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A theoretical study on the structure-activity relationships of metabolites of folates as antioxidants and its implications for rational design of antioxidants.

Abstract：

:To elucidate the structure-activity relationships of metabolites of folates as antioxidants, the O-H bond dissociation enthalpies (BDEs) and ionization potentials (IPs) for these compounds were calculated by density functional theory (DFT) on B3LYP/6-31+G(,3pd) level. Accordingly, the antioxidant activity difference for metabolites of folates can be elucidated by O-H BDE and IP values and can be further explained in terms of electronic effect and intramolecular hydrogen bond effect of substituents. Furthermore, the potential of the active center of metabolites of folates, 4-hydroxypyrimidine (4-HP), as lead antioxidant, was evaluated by comparing the BDEs and IPs of 4-HP with those of 5-hydroxypyrimidine (5-HP). It was revealed that 4-HP and 5-HP held identical IPs, but the O-H BDE of the former was 22.84 kcal/mol higher than that of the latter, which meant 4-HP was inert in H-atom donation. Nevertheless, the O-H BDE of 4-HP was very sensitive to the substituents, which made NH2-derivatives of 4-HP very active as antioxidants. Therefore, 4-HP is also a potential lead antioxidant and deserves attention in rational design of antioxidants.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Ji HF,Tang GY,Zhang HY

doi

10.1016/j.bmc.2004.11.047

subject

Has Abstract

pub_date

2005-02-15 00:00:00

pages

1031-6

issue

4

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(04)00938-1

journal_volume

13

pub_type

杂志文章

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