Coordination Chemistry of Linear Tripyrroles: Promises and Perils

REFERENCES

• Milgrom, L. R. The Colours of Life; Oxford University Press: Oxford, 1997.
   Google Scholar
• Costas, M. Coord. Chem. Rev. 2011, 255, 2912–2932.
   Web of Science ®Google Scholar
• Lu, H.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899–1909.
   PubMed Web of Science ®Google Scholar
• Aviv, I.; Gross, Z. Chem. Commun. 2007, 1987–1999.
   Google Scholar
• Ding, Y.; Tang, Y.; Zhu, W.; Xie, Y., Chem. Soc. Rev. 2015, 44, 1101–1112.
   Google Scholar
• Kesters, J.; Verstappen, P.; Kelchtermans, M.; Lutsen, L.; Vanderzande, D.; Maes, W. Adv. Energy Mater. 2015, 5, 1500218.
   Google Scholar
• Urbani, M.; Graetzel, M.; Nazeeruddin, M. K.; Torres, T. Chem. Rev. 2014, 114, 12330–12396.
   Google Scholar
• Srivatsan, A.; Missert, J. R.; Upadhyay, S. K.; Pandey, R. K. J. Porphyrins Phthalocyanines 2015, 19, 109–134.
   Google Scholar
• Ethirajan, M.; Chen, Y.; Joshi, P.; Pandey, R. K. Chem. Soc. Rev. 2011, 40, 340–362.
   PubMed Web of Science ®Google Scholar
• Sessler, J. L.; Tomat, E. Acc. Chem. Res. 2007, 40, 371–379.
   Google Scholar
• Saito, S.; Osuka, A. Angew. Chem., Int. Ed. 2011, 50, 4342–4373.
   Google Scholar
• Roznyatovskiy, V. V.; Lee, C.-H.; Sessler, J. L. Chem. Soc. Rev. 2013, 42, 1921–1933.
   PubMed Web of Science ®Google Scholar
• Lash, T. D. Chem. Asian J. 2014, 9, 682–705.
   Google Scholar
• Wood, T. E.; Thompson, A. Chem. Rev. 2007, 107, 1831–1861.
   Web of Science ®Google Scholar
• Kowada, T.; Maeda, H.; Kikuchi, K. Chem. Soc. Rev. 2015, 44, 4953–4972.
   Google Scholar
• Bessette, A.; Hanan, G. S. Chem. Soc. Rev. 2014, 43, 3342–3405.
   Google Scholar
• Hennessy, E. T.; Liu, R. Y.; Iovan, D. A.; Duncan, R. A.; Betley, T. A. Chem. Sci. 2014, 5, 1526–1532.
   Google Scholar
• Falk, H. The Chemistry of Linear Oligopyrroles and Bile Pigments; Springer-Verlag: Wien, 1989.
   Google Scholar
• Poulos, T. L., Peroxidase and catalases. In Biological Inorganic Chemistry; Bertini, I.; Gray, H. B.; Stiefel, E. I.; Valentine, J., Eds.; University Science Books: Sausalito, CA, 2007; 343–353.
   Google Scholar
• Kirkman, H. N.; Gaetani, G. F. Trends Biochem. Sci. 2007, 32, 44–50.
   Google Scholar
• Poulos, T. L. Arch. Biochem. Biophys. 2010, 500, 3–12.
   Google Scholar
• Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947–3980.
   Google Scholar
• Denisov, I. G.; Makris, T. M.; Sligar, S. G.; Schlichting, I. Chem. Rev. 2005, 105, 2253–2278.
   Google Scholar
• Chirik, P. J.; Wieghardt, K. Science 2010, 327, 794–795.
   PubMed Web of Science ®Google Scholar
• Lyaskovskyy, V.; de Bruin, B. ACS Catalysis 2012, 2, 270–279.
   Web of Science ®Google Scholar
• Luca, O. R.; Crabtree, R. H. Chem. Soc. Rev. 2013, 42, 1440–1459.
   Web of Science ®Google Scholar
• Eisenberg, R.; Gray, H. B. Inorg. Chem. 2011, 50, 9741–9751.
   Google Scholar
• Sugiyama, H.; Korobkov, I.; Gambarotta, S.; Möller, A.; Budzelaar, P. H. M. Inorg. Chem. 2004, 43, 5771–5779.
   Google Scholar
• Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13340–13341.
   Google Scholar
• Bart, S. C.; Lobkovsky, E.; Bill, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 5302–5303.
   Google Scholar
• Zarkesh, R. A.; Ziller, J. W.; Heyduk, A. F. Angew. Chem., Int. Ed. 2008, 47, 4715–4718.
   PubMed Web of Science ®Google Scholar
• Heyduk, A. F.; Zarkesh, R. A.; Nguyen, A. I. Inorg. Chem. 2011, 50, 9849–9863.
   Google Scholar
• Broere, D. L. J.; Metz, L. L.; de Bruin, B.; Reek, J. N. H.; Siegler, M. A.; van der Vlugt, J. I. Angew. Chem., Int. Ed. 2015, 54, 1516–1520.
   PubMed Web of Science ®Google Scholar
• Broere, D. L. J.; de Bruin, B.; Reek, J. N. H.; Lutz, M.; Dechert, S.; van der Vlugt, J. I. J. Am. Chem. Soc. 2014, 136, 11574–11577.
   Google Scholar
• Broring, M.; Brandt, C. D. Chem. Commun. 2001, 499–500.
   Google Scholar
• Broring, M.; Prikhodovski, S.; Tejero, E. C. Chem. Commun. 2007, 876–877.
   Google Scholar
• Jauma, A.; Farrera, J. A.; Ribo, J. M. Monatsh. Chem. 1996, 127, 935–946.
   Google Scholar
• Furstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582–3603.
   Google Scholar
• Broring, M. Beyond dipyrrins: Coordination interactions and templated macrocyclizations of open-chain oligopyrroles. In Handbook of Porphyrin Science, Vol. 8; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific: Singapore, 2010; 343–485.
   Google Scholar
• Gryko, D. T.; Gryko, D.; Lee, C.-H. Chem. Soc. Rev. 2012, 41, 3780–3789.
   Google Scholar
• Bennett, J. W.; Bentley, R. Adv. Appl. Microbiol. 2000, 47, 1–32.
   Google Scholar
• Williamson, N. R.; Fineran, P. C.; Leeper, F. J.; Salmond, G. P. C. Nat. Rev. Microbiol. 2006, 4, 887–899.
   Google Scholar
• D’Alessio, R.; Bargiotti, A.; Carlini, O.; Colotta, F.; Ferrari, M.; Gnocchi, P.; Isetta, A.; Mongelli, N.; Motta, P.; Rossi, A.; Rossi, M.; Tibolla, M.; Vanotti, E. J. Med. Chem. 2000, 43, 2557–2565.
   Google Scholar
• Furstner, A.; Grabowski, J. E. ChemBioChem 2001, 2, 706–709.
   PubMed Web of Science ®Google Scholar
• Papireddy, K.; Smilkstein, M.; Kelly, J. X.; Shweta; Salem, S. M.; Alhamadsheh, M.; Haynes, S. W.; Challis, G. L.; Reynolds, K. A. J. Med. Chem. 2011, 54, 5296–5306.
   Google Scholar
• Perez-Tomas, R.; Montaner, B.; Llagostera, E.; Soto-Cerrato, V. Biochem. Pharmacol. 2003, 66, 1447–1452.
   Google Scholar
• Perez-Tomas, R.; Vinas, M. Curr. Med. Chem. 2010, 17, 2222–2231.
   Google Scholar
• Regourd, J.; Ali, A. A.-S.; Thompson, A. J. Med. Chem. 2007, 50, 1528–1536.
   PubMed Web of Science ®Google Scholar
• Smithen, D. A.; Forrester, A. M.; Corkery, D. P.; Dellaire, G.; Colpitts, J.; McFarland, S. A.; Berman, J. N.; Thompson, A. Org. Biomol. Chem. 2013, 11, 62–68.
   Google Scholar
• Marchal, E.; Rastogi, S.; Thompson, A.; Davis, J. T. Org. Biomol. Chem. 2014, 12, 7515–7522.
   Google Scholar
• Marchal, E.; Uddin, M. I.; Hawco, C. L. A.; Thompson, A. Can. J. Chem. 2015, 93, 526–535.
   Google Scholar
• Melvin, M. S.; Wooton, K. E.; Rich, C. C.; Saluta, G. R.; Kucera, G. L.; Lindquist, N.; Manderville, R. A. J. Inorg. Biochem. 2001, 87, 129–135.
   Google Scholar
• Sessler, J. L.; Eller, L. R.; Cho, W.-S.; Nicolaou, S.; Aguilar, A.; Lee, J. T.; Lynch, V. M.; Magda, D. J. Angew. Chem., Int. Ed. 2005, 44, 5989–5992.
   Google Scholar
• Davis, J. T.; Gale, P. A.; Okunola, O. A.; Prados, P.; Iglesias-Sanchez, J. C.; Torroba, T.; Quesada, R. Nat. Chem. 2009, 1, 138–144.
   Google Scholar
• Borah, S.; Melvin, M. S.; Lindquist, N.; Manderville, R. A. J. Am. Chem. Soc. 1998, 120, 4557–4562.
   Google Scholar
• Melvin, M. S.; Tomlinson, J. T.; Saluta, G. R.; Kucera, G. L.; Lindquist, N.; Manderville, R. A. J. Am. Chem. Soc. 2000, 122, 6333–6334.
   Google Scholar
• Diaz, R. I. S.; Regourd, J.; Santacroce, P. V.; Davis, J. T.; Jakeman, D. L.; Thompson, A. Chem. Commun. 2007, 2701–2703.
   Google Scholar
• Melvin, M. S.; Calcutt, M. W.; Noftle, R. E.; Manderville, R. A. Chem. Res. Toxicol. 2002, 15, 742–748.
   Google Scholar
• Oki, Y.; Copeland, A.; Hagemeister, F.; Fayad, L. E.; Fanale, M.; Romaguera, J.; Younes, A. Blood 2012, 119, 2171–2172.
   PubMed Web of Science ®Google Scholar
• Brown, J. R.; Tesar, B.; Yu, L.; Werner, L.; Takebe, N.; Mikler, E.; Reynolds, H. M.; Thompson, C.; Fisher, D. C.; Neuberg, D.; Freedman, A. S. Leuk. Lymphoma 2015, 56, 3336–3342.
   Google Scholar
• Su, J.-C.; Chang, J.-H.; Huang, J.-W.; Chen, P. P. Y.; Chen, K.-F.; Tseng, P.-H.; Shiau, C.-W. Chem.-Biol. Interact. 2015, 228, 108–113.
   Google Scholar
• Rao, M. R.; Tiwari, M. D.; Bellare, J. R.; Ravikanth, M. J. Org. Chem. 2011, 76, 7263–7268.
   Google Scholar
• Zhang, M.; Hao, E.; Xu, Y.; Zhang, S.; Zhu, H.; Wang, Q.; Yu, C.; Jiao, L. RSC Adv. 2012, 2, 11215–11218.
   Google Scholar
• Zhang, M.; Hao, E.; Zhou, J.; Yu, C.; Bai, G.; Wang, F.; Jiao, L. Org. Biomol. Chem. 2012, 10, 2139–2145.
   Google Scholar
• Park, G.; Tomlinson, J. T.; Melvin, M. S.; Wright, M. W.; Day, C. S.; Manderville, R. A. Org. Lett. 2003, 5, 113–116.
   Google Scholar
• Chang, T. M.; Sinharay, S.; Astashkin, A. V.; Tomat, E. Inorg. Chem. 2014, 53, 7518–7526.
   Google Scholar
• Hong, T.; Song, H.; Li, X.; Zhang, W.; Xie, Y. RSC Adv. 2014, 4, 6133–6140.
   Google Scholar
• Crawford, S. M.; Ali, A. A.-S.; Cameron, T. S.; Thompson, A. Inorg. Chem. 2011, 50, 8207–8213.
   PubMed Web of Science ®Google Scholar
• Marchal, E.; Uddin, M. I.; Smithen, D. A.; Hawco, C. L. A.; Lanteigne, M.; Overy, D. P.; Kerr, R. G.; Thompson, A. RSC Adv. 2013, 3, 22967–22971.
   Google Scholar
• Marchal, E.; Smithen, D. A.; Uddin, M. I.; Robertson, A. W.; Jakeman, D. L.; Mollard, V.; Goodman, C. D.; MacDougall, K. S.; McFarland, S. A.; McFadden, G. I.; Thompson, A. Org. Biomol. Chem. 2014, 12, 4132–4142.
   Google Scholar
• Broring, M.; Brandt, C. D. J. Chem. Soc. Dalton Trans. 2002, 1391–1395.
   Google Scholar
• Broring, M.; Prikhodovski, S.; Brandt, C. D.; Consul Tejero, E.; Koehler, S.; Pietzonka, C. Inorg. Chem. 2007, 46, 917–925.
   PubMed Web of Science ®Google Scholar
• Bröring, M.; Prikhodovski, S.; Brandt, C. D. Inorg. Chim. Acta 2004, 357, 1733–1738.
   Web of Science ®Google Scholar
• Bley-Escrich, J.; Prikhodovski, S.; Brandt, C. D.; Broring, M.; Gisselbrecht, J. P. J. Porphyrins Phthalocyanines 2003, 7, 220–226.
   Google Scholar
• Sessler, J. L.; Gebauer, A.; Kral, V.; Lynch, V. M. Inorg. Chem. 1996, 35, 6636–6637.
   Google Scholar
• Broring, M.; Prikhodovski, S.; Brandt, C. D.; Consul Tejero, E., Pillars Chem. Eur. J. 2007, 13, 396–406.
   PubMed Web of Science ®Google Scholar
• Broring, M.; Prikhodovski, S.; Brandt, C. D.; Tejero, E. C.; Kohler, S. Dalton Trans. 2007, 200–208.
   Google Scholar
• Bröring, M., J. Porphyrins Phthalocyanines 2008, 12, 1242–1249.
   Google Scholar
• Balch, A. L.; Bowles, F. L., Coordination chemistry of verdohemes and open-chain oligopyrrole systems involved in heme oxidation and porphyrin destruction. In Handbook of Porphyrin Science, Vol. 8; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific: Singapore, 2010; 294–339.
   Google Scholar
• Beruter, J.; Colombo, J. P.; Schlunegger, U. P. Eur. J. Biochem. 1975, 56, 239–244.
   Google Scholar
• Yamaguchi, T.; Shioji, I.; Sugimoto, A.; Komoda, Y.; Nakajima, H. J. Biochem. 1994, 116, 298–303.
   Google Scholar
• Roth, S. D.; Shkindel, T.; Lightner, D. A. Tetrahedron 2007, 63, 11030–11039.
   PubMed Web of Science ®Google Scholar
• Dey, S. K.; Datta, S.; Lightner, D. A. Monatsh. Chem. 2009, 140, 1171–1181.
   Google Scholar
• Gautam, R.; Loughrey, J. J.; Astashkin, A. V.; Shearer, J.; Tomat, E. Angew. Chem., Int. Ed. 2015, 54, 14894–14897.
   Google Scholar
• Furuta, H.; Maeda, H.; Osuka, A. Org. Lett. 2002, 4, 181–184.
   Google Scholar
• Furuta, H.; Maeda, H.; Osuka, A. Inorg. Chem. Commun. 2003, 6, 162–164.
   Google Scholar
• Pawlicki, M.; Kańska, I.; Latos-Grażyński, L. Inorg. Chem. 2007, 46, 6575–6584.
   Google Scholar
• Rath, S. P.; Kalish, H.; Latos-Grażyński, L.; Olmstead, M. M.; Balch, A. L. J. Am. Chem. Soc. 2004, 126, 646–654.
   Google Scholar
• Rath, S. P.; Olmstead, M. M.; Latos-Grazynski, L.; Balch, A. L. J. Am. Chem. Soc. 2003, 125, 12678–12679.
   PubMed Web of Science ®Google Scholar
• Ding, Y.; Xie, Y.; Li, X.; Hill, J. P.; Zhang, W.; Zhu, W. Chem. Commun. 2011, 47, 5431–5433.
   Google Scholar