Intercalation of l-alanyl-glutamine dipeptide into layered double hydroxides: Configuration stabilization in confined interlayer region

Industrial and Engineering Chemistry Research

Volumn 51, Issue 34, 2012, Pages 11128-11136

  Wang, Yongliao ^a   Wu, Pingxiao ^a   Hou, Yakun ^a   Zhu, Nengwu ^a   Dang, Zhi ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL DRUGS; CIRCULAR DICHROISM SPECTRA; CONFORMATIONAL TRANSITIONS; DENSITY FUNCTIONAL THEORIES (DFT); DIPEPTIDE; GUEST-HOST INTERACTIONS; INTERLAYER REGIONS; LAYERED DOUBLE HYDROXIDES; REACTION TEMPERATURE; STRUCTURAL CHARACTERIZATION; SYSTEMATIC STUDY; THEORETICAL INVESTIGATIONS; UV-VIS SPECTROSCOPY;

DENSITY FUNCTIONAL THEORY; ULTRAVIOLET VISIBLE SPECTROSCOPY;

AMINO ACIDS;

EID: 84865654227     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie300406b     Document Type: Article

References (36)

1. Fogg, A. M.; Green, V. M.; Harvey, H. G. New separation science using shape-selective ion exchange intercalation chemistry Adv. Mater. 1999, 11, 1466
2. Renaudin, G.; Francois, M.; Evrard, O. Order and disorder in the lamellar hydrated tetracalcium monocarboaluminate compound Cem. Concr. Res. 1999, 29, 63
3. Khan, A. I.; O'Hare, D. Intercalation chemistry of layered double hydroxides: recent developments and applications J. Mater. Chem. 2002, 12, 3191
4. Jabbágy, M.; Regazzoni, A. E. Anion-exchange equilibrium and phase segregation in hydrotalcite systems: Intercalation of hexacyanoferrate (III) ions J. Phys. Chem. B 2005, 109, 389
5. Aisawa, S.; Ohnuma, Y.; Hirose, K.; Takahashi, S.; Hirahara, H.; Narita, E. Intercalation of nucleotides into layered double hydroxides by ion-exchange reaction Appl. Clay Sci. 2005, 28, 137
6. Géraud, E.; Rafqah, S.; Sarakha, M.; Forano, C.; Prevot, V.; Leroux, F. Three dimensionally ordered macroporous layered double hydroxides: Preparation by templated impregnation/coprecipitation and pattern stability upon calcination Chem. Mater. 2008, 20, 1116
7. Abeeló, S.; Mitchell, S.; Santiago, M.; Stocia, G.; Pérez-Ramírez, J. Perturbing the properties of layered double hydroxides by continuous coprecipitation with short residence time J. Mater. Chem. 2010, 20, 5878
8. Costantino, U.; Ambrogi, V.; Nocchetti, M.; Perioli, L. Hydrotalcite-like compounds: Versatile layered hosts of molecular anions with biological activity Microporous Mesoporous Mater. 2008, 107, 149
9. Ambrogi, V.; Fardella, G.; Grandolini, G.; Perioli, L. Intercalation compounds of hydrotalcite-like anionic clays with antiinflammatory agents - I. Intercalation and in vitro release of ibuprofen Int. J. Pharm. 2001, 220, 23
10. Ambrogi, V.; Perioli, L.; Ciarnelli, V.; Nocchetti, M.; Rossi, C. Effect of gliclazide immobilization into layered double hydroxide on drug release Eur. J. Pharm. Biopharm. 2009, 73, 285
11. Rossi, C.; Schoubben, A.; Ricci, M.; Perioli, L.; Ambrogi, V.; Latterini, L.; Aloisi, G. G.; Rossi, A. Intercalation of the radical scavenger ferulic acid in hydrotalcite-like anionic clays Int. J. Pharm. 2005, 295, 47
12. Bonina, F. P.; Giannossi, M. L.; Medici, L.; Puglia, C.; Summa, V.; Tateo, F. Adsorption of salicylic acid on bentonite and kaolin and release experiments Appl. Clay Sci. 2008, 41, 165
13. Choy, J. H.; Kwak, S. Y.; Park, J. S.; Jeong, Y. J.; Portier, J. Intercalative nanohybrids of nucleoside monophosphates and DNA in layered metal hydroxide J. Am. Chem. Soc. 1999, 121, 1399
14. Xu, Z. P.; Walker, T. L.; Liu, K.; Copper, H. M.; Lu, G. Q.; Bartlett, P. F. Layered double hydroxide nanoparticles as cellular delivery vectors of supercoiled plasmid DNA Int. J. Nanomed. 2007, 2, 163
15. Choy, J. H.; Park, M.; Oh, J. M. Bio-nanohybrids based on layered double hydroxide Curr. Nanosci. 2006, 2, 275
16. Choy, J. H.; Kwak, S. Y.; Park, J. S.; Jeong, Y. J. Cellular uptake behavior of [γ-32P] labeled ATP-LDH nanohybrids J. Mater. Chem. 2001, 11, 1671
17. Lang, K.; Bezdicki, P.; Bourdelande, J. L.; Hernando, J.; Jirka, I.; Káfunková, E.; Kovanda, F.; Kubát, P.; Mosinger, J.; Wagnerová, D. M. Layered double hydroxides with intercalated porphyrins as photofunctional materials: subtle structural changes modify singlet oxygen production Chem. Mater. 2007, 19, 3822
18. Wypych, F.; Bubniak, G. A.; Halma, M.; Nakagaki, S. Exfoliation and immobilization of anionic iron porphyrin in layered double hydroxides J. Colloid Interface Sci. 2003, 264, 203
19. Halma, M.; Castro, K. A. D. d. F.; Prévot, V.; Forano, C.; Wypych, F.; Nakagaki, S. Immobilization of anionic iron (III) porphyrins into ordered macroporous layered double hydroxides and investigation of catalytic activity in oxidation reactions J. Mol. Catal. A: Chem. 2009, 310, 42
20. Khan, A. I.; Lei, L. X.; Norquist, A. J.; O'Hare, D. Intercalation and controlled release of pharmaceutically active compounds from a layered double hydroxide Chem. Commun. 2001, 2342
21. Choy, J. H.; Kwak, S. Y.; Jeong, Y. J.; Park, J. S. Inorganic layered double hydroxides as nonviral vectors Angew. Chem., Int. Ed. 2000, 39, 4041
22. Wsol, V.; Skalova, L.; Szotakova, B. Chiral inversion of drugs: coincidence or principle? Curr. Drug Metab. 2004, 5, 517
23. Chen, Q. H.; Shi, S. X.; Liu, X. L.; Jin, L.; Wei, M. Studies on the oxidation reaction of l -cysteine in a confined matrix of layered double hydroxides Chem. Eng. J. 2009, 153, 175
24. 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. 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, 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.; Califford, 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. Gaussian 03, Revision B.01; Gaussian, Inc.: Pittsburgh PA, 2003.
25. Zhao, Y.; Li, F.; Zhang, R.; Evans, D. G.; Duan, X. Preparation of layered double-hydroxide nanomaterials with a uniform crystallite size using a new method involving separate nucleation and aging steps Chem. Mater. 2002, 14, 4286
26. Lin, Y. H.; Adebajo, M. O.; Kloprogge, J. T.; Martens, W. N.; Frost, R. L. X-ray diffraction and Raman spectroscopic studies of Zn-substituted carrboydite-like compounds Mater. Chem. Phys. 2006, 100, 174
27. Palmer, S. J.; Frost, R. L.; Nguyen, T. Hydrotalcites and their role in coordination of anions in Bayer liquors: Anion binding in layered double hydroxides Coord. Chem. Rev. 2009, 253, 250
28. Hines, D. R.; Solin, S. A.; Costantino, U.; Nocchetti, M. Physical properties of fixed-charge layer double hydroxides Phys. Rev. B 2000, 61, 11348
29. 3: LDH formation mechanism Chem. Mater. 2005, 17, 1055
30. Panda, H. S.; Srivastava, R.; Bahadur, D. In-vitro release kinetics and stability of anti cardiovascular drugs-intercalated layered double hydroxide nanohybrids J. Phys. Chem. B 2009, 113, 15090
31. Wei, M.; Yuan, Q.; Evans, D. G.; Wang, Z. Q.; Duan, X. Layered solids as a "molecular container" for pharmaceutical agents: l-tyrosine-intercalated layered double hydroxides J. Mater. Chem. 2005, 15, 1197
32. Wei, M.; Pu, Y.; Guo, J.; Han, J. B.; Li, F.; He, J.; Evans, D. G.; Duan, X. Intercalation of L-Dopa into layered double hydroxides: enhancement of both chemical and stereochemical stabilities of a drug through host-guest interactions Chem. Mater. 2008, 20, 5169
33. Pispisa, B.; Palleschi, A.; Venanzi, M.; Zanotii, G. Conformational statistics and energetics analysis of sequential peptides undergoing intramolecular transfer of excitation energy J. Phys. Chem. 1996, 100, 6835
34. Gokce, I.; Woody, R. W.; Anderluh, G.; Lakey, J. H. Single peptide bonds exhibit poly (pro) II ("random coil") circular dichroism spectra J. Am. Chem. Soc. 2005, 127, 9700
35. Oh, K. I.; Kim, W.; Joo, C.; Yoo, D. G.; Han, H.; Hwang, G. S.; Cho, M. Azido gauche effect on the backbone conformation of β-Azidoalanine peptides J. Phys. Chem. B 2010, 114, 13021
36. Lee, K. K.; Kim, E.; Joo, C.; Song, J.; Han, H.; Cho, M. Site-selective intramolecular hydrogen-bonding interactions in phosphorylated serine and threonine dipeptides J. Phys. Chem. B 2008, 112, 16782