Selective scavenging property of the indole moiety for the nitrating species of peroxynitrite

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 1, 2004, Pages 146-149

  Nakagawa, Hidehiko ^a   Takusagawa, Mitsuko ^a   Arima, Hiromi ^a   Furukawa, Kumiko ^a   Kinoshita, Takeshi ^b   Ozawa, Toshihiko ^b   Ikota, Nobuo ^a  

^a NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

^b TEIKYO UNIVERSITY   (Japan)

Author keywords

Dityrosine; Nitrotyrosine; Peroxynitrite; Scavenger; Selenium; Tryptamine

Indexed keywords

2 AMINO 3,4 DIHYDROXY 5 PHENYLSELENOPENTAN 1 OL; 3 NITROTYROSINE; 5 METHOXYTRYPTAMINE; ANTIOXIDANT; CATECHIN; CURCUMIN; GLUTATHIONE; INDOLE DERIVATIVE; MELATONIN; PEROXYNITRITE; REACTIVE NITROGEN SPECIES; SCAVENGER; SELENIUM DERIVATIVE; TROLOX C; TRYPTAMINE; TRYPTOLINE; TRYPTOPHAN; UNCLASSIFIED DRUG; URIC ACID; 13ALPHA ACETOXY 5ALPHA (3' DIMETHYLAMINO 3' PHENYL) PROPIONYLOXY 11(15 1) ABEOTAXA 4(20),11 DIENE 9ALPHA,10BETA DIOL; 13ALPHA-ACETOXY-5ALPHA-(3'-DIMETHYLAMINO-3'-PHENYL)-PROPIONYLOXY-11(15-1)-ABEOTAXA-4(20),11-DIENE-9ALPHA,10BETA-DIOL; DITERPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FREE RADICAL; PEROXYNITROUS ACID; TYROSINE;

ANTIOXIDANT ACTIVITY; ARTICLE; COMPARATIVE STUDY; FLUORESCENCE SPECTROSCOPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; INHIBITION KINETICS; NITRATION; OXIDATION KINETICS; OXIDATIVE STRESS; PHYSICAL CHEMISTRY; CHEMISTRY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; SPECTROFLUOROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DITERPENES; FREE RADICAL SCAVENGERS; FREE RADICALS; INDICATORS AND REAGENTS; INDOLES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PEROXYNITROUS ACID; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TYROSINE;

EID: 3543119459     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.146     Document Type: Article

References (36)

1. Beckman J. S., Beckman T. W., Chen J., Marshall P. A., Freeman B. A., Proc. Natl. Acad. Sci. U.S.A., 87, 1620-1624 (1990).
2. Huie R. E., Padmaja S., Free Radic. Res. Commun., 18, 195-199 (1993).
3. Whiteman M., Tritschler H., Halliwell B., FEBS Lett., 379, 74-76 (1996b).
4. Sampson J. B., Ye Y., Rosen H., Beckman J. S., Arch. Biochem. Biophys., 15, 207-213, (1998).
5. Darley-Usmar V., Wiseman H., Halliwell B., FEBS Lett., 369, 131-135 (1995).
6. Darley-Usmar V. M., Hogg N. O., Leary V. J., Wilson M. T., Moncada S., Free Radic. Res. Commun., 17, 9-20 (1992).
7. White C. R., Brock T. A., Chang L. Y., Crapo J., Briscoe P., Ku D., Bradley W. A., Gianturco S. H., Gore J., Freeman B. A., Tarpey M. M., Proc. Natl. Acad. Sci. U.S.A., 91, 1044-1048 (1994).
8. Salgo M. G., Bermudez E., Squadrito G. L., Pryor W. A., Arch. Biochem. Biophys., 322, 500-505 (1995).
9. Squadrito G. L., Jin X., Pryor W. A., Arch. Biochem. Biophys., 322, 53-59 (1995).
10. Radi R., Beckman J. S., Bush K. M., Freeman B. A., Arch. Biochem. Biophys., 288, 481-487 (1991).
11. Radi R., Beckman J. S., Bush K. M., Freeman B. A., J. Biol. Chem., 266, 4244-4250 (1991).
12. King P. A., Anderson V. E., Edwards J. O., Gustafson G., Plumb R. C., Suggs J. W., J. Am. Chem. Soc., 114, 5430-5432 (1992).
13. Pryor W. A., Jin X., Squadrito G. L., Proc. Natl. Acad. Sci. U.S.A., 91, 11173-1117 (1994).
14. Van der Vliet A. O., Neill C. A., Halliwell B., Cross C. E., Kaur H., FEBS Lett., 339, 89-92 (1994).
15. Kong S. K., Yim M. B., Stadtman E. R., Chock P. B., Proc. Natl. Acad. Sci. U.S.A., 93, 3377-3382 (1996).
16. Gow A. J., Duran D., Malcolm S., Ischiropoulos H., FEBS Lett., 385, 63-66 (1996).
17. Li X., DeSarno P., Song L., Beckman J. S., Jope R. S., Biochem. J., 331, 599-606 (1998).
18. Whiteman M., Halliwell B., Free Radic. Res., 25, 275-283 (1996a).
19. Nakagawa H., Sumiki E., Ikota N., Matsushima Y., Ozawa T., Antioxi. Redox Signaling, 1, 239-244 (1999).
20. Ikota N., Ueda J.-I., Gamage R., Shimazu Y., Hama-Inaba H., Takusakawa M., Ozawa T., Satoh T., "Biodefence Mechanisms against Environmental Stress," eds. by Ozawa T., Tatsumi K., Hori T., Kodansha, Tokyo, 1998, pp. 1-12.
21. Yoshioka T., Fujita T., Kanai K., Aigawa Y., Kurumada T., Hasegawa K., Horikoshi H., J. Med. Chem., 32, 421-428 (1989).
22. Ikota N., Heterocycles, 36, 2035-2050 (1993).
23. Pryor W. A., Cueto R., Jin X., Koppenol W. H., Ngu-Schwemlein M., Squadrito G. L., Uppu P. L., Uppu R. M., Free Radic. Biol. Med., 18, 75-83 (1995).
24. Radi R., Chem. Res. Toxicol., 11, 720-721 (1998).
25. Nakagawa H., Ohshima Y., Takusagawa M., Ikota N., Takahashi Y., Shimizu S., Ozawa T., Chem. Pharm. Bull., 49, 1547-1554 (2001).
26. N-Dithiocarboxy-L-proline (DTCP) was prepared as previously described: Nakagawa H., Ikota N., Ozawa T., Masumizu T., Kohno M., Biochem. Mol. Biol. Int., 45, 1129-1138 (1998).
27. (2S,3R,4S)-2-Amino-3,4-dihydroxy-5-phenylselenopentan-1-ol (ADPP), (2S,3R,4S)-N-ethylmercapto-3,4-dihydroxy-2-hydroxymethylpyrrolidine (NEMP), and (2S,4RS)-2-amino-4-phenylseleno-5-carboxybutan-1ol (APCB) were prepared as previously described: Nakagawa H., Sumiki E., Takusagawa M., Ikota N., Matsushima Y., Ozawa T., Chem. Pharm. Bull., 48, 261-265 (2000).
28. 1-(3′,4′-Dihydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline (3′4′DHBn-TIQ) and 1-benzyl-6,7-dihydroxy-1,2,3,4- tetrahydroisoquinoline (67DHBnTIQ) are generous gifts from Professor Shigeru Ohta and Dr. Yaichiro Kotake: Kawai H., Makino Y., Hirobe M., Ohta S., J. Neurochem., 70, 745-751 (1998).
29. 3′-Hydroxy-4′-O-methylglabridin (RK02B): Kinoshita T., Kajiyama K., Hiraga Y., Takahashi K., Tamura Y., Mizutani K., Heterocycles, 43, 581-588 (1996).
30. Glabrocoumarone A (RK18R): Kinoshita T., Kajiyama K., Hiraga Y., Takahashi K., Tamura Y., Mizutani K., Chem. Pharm. Bull., 44, 1218-1221 (1996).
31. Glabrol (RK16O): Saitoh T., Kinoshita T., Shibata S., Chem. Pharm. Bull., 24, 752-755 (1976).
32. 2′,4′,3,4-Tetrahydroxychalcone (THCL): Sogawa S., Nihiro Y., Ueda H., Miki T., Matsumoto H., Satoh T., Biol. Pharm. Bull., 17, 251-256 (1994).
33. 4-Hexyloxy-2,3,6-trimethylphenol (HTP) was prepared as previously described: Nihiro Y., Furukawa H., Sogawa S., Wang T.- C., Miyataka H., Matsumoto H., Miki T., Satoh T., Chem. Pharm. Bull., 42, 576-579 (1994).
34. 2′,4′-Dimethoxy-3,4-dihydroxy-6-fluorochalcone (DDFC) was a generous gift from the late Professor Toshio Satoh: Nakamura C., Kawasaki N., Miyataka H., Jayachandran E., Kim I.-H., Kirk K. L., Taguchi T., Takeuchi Y., Hori H., Satoh T., Bioorg. Med. Chem., 10, 699-706 (2002).
35. 2-(α-D-Glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol (TMG) was obtained from CCI Corporation, Gifu, Japan by Professor Tsutomu V. Kagiya: Murase H., Yamauchi R., Kato K., Kunieda T., Terao J., Lipids, 32, 73-78 (1997).
36. 2-Piperadino-6-methyl-5-oxo-5,6-dihydro(7H)-pyrrolo[3,4-d]pyrimidine maleate (MS-818) was a generous gift from Dr. Akira Awaya: Awaya A., Kobayashi H., Horikomi K., Tanaka S., Kabir A. M., Yokoyama K., Ohno H., Kato K., Kitahara T., Tomino I., Isayama S., Nakamura S., Biol. Pharm. Bull., 16, 248-253 (1993).