Magnetic and Spectroscopic Methods for Structural Characterization of Paramagnetic Hematoporphyrin IX Complex With Cu(II)
| 1 | University of Sofia, Faculty of Chemistry, 1, J. Bourchier Bulv., 1164 Sofia, Bulgaria |
CORRESPONDING AUTHOR
Galina G. Gencheva
Department of Analytical Chemistry, Faculty of Chemistry, “St. Kliment Ohridsky” University of Sofia, 1 J. Bourchier Boulevard, 1164 Sofia, Bulgaria
Department of Analytical Chemistry, Faculty of Chemistry, “St. Kliment Ohridsky” University of Sofia, 1 J. Bourchier Boulevard, 1164 Sofia, Bulgaria
Online publication date: 2007-10-01
Publication date: 2007-10-01
Eurasian J Anal Chem 2008;3(1):79–90
KEYWORDS
ABSTRACT
A paramagnetic metaloporphyrin type complex [Cu(II)(Hp-2H)].2H2O has been obtained during the reaction of Cu(II) and hematoporphyrin IX ((7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-21H-23H-porphyn-2,18-dipropionic acid) - Hp, I) in alkaline aqueous medium. The solution and solid state structure of the complex were studied through UV-Vis, IR and EPR spectroscopic methods. The applied simulation procedure using the parameters from the experimental EPR spectrum proved the square planar structure of the complex with symmetrical coordination of the porphyrin ligand to Cu(II) via the four pyrrole N-atoms in the porphyrin macrocycle.
REFERENCES (23)
1.
Ali H, and van Lier J E (1999) Metal complexes as photo and radiosensities. Coordination Chemistry Reviews 99: 2379.
2.
Gushikem Y, and Campos E A (1998) Cobalt(II) hematoporphyrin IX immobilized in a cellulose acetate niobium (V) oxide composite membane: Preparation and oxygen reduction study. Journal of Brazilian Chemical Society 9: 273.
3.
Ferrari R T, Colpini L M S, and Costa C M M (2003) Electrochemical Characterization of CoHP–Si Incorporated into a Carbon Paste Electrode. Microchimica Acta 142: 213.
4.
Kepczynski M, and Ehrenberg B (2002) Interaction of dicarboxylic metalloporphyrins with liposomes. The effect of pH on membrane binding revisited. Photochemistry and Photobiology 76: 486.
5.
Boyle R W, and Dolphin D (1996) Structure and biodistribution relationships of photodynamicsen sensitizers. Photochemistry 64: 469.
6.
Pottier R, and Kennedy J C (1990) The possible role of ionic species in selective biodistribution of photochemotherapeutic agents toward neoplastic tissue. Journal of Photochemistry and Photobiology B: Biology 8: 1.
7.
Brunner H, Arndt M R, and Treittinger (2004) Porphyrin platinum conjugates – new aims. Inorganica Chemica Acta 357: 1649.
8.
Zhang Ch X, and Lippard S. J. (2003) New metal complexes as potential therapeutics. Current Opinion in Chemical Biology 7: 481.
9.
Han I S (2004) Method of using a porphyrin-like molecule conjugated with an anti-cances drug for the treatment of cancer. Patent: WO/2004/041828.
10.
Lottner Ch, Knuechel, Bernhardt G, and Brunner H (2004) Distribution and subcellular localization of a water-soluble hematoporphyrin-platinum(II) complex in human bladder cancer cells. Cancer letters 215: 167.
11.
Brunner H, and Schellerer K-M (2004) New porphyrin platinum conjugates for the cytostatic and photodynamic tumour therapy. Inorganica Chimica Acta 350: 39.
12.
Lottner Ch, Bart K-Ch, Bernhardt G, and Brunner H (2002) Hematoporphyrin-derived soluble porphyrin-platinum conjugates with combined cytotoxic and phototoxic antitumor activity. Journal of Medicinal Chemistry 45: 2064.
13.
Gencheva G, Tsekova D, Gochev G, Momekov G, Tyuliev G, Skumryev V, Karaivanova M, and Bontchev P R (2007) Synthesis, structural characterization, and cytotoxic activity of novel paramagnetic hematoporphyrin IX complexes: Potent antitumor agents. Metal-Based Drugs ID 67376: 13 p (doi: 10/1155/2007/67376).
14.
Gencheva G, Tsekova D, Gochev G, Mehandjiev D, and Bontchev P R (2003) Monomeric Au(II) complexes with hematoporphyrin IX. Inorganic Chemistry Communications 6: 325.
15.
Momekov G, Ferdinandov D, Konstantinov S, Arpadjan S, Tsekova D, Gencheva G, Bontchev P R, and Karaivanova M (2007) In vitro evaluation of a stable monomeric gold(II) complex with hematoporphyrin IX: Cytotoxicity against tumor and kidney cells, cellular accumulation and induction of apoptosis. Bioinogranic Chemistry and Applications, submitted for publication with Article ID 367471, 8 pages.
16.
Tsekova D,Gencheva G, Gochev G, Momekov G, Skumryev V, Karaivanova M, and Bontchev P. R (2007) Synthesis, structural characterization and cytotoxic studies of novel designed paramagnetic palladium(III) complexes with hematoporphyrin IX. In preparation.
17.
Brisbin D A, and Balahura R J (1966) Equilibrium constants of zinc(II) and copper(II) with hematoporphyrin IX. Canadian Journal Chemistry 44: 2157 (doi:10.1139/cjc-44-18-2157).
18.
Berjot M, and Theophanides T (1980) Excitation profiles of Soret-excited resonance raman spectra of platinum-hematoporphyrin cpmplexes. Inorganica Chemica Acta 46: 281.
19.
Kunkely H, and Vogler A (1997) Photoreativity of hematoporphyrin IX-dichloroplatinum(II). Light-induced release and activation of free base hematoporphyrin. Inorganica Chimica Acta 254: 417.
20.
Zvezdina S V, Kozgova E V, Bereain M B, and Berezin B D (2007) Cadmium(II) for zinc(II) exchange reactions in deutero- and hematoporphyrin complexes in dimethyl sulfoxide. Russian Journal of Inorganic Chemistry 52: 1430 (doi: 10.1134/S0036023607090197).
21.
Christ A, and Szurkowski J (1999) Aggregation behaviour of hematoporphyrin derivates at high concentrations measured by photoacoustic spectroscopy. AIP Conf. Proc. (Proceedings of the 10th international conference on photoacoustic and photothermal phenomena) 463: 591 (doi: 10.1063/1.58224).
22.
Gochev G P,Yоrdanov N D, Antov L M (1994) A program for simulation of powder-type EPR and ENDOR spectra. Appled Magnetic Resonance 6: 183.
23.
Nakamoto K (1997) Infrared and Raman Spectra of Inorganic and Coordination Compounds. Part B: Application in Coordination, Organometallic and, Bioinorganic Chemistry, 5th Edition, p. 39.
