PHOTOSTABILITY OF BACTERIOCHLOROPHYLL a AND ITS DERIVATIVES AS POTENTIAL SENSITIZERS FOR PHOTODYNAMIC CANCER THERAPY: THE STUDY ON ACETONE-WATER AND METHANOL-WATER SOLVENTS

https://doi.org/10.22146/ijc.21403

Leenawaty Limantara(1*), Heriyanto Heriyanto(2)

(1) Industrial Engineering Study Program of Ma Chung University
(2) Ma Chung Research Center for Photosynthetic Pigments, Ma Chung University, Jl. Villa Puncak Tidar N-01, Malang 65151, East Java
(*) Corresponding Author

Abstract


The determination of photostability for Mg-BChl a, Zn-BPheo a and Cu-BPheo a irradiated with red light (≥ 630 nm, 870 lux) and equilibrated with air for 20 min in acetone-water and methanol-water solvents at various percentages of water has been done. The presence of light and oxygen in the pigment solution cause the pigment instable. The pigment stability toward photooxidation is extremely influenced by solvent properties, including oxidation potential value and solvent abilities to form coordination and aggregate. Degradation products of pigment during irradiation treatment can be detected by increment of absorption at the absorption spectrum or occurrence of new positive absorption bands at the different absorption spectra. Cu-BPheo a is a promising photosensitizer based on its stability toward photooxidation in acetone-water solvents.

Keywords


Photostability; bacteriochlorophyll a and its derivatives; acetone-water; methanol-water

Full Text:

Full Text PDF


References

[1] Oelze, J., 1985, Meth. Microbiol., 18, 257–284.

[2] Permentier, H.P., Neerken, S., Overmann, J., and Amesz, J., 2001, Biochemistry, 40, 5573–5578.

[3] Scheer, H., 2006, “An Overview of chlorophylls and Bachteriochlorophylls: Biochemistry, Biophysics, Functions and Applications” in Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications, Eds. Grimm, B., Porra, J., Rudiger, W., and Scheer, H., Advances in Photosynthesis and Respiration, 25, 1–26.

[4] Eichwurzel, I., Stiel, H., Teuchner, K., Leupold, D., Scheer, H., Salomon, Y., and Scherz, A., 2000, Photochem. Photobiol., 72, 2, 204–209.

[5] Henderson, B.W., Potter, W.R., Sumlin, A.B., Owczarczak, B.L., Dougherty, F.S., and Nowakowski, T.J., 1990, SPIE, Photodyn. Ther.: Mech. II, 1203, 211–222.

[6] Henderson, B.W., Sumlin, A.B., Owczarczak, B.L., and Dougherty, T.J., 1991, J. Photochem. Photobiol. B, 10, 303–313.

[7] Brandis, A.S., Salomon, Y., and Scherz, A., 2006, "Bacteriochlorophyll Sensitizers in Photodynamic Therapy” in Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications, Eds. Grimm, B., Porra, J., Rudiger, W. and Scheer, H., Advances in Photosynthesis and Respiration, 25, 485–494.

[8] Dougherty, T.J., Gomer, D.J., Henderson, B.W., Jori, G., Kessel, D., Korbelik, M., Moan, J., and Peng, Q., 1998, J. Natl. Cancer Inst., 90, 889–905.

[9] Moser, J.G., 1998, “Bachteriochlorophyllides, bachteriochlorins and bachteriopheophorbides” in: Photodynamic Tumor Therapy, Ed. Moser, J.G., OPA, Amsterdam, 43–49.

[10] Pandey, R.K., and Zheng, G., 2000, “Porphyrins as photosensitizers in photodynamic therapy” in The Porphyrin Handbook, Eds. Kadish, K.M., Smith, K.M., and Guilard, R., Academic Press, San Diego, 6, 157–230.

[11] Fiedor, L., Gorman, A.A., Hamblett, I., Rosenbach-Belkin, V., Salomon, Y., Scherz, A., and Tregub, I., 1993, Photochem. Photobiol., 58, 506–511.

[12] Anderson, R.R., and Parrish, J.A., 1981, J. Invest. Dermatol., 77, 1, 13–19.

[13] Spikes, J.D., and Bommer, J.C., 1991, “Chlorophyll and related pigments as photosensitizers in biology and medicine” in Chlorophylls, Ed. Scheer, H., CRC Press, Boca Raton, FL, 1181–1204.

[14] Hartwich, G., Fiedor, L., Simonin, I., Cmiel, E., Schafer, W., Noy, D., Scherz, A., and Scheer, H., 1998, J. Am. Chem. Soc., 120, 3675–3683.

[15] Fiedor, L., Scheer, H., Hunter, C.N., Tschirschwitz, F., Voigt, B., Ehlert, J., Nibbering, E., Leupold, D., and Elsaesser, T., 2000, Chem. Phys. Lett., 319, 145–152.

[16] Senge, M.O., Wiehe, A., and Ryppa, C., 2006, „Synthesis, Reactivity and Structure of Chlorophylls” in Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications, Eds. Grimm, B., Porra, J., Rudiger, W., and Scheer, H., Advances in Photosynthesis and Respiration, 25, 27–37.

[17] Yerushalmi, R., Ashur, I., and Scherz, A., 2006, “Metal-substituted Bacteriochlorophylls: Novel Molecular Tools” in Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications, Eds. Grimm, B., Porra, J., Rudiger, W., and Scheer, H., Advances in Photosynthesis and Respiration, 25, 495–506.

[18] Fiedor L., Rosenbach-Belkin, V., Sai, M., and Scherz, A., 1996, Plant Physiol. Biochem., 34, 393–398.

[19] Rosenbach-Belkin, V., Chen, L., Fiedor, L., Tregub, I., Pavlotsky, F., Brumfeld, V., Salomon, Y., and Scherz, A., 1996, Photochem. Photobiol., 64, 174–181.

[20] Scherz, A., Katz, S., Vakrat, Y., Brumfeld, V., Gabelmann, E., Leupold, D., Norris, J.R., Scheer, H., and Salomon, Y., 1998, “Bacteriochlorophyll-serine based photochemotherapy: type III PDT” in Photosynthesis: Mechanisms and Effects, Ed. Garab, G., Kluwer Academic, Dordrech, vol. V, 4207–4212.

[21] Katz, J.J., Shipman, L.L., Cotton, T.M., and Janson, T.R., 1978, “Chlorophyll aggregation: Coordination interactions in chlorophyll monomers, dimers and oligomers” in The Porphyrins, Ed. Dolphin, D., Academic Press, New York, 402–458.

[22] Quinlan, K., 1968, Arch. Biochem. Biophys., 127, 31–36.

[23] Scherz, A., and Rosenbach-Belkin, V., 1989, Proc. Natl. Acad. Sci. U.S.A., 86, 1505–1509.

[24] Fisher, J.R.E., Rosenbach-Belkin, V., and Scherz, A., 1990, Biophys. J., 58, 2, 461–470.

[25] Scherz, A., Rosenbach-Belkin, V., and Fisher, J.R.E., 1990, Proc. Natl. Acad. Sci. U.S.A., 87, 5430–5434.

[26] de Paula, J.C., Robblee, J.H., and Fasternack, R.F., 1995, Biophys. J., 68, 335–341.

[27] Oba, T., Watanabe, T., Mimuro, M., Kobayashi, M., and Yoshida, S., 1996, Photochem. Photobiol., 63, 5, 639–648.

[28] Vladkova, R., 2000, Photochem. Photobiol., 71, 1, 71–83.

[29] Susanti, N.I., Trihandaru, S., and Limantara, L., 2007, Proceeding of National Symposium: Back to Nature dengan Pigmen Alami, Satya Wacana Christian University, Salatiga, ISBN 979-978-89-2, 86-94.

[30] Heriyanto, Trihandaru, S., and Limantara, L., 2009, Indo. J. Chem., 9, 1, 113–122.

[31] Hinton, J.F., and Harpool, R.D., 1977, J. Am. Chem. Soc., 99, 2, 349–353.

[32] Fiedor, J., Fiedor, L., Kammhuber, N., Scherz, A., and Scheer, H., 2002, Photochem. Photobiol., 76, 2, 145–152.

[33] Limantara, L., 2005, Proceeding of National Conference on The Scientific Meeting, FMIPA UI, Jakarta, S3F-10.

[34] Limantara, L., Koehler, P., Wilhelm, B., Porra, R.J., and Scheer, H., 2006, Photochem. Photobiol., 82, 770–780.

[35] Heriyanto, Trihandaru, S., and Limantara, L., 2007, Proceeding of National Symposium: Back to Nature dengan Pigmen Alami, Satya Wacana Christian University, Salatiga, ISBN 979-978-89-2, 128-140.

[36] Petke, J.D., Maggiora, J.M., Shipman, L.L., and Christoffersen, R.E., 1980, Photochem. Photobiol., 32, 399–414.

[37] Connolly, J.S., Samuel, E.B., and Janzen, A.F., 1982, Photochem. Photobiol., 36, 565–574.

[38] Limantara, L., Sakamoto, S., Koyama, Y., and Nagae, H., 1997, Photochem. Photobiol., 65, 330–337.

[39] Freed, S., and Sancier, K.M., 1954, J. Am. Chem. Soc., 76, 198–205.

[40] Evans, T.A., and Katz, J.J., 1975, Biochim. Biophys. Acta, 369, 414–426.

[41] Sauer, K., Lindsay Smith, J.R., and Schultz, A.J., 1966, J. Am. Chem. Soc., 88, 2681–2688.

[42] Sauer, K., 1978, Acc. Chem. Res., 11, 257–264.

[43] Callahan, P.M., and Cotton, T.M., 1987, J. Am. Chem. Soc., 109, 7001–7007.

[44] Nishizawa, E.-I., Limantara, L., Nanjou, N., Nagae, H., Kakuno, T., and Koyama, Y., 1994, Photochem. Photobiol., 59, 2, 229–236.

[45] Koyama, Y., Limantara, L., Nishizawa, E., Misono, Y., and Itoh, K., 1995, 7th International Conference on Time-Resolved Vibrational Spectroscopy, Santa Fe, New Mexico, USA, 45–49.

[46] Bellacchio, E., and Sauer, K., 1999, J. Phys. Chem., 103, 2279–2290.

[47] Dratz, E.A., Schultz, A.J., and Sauer, K., 1966, Brookhaven Symp. Biol., 19, 303–318.

[48] Marsh, K.L., and Connolly, J.S., 1984, J. Photochem., 25, 183–195.

[49] Watanabe, T., and Kobayash, M., 1991, “Electrochemistry of chlorophylls” in Chlorophylls, Eds. Scheer, H., CRC Press, Boca Raton, 287–315.

[50] Katz, J.J., Ballschmiter, K., Garcia-Morin, M., Strain, H.H., and Uphaus, R.A., 1968, Proc. Natl. Acad. Sci. U.S.A., 60, 100–107.

[51] McNaught, A.D., and Wilkinson, A., 1997, Compendium of Chemical Terminology, 2nd Ed., The Gold Book, Blackwell Science, ISBN 0865426848.

[52] Smith, J.R.L., and Calvin, M., 1966, J. Am. Chem. Soc., 88, 19, 4500–4506.

[53] Minguez-Mosquera, M.I., and Gandul-Rojas, B., 1995, J. Chromatogr. A, 660, 161–175.

[54] Fajer, J., Brune, D.C., Davis, M.S., Forman, A., and Spaulding, L.D., 1975, Proc. Natl. Acad. Sci. U.S.A., 72, 12, 4956–4960.

[55] Davis, M.S., Forman, A., and Fajer, J., 1979, Proc. Natl. Acad. Sci. U.S.A., 76, 4170–4174.

[56] Davis, M.S., Forman, A., Hanson, L.K., Thornber, J.P., and Fajer, J., 1979, J. Phys. Chem., 83, 3325–3332.



DOI: https://doi.org/10.22146/ijc.21403

Article Metrics

Abstract views : 1620 | views : 1469


Copyright (c) 2011 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.