The Malaysian Journal of Analytical Sciences Vol 13 No 1 (2008): 505 - 512
METALLATION OF PROTOPORPHYRINS USED AS FLUORESCENT CHEMOSENSOR FOR IMIDAZOLE RECOGNITION
Kornvalai Panpae*, Chaiwat Krikrutthee, Phumthan Porntaweethum,
Panya Weerachiwcharnchai and Aekapoj Chenwittayayos
Department of Chemistry, Faculty of Science, King’s Mongkut University of Technology Thonburi, Bangkok 10140, Thailand.
* Corresponding author:kornvalai.pan@kmutt.ac.th
Abstract
Metalloporphyrin Complexes play significant roles in many biological and catalytic systems. The diversity of their functions is due in part to the variety of metals that bind in the “pocket” of the porphyrin ring system. Two kinds of metalloporphyrin derivatives, Cu (II) and Zn (II) protoporphyrins (PP), were microscale synthesized ((1) and (2)) and characterized by spectroscopic methods and magnetic measurements. A PP ligand bound to each metal center in a tetradentate fashion including four amine nitrogen atoms in the equatorial planes. These complexes were found to recognize imidazolyl groups of histidine and histamine derivatives as guest molecules by coordination and additional non-covalent interactions. These added analytes displace the selective fluorescent indicator, which when released to the solution displays its full fluorescence. Thus, analyte recognition is signaled by the sharp appearance of the fluorescence of the indicators. The binding affinities of (1) and (2) to histidine and histamine were investigated and accounted for different complexation properties. Moreover, we demonstrated that careful choice of a fluorescent indicator with tuned affinity toward the receptor can provide discrimination in sensing of a desired substrate and the role that the metal coordination plays on the hypsochromic shift and loss of fluorescence distincted characteristics of hypsoporphyrins were also discussed.
Keywords : Metallation, Imidazole recognition, Histidine, Histamine, Protoporphyrin, Fluorescent chemosensor.
References
1. Chow, C-F., B.K.W. Chiu, M.H.W. lam and W.-Y. Wong, 2003. A trinuclear heterobimetallic Ru(II)/Pt(II) complex as a chemodosimeter selective for sulfhydryl-containing amino acids and peptides. J. Am. Chem. Soc. Chem. Commun. 125 : 7802-7803.
2. Euriz, R.D and E.A. Jauregui, 1990. Study of the configurational isomerism of polar groupspresent in histamine H2-receptor antagonists. J. Mol. Stuc. : THEOCHEM, 207 : 269-283.
3. Hanaoka, K., K. Kikuchi, H. Kojima, Y. Urano and T. Nagano. 2004. Development of a zincion – selective luminescent lanthanide chemosensor for biological application. J. Am.Chem. Soc. 126 : 12470 – 12476.
4. Ho, H.A. and M. Leclerc. 2003, New colorimetric and fluorometric chemosensor based on aCatiouic polythiophene derivative for iodide-specific detection. J. Am. Chem. Soc. Chem.Commun. 125 : 4412 –4413.
5. Hortalá, L. Fabbrizzi, N. Marcotte, F. Stomeo and A. Taglietti. 2002. Designing the selectivity of the fluorescent detection of amino acids : A chemosensing ensemble for histidine. J. Am. Chem. Soc. 125 : 20 –21.
6. Kojima, T., H. Kitaguchi, Y. Tachi, M. Yasutake, Y. Naruta and Y. Matsuda. 2005. synthesis and characterization of novel Cu(II)-bipyridine complexex having functional groups and their application toword molecular recognition. Inorg. Chim. Acta. 358 : 3592 – 3600.
7. Marsh, D.F. and L.M. Mink. 1996. Microscale synthesis and electronic absorption spectroscopy of tetraphenylporphyrin H2 (TPP) and metalloporphyrins Zn(II)(TPP) and Ni(II)(TPP). J. Chem. Educ. 73 (12) : 1188 – 1190.
8. Morel, A., M. Darmon and M. Dalaage. 1990. Recognition of imidazole and histamine derivatives by monoclonal antibodies. Molec. Immun. 27 : 995 – 1000.
9. Panpae, K., T. Rerkchanchai and T. Wongsrichalalai. 2007. Synthesis of Zn(II)-oxazoline/pyridine derivative complex as a molecular sensing ensemble for aspartate and histidine. Kasetsart J. : Natural Sci. 41 : 158 – 168.
10. Saucodo, L. and L.M. Mink. 2005. Microscale synthesis and 1H NMR analysis of Zn(II) and Ni(II) tetraphenylporphyrins. J. Chem. Dduc. 82 (5) : 790 – 802.
11. Tong, A., H. Dong and L. Li. 2002. Molecular imprinting-based fluorescent chemosensor for histamine using zinc (II) – protoporphyrin as a functional monomer. Anal. Chim. Acta. 466 : 31 – 37.
12. Zheng, Y., Q. Hua, P. Kele, F.M. Andreopoulos, S. M. Pham and R.M. Leblanc. 2001. A new fluorescent chemosensor for copper ions based on tripeptide glycyl – histidyl – lysine (GHK). Org. Lett. 3 : 3277 –3280.
13. Zheng. U., X. Cao, J. Orgulescu, V. Konka, F.M. Andreopoulos, S.M. Pham and R.M. Leblanc. 2003. Peptidyl fluorescent chemosensors for the detection of divalent copper .Anal. Chem. 75 : 1706 – 1712.