CAS OpenIR
Fast coupling and detoxification of aqueous halobenzoquinones by extracellular nucleophiles: The relationship among structures, pathways and toxicity
Zhong, Chen1,2,4; Zhao, He1,2,4; Cao, Hongbin1,2,4; Huang, Ching-Hua3
2022-06-15
Source PublicationCHEMICAL ENGINEERING JOURNAL
ISSN1385-8947
Volume438Pages:13
AbstractHalobenzoquinones (HBQs), a metabolism of pentachlorophenol, arouse increasing concern for their high toxicity. This paper systematically studied the influences of 31 extracellular nucleophiles on the removal of dichlorobenzoquinones (DCBQs). The results showed that at pH 6.0-8.0, the transformation of DCBQs followed a pattern of pseudo first-order reaction. With the presence of different thiol compound (ratio 1:1), the apparent rate constant of 25DCBQ and 26DCBQ was between 0.028 and 0.204 min-1 and 0.061-0.156 min-1, respectively, which was 6.6-48.3 times faster than direct hydrolysis and 1.9-23.4 times of that with histidine, a typical amino acid. This was attributed to the different transformation pathways of DCBQs with thiol or amino groups. According to the MS spectrum and transition state theory, thiol compounds was stably incorporated into DCBQs via Michael addition or substitution, which also decreased the oxidative stress of DCBQs by 35.5-86.4% and cytotoxicity of hydrolyzed DCBQ by 44.9-100%, respectively. Conversely, amino acids promoted the hydrolysis of DCBQs by forming unstable AA-DCBQ intermediates that can be further hydrolyzed to OH-DCBQs, leading to an increased selectivity of OH-DCBQs, and increased the oxidative stress of 25DCBQs by 0.2-31.2% and cytotoxicity of hydrolyzed 25DCBQ by 42.0-52.7%. Such difference was inherently related to the nucleophilicity of different atoms. Moreover, it was revealed that the maximum condensed local nucleophilicity index of nucleophiles (Nk, max) can joint describe the relationship among nucleophilic structures, transformation pathways and toxicity of DCBQs. This paper provided a comprehensive perspective on the fast removal and detoxification of HBQs in extracellular environment.
KeywordDichlorobenzoquinone Nucleophiles Transformation pathways Toxicity Density functional theory
DOI10.1016/j.cej.2022.135525
Language英语
WOS KeywordMETAL-INDEPENDENT DECOMPOSITION ; ORGANIC HYDROPEROXIDES ; LIQUID-CHROMATOGRAPHY ; MOLECULAR-MECHANISM ; HYDROXYL RADICALS ; HYDROGEN-PEROXIDE ; AMINO-ACIDS ; WATER ; PHARMACOKINETICS ; PHARMACEUTICALS
Funding ProjectNational Natural Science Foundation of China[51978643] ; Youth Innovation Promotion Association, CAS[2014037]
WOS Research AreaEngineering
WOS SubjectEngineering, Environmental ; Engineering, Chemical
Funding OrganizationNational Natural Science Foundation of China ; Youth Innovation Promotion Association, CAS
WOS IDWOS:000779661100004
PublisherELSEVIER SCIENCE SA
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/52860
Collection中国科学院过程工程研究所
Corresponding AuthorZhao, He
Affiliation1.Chinese Acad Sci, Inst Proc Engn, Natl Key Lab Biochem Engn, Beijing, Peoples R China
2.Beijing Engn Res Ctr Proc Pollut Control, Beijing, Peoples R China
3.Georgia Inst Technol, Sch Civil & Environm Engn, Atlanta, GA 30332 USA
4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Zhong, Chen,Zhao, He,Cao, Hongbin,et al. Fast coupling and detoxification of aqueous halobenzoquinones by extracellular nucleophiles: The relationship among structures, pathways and toxicity[J]. CHEMICAL ENGINEERING JOURNAL,2022,438:13.
APA Zhong, Chen,Zhao, He,Cao, Hongbin,&Huang, Ching-Hua.(2022).Fast coupling and detoxification of aqueous halobenzoquinones by extracellular nucleophiles: The relationship among structures, pathways and toxicity.CHEMICAL ENGINEERING JOURNAL,438,13.
MLA Zhong, Chen,et al."Fast coupling and detoxification of aqueous halobenzoquinones by extracellular nucleophiles: The relationship among structures, pathways and toxicity".CHEMICAL ENGINEERING JOURNAL 438(2022):13.
Files in This Item:
There are no files associated with this item.
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Zhong, Chen]'s Articles
[Zhao, He]'s Articles
[Cao, Hongbin]'s Articles
Baidu academic
Similar articles in Baidu academic
[Zhong, Chen]'s Articles
[Zhao, He]'s Articles
[Cao, Hongbin]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Zhong, Chen]'s Articles
[Zhao, He]'s Articles
[Cao, Hongbin]'s Articles
Terms of Use
No data!
Social Bookmark/Share
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.