M. R. Bioorg. Med. Chem. 2008, 16 (18) 8403-8412
33. Boonyarattanakalin, K.; Wolschann, P.; Toochinda, P.; Lawtrakul, L. Eur. J. Pharm. Sci. 2012, 47 (4) 752-758
34. Sivasankar, T.; Antony Muthu Prabhu, A.; Karthick, M.; Rajendiran, N. J. Mol. Struct. 2012, 1028, 57-67
35. Tallury, S. S.; Smyth, M. B.; Cakmak, E.; Pasquinelli, M. A. J. Phys. Chem. B 2012, 116, 2023-2030
36. Raffaini, G.; Ganazzoli, F. J. Phys. Chem. B 2010, 114, 7133-7139
37. Raffaini, G.; Ganazzoli, F.; Malpezzi, L.; Fuganti, C.; Fronza, G.; Panzeri, W.; Mele, A. J. Phys. Chem. B 2009, 113, 9110-9122
38. Hemmateenejad, B.; Emami, L.; Sharghi, H. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 2010, 75 (1) 340-346
39. Allouche, A. R. J. Comput. Chem. 2011, 32 (1) 174-182
40. Gaussian 03, Revision C.02: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, Jr., T.; Kudin, K. N.; Burant, J. C., Gaussian, Inc., Wallingford CT, 2004.
41. OpenEye Scientific Software, www.eyesopen.com.
42. Hawkins, P. C. D.; Skillman, A. G.; Warren, G. L.; Ellingson, B. A.; Stahl, M. T. J. Chem. Inf. Model. 2010, 50 (4) 572-584
43. Omega, 2.4.3. OpenEye Scientific Software, Santa Fe, NM; http://www.eyesopen.com.
44. McGann, M. J. Comput. Aided Mol. Des. 2012, 8 (26) 1-10
45. McGann, M. J. Chem. Inf. Model. 2011, 51 (3) 578-596
46. Fred, 2.2.5. OpenEye Scientific Software, Santa Fe, NM; http://www.eyesopen.com.
47. VIDA, 4.1.2. OpenEye Scientific Software, Santa Fe, NM; http://www.eyesopen.com.
48. Case, D. A.; Cheatham, T. E., III; Darden, T.; Gohlke, H.; Luo, R.; Merz, K. M., Jr.; Onufriev, A.; Simmerling, C.; Wang, B.; Woods, R. J. J. Comput. Chem. 2005, 26 (16) 1668-1688
49. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. J. Comput. Chem. 2004, 25 (9) 1157-1174
50. Kirschner, K. N.; Yongye, A. B.; Tschampel, S. M.; González- Outeiriño, J.; Daniels, C. R.; Foley, B. L.; Woods, R. J. J. Comput. Chem. 2008, 29 (4) 622-655
51. Kuhn, B.; Gerber, P.; Schulz-Gasch, T.; Stahl, M. J. Med. Chem. 2005, 48, 4040-4048
52. Humphrey, W.; Dalke, A.; Schulten, K. J. Mol. Graph. 1996, 14 (1) 33-38
53. Turnbull, W. B.; Daranas, A. H. J. Am. Chem. Soc. 2003, 125 (48) 14859-14866
54. Indyk, L.; Fisher, H. F. Theoretical aspects of isothermal titration calorimetry. In Methods in Enzymology; Gary, K.; Ackers, M. L. J., Eds.; Academic Press: New York, 1998; Vol. 295, Chapter 17, pp 350-364.
55. Crupi, V.; Majolino, D.; Venuti, V.; Guella, G.; Mancini, I.; Rossi, B.; Verrocchio, P.; Viliani, G.; Stancanelli, R. J. Phys. Chem. A 2010, 114, 6811-6817