Pure Appl. Chem., 2012, Vol. 84, No. 10, pp. 2121-2133
http://dx.doi.org/10.1351/PAC-CON-11-11-04
Published online 2012-05-22
Green polymer chemistry: Living oxidative polymerization of dithiols
References
- 1. F. Biomaterials 30, 2180 (2009). ( , W. Hennick, Z. Zhong. http://dx.doi.org/10.1016/j.biomaterials.2009.01.026)
- 2. G. Adv. Drug Delivery Rev. 55, 199 (2003). ( , J. A. Swanson, K.-D. Lee. http://dx.doi.org/10.1016/S0169-409X(02)00179-5)
- 3. P. E. Cancer Res. 47, 5924 (1987). , P. M. Wallace, P. P. Knowles, M. G. Relf, A. N. Brown, G. J. Watson, R. E. Knyba, E. J. Wawrzynczak, D. C. Blakey.
- 4. C. J. Biol. Chem. 75, 1385 (2006). , I. Knight, P. G. Winyard.
- 5. J. P. J. Am. Chem. Soc. 82, 2511 (1960). ( , C. J. Noel. http://dx.doi.org/10.1021/ja01495a028)
- 6. P. J. Am. Chem. Soc. 82, 795 (1960). ( , F. A. Long. http://dx.doi.org/10.1021/ja01489a008)
- 7. L. S. J. Biol. Chem. 259, 5606 (1984). , C. Mottley, R. Mason.
- 8. A. Holmgren. In Methods in Enzymology, 107, K. M. Finn Wold (Ed.), pp. 295–350, Academic Press, New York (1984).
- 9. S. Oae. Organic Sulfur Chemsitry: Structure and Mechanism, CRC Press, Ann Arbor, MI (1991).
- 10. R. L. Augustine (Ed.). Oxidation: Techniques and Applications in Organic Synthesis, 1, pp. 247–248, Marcel Dekker, New York (1969).
- 11. L. O. J. Biol. Chem. 164, 521 (1946). .
- 12. K. Faber. Biotransformations in Organic Chemistry, 5th ed., pp. 226, 378–381 Springer-Verlag, New York (2004).
- 13. Y. Chem. Commun. 5, 1031 (1984). , M. Oshima, S. Suto, M. Nakazato.
- 14. Y. J. Chem. Soc., Perkins Trans. 2 6, 753 (1985). ( , M. Oshima, I. Yatsu, S. Sutoh. http://dx.doi.org/10.1039/p29850000753)
- 15. J. W. Aust. J. Chem. 30, 1387 (1977). ( , L. Main. http://dx.doi.org/10.1071/CH9771387)
- 16. G. M. J. Org. Chem. 42, 332 (1977). ( , J. E. Lilburn, R. P. Szajewski. http://dx.doi.org/10.1021/jo00422a034)
- 17. X.-L. J. Controlled Release 120, 250 (2007). ( , R. Jensen, Z.-R. Lu. http://dx.doi.org/10.1016/j.jconrel.2007.05.014)
- 18. Y.-M. Polymer 46, 4619 (2005). ( , B.-H. Huang, J.-J. Lin. http://dx.doi.org/10.1016/j.polymer.2005.04.013)
- 19. S. Biomacromolecules 10, 119 (2009). ( , R. J. Christie, N. Nishiyama, K. Miyata, A. Ishii, M. Oba, H. Koyama, Y. Yamasaki, K. Kataoka. http://dx.doi.org/10.1021/bm800985e)
- 20. S. Adv. Drug Delivery Rev. 60, 3 (2008). ( , A. Godwin, S. Balan, J. Choi, M. Zloh, S. Shaunak. http://dx.doi.org/10.1016/j.addr.2007.06.014)
- 21. W. Biomaterials 30, 2180 (2009). ( , R. Lammertink, J. K. Sakata, J. A. Kornfield, D. A. Tirell. http://dx.doi.org/10.1016/j.biomaterials.2009.02.004)
- 22. R. P. J. Am. Chem. Soc. 123, 4408 (2001). ( , W. M. Atkin. http://dx.doi.org/10.1021/ja0040417)
- 23. G. E. Environ. Toxicol. Pharmacol. 10, 153 (2001). ( , H. Sies. http://dx.doi.org/10.1016/S1382-6689(01)00078-3)
- 24. A. Coord. Chem. Rev. 253 1692 (2009). ( , M. P. Rigobello, G. Scutari, C. Cabbiani, A. Casini, L. Messori. http://dx.doi.org/10.1016/j.ccr.2009.02.026)
- 25. A. Holmgren, M. Bjornstedt. In Methods in Enzymology, 252, L. Packer (Ed.), pp. 199–208, Academic Press, New York (1995).
- 26. S. N. J. Biol. Chem. 271, 8101 (1996). , P. A. Karplus.
- 27. E. S. Pilka, C. Johannson, K. Guo, O. Gileadi, A. Rojkowa, F. von Delft, A. C. W. Pike, K. L. Kavanagh, M. Sundstrom, W. H. Lee, S. Muller, B. D. Marsden, C. Bountra, U. Oppermann. GPX3: Human glutathione peroxidase 3, PDB Code: 2R37 (2007).
- 28. B. A. Shirley (Ed.). Protein Stability and Folding: Theory and Practice, Humana Press, New York (1995).
- 29. B. S. Annu. Rev. Cell Dev. Biol. 24, 211 (2008). ( , J. C. Bardwell. http://dx.doi.org/10.1146/annurev.cellbio.24.110707.175333)
- 30. C. V. Toxicol. Appl. Pharmacol. 140, 1 (1996). ( , D. P. Jones, T. M. Guenther, L. H. Lash, B. H. Lauterburg. http://dx.doi.org/10.1006/taap.1996.0191)
- 31. A. Macromol. Chem. Phys. 208, 2642 (2007). ( , M. Pechar, R. Laga, K. Ulbrich. http://dx.doi.org/10.1002/macp.200700315)
- 32. F. Q. Free Radical Biol. Med. 30, 1191 (2001). ( , G. R. Buettner. http://dx.doi.org/10.1016/S0891-5849(01)00480-4)
- 33. C. Electrophoresis 25, 882 (2004). ( , L. Deiana, S. Sotgia, G. M. Pes, A. Zinellu. http://dx.doi.org/10.1002/elps.200305768)
- 34. A. Electrophoresis 26, 1963 (2005). ( , S. Sotgia, M. F. Usai, R. Chessa, L. Deiana, C. Carru. http://dx.doi.org/10.1002/elps.200400042)
- 35. Y. FEBS Lett. 302, 18 (1992). ( , M. Maeda, M. Futai. http://dx.doi.org/10.1016/0014-5793(92)80274-K)
- 36. A. M. J. Appl. Physiol. 63, 152 (1987). , S. L. North, R. C. Hubbard, R. G. Crystal.
- 37. D. Bioconjugate Chem. 4, 521 (1993). ( , P. A. Trail, S. J. Hofstead, H. D. King, S. J. Lasch, G. R. Braslawsky, R. S. Greenfield, T. Kaneko, R. A. Firestone. http://dx.doi.org/10.1021/bc00024a015)
- 38. P. D. J. Org. Chem. 55, 2975 (1990). ( , W. E. Pearce, R. S. Greenfield. http://dx.doi.org/10.1021/jo00296a082)
- 39. A. N. Chem. Commun. 48, 6570 (2008). ( , H. J. Lee, S. E. Kim, J. H. Chang, C. Park, C. Kim, J. H. Park, S. C. Lee. http://dx.doi.org/10.1039/b815918a)
- 40. S. Biomacromolecules 8, 1966 (2007). ( , D. Velluto, J. A. Hubbell. http://dx.doi.org/10.1021/bm070085x)
- 41. T. M. Adv. Drug Delivery Rev. 13, 285 (1994). ( . http://dx.doi.org/10.1016/0169-409X(94)90016-7)
- 42. S. Adv. Mater. 21, 3286 (2009). ( , C. Hozsa, M. Breunig, A. Gopferich. http://dx.doi.org/10.1002/adma.200802453)
- 43. Y. Biomaterials 27, 3782 (2006). ( , K. Ghosh, X. Z. Shu, B. Li, J. C. Sokolov. G. D. Prestwich, A. F. Richard, M. H. Rafailovich. http://dx.doi.org/10.1016/j.biomaterials.2006.02.037)
- 44. X. Z. Biomaterials 3, 1304 (2002). , Y. Liu, M. C. Roberts, G. D. Prestwich.
- 45. X. Z. Biomaterials 24, 3825 (2003). ( , Y. Liu, F. Palumbo, G. D. Prestwich. http://dx.doi.org/10.1016/S0142-9612(03)00267-9)
- 46. Z. M. Eur. J. Pharm. Sci. 37 198 (2009). ( , X. G. Zhang, C. Zheng, C. X. Li, S. M. Zhang, R. N. Dong, D. M. Yu. http://dx.doi.org/10.1016/j.ejps.2009.01.010)
- 47. J. Biomaterials 29, 4521 (2008). ( , A. Skardal, G. D. Prestwich. http://dx.doi.org/10.1016/j.biomaterials.2008.08.008)
- 48. N. Biomed. Mater. Res. 40, 115 (1998). ( , M. Noriyuki, H. Iwata, Y. Ikada. http://dx.doi.org/10.1002/(SICI)1097-4636(199804)40:1<115::AID-JBM13>3.0.CO;2-N)
- 49. R. Munday. In Methods in Enzymology, 251, L. Packer (Ed.), pp. 117–120, Academic Press, New York (1995).
- 50. R. Free Radical Biol. Med. 7, 659 (1989). ( . http://dx.doi.org/10.1016/0891-5849(89)90147-0)
- 51. E. Cadenas. In Methods in Enzymology, 251, L. Packer (Ed.), pp. 106–116, Academic Press, New York (1995).
- 52. J. C. Patrick. U.S. Patent 1890 191, Issued 6 Dec 1932.
- 53. J. C. Patrick. U.S. Patent 2553 206, Issued 15 May 1951.
- 54. J. C. Patrick, N. M. Mnookin, J. C. Patrick. U.S. Patent 1996 486, Issued 2 April 1935.
- 55. E. M. Ind. Eng. Chem. Res. 42, 2217 (1950). , J. S. Jorczak.
- 56. K. Adv. Polym. Sci. 121, 83 (1995). , K. Ganesh.
- 57. J. C. Patrick. U.S. Patent 2363 614, Issued 28 Nov 1944.
- 58. C. S. J. Am. Chem. Soc. 79, 3089 (1957). ( , L. E. Olson. http://dx.doi.org/10.1021/ja01569a027)
- 59. P. V. J. Org. Chem. 25, 237 (1960). ( , C. S. Marvel, S. Banerjee. http://dx.doi.org/10.1021/jo01072a024)
- 60. E. J. Macromol. Chem. Phys. 119, 249 (1968). , C. Sillis.
- 61. Z. J. Appl. Microbiol. Biotechnol. 69, 237 (2005). ( , J. M. Culhane. http://dx.doi.org/10.1007/s00253-005-0156-x)
- 62. R. L. J. Polym. Sci., Part A: Polym. Chem. 5, 2111 (1967). ( , D. J. Hoffman. http://dx.doi.org/10.1002/pol.1967.150050827)
- 63. W. J. Polym. Sci., Part A: Polym. Chem. 36, 79 (1998). ( , F. Sanda, N. Kihara, T. Endo. http://dx.doi.org/10.1002/(SICI)1099-0518(19980115)36:1<79::AID-POLA11>3.0.CO;2-A)
- 64. Y. Z. Polym. Adv. Technol. 15, 564 (2004). ( , A. R. Hllil, A. S. Hay. http://dx.doi.org/10.1002/pat.497)
- 65. Y. Z. J. Appl. Polym. Sci. 74, 3069 (1999). ( , A. S. Hay. http://dx.doi.org/10.1002/(SICI)1097-4628(19991220)74:13<3069::AID-APP9>3.0.CO;2-I)
- 66. Y. Z. Polymer 42, 5215 (2001). ( , S. C. Tjong, A. S. Hay. http://dx.doi.org/10.1016/S0032-3861(01)00007-6)
- 67. H. Bull. Korean Chem. Soc. 26, 2069 (2005). , G. Jin, Y. Lee, H. Mo, M. Cho, J.-S. Park.
- 68. Y. Biomacromolecules 6, 24 (2005). ( , H. Koo, G. Jin, H. Mo, M. Cho, J.-Y. Park, J. Choi, J.-S. Park. http://dx.doi.org/10.1021/bm049658l)
- 69. H. Int. J. Pharm. 374, 58 (2009). ( , G. Jin, H. Kang, Y. Lee, H. Y. Nam, H.-S. Jang, J.-S. Park. http://dx.doi.org/10.1016/j.ijpharm.2009.03.010)
- 70. M. Macromolecules 39, 9028 (2006). ( , Y.-K. Goh, H. Gemici, T. Legge, S. Perrier, M. Montiero. http://dx.doi.org/10.1021/ma061070e)
- 71. Y. Z. Biomacromolecules 8, 2038 (2007). ( , D. S. Manickam, Q.-H. Zhou, D. Oupicky. http://dx.doi.org/10.1021/bm0702049)
- 72. N. V. Macromolecules 35, 9009 (2002). ( , K. Matyjaszewski. http://dx.doi.org/10.1021/ma021061f)
- 73. J. E. Puskas, E. Q. Rosenthal. U.S. Patent Application 20110218298, Filed 4 March 2011.
- 74. E. Q. Biomacromolecules 13, 154 (2011). ( , J. E. Puskas, C. Wesdemiotis. http://dx.doi.org/10.1021/bm201395t)