Synthesis and in vitro photodynamic activities of pegylated distyryl boron dipyrromethene derivatives

Journal of Medicinal Chemistry

Volumn 54, Issue 8, 2011, Pages 3097-3102

  He, Hui ^a   Lo, Pui Chi ^a   Yeung, Sin Lui ^a   Fong, Wing Ping ^a   Ng, Dennis K P ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; POLYSORBATE 80; STYRENE DERIVATIVE; TRIETHYLENE GLYCOL;

APOPTOSIS; ARTICLE; CANCER CELL; COLORECTAL CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SYNTHESIS; ENDOPLASMIC RETICULUM; FLUORESCENCE; HUMAN; HUMAN TISSUE; IC 50; ILLUMINATION; IN VITRO STUDY; PHOTODYNAMICS;

HUMANS; PHOTOCHEMOTHERAPY; POLYETHYLENE GLYCOLS; PORPHOBILINOGEN;

EID: 79955461251     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101637g     Document Type: Article

References (23)

1. Loudet, A.; Burgess, K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties Chem. Rev. 2007, 107, 4891-4932 (Pubitemid 350225866)
2. Domaille, D. W.; Zeng, L.; Chang, C. J. Visualizing ascorbate-triggered release of labile copper within living cells using a ratiometric fluorescent sensor J. Am. Chem. Soc. 2010, 132, 1194-1195
3. Rosenthal, J.; Lippard, S. J. Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex J. Am. Chem. Soc. 2010, 132, 5536-5537
4. 60 pentad Chem.-Eur. J. 2011, 17, 1605-1613 and references cited therein
5. Bozdemir, O. A.; Guliyev, R.; Buyukcakir, O.; Selcuk, S.; Kolemen, S.; Gulseren, G.; Nalbantoglu, T.; Boyaci, H.; Akkaya, E. U. Selective manipulation of ICT and PET processes in styryl-BODIPY derivatives: applications in molecular logic and fluorescence sensing of metal ions J. Am. Chem. Soc. 2010, 132, 8029-8036
6. Rousseau, T.; Cravino, A.; Bura, T.; Ulrich, G.; Ziessel, R.; Roncali, J. BODIPY derivatives as donor materials for bulk heterojunction solar cells Chem. Commun. 2009, 1673-1675
7. Pochorovski, I.; Breiten, B.; Schweizer, W. B.; Diederich, F. FRET studies on a series of BODIPY-dye-labeled switchable resorcin[4]arene cavitands Chem.-Eur. J. 2010, 16, 12590-12602
8. Jiang, X.-J.; Yeung, S.-L.; Lo, P.-C.; Fong, W.-P.; Ng, D. K. P. Phthalocyanine-polyamine conjugates as highly efficient photosensitizers for photodynamic therapy J. Med. Chem. 2011, 54, 320-330 and references cited therein
9. Atilgan, S.; Ekmekci, Z.; Dogan, A. L.; Guc, D.; Akkaya, E. U. Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy Chem. Commun. 2006, 4398-4400 (Pubitemid 44611702)
10. Ozlem, S.; Akkaya, E. U. Thinking outside the silicon box: molecular AND logic as an additional layer of selectivity in singlet oxygen generation for photodynamic therapy J. Am. Chem. Soc. 2009, 131, 48-49
11. Lim, S. H.; Thivierge, C.; Nowak-Sliwinska, P.; Han, J.; van den Bergh, H.; Wagnières, G.; Burgess, K.; Lee, H. B. In vitro and in vivo photocytotoxicity of boron dipyrromethene derivatives for photodynamic therapy J. Med. Chem. 2010, 53, 2865-2874
12. Yogo, T.; Urano, Y.; Ishitsuka, Y.; Maniwa, F.; Nagano, T. Highly efficient and photostable photosensitizer based on BODIPY chromophore J. Am. Chem. Soc. 2005, 127, 12162-12163 (Pubitemid 41279207)
13. He, H.; Ng, D. K. P. A ratiometric near-infrared pH-responsive fluorescent dye based on distyryl BODIPY. Org. Biomol. Chem. 2011, DOI: 10.1039/C0OB01252A.
14. Bailon, P.; Won, C. Y. PEG-modified biopharmaceuticals Expert Opin. Drug Delivery 2009, 6, 1-16
15. Hajri, A.; Wack, S.; Meyer, C.; Smith, M. K.; Leberquier, C.; Kedinger, M.; Aprahamian, M. In vitro and in vivo efficacy of Photofrin and pheophorbide a, a bacteriochlorin, in photodynamic therapy of colonic cancer cells Photochem. Photobiol. 2002, 75, 140-148
16. Hofman, J.-W.; van Zeeland, F.; Turker, S.; Talsma, H.; Lambrechts, S. A. G.; Sakharov, D. V.; Hennink, W. E.; van Nostrum, C. F. Peripheral and axial substitution of phthalocyanines with solketal groups: synthesis and in vitro evaluation for photodynamic therapy J. Med. Chem. 2007, 50, 1485-1494 (Pubitemid 46564370)
17. Li, H.; Jensen, T. J.; Fronczek, F. R.; Vicente, M. G. H. Synthesis and properties of a series of cationic water-soluble phthalocyanines J. Med. Chem. 2008, 51, 502-511 (Pubitemid 351252278)
18. Teiten, M.-H.; Bezdetnaya, L.; Morlière, P.; Santus, R.; Guillemin, F. Endoplasmic reticulum and Golgi apparatus are the preferential sites of Foscan localisation in cultured tumour cells Br. J. Cancer 2003, 88, 146-152 (Pubitemid 36241232)
19. Gallagher, W. M.; Allen, L. T.; O'Shea, C.; Kenna, T.; Hall, M.; Gorman, A.; Killoran, J.; O'Shea, D. F. A potent nonporphyrin class of photodynamic therapeutic agent: cellular localization, cytotoxic potential and influence of hypoxia Br. J. Cancer 2005, 92, 1702-1710 (Pubitemid 40756482)
20. Vermes, I.; Haanen, C.; Steffens-Nakken, H.; Reutelingsperger, C. A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V J. Immunol. Methods 1995, 184, 39-51
21. Lottner, C.; Bart, K.-C.; Bernhardt, G.; Brunner, H. Soluble tetraarylporphyrin-platinum conjugates as cytotoxic and phototoxic antitumor agents J. Med. Chem. 2002, 45, 2079-2089 (Pubitemid 34477720)
22. Nielsen, C. B.; Johnsen, M.; Arnbjerg, J.; Pittelkow, M.; McIlroy, S. P.; Ogiby, P. R.; Jørgensen, M. Synthesis and characterization of water-soluble phenylene-vinylene-based singlet oxygen sensitizers for two-photon excitation J. Org. Chem. 2005, 70, 7065-7079 (Pubitemid 41235471)
23. Rivera, E.; Belletête, M.; Natansohn, A.; Durocher, G. Synthesis, characterization, and optical properties of a novel azo-dye bearing an oligo(ethylene glycol) methyl ether side chain in solution and in the solid state Can. J. Chem. 2003, 81, 1076-1082 (Pubitemid 37463911)