D. Skrzypek et al. / Journal of Molecular Structure 876 (2008) 177–185
185
imply that synthetic porphyrin (such as investigated TTP)
[20] D. Inniss, S.M. Soltis, C.E. Strouse, J. Am. Chem. Soc. 110 (1988)
644.
5
exhibit lower U values (Table 4) than earlier investigated
F
[21] F.A. Walker, Coord. Chem. Rev. 185–186 (1999) 471, and references
therein.
natural porphyrin [54,55], hence they rather cannot be a
promising candidate as photomarkers for diagnosis.
It is known that the yield of singlet oxygen formation
[22] J. Kliava, Phys. Stat. Solids (b) 134 (1986) 411.
[23] T.D. Smith, J.R. Pilbrow, in: L.J. Berliner, J. Reuben (Eds.),
Biological Magnetic Resonance, vol. 2, Plenum Press, New York
and London, 1980, pp. 85–168, and references therein.
(
U ) as a result of dye triplet interaction with oxygen can
D
be given by the relation: U = U S . The value of S coef-
D
T
D
D
[
[
24] R. Cammack, C.E. Cooper, Methods in Enzymology 227 (1993) 353.
25] A. Abragam, B. Bleaney, Electron Paramagnetic Resonance of
Transition Ions, Clarendon Press, Oxford, 1970.
ficient is close to 1 for TTP–NHCO–Pro–Cbz and indicate
that the very efficient excitation energy transfer between
dye and molecular oxygen caused the singlet oxygen forma-
tion. It was also found out that for TTP–CONH–Pro–
COOCH C H the S value is about 0.81 confirmed that
[26] (a) R.M. Golding, T. Singhasuwich, W.C. Tennant, Mol. Phys. 34
(1977) 1343, and references therein;
(
b) D.G. McGavin, W.C. Tennant, Mol. Phys. 45 (1982) 77.
2
6
5
D
[
[
27] E.M. Yahiaoui, R. Berger, Y. Servant, J. Kliava, L. Cugunov, A.
Mednis, J. Phys. Condens. Matter 6 (1994) 9415.
28] J. Kliava, R. Berger, Mol. Phys. Rep. 39 (2004) 130.
the triplet state of this dye could be still able to participate
directly (not only mediated by singlet oxygen) in photody-
namic reaction. The result shows as small structural differ-
ences in porphyrins provide to the differentiations in their
spectroscopic behaviour and therefore can affect the dye’s
effectiveness of photodynamic ability.
[29] Y.V. Yablokov, V.V. Zelentsov, M. Augustyniak-Jablokow, A.
Krupska, J. Mrozinski, Mater. Sci. 21 (2003) 215.
[30] D. Skrzypek, I. Madejska, J. Habdas, J. Phys. Chem. Sol. 66 (2005)
9
1.
[
[
31] F.A. Walker, J. Magn. Res. 15 (1974) 201.
32] J.A. Pilbrow, Transition Ion Electron Paramagnetic Resonance,
Clarendon, Oxford, 1990.
Acknowledgement
[
[
[
[
33] A. Bencini, I. Bertini, G. Canti, D. Gatteschi, C. Luchinat, J. Inorg.
Biochem. 14 (1981) 81.
One of us (A.D.) thanks Mrs Ewa Teslak for assistance
with the LIOAS measurements.
34] L. Banci, A. Bencini, C. Benelli, D. Gatteschi, C. Zanchini, Structure
and Bonding, vol. 52, Springer Verlag, Berlin, Heidelberg, 1982.
35] J. Subramanian, in: K.M. Smith (Ed.), Porphyrins and Metallopor-
phyrins, Elsevier, Amsterdam, 1975, pp. 555–589, Chapter 13.
36] T. Gianferrara, B. Serli, E. Zangrando, E. Iengo Alesslo, New J.
Chem. 29 (2005) 895.
References
[
[
[
1] R. Bonnett, Chemical Aspects of Photodynamic Therapy, Gordon
and Breach Science Publishers, London, 2000.
2] J. Poltowicz, E.M. Serwicka, E. Bastardo-Gonzalez, W. Jones, R.
Mokaya, Appl. Catal. A. General 218 (2001) 211.
[37] B.B. Wayland, M.E. Abd-Elmageed, J. Am. Chem. Soc. 96 (1974)
4809.
[38] F.A. Walker, J. Am. Chem. Soc. 92 (1970) 4235.
[39] J.S. Taylor, J.E. Coleman, J. Biol. Chem. 246 (1971) 7058.
[40] G.N. La Mar, F.A. Walker, J. Am. Chem. Soc. 95 (1973) 1790.
[41] S.A. Cockle, Biochem. J. 137 (1974) 587.
3] (a) A. Yaron, F. Naider, Biochem. Mol. Biol. 28 (1993) 3;
(
b) J. Habdas, in: H. Gorecki, Z. Dobrzanski, P. Kafarski (Eds.),
Chemistry for Agriculture, vol. 5, Czech-Pol-Trade, Preque-Brissels,
004, pp. 96–100.
[42] E. Di Iorio, E. Fioretti, I. Ariani, F. Ascoli, G. Rotilio, M. Brunori,
FEBS Lett. 105 (1979) 229.
2
[
4] A.D. Adler, F.R. Longo, J.D. Finarelli, J. Goldmacher, J. Assour, L.
Korsakoff, J. Org. Chem. 32 (1967) 476.
5] J.C. Sheehan, G.P. Hess, J. Am. Chem. Soc. 77 (1955) 1067.
6] J. Habdas, B. Boduszek, Phosphorus, Sulfur Silicon 180 (2005) 2039.
7] J.E. Falk, Porphyrins and Metalloporphyrins, Elsevier, Amsterdam,
[43] B.R. Mc Garvey, Can. J. Chem. 53 (1975) 2498.
[44] M. Barzaghi, T. Beringhelli, F. Morazzoni, J. Mol. Catal. 14 (1982)
357.
[45] B.B. Wayland, J.V. Minkiewicz, M.E. Abd-Elmageed, J. Am. Chem.
Soc. 96 (1974) 2795.
[
[
[
1
975.
[46] R. Koerner, M. Olmstead, A. Ozarowski, S.L. Phillips, P.M. Van
Calcar, K. Winkler, A.L. Balch, J. Am. Chem. Soc. 120 (1998) 1274.
[47] Z. Sojka, Catal. Rev. Sci. Eng. 37 (1995) 461.
[48] A. Dudkowiak, E. Te s´ lak, J. Habdas, J. Mol. Struct. 792/793 (2006)
93.
[49] M. Pineiro, A.L. Carvalho, M.M. Pereira, AMd’A. Rocha Gonsalves,
L.G. Arnaut, Chem. Eur. J. 4 (1998) 2299.
[50] E. Zenkevich, E. Sagun, V. Knyukshto, A. Shulga, A. Mironov, O.
Efremova, R. Bonnett, S.P. Songca, M. Kassem, J. Photochem.
Photobiol. B. Biol. 33 (1996) 171.
[
[
8] E. Braslavsky, G.E. Heibel, Chem. Rev. 92 (1992) 1381.
9] D. Fr a˛ ckowiak, A. Dudkowiak, K. Wiktorowicz, J. Phys. IV 109
(2003) 33.
[
[
[
10] H. Ogoshi, Y. Saito, K. Nakamoto, J. Chem. Phys. 57 (1972) 4194.
11] L.J. Boucher, J.J. Katz, J. Am. Chem. Soc. 89 (1967) 1340.
12] M.M. El-Nahass, H.M. Zeyada, M.S. Aziz, M.M. Makhlouf,
Spectrochim. Acta A 61 (2005) 3026.
13] M. Gouterman, in: D. Dolphin (Ed.), The Porphyrins, vol. 3,
Academic press, New York, 1978, Chapter 1.
[
[
14] E.J. Baerends, G. Ricciard, A. Rosa, S.J. van Gisbergen, Coord.
Chem. Rev. 230 (2002) 5.
[51] C. Marti, S. Nonell, M. Nicolaus, T. Torres, Photochem. Photobiol.
71 (2000) 53.
[
[
[
15] Y. Kaizu, M. Asano, H. Kobayashi, J. Phys. Chem. 90 (1986) 3906.
16] W.E. Blumberg, Methods Enzymol. 76 (1981) 312.
17] F.A. Walker, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The
Porphyrin Handbook, vol. 5, Academic Press, New York, 2000, pp.
[52] J.R. Small, L.J. Libertini, E.W. Small, Biophys. Chem. 42 (1992) 29.
[53] D. Wr o´ bel, A. Dudkowiak, Mol. Cryst. Liq. Cryst. 448 (2006) 617.
[54] E. Sta s´ kowiak, A. Dudkowiak, Spectrochim. Acta A. 61 (2005) 2033.
[55] A. Dudkowiak, E. Te s´ lak, J. Habdas, in: A. Pawełczyk (Ed.),
Chemistry and Biochemistry in the Agricultural Production, Envi-
ronment Protection, Human and Animal Health, Series: Chemistry
for Agriculture, vol. 7, Czech-Pol-Trade, Prague, Brussels, 2006, pp.
954–959.
81–183, and references therein.
[
[
18] J.C. Salerno, J.S. Leigh, J. Am. Chem. Soc. 106 (1984) 2156.
19] F.A. Walker, B.H. Huynh, W.R. Scheidt, S.R. Osvath, J. Am. Chem.
Soc. 108 (1986) 5288.