PHOTOPHYSICAL AND PHYSICOCHEMICAL PROPERTIES OF Cu(II)CHLORIN e4 AND Cu(II)CHLORIN e6 AS A LEAD COMPOUND OF PHOTOSENSITIZER FOR PDT

Eva Susanty Simaremare, Asmiyenti D. Djalil, Daryono H. Tjahjono

Abstract


Porphyrin derivatives are potential compounds for diagnostic agent and photosensitizer in photodynamic therapy. However, they have a weakness in molar absorptivity, especially in visible region of Q band which used to excite them. Due to incapabilities of porphyrin, other tetrapyrole derivatives, such as chlorophyllin can be alternative for a lead compound of photosensitizer. In the present research, two chlorin derivatives were isolated from commercial chlorophyllin product. Their photophysical and physicochemical properties, i.e. molar absorptivity, quantum yield of fluorescence and quantum yield of singlet oxygen were determined. Chlorophyllin carboxylic acid form, Cu(II)-chlorin e4 and Cu(II)-chlorin e6,were successfully isolated with recovery of 11.33% and 16.46%, respectively.         The absorption spectrum of Cu(II)-chlorin e4 showed an intense Soret band at 406 nm and two weaker Q bands at 628nm, 658nm. Fluorescence efficiency was 0.09 while efficiency for singlet oxygen at  pH 6.3 and 7.4 were 0.0052±0.0017 and 0.0066±0.0012. Cu(II)-chlorin e6 displayed soret band at 407nm and Q bands at 627nm, 663nm. Singlet oxygen at pH 6.3 was 0.0029±0.0007, while at pH 7.4 was 0.0034±0.0001. However,  Cu(II)-chlorin e6 did not show fluorescence.

Key words: Chlorophyllin, Cu(II)-chlorin e4, Cu(II)-chlorin e6, singlet oxygen fluorescence


Full Text:

PDF (PP.29-36)

References


Bonnett R., 2000. Chemical Aspect of Photodynamic Therapy. Gordon and Breach Publishers, London. pp 39-56.

Castano AP., Demidova TN., Hamblin MR., 2005. Mechanisms in photodynamic therapy: part three-fotosensitisers pharmacokinetics, biodistribution, tumor localization and modes of tumor destruction. Photodiagnosis and Photodynamic Therapy. 2: 91-106.

Dougherty TJ., Gomer CJ., Henderson BW., Jori G., Kessel M., Korbelik M., Moan J., Peng Q., 1998. Photodynamic therapy: review. J. Natl. Cancer Inst. 90: 889-902.

Fahey JW., Peng K., Stephenson K., Kostova ATD., Egner PA., Kensler TW., P Talalay ., 2005. Chlorophyll, chlorophyllin, and related tetrapyrroles are significant inducers of mammalian phase 2 cytoprotective genes. Carcinogenesis. 26(7): 1247-1255.

Inoue H., Yamashitaa H., Furuyaa K., Nonomuraa N., Yoshioka N., 1994. Determination of copper (II) chlorophyllin by reversed-phase HPLC. J. Chromatography. 679: 99-100.

Jichlinski P., Jacqmin D., 2008. Photodynamic Diagnosis in Non-Muscle-Invasive Bladder Cancer. European Association of Urology. 7: 529-539.

Jobin A., Guide to Recording Fluorescence Quantum Yields, HORIBA Jobin Yvon Inc.http://www.jobinyvon.com/usadivisions/fluorescence/applications/quantumyieldstrad. pdf. (last date accessed: 08.03.2012)

Kraljic I., El Mohsni S., 1978. A New method for the detection of singlet oxygen in aqueous solutions. Photochemistry and Photobiology. 28:577-581.

Mac Donald IJ., Dougherty TJ., 2001. Basic principles of photodynamic therapy. J Porp. Phth.. 5: 105–129.

Mathai S., Trevor A. Smith, Ghiggino KP., 2007. Singlet oxygen quantum yields of potential porphyrin-based photosensitisers for photodynamic therapy. Phot. Phot. Scie. 6: 995–1002.

Mortensen A. Geppel A., 2007. HPLC-MS Analysis of the Green Food Colorant Sodium Copper Chlorophyllin. Innov. Food Res. Emerg. Technology. 8: 419-425

Murthy NN., Karlin KD., Bertini I., Luchinat C., 1997. NMR and Electronic Relaxation in Paramagnetic Dicopper (II)Compounds, J. Am. Chem. Soc. 119, 2156-2162

Pandey RK., Zheng G., 2000. Porphyrins as Fotosensitisers in Photodynamic Therapy. The Porphyrin Handbook, ed. K.M. Kadish, K.M. Smith, and R. Guilard. Academic Press. San Diego.

Scotter MJ., Castle L., Roberts D., 2005. Method development and HPLC analysis of retail foods and beverages for copper chlorophyll (E141[i]) and chlorophyllin (E141[ii]) food colouring materials. Food Add. Contaminants. 22(12): 1163-1175.

Setyoko KD., 2010. Gambaran Umum Photodynamics Therapy (PDT). Sebuah pengantar dalam dunia Fisika Medis. Surabaya, 1-5.

Skutnik BJ., Neuberger W., Spaniol S., 2004. Optical Fibers for Improved Light Delivery in Photodynamic Therapy and Diagnosis. Society of Photo-Optical Instrumentation Engineers.

Tjahjono HD., 2006. Porphyrin Structure-based Molecules for Photodynamic Therapy of cancer. Acta Pharmaceutical Indonesia. 32: 1-6.

Wang I., 1999. Photodynamic therapy and laser-based diagnostic studies. The Jubileum Institute Department of Oncology Lund University Hospital of malignant tumours.




DOI: http://dx.doi.org/10.14499/indonesianjpharm26iss1pp29

Refbacks

  • There are currently no refbacks.




Copyright (c) 2017 INDONESIAN JOURNAL OF PHARMACY

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

Indonesian J Pharm indexed by:

                                                

web
analytics View My Stats