Photochemical transformation of the uricosuric drug benzbromarone in aqueous solutions exposed to UV irradiation

IF 11.4 1区环境科学与生态学 Q1 ENGINEERING, ENVIRONMENTAL

Water Research Pub Date : 2025-04-22 DOI:10.1016/j.watres.2025.123705

Yan Cai, Xiaoci Li, Peizeng Yang, Jing Chen, Junhe Lu, Jean-Marc Chovelon, Yuefei Ji

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Abstract

As one of benzophenone-derived drugs, benzbromarone (BBM) has been widely used to reduce blood uric acid, treat gout, and gouty arthritis. Understanding the transformation and fate of BBM in natural and engineered systems is critical for its ecological risk assessment. In this study, we systematically investigated the photochemical behavior of BBM in aqueous solutions under laboratory UV₂₅₄ irradiation. UV-vis spectra show that an aqueous solution of BBM is capable of absorbing UV photons at 200 - 400 nm. Spectroscopic titration indicates that BBM with a pK_a value of 4.83 ± 0.17 is present mainly as the phenolate form under circumneutral conditions. BBM undergoes rapid direct photolysis when exposed to UV₂₅₄ irradiation and the quantum yields were determined to be 0.0105 and 0.0196 mol E⁻¹ for phenol and phenolate forms, respectively. The heavy atom effect of bromine and spin-orbit coupling effect of aromatic ketone make dibromophenol and carbonyl moieties the critical chromophores accounting for the high photoreactivity of BBM. Laser flash photolysis and electron paramagnetic resonance studies suggest that the photolysis of BBM is initiated by ultrafast photodebromination and Norrish I cleavage. The high yield of bromide determined by ion chromatograph highlights the importance of photodebromination. Due to the light screening effect of wastewater components, the photolysis of BBM in hospital wastewater is inhibited. Photo-induced modification of the dibromophenol moiety of BBM likely generates photoproducts showing toxicity to luminescent bacteria. Overall, our results reveal that photochemical reaction under UV irradiation plays an important role in the attenuation of BBM in engineered water.

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紫外光照射下尿用药物苯溴马隆水溶液的光化学转化

苯溴马隆（BBM）作为二苯甲酮类衍生药物之一，被广泛用于降低血尿酸、治疗痛风、痛风性关节炎等。了解BBM在自然和工程系统中的转变和命运对其生态风险评估至关重要。在这项研究中，我们系统地研究了在实验室UV254照射下，BBM在水溶液中的光化学行为。紫外可见光谱表明，BBM水溶液能够吸收200 ~ 400 nm的紫外光子。光谱滴定表明，在环中性条件下，pKa值为4.83±0.17的BBM主要以酚酸盐形式存在。在UV254照射下，BBM发生了快速的直接光解，苯酚和酚酸形式的量子产率分别为0.0105和0.0196 mol E−1。溴的重原子效应和芳香酮的自旋轨道耦合效应使二溴酚和羰基基团成为BBM具有高光反应性的关键发色团。激光闪光光解和电子顺磁共振研究表明，BBM的光解是由超快光脱溴和诺里什ⅰ解理引发的。离子色谱仪测定溴化物的高收率突出了光脱溴的重要性。由于废水组分的挡光作用，医院废水中BBM的光解受到抑制。光诱导修饰BBM的二溴酚部分可能产生对发光细菌具有毒性的光产物。综上所述，我们的研究结果表明，紫外线照射下的光化学反应在工程水中BBM的衰减中起着重要作用。

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来源期刊

Water Research 环境科学-工程：环境

CiteScore

20.80

自引率

9.40%

发文量

1307

审稿时长

38 days

期刊介绍： Water Research, along with its open access companion journal Water Research X, serves as a platform for publishing original research papers covering various aspects of the science and technology related to the anthropogenic water cycle, water quality, and its management worldwide. The audience targeted by the journal comprises biologists, chemical engineers, chemists, civil engineers, environmental engineers, limnologists, and microbiologists. The scope of the journal include: •Treatment processes for water and wastewaters (municipal, agricultural, industrial, and on-site treatment), including resource recovery and residuals management; •Urban hydrology including sewer systems, stormwater management, and green infrastructure; •Drinking water treatment and distribution; •Potable and non-potable water reuse; •Sanitation, public health, and risk assessment; •Anaerobic digestion, solid and hazardous waste management, including source characterization and the effects and control of leachates and gaseous emissions; •Contaminants (chemical, microbial, anthropogenic particles such as nanoparticles or microplastics) and related water quality sensing, monitoring, fate, and assessment; •Anthropogenic impacts on inland, tidal, coastal and urban waters, focusing on surface and ground waters, and point and non-point sources of pollution; •Environmental restoration, linked to surface water, groundwater and groundwater remediation; •Analysis of the interfaces between sediments and water, and between water and atmosphere, focusing specifically on anthropogenic impacts; •Mathematical modelling, systems analysis, machine learning, and beneficial use of big data related to the anthropogenic water cycle; •Socio-economic, policy, and regulations studies.