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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
REVIEW

Profluorescent Nitroxides as Sensitive Probes of Oxidative Change and Free Radical Reactions

James P. Blinco A C , Kathryn E. Fairfull‐Smith B , Benjamin J. Morrow B and Steven E. Bottle B C
+ Author Affiliations
- Author Affiliations

A Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesser Strasse 18, 76128 Karlsruhe, Germany.

B Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Queensland University of Technology, Brisbane, Qld 4001, Australia.

C Corresponding authors. Email: james.blinco@kit.edu, s.bottle@qut.edu.au

Australian Journal of Chemistry 64(4) 373-389 https://doi.org/10.1071/CH10442
Submitted: 6 December 2010  Accepted: 28 January 2011   Published: 18 April 2011

Abstract

This paper presents a review on the use of tethered nitroxide–fluorophore molecules as probes of oxidative change and free radical generation and reaction. The proximity of the nitroxide free radical to the fluorophore suppresses the normal fluorescence emission process. Nitroxide free radical scavenging, metabolism or redox chemistry return the system to its natural fluorescent state and so these tethered nitroxide–fluorophore molecules are described as being profluorescent. A survey of profluorescent nitroxides found in the literature is provided as well as background on the mechanism of action and applications of these compounds as fluorometric probes within the fields of biological, materials and environmental sciences.


References

[1]  L. Stryer, H. O. Griffith, Proc. Natl. Acad. Sci. USA 1965, 54, 1785.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF28XntVerug%3D%3D&md5=b806c2d1f07fde9aafd46301be09b336CAS |

[2]  I. M. Bystryak, G. I. Likhtenshtein, A. I. Kotelnikov, O. H. Hankovsky, K. Hideg, Russ. J. Phys. Chem. 1986, 60, 1679.

[3]  J. L. Gerlock, P. J. Zacamanidis, D. R. Bauer, D. J. Simpson, N. V. Blough, Free Radic. Res. Commun. 1990, 10, 119.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXksVGnsL0%3D&md5=54b574dc6c29495278a1f23f87f23594CAS | 2165981PubMed |

[4]  J. A. Green, D. J. Simpson, G. Zhou, P. S. Ho, N. V. Blough, J. Am. Chem. Soc. 1990, 112, 7337.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXlslWgt7g%3D&md5=6a5bb8052f224b95212babe0d74a03e3CAS |

[5]  N. V. Blough, D. J. Simpson, J. Am. Chem. Soc. 1988, 110, 1915.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXhtlSrurc%3D&md5=31377cf580f435a63b5252c18e6bceedCAS |

[6]  A. S. Micallef, J. P. Blinco, G. A. George, D. A. Reid, E. Rizzardo, S. H. Thang, S. E. Bottle, Polym. Degrad. Stabil. 2005, 89, 427.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltlemu7s%3D&md5=74482f9dd53bc8b372b2076b8cfadf97CAS |

[7]  C. Coenjarts, O. Garcia, L. Llauger, J. Palfreyman, A. L. Vinette, J. C. Scaiano, J. Am. Chem. Soc. 2003, 125, 620.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xpsl2jtLk%3D&md5=631cb8a63354865e5e7ee42f9eb921aeCAS | 12526647PubMed |

[8]  K. Hideg, T. Kalai, C. P. Sar, J. Heterocycl. Chem. 2005, 42, 437.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjs12rsrw%3D&md5=91036f574e31cde09650f22405acd547CAS |

[9]  N. Medvedeva, V. V. Martin, A. L. Weis, G. I. Likhtenshten, J. Photochem. Photobiol. A 2004, 163, 45.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhs1Gjtbs%3D&md5=5cac14e4e2fe073a0fd13f78f4862489CAS |

[10]  F. S. Abrams, E. London, Biochemistry 1993, 32, 10826.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXlvFyqs7w%3D&md5=b34c2a3bfd30c1af3f88eaf38d0fcaa3CAS | 8399232PubMed |

[11]  E. Asuncion‐Punzalan, E. London, Biochemistry 1995, 34, 11460.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXns1CisrY%3D&md5=c28261de33645b5cd21e90d09ac05833CAS | 7547874PubMed |

[12]  R. D. Kaiser, E. London, Biochemistry 1998, 37, 8180.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXivFCisLs%3D&md5=4b0bc1e72ef7d5476050227ffe79e319CAS | 9609714PubMed |

[13]  K. Kachel, E. Asuncion‐Punzalan, E. London, Biochemistry 1995, 34, 15475.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXptFSqtbw%3D&md5=2bf504cd4c35ad050765162f6aba2fdbCAS | 7492549PubMed |

[14]  D. S. Weiss, J. Photochem. 1977, 6, 301.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2sXhsFCrsrk%3D&md5=6c781d33ecfba1853ef5634f92341770CAS |

[15]  A. R. Watkins, Chem. Phys. Lett. 1974, 29, 526.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXosFGksg%3D%3D&md5=9bc0bcc09fc702acf4919dc52b7b4486CAS |

[16]  S. K. Chattopadhyay, P. K. Das, G. L. Hug, J. Am. Chem. Soc. 1983, 105, 6205.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXltl2iurY%3D&md5=31425552358a1ca6b76afdbabf906753CAS |

[17]  O. L. Gijzeman, F. Kaufman, G. Porter, J. Chem. Soc., Faraday Trans. II 1973, 69, 727.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXhsFyltr0%3D&md5=43c236499efcbe3711cf3ad7a3c2a781CAS |

[18]  J. A. Green, L. A. Singer, J. Am. Chem. Soc. 1988, 110, 1915.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  G. I. Likhtenstein, K. Ishii, S. I. Nakatsuji, Photochem. Photobiol. 2007, 83, 871.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXoslOjsrY%3D&md5=bd45b1cd5d6e43c975f45b3b25f1d075CAS | 17645658PubMed |

[20]  J. Matko, K. Ohki, M. Edidin, Biochemistry 1992, 31, 703.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XlsVyktw%3D%3D&md5=d0bd6efa5ae1f79930f1c628af21689dCAS | 1731926PubMed |

[21]  G. Moad, D. Shipp, T. A. Smith, D. H. Solomon, J. Phys. Chem. A 1999, 103, 6580.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXlt1Wjsr4%3D&md5=27323dc6076a1161a4c098ab785dbc81CAS |

[22]  Z.‐Y. Bian, X.‐Q. Guo, Y.‐B. Zhao, J.‐O. Du, Anal. Sci. 2005, 21, 553.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXksFahurw%3D&md5=c4766d3c61ce41c2a1174d10590330f7CAS | 15913147PubMed |

[23]  X.‐F. Yang, X.‐Q. Guo, Anal. Chim. Acta 2001, 434, 169.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjtFOrtL4%3D&md5=7cbddd727d23f4250d88bda96a5b8936CAS |

[24]  N. J. Turro, G. Lem, I. S. Zavarine, Macromolecules 2000, 33, 9782.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXptVCmurs%3D&md5=b56e251542165c3f222f8180ed5d7ed4CAS |

[25]  G. I. Likhtenshtein, Appl. Biochem. Biotechnol. 2009, 152, 135.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXks1Sru7Y%3D&md5=7a4123c764ed02d8a67d7a47fce43c5eCAS | 18654744PubMed |

[26]  T. Kálai, E. Hideg, I. Vass, K. Hideg, Free Radic. Biol. Med. 1998, 24, 649.
         | Crossref | GoogleScholarGoogle Scholar | 9559877PubMed |

[27]  G. I. Likhtenshtein, Pure Appl. Chem. 2008, 80, 2125.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlWnsbvE&md5=bf2bc7690f86eea3954184543f241f82CAS |

[28]  E. Lozinsky, V. V. Matin, T. A. Berezina, A. I. Shames, D. L. Weis, G. I. Likhtenshtein, J. Biochem. Biophys. Methods 1999, 38, 29.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXnvVSqur8%3D&md5=cee5add10fc323b69ed1bbc5fb2a1c7fCAS | 10078871PubMed |

[29]  M. Danko, S. Chmela, P. Hrdlovic, Polym. Degrad. Stabil. 2003, 79, 333.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XpsVeksrc%3D&md5=6e6f18837a6b7395537a55fbb83c627eCAS |

[30]  J. Kollár, P. Hrdlovic, S. Chmela, J. Photochem. Photobiol. A 2009, 204, 191.
         | Crossref | GoogleScholarGoogle Scholar |

[31]  X.‐F. Yang, X.‐Q. Guo, Analyst 2001, 126, 1800.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXnsVGnurs%3D&md5=247649a70cfc5aeb0133bd4c139352b7CAS | 11693627PubMed |

[32]  P. Hrdlovic, S. Chmela, M. Danko, J. Photochem. Photobiol. A 1998, 112, 197.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhtlaqsLg%3D&md5=9101885e3f0852629123884b6999436aCAS |

[33]  Y.‐M. Dang, X.‐Q. Guo, Appl. Spectrosc. 2006, 60, 203.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xit1Sns74%3D&md5=ae77b3f2a1240f44c17af372a7536d5bCAS | 16542572PubMed |

[34]  P. Hrdlovič, S. Chmela, M. Danko, M. Sarakha, G. Guyot, J. Fluoresc. 2008, 18, 393.
         | Crossref | GoogleScholarGoogle Scholar | 18060482PubMed |

[35]  S. Jockusch, G. Dedola, G. Lem, N. J. Turro, J. Phys. Chem. B 1999, 103, 9126.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjs1Witbw%3D&md5=36b0e32b43261047779687a109bc73f2CAS |

[36]  M. G. Ivan, J. C. Scaiano, Photochem. Photobiol. 2003, 78, 416.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosV2rt78%3D&md5=f2bd0ccce96263159435479379815983CAS | 14626672PubMed |

[37]  A. Aspée, L. Maretti, J. C. Scaiano, Photochem. Photobiol. Sci. 2003, 2, 1125.
         | Crossref | GoogleScholarGoogle Scholar | 14690224PubMed |

[38]  A. Goto, J. C. Scaiano, L. Maretti, Photochem. Photobiol. Sci. 2007, 6, 833.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXosVSktrw%3D&md5=4c78c15bcdef79853d464ea89142f5ccCAS | 17668111PubMed |

[39]  C. Bueno, L. Mikelsons, L. Maretti, J. C. Scaiano, A. Aspee, Photochem. Photobiol. 2008, 84, 1535.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVWkt7vO&md5=f99664ec6869d42f23e208f116b843d6CAS | 18627524PubMed |

[40]  A. Aspée, O. Garcia, L. Maretti, R. Sastre, J. C. Scaiano, Macromolecules 2003, 36, 3550.
         | Crossref | GoogleScholarGoogle Scholar |

[41]  S. Sato, M. Suzuki, T. Soma, M. Tsunoda, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2008, 70, 799.
         | Crossref | GoogleScholarGoogle Scholar | 18029225PubMed |

[42]  A. Aspee, C. Aliaga, J. C. Scaiano, Photochem. Photobiol. 2007, 83, 481.
         | 1:CAS:528:DC%2BD2sXntV2hu7o%3D&md5=7d279446637cdc2895ac564009bfcd33CAS | 17094718PubMed |

[43]  C. Aliaga, J. M. Juarez‐Ruiz, J. C. Scaiano, A. Aspee, Org. Lett. 2008, 10, 2147.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXls1Whsb8%3D&md5=2c51ae6b4a34a9eab0f1bfee56f92039CAS | 18465870PubMed |

[44]  W. Chen, X. Wang, X. Tu, D. Pei, Y. Zhao, X. Guo, Small 2008, 4, 759.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXosFyntLs%3D&md5=f4f8662f1959436437544f9887a18be0CAS | 18500770PubMed |

[45]  B. Bognár, E. Osz, K. Hideg, T. Kalai, J. Heterocycl. Chem. 2006, 43, 81.
         | Crossref | GoogleScholarGoogle Scholar |

[46]  C. Tansakul, E. Lilie, E. D. Walter, F. Rivera, A. Wolcott, J. Z. Zhang, G. L. Millhauser, R. Braslau, J. Phys. Chem. C 2010, 114, 7793.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXktFOjtLo%3D&md5=2a27a336f88daf50840d4a5d48f4baf6CAS |

[47]  O. G. Ballesteros, L. Maretti, R. Sastre, J. C. Scaiano, Macromolecules 2001, 34, 6184.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXlsFWhsrg%3D&md5=03ca8c9e2985f904636aceda32c9f0b8CAS |

[48]  T. Maki, N. Soh, T. Fukaminato, H. Nakajima, K. Nakano, T. Imato, Anal. Chim. Acta 2009, 639, 78.
         | 1:CAS:528:DC%2BD1MXktF2ltLw%3D&md5=a41e96994f277504664e3bd149926b4eCAS | 19345762PubMed |

[49]  S. E. Herbelin, N. V. Blough, J. Phys. Chem. B 1998, 102, 8170.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXms1Kjs7o%3D&md5=10bcc9aacf0199c18308b82ac24d8abeCAS |

[50]  M. Jia, Y. Tang, Y.‐F. Lam, S. A. Green, N. V. Blough, Anal. Chem. 2009, 81, 8033.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFWqtbzI&md5=22a9d35463ec9e43ef3b6438e9df7cafCAS | 19788316PubMed |

[51]  P. Parkhomyuk‐Ben Arye, N. Strashnikova, G. I. Likhtenshtein, J. Biochem. Biophys. Methods 2002, 51, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhslWjur0%3D&md5=daf3429867e9a00d661b0bd210c2562fCAS | 11879915PubMed |

[52]  M. A. Nejad, S. A. Green, ArXiv.org 2010. https://doi.org/arXiv:1009.2291v1

[53]  D. J. Kieber, N. V. Blough, Free Radic. Res. Commun. 1990, 10, 109.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXit1aqs7Y%3D&md5=bd4df9361db766c45f8c7ae97af32a8aCAS | 2165979PubMed |

[54]  D. J. Kieber, N. V. Blough, Anal. Chem. 1990, 62, 2275.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXnsVGjtg%3D%3D&md5=20791781a95de5e0e59d611bdf8cd2b7CAS |

[55]  B. Li, P. L. Gutierrez, N. V. Blough, Anal. Chem. 1997, 69, 4295.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXmt12ms78%3D&md5=d1795b8dcee6bba985e3089c4d24622fCAS | 9360488PubMed |

[56]  T. Thomas‐Smith, N. V. Blough, Environ. Sci. Technol. 2001, 35, 2721.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjvVOhurk%3D&md5=d00b99bd88a8a74bc14525a5f338a575CAS | 11452598PubMed |

[57]  P. P. Vaughan, N. V. Blough, Environ. Sci. Technol. 1998, 32, 2947.
         | Crossref | GoogleScholarGoogle Scholar |

[58]  Y. Suzuki, T. Katagi, J. Agric. Food Chem. 2008, 56, 10811.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlaktbrO&md5=ddc4a351c85c6c076b909cc2ef941077CAS | 18983159PubMed |

[59]  B. Li, N. V. Blough, P. L. Guiterrez, Free Radic. Biol. Med. 2000, 29, 548.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXnt1Sisrw%3D&md5=95850d82ddd90cacb92dc175744c2d62CAS | 11025198PubMed |

[60]  B. Li, P. L. Guiterrez, P. Amstad, N. V. Blough, Chem. Res. Toxicol. 1999, 12, 1042.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmt12mt78%3D&md5=f3fce6526395c2c17c1e3ba653173c8eCAS | 10563829PubMed |

[61]  C. G. Johnson, S. Caron, N. V. Blough, Anal. Chem. 1996, 68, 867.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xntlymuw%3D%3D&md5=f8ab9834f32898f9f6286351f009d648CAS | 8779444PubMed |

[62]  C. A. Cohn, S. R. Simon, M. A. A. Schoonen, Part. Fibre Toxicol. 2008, 5,
         | Crossref | GoogleScholarGoogle Scholar |

[63]  T. M. Flicker, S. A. Green, Anal. Chem. 1998, 70, 2008.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXit1WnsLg%3D&md5=15abd290bfa77cfaea2b4082bb04f0beCAS |

[64]  A. G. Matveeva, D. V. Stass, E. M. Glebov, V. P. Grivin, V. V. Korolev, V. F. Plyusnin, V. A. Reznikova, Russ. Chem. Bull. Int. Ed. 2010, 59, 771.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlWrur3P&md5=b22bbcff445b87c80f05bdf74190a334CAS |

[65]  H. Wang, D. Zhang, X. Guo, L. Zhu, Z. Shuai, D. Zhu, Chem. Commun. 2004, 670.
         | Crossref | GoogleScholarGoogle Scholar |

[66]  J. Li, M. Wang, H. M. Ma, D. Q. Zhang, S. X. Xiong, Chin. J. Chem. 2005, 16, 1125.
         | 1:CAS:528:DC%2BD2MXpsVeht7o%3D&md5=c6ed006bc711103854667d9b1e0ddba0CAS |

[67]  E. M. Lozinsky, L. V. Martina, A. I. Shames, N. Uzlaner, A. Masarwa, G. I. Likhtenshtein, D. Meyerstein, V. V. Martin, Anal. Biochem. 2004, 326, 139.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhslegtLg%3D&md5=4815bfaadd1bb1f8e5c6da6c811ff32aCAS | 15003554PubMed |

[68]  R. Ziessel, C. Stroh, Org. Lett. 2003, 5, 2397.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXks1Krt7g%3D&md5=72e15b8b2acd2d5a362aa56fa2c91f9dCAS | 12841739PubMed |

[69]  R. Ziessel, C. Stroh, Synthesis 2003, 14, 2145.
         | Crossref | GoogleScholarGoogle Scholar |

[70]  N. Barhate, P. Cekan, A. P. Massey, S. T. Sigurdsson, Angew. Chem. Int. Ed. 2007, 46, 2655.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXksVWru7w%3D&md5=99a9674c6a77ea4962f411048a780b72CAS |

[71]  S. Sato, M. Tsunoda, M. Suzuki, M. Kutsuna, K. Takido‐uchi, M. Shindo, H. Mizugushi, H. Obara, H. Ohya, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2009, 71, 2030.
         | Crossref | GoogleScholarGoogle Scholar | 18790663PubMed |

[72]  T. Yoshioka, S. Higashida, A. Morimura, K. Murayama, Bull. Chem. Soc. Jpn. 1971, 44, 2207.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXlt12ju7c%3D&md5=121ba903f4cce0e1c3f5e27f1401796cCAS |

[73]  C. H. Han, M. Drache, H. Baethge, G. Schmidt‐Naake, Macromol. Chem. Phys. 1999, 200, 1779.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXkvF2lsr0%3D&md5=43625a67dd7c8a749df79899d6d3672fCAS |

[74]  D. F. Bowman, T. Gillan, K. U. Ingold, J. Am. Chem. Soc. 1971, 93, 6555.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38XisVamsA%3D%3D&md5=5cb92399afd2955563c3dbe11ecfd014CAS |

[75]  A. R. Forrester, J. M. Hay, R. H. Thomson, in Organic Chemistry of Stable Free Radicals 1968, p. 201 (Academic Press: London).

[76]  G. A. Abakumov, V. D. Tikhonov, Izv Akad Nauk Gruz SSR Ser Khim 1969, 796.
         | 1:CAS:528:DyaF1MXkt1ajsro%3D&md5=36e7c5353b8dd3f610f7269066ce3a9cCAS |

[77]  V. A. Golubev, G. N. Boronina, Izv Akad Nauk Gruz SSR Ser Khim 1972, 2089.
         | 1:CAS:528:DyaE3sXjs1Sr&md5=57b4329c4e85397b24808c1a88df0467CAS |

[78]  T. Gnewuch, G. Sosnovsky, Chem. Rev. 1986, 86, 203.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XhsV2ht7g%3D&md5=c6b496b738fb9c82a8e254cca9d2bc95CAS |

[79]  E. F. Ullman, L. Call, J. H. Osiecki, J. Org. Chem. 1970, 35, 3623.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXpvFahtw%3D%3D&md5=584fc54b7c7c8cbacbe9a564171b7c8dCAS |

[80]  E. Y. Fursova, V. I. Ovcharenko, G. V. Romanenko, E. V. Tretyakov, Tetrahedron Lett. 2003, 44, 6397.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlvFOmtLg%3D&md5=be389f39ff4c182989d41d2a7d34cd5dCAS |

[81]  E. Tretyakov, S. Tolstikov, A. Mareev, A. Medvedeva, G. Romanenko, D. Stass, A. Bogomyakov, V. Ovcharenko, Eur. J. Org. Chem. 2009, 2548.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXls1Kitbs%3D&md5=0cceb4742fb52fcecf76f5d45f482b78CAS |

[82]  D. J. Kieber, C. G. Johnson, N. V. Blough, Free Radic. Res. Commun. 1992, 16, 35.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XkvValuro%3D&md5=91107367061ba4a8b5cb1eb7fc2655a6CAS | 1516847PubMed |

[83]  D. J. Keddie, T. E. Johnson, D. P. Arnold, S. E. Bottle, Org. Biomol. Chem. 2005, 3, 2593.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlvVSlurg%3D&md5=eaee8168deb372bc08aef19160de1bddCAS | 15999192PubMed |

[84]  T. Kálai, M. Balog, J. Jeko, W. L. Hubbell, K. Hideg, Synthesis 2002, 16, 2365.

[85]  D. J. Keddie, K. E. Fairfull‐Smith, S. E. Bottle, Org. Biomol. Chem. 2008, 6, 3135.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXpslWmtrg%3D&md5=ed9f05f13da06ade70a5798fdf228473CAS | 18698473PubMed |

[86]  K. E. Fairfull‐Smith, J. P. Blinco, D. J. Keddie, G. A. George, S. E. Bottle, Macromolecules 2008, 41, 1577.
         | 1:CAS:528:DC%2BD1cXhvV2ntrw%3D&md5=c60493b216cd67a1511c13ca418a6aafCAS |

[87]  K. E. Fairfull‐Smith, S. E. Bottle, Eur. J. Org. Chem. 2008, 5391.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsFWmtLjN&md5=18f38ca202ae4f7fd95f09a27342fd25CAS |

[88]  C. Stroh, M. Mayor, C. v. Hanisch, Eur. J. Org. Chem. 2005, 3697.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpvF2lu7c%3D&md5=77e0b78f30de49f7cf8864e488f5e80eCAS |

[89]  B. J. Morrow, D. J. Keddie, N. Gueven, M. F. Lavin, S. E. Bottle, Free Radic. Biol. Med. 2010, 49, 67.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmsVGgs7Y%3D&md5=5597469aae8a0a1deda617b6c59731a0CAS | 20350596PubMed |

[90]  J. P. Blinco, D. J. Keddie, T. Wade, P. J. Barker, G. A. George, S. E. Bottle, Polym. Degrad. Stabil. 2008, 93, 1613.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVyju7vE&md5=5ed91c2a2b66532f7e52bbc2aebf9058CAS |

[91]  J. P. Blinco, K. E. Fairfull‐Smith, A. S. Micallef, S. E. Bottle, Polym. Chem. 2010, 1, 1009.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtl2ms7bJ&md5=4b8d5a0d3e4eebcb256cb5ff0d7fbd00CAS |

[92]  J. M. Colwell, J. R. Walker, J. P. Blinco, A. S. Micallef, G. A. George, S. E. Bottle, Polym. Degrad. Stabil. 2010, 95, 2101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFWqu7bL&md5=9b9c54c8ca5e1d5b68c631bfc98edb3bCAS |

[93]  B. Miljevic, K. E. Fairfull‐Smith, S. E. Bottle, Z. D. Ristovski, Atmos. Environ. 2010, 44, 2224.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXlslCjsr0%3D&md5=aaea5ca3522235298e65793c6f7bcf93CAS |

[94]  B. Miljevic, M. F. Heringa, A. Keller, N. K. Meyer, J. Good, A. Lauber, P. F. Decarlo, K. E. Fairfull‐Smith, T. Nussbaumer, H. Burtscher, A. S. H. Prevot, U. Baltensperger, S. E. Bottle, Z. D. Ristovski, Environ. Sci. Technol. 2010, 44, 6601.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXpslWjsrw%3D&md5=a825146546fc0d248dab5ca561709ad6CAS | 20684503PubMed |

[95]  N. C. Surawski, B. Miljevic, B. A. Roberts, R. L. Modini, R. Situ, R. J. Brown, S. E. Bottle, Z. D. Ristovski, Environ. Sci. Technol. 2010, 44, 229.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFaks7fP&md5=cfae5ebfc08836cad8cb9e1e9e6dae51CAS | 19994903PubMed |

[96]  J. P. Blinco, J. C. McMurtrie, S. E. Bottle, Eur. J. Org. Chem. 2007, 4638.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFyitbfJ&md5=79e619dc6fde7995cd20cccac7d8073dCAS |

[97]  A. S. Micallef, S. E. Bottle, J. P. Blinco, G. A. George, ACS Symposium Series 2008, 978(Polymer Durability and Radiation Effects) 2008, pp. 59–69, in press.

[98]  L. Moghaddam, J. P. Blinco, J. M. Colwell, P. J. Halley, S. E. Bottle, P. M. Fredericks, G. A. George, Polym. Degrad. Stabil. 2011, in press.in press
         | Crossref | GoogleScholarGoogle Scholar |

[99]  J. M. Colwell, J. P. Blinco, C. Hulbert, K. E. Fairfull‐Smith, S. E. Bottle, Aust. J. Chem. 2011, in press.
         | Crossref | GoogleScholarGoogle Scholar |

[100]  B. Bognár, J. Jeko, T. Kalai, K. Hideg, Dyes Pigm. 2010, 87, 218.
         | Crossref | GoogleScholarGoogle Scholar |

[101]  M. Laferriére, R. E. Galian, V. Maurel, J. C. Scaiano, Chem. Commun. 2006, 257.
         | Crossref | GoogleScholarGoogle Scholar |

[102]  J. C. Scaiano, M. Laferriére, R. E. Galian, V. Maurel, P. Billone, Phys. Status Solidi, A 2006, 203, 1337.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XltlGjsLo%3D&md5=d9708d30788a8ca78741aace2b88bd9fCAS |

[103]  V. Maurel, M. Laferriére, P. Billone, R. Godin, J. C. Scaiano, J. Phys. Chem. B 2006, 110, 16353.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xntl2gs7Y%3D&md5=5ead63686d53cff764bb7e63a01e5e27CAS | 16913763PubMed |

[104]  W. Chen, X. Wang, X. Tu, D. Pei, Y. Zhao, X. Guo, Small 2008, 4, 759.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXosFyntLs%3D&md5=f4f8662f1959436437544f9887a18be0CAS | 18500770PubMed |

[105]  Y. Tang, F. He, M. Yu, S. Wang, Y. Li, D. Zhu, Chem. Mater. 2006, 18, 3605.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xmsl2ksb4%3D&md5=6abd0f5754026cb5c5bc668fbb287d08CAS |

[106]  E. Lozinsky, A. Novoselsky, A. I. Shames, O. Saphier, G. I. Likhtenshtein, D. Meyerstein, Biochim. Biophys. Acta 2001, 1526, 53.
         | 1:CAS:528:DC%2BD3MXisVWgtbc%3D&md5=a442a8680ab909af25925f31fc41bb16CAS | 11287122PubMed |

[107]  O. Saphier, T. Silberstein, A. I. Shames, G. I. Likhtenshtein, E. Maimon, D. Mankuta, M. Mazor, M. Katz, D. Meyerstein, N. Meyerstein, Free Rad. Res. 37, 301.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtFKhtrc%3D&md5=45ebdc5cff07088146230b565394a390CAS |

[108]  E. C. I. Veerman, K. Nazmi, W. Van’t Hof, J. G. M. Bolscher, A. L. D. Hertog, A. V. Nieuw Amerongen, Biochem. J. 2004, 381, 447.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXlslGnt70%3D&md5=feb75060723f1ee0af049b05705476d5CAS | 15109304PubMed |

[109]  G. G. Borisenko, I. Martin, Q. Zhao, A. A. Amoscato, Y. Y. Tyurina, V. E. Kagan, J. Biol. Chem. 2004, 279, 23453.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXkt1GitL4%3D&md5=cddf00d496a508a6fbd04a341a262c21CAS | 15039448PubMed |

[110]  G. G. Borisenko, I. Martin, Q. Zhao, A. A. Amoscato, V. E. Kagan, J. Am. Chem. Soc. 2004, 126, 9221.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXlsFemtb0%3D&md5=78a704c9db4ac6a1b3a79d9875b462a4CAS | 15281811PubMed |

[111]  P. Cekan, A. L. Smith, N. Barhate, B. H. Robinson, S. T. Sigurdsson, Nucleic Acids Res. 2008, 36, 5946.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1Knsr7M&md5=8f3a9df8c8b390106475330dae87c7baCAS | 18805908PubMed |

[112]  R. Braslau, Patent: WO 2009139864 2009.

[113]  M. Bätz, H.‐G. Korth, R. Sustmann, Angew. Chem. Int. Ed. Engl. 1997, 36, 1501.
         | Crossref | GoogleScholarGoogle Scholar |

[114]  P. Meineke, U. Rauen, H. d. Groot, H.‐G. Korth, R. Sustmann, Biol. Chem. 2000, 381, 575.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXmvFShs7k%3D&md5=30ab4ebab2906b60ceef8150ec61160eCAS | 10987364PubMed |

[115]  P. Meineke, U. Rauen, H. d. Groot, H.‐G. Korth, R. Sustmann, Chemistry 1999, 5, 1738.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjvVamtbY%3D&md5=c676043a62498bdde28afd47db81dc68CAS |

[116]  P. M. Düppe, P. M. Talbierski, F. S. Hornig, U. Rauen, H.‐G. Korth, T. Wille, R. Boese, T. Omlor, H. d. Groot, R. Sustmann, Chemistry 2010, 16, 11121.
         | Crossref | GoogleScholarGoogle Scholar | 20680937PubMed |

[117]  A. L. J. Beckwith, V. W. Bowry, K. U. Ingold, J. Am. Chem. Soc. 1992, 114, 4983.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XktVOhu74%3D&md5=59339e7bd38e504da682658276444c4aCAS |

[118]  W. K. Busfield, K. Heiland, I. D. Jenkins, Tetrahedron Lett. 1994, 35, 6541.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXlvVSgs7w%3D&md5=9c63d991816c0008b9f38be26cedf149CAS |

[119]  W. K. Busfield, I. D. Grice, I. D. Jenkins, Aust. J. Chem. 1995, 48, 625.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXksFyiur4%3D&md5=7a74bbf5ee9c3accc957acd13c7f2420CAS |

[120]  G. Moad, D. Shipp, T. A. Smith, D. H. Solomon, Macromolecules 1997, 30, 7627.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXnt1Wgsro%3D&md5=848e12c27aac892ae4790e0960d5155cCAS |

[121]  D.‐L. Versace, J. Lalevee, J.‐P. Fouassier, Y. Guillaneuf, D. Bertin, D. Gigmes, Macromol. Rapid Commun. 2010, 31, 1383.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXps1GjsLY%3D&md5=6773f7fc4fcd49add64f2b870f7da8aaCAS |

[122]  Y. Guillaneuf, D. Bertin, D. Gigmes, D.‐L. Versace, J. Lalevee, J.‐P. Fouassier, Macromolecules 2010, 43, 2204.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhvVKjsL8%3D&md5=7410e77d60b797573a67317a8386acc7CAS |

[123]  M. Alaghmand, N. V. Blough, Environ. Sci. Technol. 2007, 41, 2364.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXisVOmsLY%3D&md5=c8ad6d4092f2c0e683b32f8d5db53a4aCAS | 17438788PubMed |

[124]  T. M. Flicker, J. A. Green, Environ. Health Perspect. 2001, 109, 765.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXntFamsbg%3D&md5=20c9b94a4df151b8aa12564863d0c5f0CAS |

[125]  J. Bartalis, W. G. Chan, J. B. Wooten, Anal. Chem. 2007, 79, 5103.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXlslGgs7s%3D&md5=2e071be7fd1bf6318f4c6cea8314b4daCAS | 17530742PubMed |

[126]  J. Bartalis, Y.‐L. Zhao, J. W. Flora III, J. B. Wooten, Anal. Chem. 2009, 81, 631.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsFais77O&md5=6f9684940921cbc2542063f94fcef1b6CAS | 19093757PubMed |