Reaction of 3′,5′-di-O-acetyl-2′-deoxyguansoine with hypobromous acid

Suzuki, Toshinori; Nakamura, Asuka; Inukai, Michiyo

doi:10.1016/j.bmc.2013.04.060

Cited by 8 publications

(12 citation statements)

References 29 publications

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“…The dXpT isomer of d(DGh)pT, that formed during the lyophilization of HPLC elution buffer, was not identified in the present work but may be tentatively attributed to oxidized iminoallantoin derivative (Iaox). 37,38 A minor amount of parabanic acid lesion, d(Pa)pT eluted at 34 min was noted.…”

Section: Resultsmentioning

confidence: 99%

Formation of the carboxamidine precursor of cyanuric acid from guanine oxidative lesion dehydro-guanidinohydantoin

Irvoas

Trzcionka

Pratviel

2014

Bioorganic & Medicinal Chemistry

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Section: Resultsmentioning

confidence: 99%

Formation of the carboxamidine precursor of cyanuric acid from guanine oxidative lesion dehydro-guanidinohydantoin

Irvoas

Trzcionka

Pratviel

2014

Bioorganic & Medicinal Chemistry

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“…102 The oxidation process of cytosine was demonstrated toward the formation of 5-hydroxyhydantoin nucleosides (Scheme 16). 103−105 Oxidative sources leading to hydantoins, other than singlet oxygen, were also reported, including chromium(V) complexes, 106 azo-compound derived radicals, 107 hydrobromous acid, 108 or Fenton-like systems with Cu(II) 109 or Fe(II). 110 The most usual way to substitute the N-3 position of hydantoins is alkylation with halides in the presence of a base (usually potassium carbonate).…”

Section: Miscellaneousmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

et al. 2017

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The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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“…In in vitro studies, 8-bromo-2′-deoxyguanosine (8-BrdGuo) and 5-bromo-2′-deoxycytidine (5-Br-Cyd) were generated from dGuo and dCyd by reactions with reagent HOBr, an EPO/H 2 O 2 /Br − system, and other oxidant/Br − systems. [10][11][12][13] Recently, 8-Br-dGuo was detected in urine from healthy volunteers. 14) In diabetic patients, the urinary 8-Br-dGuo level was found to be 8-fold higher than that in healthy volunteers.…”

Section: ) Epo Uses the Plasma Concentration Of Brmentioning

confidence: 99%

Formation of 8-<i>S</i>-L-Cysteinyladenosine from 8-Bromoadenosine and Cysteine

Suzuki

Ogishi

Shinohara

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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When 8-bromoadenosine was incubated with cysteine at pH 7.2 and 37°C, an exclusive product was generated. This product was identified as a cysteine substitution derivative of adenosine at the 8 position, 8-S-Lcysteinyladenosine. The reaction accelerated as pH increased from mildly acidic to basic conditions. The isolated cysteine adduct of adenosine decreased with a half-life of 15 h at pH 7.2 and 37°C. Similar results were obtained for the incubation of 8-bromo-2′-deoxyadenosine and 8-bromoadenosine 3′,5′-cyclic monophosphate with cysteine. These results suggest that 8-bromoadenine in nucleotides, RNA, and DNA can react with thiols, resulting in adducts under physiological conditions. Key words 8-bromoadenosine; cysteine; cysteinyladenosine; 8-bromo-2′-deoxyadenosine; 8-bromo-cAMP HOBr can react with nucleic acid bases. HOBr reacted with thymidine, resulting in thymidine glycol and its phosphate derivative in phosphate buffer. 9) 2′-Deoxyguanosine (dGuo) and 2′-deoxycytidine (dCyd) are major targets in the reaction of HOBr. In in vitro studies, 8-bromo-2′-deoxyguanosine (8-BrdGuo) and 5-bromo-2′-deoxycytidine (5-Br-Cyd) were generated from dGuo and dCyd by reactions with reagent HOBr, an EPO/H 2 O 2 /Br − system, and other oxidant/Br − systems. 10-13)Recently, 8-Br-dGuo was detected in urine from healthy volunteers. 14) In diabetic patients, the urinary 8-Br-dGuo level was found to be 8-fold higher than that in healthy volunteers. This implies that nucleoside bromination occurs naturally in healthy humans and that inflammatory diseases greatly increase its level. For adenine (Ade) in nucleoside, the reactivity with HOBr is low. However, it has been reported that 8-bromoadenine (8-Br-Ade) is the major purine oxidation product generated in double-stranded DNA by either reagent HOBr or an EPO/H 2 O 2 /Br − system. 15)In our previous paper, we reported that the incubation of 8-bromoguanosine (8-Br-Guo) with L-cysteine (Cys) under physiological conditions (pH 7.4 and 37°C) generated 8-S-Lcysteinylguanosine (Cys-Guo) and guanosine (Guo). 16) In the present study, we investigated the reaction of 8-bromoadenosine (8-Br-Ado), 8-bromo-2′-deoxyadenosine (8-BrdAdo), and 8-bromoadenosine 3′,5′-cyclic monophosphate (8-Br-cAMP) with Cys, and report here the identification of the product and its comparison with the reaction of 8-Br-Guo with Cys. ResultsA solution of 100 µM 8-Br-Ado and 50 mM Cys was incubated in 100 mM potassium phosphate buffer at pH 7.2 and at a temperature of 37°C for 4 h. When the reaction mixture was analyzed by reversed phase (RP) HPLC, an unknown product peak showing a UV spectrum with λ max =279 nm was eluted at the retention time of 4.4 min in the chromatogram with a small peak of adenosine (Ado) (Fig. 1). Ado was confirmed by coincidence of the RP-HPLC retention time and UV and MS spectra of an authentic Ado. The unknown product was collected and subjected to spectrometric measurements. The product showed an electrospray ionization time of flight (ESI-TOF) MS spectrum with m/z=298 and 385 in the nega...

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Reaction of 3′,5′-di-O-acetyl-2′-deoxyguansoine with hypobromous acid

Cited by 8 publications

References 29 publications

Formation of the carboxamidine precursor of cyanuric acid from guanine oxidative lesion dehydro-guanidinohydantoin

Formation of the carboxamidine precursor of cyanuric acid from guanine oxidative lesion dehydro-guanidinohydantoin

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

Formation of 8-<i>S</i>-L-Cysteinyladenosine from 8-Bromoadenosine and Cysteine

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