Novel boronated chlorin e6-based photosensitizers: synthesis, binding to albumin and antitumour efficacy

Bioorganic & Medicinal Chemistry
Valentina A Ol'shevskayaAlexander A Shtil

Abstract

Chlorins, a class of plant porphyrins, are perspective as photosensitizing agents due to light absorption in the long wavelength spectral region and deeper photodamage of tissues. Aiming at optimization of antitumour properties of chlorins, we synthesized a series of boronated derivatives of chlorin e(6) and their complexes containing Zn(II), Pd(II) or Sn(IV). The compounds were synthesized by alkylation of amino or hydroxy derivatives of chlorin e(6) with 1-trifluoromethanesulfonylmethyl-o-carborane. Chlorin e(6) 13(1)-N-{2-[N-(o-carboran-1-yl)methyl]aminoethyl}amide-15(2), 17(3)-dimethyl ester (compound 5) formed complexes with serum albumin, a major porphyrin carrier. The binding constant of these complexes was approximately 4 times bigger than the respective value for the complexes of albumin with boron-free aminochlorin e(6). Compound 5 potently sensitized rat fibroblasts to illumination with monochromatic red light: >98% of cells were necrotic by 24h post-illumination with 1 microM of 5. This compound demonstrated high efficacy in photodynamic therapy of rat M-1 sarcoma. After PDT with 25mg/kg of 5 the residual tumours were significantly smaller than in animals subjected to PDT with equal concentration of boron-free amino...Continue Reading

References

Jan 1, 1991·Photochemistry and Photobiology·R K PandeyT J Dougherty
Jun 1, 1987·Photochemistry and Photobiology·D KesselK D Nantwi
Dec 1, 1996·Photochemistry and Photobiology·P G SpizzirriK P Ghiggino
Nov 1, 1996·Journal of Photochemistry and Photobiology. B, Biology·H KostronR Jakober
Jul 7, 1999·Journal of Photochemistry and Photobiology. B, Biology·V O MelnikovaF Guillemin
Oct 19, 1999·International Journal of Radiation Oncology, Biology, Physics·D E CallahanE A Blakely
Jan 30, 2002·Bioorganic & Medicinal Chemistry·Prapai WongsinkongmanKuo-Hsiung Lee
Feb 19, 2002·Chemical Reviews·Albert H. SolowayJ. Gerald Wilson
Oct 8, 2003·Current Medicinal Chemistry. Anti-cancer Agents·Rima P EvstigneevaAlexander A Shtil
Jan 21, 2004·Journal of Photochemistry and Photobiology. B, Biology·Emma S Nyman, Paavo H Hynninen
Jan 22, 2005·Journal of Medicinal Chemistry·Paola DozzoStephen B Kahl
Feb 24, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·V N KalininE Hey-Hawkins
Mar 19, 2005·Journal of Controlled Release : Official Journal of the Controlled Release Society·Shun-ichiro OguraIchiro Okura
May 18, 2005·Journal of Photochemistry and Photobiology. B, Biology·Robert A WeersinkBrian C Wilson
Jun 9, 2005·Chemical Reviews·Konrad SzaciłowskiGrazyna Stochel
Jul 30, 2005·International Journal of Cancer. Journal International Du Cancer·Josephine H WoodhamsStephen G Bown
Sep 24, 2005·Photochemistry and Photobiology·Thomas H FosterChad E Bigelow
Sep 28, 2005·Bioorganic & Medicinal Chemistry·Valentina A Ol'shevskayaAlexander A Shtil
Nov 22, 2005·Bioorganic & Medicinal Chemistry·Vijay GottumukkalaM Graça H Vicente
Apr 18, 2006·The International Journal of Biochemistry & Cell Biology·Sara NovickMichael R Quastel
May 18, 2006·Bioconjugate Chemistry·K Eszter BorbasJonathan S Lindsey
Jun 7, 2006·Bioorganic & Medicinal Chemistry·Raymond LuguyaM Graça H Vicente
Oct 7, 2006·Organic & Biomolecular Chemistry·Valentina A Ol'shevskayaAlexander A Shtil
Jan 27, 2007·Journal of Medicinal Chemistry·Myoung-Seo KooStephen B Kahl
Nov 2, 2007·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Anna NazarovaJean-Claude Maurizot
Mar 18, 2008·The Journal of Organic Chemistry·K Eszter BorbasJonathan S Lindsey
Mar 26, 2008·British Journal of Pharmacology·L B Josefsen, R W Boyle
Apr 4, 2008·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Noémie ThomasMuriel Barberi-Heyob
Apr 9, 2008·Anti-cancer Agents in Medicinal Chemistry·Xiang Zheng, Ravindra K Pandey
Apr 9, 2008·Anti-cancer Agents in Medicinal Chemistry·Mark Wainwright
Dec 1, 2006·Photodiagnosis and Photodynamic Therapy·Timothy C Zhu, Jarod C Finlay

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Citations

Sep 23, 2011·Journal of Medicinal Chemistry·R G Waruna JinadasaKevin M Smith
Nov 30, 2013·Biochimica Et Biophysica Acta·Yuri N AntonenkoMikhail P Kirpichnikov
Jul 9, 2013·Ultrasound in Medicine & Biology·Haiping WangQuanhong Liu
May 26, 2016·Photochemistry and Photobiology·Kathrin ButzbachBernd Epe
Feb 14, 2018·Photochemistry and Photobiology·Niluksha WalalawelaAlexander Greer
Aug 29, 2018·Chemical Society Reviews·Verónica Almeida-MarreroAndrés de la Escosura
Nov 5, 2015·PloS One·Elena O OmarovaYuri N Antonenko
Nov 1, 2017·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·P Sarbadhikary, A Dube
Dec 11, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Vladimíra PavlíčkováTomáš Ruml
Jan 21, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Anastasija V EfremenkoAlexey V Feofanov

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