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Synthesis and Photophysicochemical Properties of Octadodecyloxy Silicon(IV) Phthalocyanine for Photodynamic Therapy

Year 2019, Volume: 9 Issue: 3, 1513 - 1519, 01.09.2019
https://doi.org/10.21597/jist.540771

Abstract

Octadodecyloxysilicon(IV) phthalocyanine derivative was synthesized and its structure was determined by spectrophotometric methods. The synthesized phthalocyanine compound exhibits good solubility in tetrahydrofuran, ethyl acetate, CH2Cl2, N,Ndimethylformamide, diethyl ether, CHCl3, ethyl alcohol and acetonitrile. The photophysicochemical properties of the silicon phthalocyanine compound in photodynamic therapy were investigated in DMF. Singlet oxygen, photodegradation and aggregation properties were compared with standard unsaturated silicon phthalocyanine and zinc phthalocyanine. Singlet oxygen quantum yield (ΦΔ) was found to be very close to the value of Si (IV) Pc used as standard.

References

  • Atmaca G Y, Dizman C, ErenT, Erdoğmuş A, 2015.Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties. A Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 137 (2) 244-249.
  • Bonnett R, 1995. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy Chemical Society Reviews, 24 (1), 19-33.
  • Braichotte D.R, Savary JF, Monnier P, van den Bergh H.E, 1996. Optimizing light dosimetry in photodynamic therapy of early stage carcinomas of the esophagus using fluorescence spectroscopy. Lasers Surgery and Medicine 19 (3) 340–346.
  • Durmuş M. 2012. Photosensitizers in Medicine, Environment, and Security. Bölüm 4, sayfa 135-266. Editors: Tebello Nyokong, Vefa Ahsen. Springer Dordrecht Heidelberg London New York. 2012. e-ISBN 978-90-481-3872-2. DOI 10.1007/978-90-481-3872-2.
  • Durmus M, Yaman H, Göl C, Ahsen V, 2011. Nyokong. T.Water-soluble quaternized mercaptopyridine-substituted zinc-phthalocyanines: Synthesis, photophysical, photochemical and bovine serum albumin binding properties. Dyes and Pigments, 91 (2): 153-163.
  • Durmuş M, Yeşilot S, Ahsen V, 2006. Separation and mesogenic properties of tetraalkoxy-substituted phthalocyanine isomers. New J. Chem.,30 (5): 675–678.
  • Ertem B, Yalazan H, Güngör Ö, Sarkı G, Durmuş M, Saka E T, Kantekin H, 2018. Synthesis, structural characterization, and investigation on photophysical and photochemical features of new metallophthalocyanines. Journal of Luminescence, 204 (3) 467-471.
  • Gillenwater A, Jacob R, Kortum RR, 1998. Fluorescence spectroscopy: A technique with potential to improve the early detection of aerodigestive tract neoplasia. Head Neck 20 (6) 556–562.
  • Gu D, Chen Q, Tang X, Gan F, Shen S, Liu K, Xu H, 1995. Application of phthalocyanine thin films in optical recording. Optics Communications,121 (4): 125–129.
  • Guillaud G, Simon J, Germain JP, 1998. Metallophthalocyanines: Gas sensors, resistors and field effect transistors. Coordination Chemistry Reviews, 178 (2): 1433–1484.
  • Güngör Ö, Durmuş M, Ahsen V, 2016 Investigation of photochemical and photophysical properties of novel silicon(IV) phthalocyanines and their -oxo dimers, Turkish Journal of Chemistry. 41 (6), 803-812.
  • Gürol İ, Gümüş G, Tarakci DK, Güngör Ö, Durmuş M, Ahsen V, 2018. Photophysical and photochemical properties of fluoroether-substituted zinc (II) and titanium (IV) phthalocyanines, Journal of Porphyrins and Phthalocyanines. 22 (1) 46–55.
  • Gürol I, Durmuş M, Ahsen V, Nyokong T, 2007. Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines. Dalton Trans., 34 (): 3782-3791.
  • Gürek AG, Bekaroğlu O, 1994. Octakis(alkylthio)-substituted phthalocyanines and their Interactions with Silver(I) and Palladium(II) Ions, J.Chem.Soc.Dalton Trans, 9 (3): 1419-1423.
  • Kadish K.M, Smith K.M, Guilard R, 2000. The Porphyrin Handbook, Academic Press, Amsterdam, Vol. 1–10. e-ISBN: 9780080923857
  • Leznoff CC, Lever ABP, 1993. Phthalocyanines: Properties and Applications, New York Vol. 2. pp: 197-223. ISBN: 1-56081-544-2.
  • Phillips, D, 1995.The photochemistry of sensitisers for photodynamic therapy, Pure and Applied Chemistry, 67 (1), 117-126.

Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri

Year 2019, Volume: 9 Issue: 3, 1513 - 1519, 01.09.2019
https://doi.org/10.21597/jist.540771

Abstract

Bu çalışmada, oktadodesiloksi silisyum(IV) ftalosiyanin türevi sentezlenmiş ve yapısı spektrofotometrik yöntemlerle aydınlatılmıştır. Sentezlenen ftalosiyanin bileşiği tetrahidrofuran, etil asetat, CH2Cl2, N,N dimetilformamid, dietil eter, CHCl3, etil alkol, ve asetonitril içinde iyi bir çözünürlük sergilemektedir. Silisyum ftalosiyanin bileşiğinin fotodinamik terapide fotoduyarlaştırıcı olarak kullanılabilirliğini araştırmak için fotofizikokimyasal özellikleri DMF içerisinde araştırılmıştır. Singlet oksijen, fotobozunma ve agregasyon özellikleri standart unsubstitüe silisyum ftalosiyanin ve çinko ftalosiyanin ile karşılaştırılmıştır. Singlet oksijen kuantum verimi’nin (ΦΔ) standart olarak kullanılan Si(IV)Pc’nin değerine çok yakın olduğu görülmüştür.

References

  • Atmaca G Y, Dizman C, ErenT, Erdoğmuş A, 2015.Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties. A Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 137 (2) 244-249.
  • Bonnett R, 1995. Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy Chemical Society Reviews, 24 (1), 19-33.
  • Braichotte D.R, Savary JF, Monnier P, van den Bergh H.E, 1996. Optimizing light dosimetry in photodynamic therapy of early stage carcinomas of the esophagus using fluorescence spectroscopy. Lasers Surgery and Medicine 19 (3) 340–346.
  • Durmuş M. 2012. Photosensitizers in Medicine, Environment, and Security. Bölüm 4, sayfa 135-266. Editors: Tebello Nyokong, Vefa Ahsen. Springer Dordrecht Heidelberg London New York. 2012. e-ISBN 978-90-481-3872-2. DOI 10.1007/978-90-481-3872-2.
  • Durmus M, Yaman H, Göl C, Ahsen V, 2011. Nyokong. T.Water-soluble quaternized mercaptopyridine-substituted zinc-phthalocyanines: Synthesis, photophysical, photochemical and bovine serum albumin binding properties. Dyes and Pigments, 91 (2): 153-163.
  • Durmuş M, Yeşilot S, Ahsen V, 2006. Separation and mesogenic properties of tetraalkoxy-substituted phthalocyanine isomers. New J. Chem.,30 (5): 675–678.
  • Ertem B, Yalazan H, Güngör Ö, Sarkı G, Durmuş M, Saka E T, Kantekin H, 2018. Synthesis, structural characterization, and investigation on photophysical and photochemical features of new metallophthalocyanines. Journal of Luminescence, 204 (3) 467-471.
  • Gillenwater A, Jacob R, Kortum RR, 1998. Fluorescence spectroscopy: A technique with potential to improve the early detection of aerodigestive tract neoplasia. Head Neck 20 (6) 556–562.
  • Gu D, Chen Q, Tang X, Gan F, Shen S, Liu K, Xu H, 1995. Application of phthalocyanine thin films in optical recording. Optics Communications,121 (4): 125–129.
  • Guillaud G, Simon J, Germain JP, 1998. Metallophthalocyanines: Gas sensors, resistors and field effect transistors. Coordination Chemistry Reviews, 178 (2): 1433–1484.
  • Güngör Ö, Durmuş M, Ahsen V, 2016 Investigation of photochemical and photophysical properties of novel silicon(IV) phthalocyanines and their -oxo dimers, Turkish Journal of Chemistry. 41 (6), 803-812.
  • Gürol İ, Gümüş G, Tarakci DK, Güngör Ö, Durmuş M, Ahsen V, 2018. Photophysical and photochemical properties of fluoroether-substituted zinc (II) and titanium (IV) phthalocyanines, Journal of Porphyrins and Phthalocyanines. 22 (1) 46–55.
  • Gürol I, Durmuş M, Ahsen V, Nyokong T, 2007. Synthesis, photophysical and photochemical properties of substituted zinc phthalocyanines. Dalton Trans., 34 (): 3782-3791.
  • Gürek AG, Bekaroğlu O, 1994. Octakis(alkylthio)-substituted phthalocyanines and their Interactions with Silver(I) and Palladium(II) Ions, J.Chem.Soc.Dalton Trans, 9 (3): 1419-1423.
  • Kadish K.M, Smith K.M, Guilard R, 2000. The Porphyrin Handbook, Academic Press, Amsterdam, Vol. 1–10. e-ISBN: 9780080923857
  • Leznoff CC, Lever ABP, 1993. Phthalocyanines: Properties and Applications, New York Vol. 2. pp: 197-223. ISBN: 1-56081-544-2.
  • Phillips, D, 1995.The photochemistry of sensitisers for photodynamic therapy, Pure and Applied Chemistry, 67 (1), 117-126.
There are 17 citations in total.

Details

Primary Language Turkish
Subjects Chemical Engineering
Journal Section Kimya / Chemistry
Authors

Ömer Güngör 0000-0002-3835-2920

Hatice Uluşan This is me 0000-0003-1449-0904

Zafer Yazıcıgil This is me 0000-0001-7048-7940

Publication Date September 1, 2019
Submission Date March 15, 2019
Acceptance Date April 29, 2019
Published in Issue Year 2019 Volume: 9 Issue: 3

Cite

APA Güngör, Ö., Uluşan, H., & Yazıcıgil, Z. (2019). Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri. Journal of the Institute of Science and Technology, 9(3), 1513-1519. https://doi.org/10.21597/jist.540771
AMA Güngör Ö, Uluşan H, Yazıcıgil Z. Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri. J. Inst. Sci. and Tech. September 2019;9(3):1513-1519. doi:10.21597/jist.540771
Chicago Güngör, Ömer, Hatice Uluşan, and Zafer Yazıcıgil. “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi Ve Fotofizikokimyasal Özellikleri”. Journal of the Institute of Science and Technology 9, no. 3 (September 2019): 1513-19. https://doi.org/10.21597/jist.540771.
EndNote Güngör Ö, Uluşan H, Yazıcıgil Z (September 1, 2019) Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri. Journal of the Institute of Science and Technology 9 3 1513–1519.
IEEE Ö. Güngör, H. Uluşan, and Z. Yazıcıgil, “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri”, J. Inst. Sci. and Tech., vol. 9, no. 3, pp. 1513–1519, 2019, doi: 10.21597/jist.540771.
ISNAD Güngör, Ömer et al. “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi Ve Fotofizikokimyasal Özellikleri”. Journal of the Institute of Science and Technology 9/3 (September 2019), 1513-1519. https://doi.org/10.21597/jist.540771.
JAMA Güngör Ö, Uluşan H, Yazıcıgil Z. Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri. J. Inst. Sci. and Tech. 2019;9:1513–1519.
MLA Güngör, Ömer et al. “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi Ve Fotofizikokimyasal Özellikleri”. Journal of the Institute of Science and Technology, vol. 9, no. 3, 2019, pp. 1513-9, doi:10.21597/jist.540771.
Vancouver Güngör Ö, Uluşan H, Yazıcıgil Z. Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri. J. Inst. Sci. and Tech. 2019;9(3):1513-9.