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

Yıl 2019, Cilt: 9 Sayı: 3, 1513 - 1519, 01.09.2019
https://doi.org/10.21597/jist.540771

Öz

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.

Kaynakça

  • 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

Yıl 2019, Cilt: 9 Sayı: 3, 1513 - 1519, 01.09.2019
https://doi.org/10.21597/jist.540771

Öz

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.

Kaynakça

  • 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.
Toplam 17 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Ömer Güngör 0000-0002-3835-2920

Hatice Uluşan Bu kişi benim 0000-0003-1449-0904

Zafer Yazıcıgil Bu kişi benim 0000-0001-7048-7940

Yayımlanma Tarihi 1 Eylül 2019
Gönderilme Tarihi 15 Mart 2019
Kabul Tarihi 29 Nisan 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 9 Sayı: 3

Kaynak Göster

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. Iğdır Üniv. Fen Bil Enst. Der. Eylül 2019;9(3):1513-1519. doi:10.21597/jist.540771
Chicago Güngör, Ömer, Hatice Uluşan, ve Zafer Yazıcıgil. “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi Ve Fotofizikokimyasal Özellikleri”. Journal of the Institute of Science and Technology 9, sy. 3 (Eylül 2019): 1513-19. https://doi.org/10.21597/jist.540771.
EndNote Güngör Ö, Uluşan H, Yazıcıgil Z (01 Eylül 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, ve Z. Yazıcıgil, “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi ve Fotofizikokimyasal Özellikleri”, Iğdır Üniv. Fen Bil Enst. Der., c. 9, sy. 3, ss. 1513–1519, 2019, doi: 10.21597/jist.540771.
ISNAD Güngör, Ömer vd. “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi Ve Fotofizikokimyasal Özellikleri”. Journal of the Institute of Science and Technology 9/3 (Eylül 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. Iğdır Üniv. Fen Bil Enst. Der. 2019;9:1513–1519.
MLA Güngör, Ömer vd. “Fotodinamik Terapi İçin OktadodesiloksiSilicon(IV) Ftalosiyanin Bileşiğinin Sentezi Ve Fotofizikokimyasal Özellikleri”. Journal of the Institute of Science and Technology, c. 9, sy. 3, 2019, ss. 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. Iğdır Üniv. Fen Bil Enst. Der. 2019;9(3):1513-9.