Purine N-Oxides and Cancer

Brown, George Bosworth

doi:10.1016/s0079-6603(08)60547-4

Cited by 45 publications

(8 citation statements)

References 206 publications

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“…indicator glass electrode  system studied  modified calomel electrode BHClO 4 at the same concentration as that of the titrand (to keep the formal ionic strength constant for all titration points). The electromotive force (e.m.f.)…”

Section: Methodsmentioning

confidence: 99%

“…However, the mechanism of these activities has been neither recognized nor explained. According to recent reports, the N-oxides of heterocyclic amines play an important role in reactions of the modification of enzymes and biological reductive systems, as well as factors substituting some functions of nucleic acids [3,4]. Referring to the 2-halo-4-nitropicoline N-oxides studied here, an important feature is [5] that the presence of the nitro group has been crucial for developing antifungal efficacy of these compounds.…”

Section: Introductionmentioning

confidence: 95%

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A Study of Acid-Base Equilibria in Acetonitrile Systems of 2-Halo(Cl,Br,I)-4-nitropicoline(3,5,6) N-oxides

et al. 1999

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An attempt has been made to determine potentiometrically (1) acid dissociation constants of cations obtained by protonation of nine trisubstituted pyridine N-oxides, namely 2-halo(Cl, Br and I)-4-nitropicoline N-oxides with the methyl group at positions 3, 5, and 6, as well as (2) the cationic homoconjugation constants of these cationic acids with conjugated N-oxides in acetonitrile. On the basis of the substitution effect, variations of the acid dissociation constants of the trisubstituted pyridine N-oxide cations are discussed. The determined pK a values of the protonated 2-halo-4-nitropicoline N-oxides are compared with the previously determined equilibrium constants of the cationic acids conjugated with the mono-and disubstituted pyridine N-oxides in acetonitrile. Further, based on the pK a values of the protonated 2-halo-4-nitropicoline N-oxides in acetonitrile, supplemented with correlations between pK a 's of the protonated mono-and disubstituted pyridine N-oxides in acetonitrile and water, the pK a 's of the acids conjugated with the trisubstituted N-oxides studied in aqueous solutions have been estimated. Moreover, it has been concluded that the cationic homoconjugation constants cannot be determined by potentiometric titration in acetonitrile solutions of the 2-halo-4-nitropicoline N-oxide systems.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 95%

A Study of Acid-Base Equilibria in Acetonitrile Systems of 2-Halo(Cl,Br,I)-4-nitropicoline(3,5,6) N-oxides

et al. 1999

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“…Nitroquinoline N-oxide (22) is a potent carcinogen, in which the N O function appears to be essential to carcinogenic activity; conversion to the proximate carcinogen requires reduction of the nitro group to yield 4-hydroxylaminoquinoline Noxide 83 . Similarly, some purine N-oxides have been demonstrated to induce malignant tumors 84 .…”

Section: B Occurrence In Synthetic Compoundsmentioning

confidence: 99%

“…Analogous light-induced transformation to a toxic oxaziridine has also been reported for the di-N-oxide olaquindox (49), which elicits severe photoallergic reactions in animals and man 164,201 . Finally, oxaziridines can arise from the photolysis of purine N-oxides 84 …”

Section: Photochemical Reactionsmentioning

confidence: 99%

N‐Oxidative Transformations ofCNGroups as Means of Toxification and Detoxification

Hlavica

Lehnerer

2009

Patai's Chemistry of Functional Groups

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Introduction Chemical Aspects of the N ‐Oxygenation of the C  N Functionality Occurrence of N ‐Oxygenated C  N Functionalities in Natural and Synthetic Compounds and Biological Activity Metabolic in Vivo and in Vitro Formation of N ‐Oxygenated C  N Functionalities Enzymology of the Formation of N ‐Oxygenated C  N Functionalities Further Transformations of N ‐Oxygenated C  N Functionalities Conclusions

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“…The oxidative transformation of purines into their N-oxide derivatives which are potent oncogenic agents introduces the possibility that such derivatives play an important role in various biological and clinical processes. [1][2][3] The presence of the N-oxide group in purines has been found to induce antibiotic activity. 4 Several purine N-oxides have been reviewed in relation to their oncogenic 5 and antitumor properties.…”

Section: Introductionmentioning

confidence: 99%

Oxidation chemistry of adenine N1-oxide, a potent oncogenic agent, at a pyrolytic graphite electrode

Goyal

Sangal

2002

J. Chem. Soc., Perkin Trans. 2

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Purine N-Oxides and Cancer

Cited by 45 publications

References 206 publications

A Study of Acid-Base Equilibria in Acetonitrile Systems of 2-Halo(Cl,Br,I)-4-nitropicoline(3,5,6) N-oxides

A Study of Acid-Base Equilibria in Acetonitrile Systems of 2-Halo(Cl,Br,I)-4-nitropicoline(3,5,6) N-oxides

N‐Oxidative Transformations ofCNGroups as Means of Toxification and Detoxification

Oxidation chemistry of adenine N1-oxide, a potent oncogenic agent, at a pyrolytic graphite electrode

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