Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Properties of Soluble and Stable Silyl End-capped Bis-thienylanthracene Oligomers

  • Choi, Jung-Hei (Department of Chemistry and the Center for Plastic Information System, Pusan National University) ;
  • Cho, Dae-Won (Department of Chemistry and the Center for Plastic Information System, Pusan National University) ;
  • Sung, Nam-Kyoung (Department of Chemistry and the Center for Plastic Information System, Pusan National University) ;
  • Jin, Sung-Ho (Department of Chemistry Education and the Center for Plastic Information System, Pusan National University) ;
  • Yoon, Ung-Chan (Department of Chemistry and the Center for Plastic Information System, Pusan National University)
  • Published : 2007.11.20
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Abstract

Analyzed are recent advances in design of novel boronared conjugates of synthetic and natural porphyrins and chlorins. These compounds showed high efficacy as cytotoxic agents for tumor cells in culture and as phototoxins in photodynamic therapy of tumor xenografts. Thus, boronated porphyrins and chlorins emerge as promising class of anticancer agents with potentially multiple advantages: the chemotherapeutic drugs alone and photo- and radiosensitizers in binary treatments.

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References

  1. Barbarella, G.; Favaretto, L.; Sotgiu, G.; Zambianchi, M.; Bongini, A.; Arbizzani, C.; Mastragostino, M.; Anni, M.; Gigli, G.; Cingolani, R. J. Am. Chem. Soc. 2000, 122, 11971 https://doi.org/10.1021/ja002037p
  2. Ho, H. A.; Brisset, H.; Elandaloussi, E. H.; Frere, P.; Roncali, J. Adv. Mater. 1996, 8, 990 https://doi.org/10.1002/adma.19960081210
  3. Hicks, R. G.; Nodwell, M. B. J. Am. Chem. Soc. 2000, 122, 6746 https://doi.org/10.1021/ja000752t
  4. Lee, B. H.; Cho, Y. H.; Shin, H.; Kim, J.; Lee, J.; Lee, H.; Sung, M. M. Bull. Korean Chem. Soc. 2006, 27, 1633 https://doi.org/10.5012/bkcs.2006.27.10.1633
  5. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burn, P. L.; Holmes, A. B. Nature 1990, 347, 539 https://doi.org/10.1038/347539a0
  6. Lee, W. L.; An, J.-G.; Yoon, H.-K.; Jang, H.; Kim, N. G.; Do, Y. Bull. Korean Chem. Soc. 2005, 26, 1569 https://doi.org/10.5012/bkcs.2005.26.10.1569
  7. Horowitz, G. Adv. Mater. 1998, 10, 365 https://doi.org/10.1002/(SICI)1521-4095(199803)10:5<365::AID-ADMA365>3.0.CO;2-U
  8. Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y. Y.; Dodabalapur, A. Nature 2000, 404, 478 https://doi.org/10.1038/35006603
  9. Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474 https://doi.org/10.1126/science.258.5087.1474
  10. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789 https://doi.org/10.1126/science.270.5243.1789
  11. Halik, M.; Klauk, U. T.; Schmid, G.; Ponomarenko, S.; Kirchmeyer, S.; Weber, W. Adv. Mater. 2003, 15, 917 https://doi.org/10.1002/adma.200304654
  12. Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 115, 8716 https://doi.org/10.1021/ja00072a026
  13. Servet, B.; Horowitz, G.; Ries, S.; Lagorsse, O.; Alnot, P.; Yassar, A.; Deloffre, F.; Srivastava, P.; Hajlaoui, R.; Lang, P.; Garnier, F. Chem. Mater. 1994, 6, 1809 https://doi.org/10.1021/cm00046a039
  14. Fichou, D. Handbook of Oligo- and Polythiophenes; Wiley-VCH: New York, 1998
  15. Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359 https://doi.org/10.1021/ar990114j
  16. Hong, X. M.; Katz, H. E.; Lovinger, A. J.; Wang, B.-C.; Raghavachari. K. Chem. Mater. 2001, 13, 4686
  17. Tian, H.; Wang, J.; Shi, J.; Yan, D.; Wang, L.; Geng, Y.; Wang, F. J. Mater. Chem. 2005, 15, 3026 https://doi.org/10.1039/b504044b
  18. Choi, J. H.; Cho, D. W.; Jin. S.-H.; Yoon, U. C. Bull. Korean Chem. Soc. 2007, 28(7), 1175 https://doi.org/10.5012/bkcs.2007.28.7.1175
  19. Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13480 https://doi.org/10.1021/ja048988a
  20. Facchetti, A.; Deng, H.; Wang, A. C.; Koide, Y.; Sirrinhaus, H.; Marks, T. J.; Friend, R. H. Angew. Chem. Int. Ed. 2000, 39, 4547 https://doi.org/10.1002/1521-3773(20001215)39:24<4547::AID-ANIE4547>3.0.CO;2-J
  21. Nessakh, B.; Horowitz, G.; Garnier, F.; Deloffre, F.; Srivastava, P.; Yassar, A. J. Electroanal. Chem. 1995, 399, 97 https://doi.org/10.1016/0022-0728(95)04224-5

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