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Volumn 122, Issue 29, 2000, Pages 6911-6916

Nitration and nitrosation by peroxynitrite: Role of CO2 and evidence for common intermediates

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; MORPHOLINE; MORPHOLINE DERIVATIVE; NITRO DERIVATIVE; NITROSO DERIVATIVE; PEROXYNITRITE;

EID: 0034718053     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000270h     Document Type: Article
Times cited : (48)

References (84)
  • 1
    • 0343537170 scopus 로고    scopus 로고
    • note
    • - and ONOOH.
  • 7
    • 0001797233 scopus 로고    scopus 로고
    • Lancaster, J., Jr., Ed.; Academic Press: San Diego
    • Beckman, J. S. In Nitric Oxide. Principles and Actions; Lancaster, J., Jr., Ed.; Academic Press: San Diego, 1996; pp 1-82.
    • (1996) Nitric Oxide. Principles and Actions , pp. 1-82
    • Beckman, J.S.1
  • 25
    • 11944262823 scopus 로고
    • Carbonate is present in concentrations up to 25 mM in all physiological fluids, and about 7% of carbonate exists as free COj at pH 7.2. Peroxynitrite anion reacts with COz to form ONOOCOa" (fa = 6 x 104 M"1 s~' at 37 °C). In the absence of peroxidases, virtually all of the peroxynitrite generated in biological environments will react with CU2 before it can react with any other molecules. Therefore, it has become imperative to study the reactions of peroxynitrite with biomolecules in the presence of purposefully added carbonate; it also is wise to do experiments that do not have added carbonate but contain only adventitious carbonate. See: (a) Lymar, S. V.; Hurst, J. K. J. Am. Chem. Soc. 1995, 117, 8867.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8867
    • Lymar, S.V.1    Hurst, J.K.2
  • 41
    • 0342666939 scopus 로고    scopus 로고
    • note
    • We have examined the yields of nitrosation of MorH at various low and high initial concentrations of peroxynitrite (0-2 mM) at pH 10.2. Nitrosation of MorH occurs at all concentrations of peroxynitrite, much in the same way as described for pheno!5c and 1, 2-phenylenediamine.15 In these systems, the dependence of nitrosation on peroxynitrite concentration is somewhat curvilinear (for example, see Figure 3A in ref 5c), particularly in reactions performed without added carbonate but supposedly containing some adventitious carbonate."b-'3a
  • 44
    • 33847561864 scopus 로고    scopus 로고
    • For the sake of simplicity, we show HO" in Scheme 1. However, the mechanism does not necessarily depend on HO'; it only requires an activated species from ONOOH.
    • For the sake of simplicity, we show HO" in Scheme 1. However, the mechanism does not necessarily depend on HO'; it only requires an activated species from ONOOH.
  • 64
    • 0343973033 scopus 로고    scopus 로고
    • note
    • A reviewer asked if ONOOCO2~ could react with ONOO", forming NO and other products as shown in eq i ONOOCO2" + ONOCT -CO32~ + NO2~ + O2 + 'NO (i) The adduct ONOOCOr has a very short half-life11-0-14 and a similar adduct, RCH(O")OONO, formed in reactions of ONOO" with aldehydes, does not have significant oxidative capability.296 Therefore, we believe that ONOOCOr does not oxidize ONOO~. Even if ONOOCO2~ would react with peroxynitrite directly, the reaction is indistinguishable from those of HO" and CO3'- with ONOQ- (eq 3).
  • 66
    • 0343101241 scopus 로고    scopus 로고
    • note
    • The dissociation constant for ONOO~ giving 'NO plus O2" is 0.017 s~', 23a whereas the rate constants for reactions of HO' and COj~ with ONOO- are (4-5) x I0923b'c and 8 x 107 M~' s-', 23c respectively. Therefore, the relative yields of'NO from reactions 3 and 4 depend on pH, carbonate and buffer concentrations, and impurities present in the system.
  • 70
    • 0343973031 scopus 로고    scopus 로고
    • note
    • 3 may be formed (eq 6) in reactions of peroxynitrite in the absence of purposefully added carbonate.
  • 73
    • 0343973032 scopus 로고    scopus 로고
    • note
    • 2/MorH system. This is consistent with our hypothesis that peroxynitrite-mediated oxidations are predominantly free radical processes.
  • 76
    • 33847554339 scopus 로고    scopus 로고
    • 2 that we could not observe in our RP-HPLC analysis of the products
    • 2 that we could not observe in our RP-HPLC analysis of the products.
  • 78
    • 0032588709 scopus 로고    scopus 로고
    • -) causes nitrosation in vivo. 'NO autoxidation generates nitrosating intermediates (like NjOj), and these can react directly with ONOO" (Goldstein, G.; Czapski, G.; Lind, J.; Merényi, G. Chem. Res. Toxicol 1999, 12, 132). Thus, by adding 'NO, one would introduce a peroxynitrite-independent pathway for nitrosation as well as potentially interfering cross reactions. The system the reviewer proposes is even more complex than our system, and finding increased nitrosation, as one would expect, could not be easily interpreted.
    • (1999) Chem. Res. Toxicol , vol.12 , pp. 132
    • Goldstein, G.1    Czapski, G.2    Lind, J.3    Merényi, G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.