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Preparation and Characterization of a Novel Ala-Gln Dipeptide-Zn2+ Complex
Corresponding Author(s) : Dan Wang
Asian Journal of Chemistry,
Vol. 25 No. 8 (2013): Vol 25 Issue 8
Abstract
Peptide-trace elements complex with constant coordination ratio and high biological activity has drawn wide attention around the world. The aim of the present study was to synthesize and characterizes Ala-Gln dipeptide-Zn2+ complex as an oral medicine. A freeze-dry powder containing Ala-Gln dipeptide and Zn2+, of which a chelating ratio of the dipeptide to Zn2+ is 2 to 1, was obtained in this study. Cyclic voltammetry analysis showed that ZnSO4 has only cathodic peak, while the dipeptide and the complex have both cathodic and anodic ones. The analysis of the complex by differential thermal analyzer showed that a new endothermic peak at 537.3 ºC appeared. It may be deduced that the coordination bond between carbonyl oxygen and Zn2+ broke. The endothermic peak at 279.5 ºC belonged to ionic bond fission between the carboxyl oxygen and Zn2+. Infrared analysis of the complex showed that absorption at 3334 cm-1 disappeared, which belonged to hydroxyl hydrogen of carboxylic acid. These characteristics suggested that an ionic bond formed between the carboxyl group of C8 and Zn2+, and the carbonyl oxygen in amide plane of C4 and carbonyl oxygen of carboxyl of C8 formed coordinate bond with Zn2+, respectively, providing lone pair electrons to the p empty orbital of Zn2+. Quantitative and biological qualitative evaluations showed that this Ala-Gln dipeptide-Zn2+ complex may serve as an effective oral medication for adsorption of the peptide and Zn2+ simultaneously in vivo.
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- M. Stefanidou, C. Maravelias and A. Dona, Arch. Toxicol., 80, 1 (2006).
- H. Scherz and E. Kirchhoff, J. Food Compos. Anal., 19, 420 (2006).
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- H. Fujita, K. Yokoyama and M. Yoshikawa, J. Food Sci., 65, 564 (2000).
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- M.J.S. Apines, S. Satoh and V. Kiron, Fisheries Sci., 69, 722 (2003).
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- S.K. Morcos, Eur. J. Radiol., 66, 175 (2008).
- J. Geng, H.J. Yu, J.S. Ren and X.G. Qu, Electrochem. Commun., 10, 1797 (2008).
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- D.K. Kundiyana, D.D. Bellmer, R.L. Huhnke, M.R. Wilkins and P.L. Claypool, Biomass Bioenergy, 34, 1481 (2010).
- L. Laopaiboon, S. Nuanpeng, P. Srinophakun, P. Klanrit and P. Laopaiboon, Bioresour. Technol., 100, 4176 (2009).
- M.A. Santos, R. Grazina, A.Q. Neto, G. Cantinho, L. Gano and L. Patricio, J. Inorg. Biochem., 78, 303 (2000).
- J.A. Lindsay and S.J. Foster, Microbiology, 147, 1259 (2001).
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References
M. Stefanidou, C. Maravelias and A. Dona, Arch. Toxicol., 80, 1 (2006).
H. Scherz and E. Kirchhoff, J. Food Compos. Anal., 19, 420 (2006).
D.K. Heyland, R. Dhaliwal and U. Suchner, Intens Care Med., 31, 327 (2005).
A. Ojo and C.M. Wood, Aquatic Toxicol., 89, 55 (2008).
R.J. Cousins, J.P. Liuzzi and L.A. Lichten, J. Biol. Chem., 281, 24085 (2006).
R.J. Cousins, Physiol. Rev., 65, 238 (1985).
E. Daniela, C. Salvatore and T. Giulio, Nutrition, 18, 743 (2002).
H. Fujita, K. Yokoyama and M. Yoshikawa, J. Food Sci., 65, 564 (2000).
T. Kawasaki, E. Seki and K. Osajima, J. Hum. Hypertens, 14, 519 (2000).
Y.S. Liu, S.F. Kong and Y.Q. Li, J. Hazard. Mater., 171, 1159 (2009).
M.S.A. Sarker, S. Satoh and V.h Kiron, Aquaculture, 262, 436 (2007).
A. Yiannikouris, C. Connolly and R. Power, Metallomics, 1, 235 (2009).
M.J.S. Apines, S. Satoh and V. Kiron, Fisheries Sci., 69, 722 (2003).
D.T.S. Rijkers, G.W. van Esse and R. Merkx, Chem. Commun., 36, 4581 (2005).
H.J. Olivos, P.G. Alluri, M.M. Reddy, D. Salony and T. Kodadek, Org. Lett., 4, 4057 (2002).
A. Olaya, S. Moreno and R. Molina, Appl. Catal. A-Gen., 370, 7 (2009).
H.X. Liu, C. Hu and X.J. Zhu, Mater. Chem. Phys., 88, 290 (2004).
A.K. Bose, H.I. Yao, N. Lavlinskaia, C. Sareen, B.N. Pramanik, L.B. Peter, H.L. Yan and L. Heimark, J. Am. Soc. Mass Spectr., 13, 839 (2002).
P. Dechelotte, M. Hasselmann, L. Cynober, B. Allaouchiche, M. Coeffier, B. Hecketsweiler, V. Merle, M. Mazerolles, D. Samba, Y.M. Guillou, J. Petit, O. Mansoor, G. Colas, R. Cohendy, D. Barnoud, P. Czernichow and G. Bleichner, Crit. Care Med., 34, 598 (2006).
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V. Gebbia and C. Puozzo, Expert Opin. Drug Safety, 4, 915 (2005).
M. Vogeser, P. Moehnle and J. Briegel, Clin. Chem. Lab. Med., 45, 521 (2007).
N.J. Waters, R. Jones, G. Williams and B. Sohal, J. Pharm. Sci., 97, 4586 (2008).
S.K. Morcos, Eur. J. Radiol., 66, 175 (2008).
J. Geng, H.J. Yu, J.S. Ren and X.G. Qu, Electrochem. Commun., 10, 1797 (2008).
H. Yuan, W. Meng, W. Duo, L.G. Xue and J.G. Cong, J. Membr. Sci., 319, 5 (2008).
K. Osz, Z. Nagy, G. Pappalardo, G. Di Natale, D. Sanna, G. Micera, E. Rizzarelli and I. Sóvágó, Chem.-A Eur. J., 13, 7129 (2007).
T.E. Haynes, P. Li, X.L. Li, K. Shimotori, H. Sato, N.E. Flynn, J.J. Wang, D.A. Knabe and G.Y. Wu, Amino Acids, 37, 131 (2009).
D.K. Kundiyana, D.D. Bellmer, R.L. Huhnke, M.R. Wilkins and P.L. Claypool, Biomass Bioenergy, 34, 1481 (2010).
L. Laopaiboon, S. Nuanpeng, P. Srinophakun, P. Klanrit and P. Laopaiboon, Bioresour. Technol., 100, 4176 (2009).
M.A. Santos, R. Grazina, A.Q. Neto, G. Cantinho, L. Gano and L. Patricio, J. Inorg. Biochem., 78, 303 (2000).
J.A. Lindsay and S.J. Foster, Microbiology, 147, 1259 (2001).
W.H. McClain, K. Gabriel, D. Lee and S.H. Otten, RNA, 5, 795 (2004)