Supramolecular ferric porphyrins as cyanide receptors in aqueous solution

ACS Medicinal Chemistry Letters

Volumn 2, Issue 12, 2011, Pages 943-947

  Watanabe, Kenji ^a   Kitagishi, Hiroaki ^a   Kano, Koji ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

cyanide binding; cyanide receptor; Cyclodextrin dimer; ferric porphyrin; supramolecules

Indexed keywords

5,10,15,20 TETRAKIS(2,4,6 TRIMETHYL 3 SULFONATOPHENYL)PORPHINATOIRON HEPTAKIS[2,3 DI O ACETYL 6 (1 BUTYL 1H IMIDAZOL 2 YL) 6 DESOXY] BETA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYANIDE; CYANIDE RECEPTOR; IMIDAZOLE DERIVATIVE; PORPHYRIN DERIVATIVE; RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; CONTROLLED STUDY; CYANIDE POISONING; DRUG EFFECT; DRUG EFFICACY; DRUG SYNTHESIS; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; REACTION ANALYSIS;

EID: 83455172844     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200231x     Document Type: Article

References (26)

1. Shepherd, G.; Velez, L. I. Role of hydroxocobalamin in acute cyanide poisoning Ann. Pharmacother. 2008, 42, 661-669 (Pubitemid 351619937)
2. Ma, J.; Dasgupta, P. K. Recent developments in cyanide detection: A review Anal. Chim. Acta 2010, 673, 117-125
3. Hudnall, T. W.; Gabbaï, F. P. Ammonium boranes for the selective complexation of cyanide or fluoride ions in water J. Am. Chem. Soc. 2007, 129, 11978-11986 (Pubitemid 47512026)
4. Lin, T.-P.; Chen, C.-Y.; Wen, Y.-S.; Sun, S.-S. Synthesis, photophysical, and anion-sensing properties of quinoxalinebis(sulfonamide) functionalized receptors and their metal complexes Inorg. Chem. 2007, 46, 9201-9212
5. Miyaji, H.; Kim, D.-S.; Chang, B.-Y.; Park, E.; Park, S.-M.; Ahn, K. H. Highly cooperative ion-pair recognition of potassium cyanide using a heteroditopic ferrocene-based crown ether-trifluoroacetylcarboxanilide receptor Chem. Commun. 2008, 753-755 (Pubitemid 351171427)
6. Hall, A. H.; Dart, R.; Bogdan, G. Sodium thiosulfate of hydroxocobalamin for the empiric treatment of cyanide poisoning? Ann. Emerging Med. 2007, 49, 806-813 (Pubitemid 46778875)
7. Hall, A. H.; Saiers, J.; Baud, F. Which cyanide poisoning? Crit. Rev. Toxicol. 2009, 39, 541-552
8. Marques, H. M.; Brown, K. L.; Jacobsen, D. W. Kinetics and activation parameters of the reaction of cyanide with free aquocobalamin and aquocobalamin bound to a haptocorrin from chicken serum J. Biol. Chem. 1988, 263, 12378-12383 (Pubitemid 19000416)
9. Péry-Man, N.; Houeto, P.; Coirault, C.; Suard, I.; Perennec, J.; Riou, B.; Lecarpentier, Y. Hydroxocobalamin vs cobalt toxicity on rat cardiac and diaphragmatic muscles Intensive Care Med. 1996, 22, 108-115 (Pubitemid 26074905)
10. Kano, K.; Kitagishi, H.; Kodera, M.; Hirota, S. Dioxygen binding to a simple myoglobin model in aqueous solution Angew. Chem., Int. Ed. 2005, 44, 435-438 (Pubitemid 40138351)
11. Kano, K.; Kitagishi, H.; Dagallier, C.; Kodera, M.; Matsuo, T.; Hayashi, T.; Hisaeda, Y.; Hirota, S. Iron porphyrin-cyclodextrin supramolecular complex as a functional model of myoglobin in aqueous solution Inorg. Chem. 2006, 45, 4448-4460
12. Kano, K.; Kitagishi, H.; Mabuchi, T.; Kodera, M.; Hirota, S. A myoglobin functional model composed of a ferrous porphyrin and a cyclodextrin dimer with an imidazole linker Chem. Asian J. 2006, 1, 358-366 (Pubitemid 44475589)
13. 2, CO, NO) in aqueous solution J. Am. Chem. Soc. 2008, 130, 8006-8015 (Pubitemid 351875076)
14. Kitagishi, H.; Negi, S.; Kiriyama, A.; Honbo, A.; Sugiura, Y.; Kawaguchi, A. T.; Kano, K. A diatomic molecule receptor that removes CO in a living organism Angew. Chem., Int. Ed. 2010, 49, 1312-1315
15. Wang, J.-T.; Yeh, H. J. C.; Johnson, D. F. Proton nuclear magnetic resonance study of equilibriums and paramagnetisms of ferriprotoporphyrin IX-ligand complexations J. Am. Chem. Soc. 1978, 100, 2400-2405
16. Scheidt, W. R.; Haller, K. J.; Hatano, K. Preparation and characterization of the anionic complex potassium dicyano(mesotetraphenylporphinato)iron(III) bis(acetone) J. Am. Chem. Soc. 1980, 102, 3017-3021
17. Inniss, D.; Soltis, S. M.; Strouse, C. E. The electronic structure of highly anistropic low-spin ferric porphyrin complexes based on single-crystal EPR measurements J. Am. Chem. Soc. 1988, 110, 5644-5650
18. -, caused by the nonplanarity of the porphyrin ring J. Am. Chem. Soc. 1997, 119, 6284-6291 (Pubitemid 27364242)
19. Li, J.; Noll, B. C.; Schulz, C. E.; Scheidt, W. R. New insights on the electronic and molecular structure of cyanide-ligated iron(III) porphyrinates Inorg. Chem. 2007, 46, 2286-2298
20. Patra, R.; Rath, S. P. Cyanide binding to iron in a highly distorted porphyrin macrocycle: synthesis and structure of low-spin Fe(II) dicyano porphyrin Inorg. Chem. Commun. 2009, 12, 515-519
21. Oszajca, M.; Franke, A.; Brindell, M.; Stochel, G.; van Eldik, R. Mechanistic studies on the reactions of cyanide with a water-soluble Fe(III) porphyrin and their effect on the binding of NO Inorg. Chem. 2011, 50, 3413-3424
22. Kano, K.; Kitagishi, H.; Tamura, S.; Yamada, A. Anion binding to a ferric porphyrin complexed with per- O -methylated β-cyclodextrin in aqueous solution J. Am. Chem. Soc. 2004, 126, 15202-15210 (Pubitemid 39557278)
23. 2 J. Phys. Chem. 1979, 83, 3307
24. Reenstra, W. W.; Jencks, W. P. Reaction of cyanide with cobalamins J. Am. Chem. Soc. 1979, 101, 5780-5791
25. Brunori, M.; Amiconi, G.; Antonini, E.; Wyman, J.; Zito, R.; Fanelli, A. R. The transition between acid and alkaline ferric heme proteins Biochim. Biophys. Acta 1968, 154, 315-322
26. George, P.; Hanania, G. Ionization of acidic memyoglobin Biochem. J. 1952, 52, 517-523