Theoretical and experimental study of the tetracain/β-cyclodextrin inclusion complex

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 74, Issue 1-4, 2012, Pages 211-221

  Chekirou, N L ^a   Benomrane, I ^a   Lebsir, F ^a   Krallafa, A M ^a  

^a UNIVERSITY OF ORAN   (Algeria)

Author keywords

Cyclodextrin; Fukui functions; Inclusion process; Quantum calculation; Raman spectroscopy; Tetracain

Indexed keywords

EID: 84864461259     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-0102-8     Document Type: Article

References (44)

1. KA Connors 1997 The stability of cyclodextrin complexes in solution Chem. Rev. 97 1325 10.1021/cr960371r 1:CAS:528:DyaK2sXksV2kurs%3D
2. VT D'Souza KB Lipkowitz 1998 Cyclodextrins: introduction Chem. Rev. 98 1741 10.1021/cr980027p
3. Sun, X.Q.; Meng, Q.; Yan, H.B.: Introduction of supermolecular chemistry, p. 11. Chinese Petrochemistry Press, Beijing (1997)
4. T Loftsson ME Brewster 1996 Pharmaceutical applications of cyclodextrins J. Pharm. Sci. 85 10 1017 10.1021/js950534b 1:CAS:528:DyaK28XlsFSrsr4%3D (Pubitemid 26338912)
5. SH Gellman 1997 Introduction: molecular recognition Chem. Rev. 97 1231 10.1021/cr970328j 1:CAS:528:DyaK2sXksFSru74%3D
6. R Breslow SD Dong 1998 Biomimetic reactions catalyzed by cyclodextrins and their derivatives Chem. Rev. 98 1997 10.1021/cr970011j 1:CAS:528: DyaK1cXksFSksL0%3D
7. JA Hamilton MN Sabesan 1982 Structure of inclusion complexes of cyclomaltoheptaose (cycloheptaamylose): crystal structure of the benzocaine adduct Carbohydr. Res. 102 31 10.1016/S0008-6215(00)88048-9 1:CAS:528: DyaL38XhsFeht74%3D
8. K Uekama F Hirayama T Irie 1998 Cyclodextrin drug carrier systems Chem. Rev. 98 2045 10.1021/cr970025p 1:CAS:528:DyaK1cXksV2itr0%3D
9. P Caliceta S Salmaso A Semenzato T Carofiglio R Fornasier M Fermeglia M Ferrone S Pricl 2003 Synthesis and physicochemical characterization of folate-cyclodextrin bioconjugate for active drug delivery Bioconjug. Chem. 14 899 10.1021/bc034080i (Pubitemid 37152948)
10. F Djedaini B Perly 1990 Organic shift reagents for the NMR analysis of cyclodextrins J. Mol. Struct. 239 161 10.1016/0022-2860(90)80209-3 1:CAS:528:DyaK3MXmt1Gmtw%3D%3D
11. L Szente J Szejtli 1998 Non-chromatographic analytical uses of cyclodextrins Analyst 123 735 10.1039/a707413a 1:CAS:528:DyaK1cXhvFOhsLc%3D (Pubitemid 28196141)
12. Frömming, K.-H.; Szejtl, J.: Cyclodextrin in pharmacy: topics in inclusion science. Kluwer Academic Publishers, The Netherland (1994)
13. K Uekama T Fujinaga F Hirayama M Otagiri M Yamasaki 1982 Inclusion complexations of steroid hormones with cyclodextrins in water and in solid phase Int. J. Pharm. 10 1 10.1016/0378-5173(82)90057-6 1:CAS:528:DyaL38XhsV2jtrg%3D (Pubitemid 12145049)
14. J Kang V Kumar D Yang PR Chowdhury RJ Hohl 2002 Cyclodextrin complexation: influence on the solubility, stability, and cytotoxicity of camptothecin, an antineoplastic agent Eur. J. Pharm. Sci. 15 163 10.1016/S0928-0987(01)00214-7 1:CAS:528:DC%2BD38Xht1ansbs%3D (Pubitemid 34155378)
15. N Li YH Zhang XL Xiong ZG Li HH Jin YN Wu 2005 Study of the physicochemical properties of trimethoprim with beta-cyclodextrin in solution J. Pharm. Biomed. Anal. 38 370 10.1016/j.jpba.2005.01.014 1:CAS:528: DC%2BD2MXltVegtL4%3D (Pubitemid 40733169)
16. ME Brewster T Loftsson 2007 Cyclodextrins as pharmaceutical solubilizers Adv. Drug Deliv. Rev. 59 645 10.1016/j.addr.2007.05.012 1:CAS:528: DC%2BD2sXpsFGks7g%3D (Pubitemid 47299263)
17. Bowman, W.C.; Rand, M.J.: Textbook of pharmacology. Blackwell, Cambridge (1990)
18. Avendaño, C.: Introducción a la Química FarmacéUtica. McGraw-Hill Interamaricana, Madrid (1993)
19. W Qin Z Jiao M Zhong XJ Shi J Zhang Z Li X Cui 2010 Simultaneous determination of procaine, lidocaine, ropivacaine, tetracaine and bupivacaine in human plasma by high-performance liquid chromatography J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 15-16 1185 10.1016/j.jchromb.2010.03.003
20. Atwood, J.L.; Davies, J.E.D.; MacNicol, D.D.; Vögtle, F.: Comprehensive supramolecular chemistry. Pergamon, Oxford (1996)
21. HJ Schneider F Hacket V Rüdiger H Ikeda 1998 NMR studies of cyclodextrins and cyclodextrin complexes Chem. Rev. 98 1755 10.1021/cr970019t 1:CAS:528:DyaK1cXksV2iur0%3D
22. K Harata 1998 Structural aspects of stereodifferentiation in the solid state Chem. Rev. 98 1803 10.1021/cr9700134 1:CAS:528:DyaK1cXksV2itbk%3D
23. L Liu L Xiao-Song K-S Song Q-X Guo 2000 PM3 studies on the complexation of α-cyclodextrin with benzaldehyde and acetophenone J. Mol. Struct. Theochem 531 127 10.1016/S0166-1280(00)00440-1 1:CAS:528:DC%2BD3cXntFyjtb0%3D
24. Li, X.; Liu, L.; Guo, Q.X.; Chu, S.D.; Liu, YC. PM3 molecular orbital calculations on the complexation of alpha-cyclodextrin with acetophenone. Chem. Phys. Lett. 307 (1999)
25. Li, X.; Liu, L.; Mu, T.W.; Guo, Q.X. A Systematic Quantum Chemistry Study on Cyclodextrins. Monatsh. Chem. 131 (2000)
26. L Liu X Li QX Guo YC Liu 1999 Hartree-Fock and density functional theory studies on the molecular recognition of the cyclodextrin. Hartree-Fock and density functional theory studies on the molecular recognition of the cyclodextrin Chin. Chem. Lett. 10 1053 1:CAS:528:DC%2BD3cXislSjtQ%3D%3D
27. E-C Yang X-J Zhao F Hua J-K Hao 2004 Semi-empirical PM3 study upon the complexation of β-cyclodextrin with 4,4′-benzidine and o-tolidine J. Mol. Struct. Theochem 712 75 10.1016/j.theochem.2004.08.045 1:CAS:528: DC%2BD2cXhtFeitrfE (Pubitemid 40022546)
28. C Yan L Xiaohui Z Xiu C Hao 2006 A quantum-mechanical study on the complexation of β-cyclodextrin with quercetin J. Mol. Struct. Theochem. 764 95 10.1016/j.theochem.2006.02.008 1:CAS:528:DC%2BD28XlvFGhu7o%3D
29. CL Yan ZL Xiu XH Li C Hao 2007 Molecular modeling study of β-cyclodextrin complexes with (+)-catechin and (-)-epicatechin J. Mol. Graph. Modelling 26 420 10.1016/j.jmgm.2007.01.010 1:CAS:528: DC%2BD2sXpvFKhur0%3D (Pubitemid 47333207)
30. Blidi Boukamel, N.; Krallafa, A.; Bormann, D.; Caron, L.; Canipelle, M.; Tilloy, S.; Monflier, E. Theoretical investigations of inclusion processes of (4-tert-butylphenyl)(3-sulfonatophenyl)(phenyl) phosphine in the β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 42 269 (2002)
31. NL Chekirou A Krallafa D Bormann 2005 Theoretical investigations and mechanisms of the inclusion processes of bi(3-sulfonatophenyl) (4-tert-butylphenyl) phosphine in the beta-cyclodextrin J. Incl. Phenom. Macrocycl. Chem. 53 89 10.1007/s10847-005-1762-z 1:CAS:528:DC%2BD2MXmtlWis70%3D (Pubitemid 41016364)
32. JJP Stewart 1989 Optimization of parameters for semi-empirical methods I-method J. Comp. Chem. 10 209 10.1002/jcc.540100208 1:CAS:528: DyaL1MXkt1ylu70%3D
33. K-S Song C-R Hou L Liu L Xiao-Song Q-X Guo 2001 A quantum-chemical study on the molecular recognition of β-cyclodextrin with ground and excited xanthones J. Photochem. Photobiol. A Chem. 139 105 10.1016/S1010-6030(01)00385-9 1:CAS:528:DC%2BD3MXhs1Wjtrc%3D
34. DE Bugay 2001 Characterization of the solid-state: spectroscopic techniques Adv. Drug Deliv. Rev. 48 43 10.1016/S0169-409X(01)00101-6 1:CAS:528:DC%2BD3MXivFejsrk%3D (Pubitemid 32452291)
35. J Johansson S Pettersson LS Taylor 2002 Infrared imaging of laser-induced heating during Raman spectroscopy of pharmaceutical solids J. Pharm. Biomed. Anal. 30 1223 10.1016/S0731-7085(02)00461-2 1:CAS:528:DC%2BD38Xot1CjsLo%3D (Pubitemid 35284334)
36. L Bondesson KV Mikkelsen Y Luo P Garberg H Agren 2007 Hydrogen bonding effects on infrared and Raman spectra of drug molecules Spectrochim. Acta A Mol. Biomol. Spectrosc. 66 213 10.1016/j.saa.2006.02.045 (Pubitemid 46027666)
37. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A. Jr.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A. GAUSSIAN03, Revision C.02, Gaussian, Inc.; Pittsburgh (PA) 2003
38. Parr, R.G.; Yang, W.: Density functional theory of atoms and molecules. Oxford University Press, New York (1989)
39. MW Schmidt KK Baldridge JA Boatz ST Elbert MS Gordon JH Jensen S Koseki N Matsunaga KA Nguyen SJ Su TL Windus M Dupuis JA Montgomery 1993 GAMESS: general atomic and molecular electronic structure system J. Comput. Chem. 14 1347 10.1002/jcc.540141112 1:CAS:528:DyaK2cXhsFaqtQ%3D%3D
40. RR Contreras P Fuentealba M Galvan P Perez 1999 A simple formalism devised to calculate the condensed-to-atoms Fukui function Chem. Phys. Lett. 304 405 10.1016/S0009-2614(99)00325-5 1:CAS:528:DyaK1MXislWlt70%3D
41. C Moller MS Plesset 1934 Note on an approximation treatment for many-electron systems Phy. Rev. 46 618 10.1103/PhysRev.46.618 1:CAS:528:DyaA2MXnvVCq
42. P Geerlings F De Proft W Langenaeker 2003 Conceptual density functional theory Chem. Rev. 103 1793 10.1021/cr990029p 1:CAS:528:DC%2BD3sXivFGgu7g%3D
43. Pearson, R.G.: Chemical hardness: applications from molecules to solids. Wiley-VCH Verlag GMBH, Weinheim (1997)
44. Koopmans, T.A.: Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica 1, 104 (1934)