深入了解 1,8-二羟基萘异黑素纳米颗粒的抗氧化活性,Antioxidants

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深入了解 1,8-二羟基萘异黑素纳米颗粒的抗氧化活性
Antioxidants ( IF 6.0 ) Pub Date : 2023-07-28 , DOI: 10.3390/antiox12081511
Alexandra Mavridi-Printezi ₁ , Fabio Mollica ₁ , Rosa Lucernati ₁ , Marco Montalti ₁ , Riccardo Amorati ₁

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黑色素是稳定且无毒的色素，在医疗和化妆品应用中作为抗氧化应激的化学预防剂具有巨大的潜力。别黑素是一类常见于真菌中的无氮黑色素。最近表明，通过 1,8-二羟基萘 (DHN) 聚合获得的人工异黑素，聚 DHN (PDHN)，是比聚多巴胺 (PDA) 更好的自由基猝灭剂，聚多巴胺 (PDA) 是通过多巴胺 (DA) 聚合获得的黑色素模型。）；然而，这种差异背后的化学机制尚不清楚。在这里，我们通过实验和理论方法研究了 PDHN 纳米粒子 (PDHN-NP) 与 PDA-NP 相比捕获参与过氧化传播的烷基过氧化基 (ROO•) 和氢过氧化基 (HOO•) 自由基的能力在真实条件下。我们的结果表明，相对于 PDA-NP，PDHN-NP 对 pH 7.4 水中的 ROO• 以及乙腈中的混合 ROO• 和 HOO• 表现出更高的抗氧化效率，显示出催化交叉终止活性。PDHN-NP 在水中的抗氧化能力为 0.8 mmol/g（ROO• 自由基被 1 g PDHN-NP 猝灭），每个反应部分的速率常数为 3 × 105 M−1 s−1。量子力学计算表明，由于氢键网络的形成，PDHN-NP 中的醌对氢原子具有高亲和力，从而证明了实验观察到的PDHN-NP 与HOO• 的高反应性。

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Insight into the Antioxidant Activity of 1,8-Dihydroxynaphthalene Allomelanin Nanoparticles

Melanins are stable and non-toxic pigments with great potential as chemopreventive agents against oxidative stress for medical and cosmetic applications. Allomelanin is a class of nitrogen-free melanin often found in fungi. The artificial allomelanin obtained by the polymerization of 1,8-dihydroxynaphthalene (DHN), poly-DHN (PDHN), has been recently indicated as a better radical quencher than polydopamine (PDA), a melanin model obtained by the polymerization of dopamine (DA); however, the chemical mechanisms underlying this difference are unclear. Here we investigate, by experimental and theoretical methods, the ability of PDHN nanoparticles (PDHN-NP), in comparison to PDA-NP, to trap alkylperoxyl (ROO•) and hydroperoxyl (HOO•) radicals that are involved in the propagation of peroxidation in real conditions. Our results demonstrate that PDHN-NP present a higher antioxidant efficiency with respect to PDA-NP against ROO• in water at pH 7.4 and against mixed ROO• and HOO• in acetonitrile, showing catalytic cross-termination activity. The antioxidant capacity of PDHN-NP in water is 0.8 mmol/g (ROO• radicals quenched by 1 g of PDHN-NP), with a rate constant of 3 × 105 M−1 s−1 for each reactive moiety. Quantum-mechanical calculations revealed that, thanks to the formation of a H-bond network, the quinones in PDHN-NP have a high affinity for H-atoms, thus justifying the high reactivity of PDHN-NP with HOO• observed experimentally.

更新日期：2023-07-28

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