A diatomic molecule receptor that removes CO in a living organism

Angewandte Chemie - International Edition

Volumn 49, Issue 7, 2010, Pages 1312-1315

  Kitagishi, Hiroaki ^a   Negi, Shigeru ^b   Kiriyama, Akiko ^b   Honbo, Akino ^b   Sugiura, Yukio ^b   Kawaguchi, Akira T ^c   Kano, Koji ^a  

^a DOSHISHA UNIVERSITY   (Japan)

^b DOSHISHA WOMEN'S COLLEGE OF LIBERAL ARTS   (Japan)

^c TOKAI UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

Carbon monoxide; Cyclodextrins; In vivo experiments; Porphyrinoids; Supramolecular chemistry

Indexed keywords

CHEMICAL EQUATIONS; CORECEPTORS; DIATOMIC MOLECULES; IN-VIVO EXPERIMENTS; LIGAND EXCHANGES; LIVING ORGANISMS; PORPHYRINOIDS; SUPRAMOLECULAR COMPLEXES;

BIOLOGY; CARBON MONOXIDE; CHEMICAL REACTIONS; CYCLODEXTRINS; IRON COMPOUNDS; MACROMOLECULES; PORPHYRINS; SILANES;

SUPRAMOLECULAR CHEMISTRY;

5,10,15,20 TETRAKIS(4 SULFONATOPHENYL)PORPHYRINATO IRON(III) CHLORIDE; 5,10,15,20-TETRAKIS(4-SULFONATOPHENYL)PORPHYRINATO IRON(III) CHLORIDE; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CARBON MONOXIDE; METALLOPORPHYRIN; OXYGEN; PYRIDINE; PYRIDINE DERIVATIVE;

ANIMAL; ARTICLE; CHEMISTRY; METABOLISM; RAT; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; BETA-CYCLODEXTRINS; CARBON MONOXIDE; METALLOPORPHYRINS; OXYGEN; PYRIDINES; RATS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 76349121554     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906149     Document Type: Article

References (26)

1. Y. Murakami, J. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721-758.
2. M. L. Bender, B. W. Turnquest, J. Am. Chem. Soc. 1957, 79, 1656-1662.
3. G. R. Schonbaum, M. L. Bender, J. Am. Chem. Soc. 1960, 82, 1900-1904.
4. J. H. Fendler, E. J. Fendler, Catalysis in Micellar and Macromolecular Systems, Academic Press, London, 1975.
5. R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997-2012.
6. T. Kunitake, Y. Okahata, J. Am. Chem. Soc. 1977, 99, 3860-3861.
7. C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036.
8. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, Wiley-VCH, Weinheim, 1995.
9. J. P. Coliman, R. Boulatov, C. J. Sunderland, L. Fu, Chem. Rev. 2004, 104, 561-588.
10. M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Jr., Chem. Rev. 2004, 104, 939-986.
11. J. P. Coliman, R. R. Gagne, T. R. Halbert, J. C. Marchon, C. A. Reed, J. Am. Chem. Soc. 1973, 95, 7868-7870.
12. K. Kano, H. Kitagishi, M. Kodera, S. Hirota, Angew. Chem. 2005, 117, 439-442;
13. Angew. Chem. Int. Ed. 2005, 44, 435-438.
14. 2 and CO.
15. K. Kano, H. Kitagishi, C. Dagallier, M. Kodera, T. Matsuo, T. Hayashi, Y. Hisaeda, S. Hirota, Inorg. Chem. 2006, 45, 4448-4460.
16. S. W. Ryter, J. Alam, A. M. K. Choi, Physiol. Rev. 2006, 86, 583-650.
17. L. Wu, R. Wang, Pharmacol. Rev. 2005, 57, 585-630.
18. Since the spectral patterns (UV/Vis and rR) of the urine are in agreement with those of CO-hemoCD, the supramolecular structure of hemoCD should be maintained after circulation in the body. In addition, the unchanged Py3CD scaffold was detected in the urine by means of MALDI-TOF mass spectrometry (Figure S1 in the Supporting Information).
19. IIITPPS as the control.
20. In the case of the infusion of met-hemoCD, the excreted urine solution also contained CO-hemoCD (Figure S2 in the Supporting Information), thus indicating that the reduction of methemoCD to hemoCD occurred in the rat body.
21. T. T. Tominaga, V. E. Yushmanov, I. E. Borissevitch, H. Imasato, M. Tabak, J. Inorg. Biochem. 1997, 65, 235-244.
22. co is given in the Supporting Information.
23. -1 of CO production (see Reference [15] and R. F. Coburn, W. S. Blakemore, R. E. Forster, J. Clin. Invest. 1963, 42, 1172-1178) based on the assumptions of a human body weight of 60 kg and body temperature of 37 °C.
24. Nitric oxide (NO), which is a potent ligand to the ferrous porphyrin, does not bind to hemoCD, though NO slightly decomposes hemoCD, see: K. Kano, Y. Itoh, H. Kitagishi, T. Hayashi, S. Hirota, J. Am. Chem. Soc. 2008, 130, 8006-8015.
25. The biochemical tests of rat plasma were performed by an IDEXX VetTest chemistry analyzer before and after the infusion of oxy-hemoCD (Table S2 in the Supporting Information). The rat heart rate and the blood pressure were preliminarily monitored during the infusion.
26. In the case of the infusion of oxy-hemoCD into the CO-exposed rat, the amount of excreted CO in the urine was greatly enhanced (Figure S6 in the Supporting Information), thus suggesting that hemoCD is also able to remove exogenously inhaled CO from the rat body.