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Tytuł:
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Amino and hydroxy substitution influences pyrene-DNA binding.
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Autorzy:
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Qin C; Institute of Organic Contaminant Control and Soil Remediation, College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.
Hu X; Institute of Organic Contaminant Control and Soil Remediation, College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.
Waigi MG; Institute of Organic Contaminant Control and Soil Remediation, College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.
Yang B; Institute of Organic Contaminant Control and Soil Remediation, College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China.
Gao Y; Institute of Organic Contaminant Control and Soil Remediation, College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing 210095, China. Electronic address: .
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Źródło:
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The Science of the total environment [Sci Total Environ] 2020 Jul 10; Vol. 725, pp. 138542. Date of Electronic Publication: 2020 Apr 07.
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Typ publikacji:
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Journal Article
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Język:
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English
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Imprint Name(s):
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Original Publication: Amsterdam, Elsevier.
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MeSH Terms:
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Polycyclic Aromatic Hydrocarbons*
Pyrenes*
DNA Damage
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Contributed Indexing:
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Keywords: Carcinogenesis; DNA; Functional groups; PAHs
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Substance Nomenclature:
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0 (Polycyclic Aromatic Hydrocarbons)
0 (Pyrenes)
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Entry Date(s):
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Date Created: 20200419 Date Completed: 20200710 Latest Revision: 20200710
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Update Code:
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20240104
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DOI:
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10.1016/j.scitotenv.2020.138542
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PMID:
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32304974
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Polycyclic aromatic hydrocarbon (PAH)-DNA binding is an essential step in PAH-induced carcinogenesis. A large number of PAHs contain substituents, it is unclear whether functional groups will influence the PAH-DNA binding. Here, we investigated amino (-NH 2 ) and hydroxy (-OH) substitution on pyrene-DNA binding. Because of the considerable effects of electrostatic surface potential (ESP), -NH 2 substitution significantly facilitated binding by increasing the binding constant (log K A ) from 4.14 L mol -1 to 12.31 L mol -1 , while -OH substitution inhibited binding by reducing log K A to 3.68 L mol -1 . Spectroscopy results revealed that pyrene and its derivatives were able to bind with thymine to induce DNA damage or double helix distortion. Quantum chemical calculations showed that -NH 2 substitution induces hydrogen bond formation, thereby enhancing the binding of pyrene with DNA; moreover, binding force changes due to -OH substitution may not be an essential factor. All structural descriptors were not correlated with the quenching constant (K SV ) or binding constant, indicating that changes in physicochemical properties shows no influence on pyrene-DNA binding. The results of this study will improve our understanding of the contribution of functional groups to PAH-DNA binding.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2020 Elsevier B.V. All rights reserved.)
