Mechanistic insights into the specificity of human cytosolic sulfotransferase 2A1 (hSULT2A1) for hydroxylated polychlorinated biphenyls through the use of fluoro-tagged probes
Abstract Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR)...
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| Autor*in: |
Ekuase, E. J. [verfasserIn] |
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| Format: |
Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2015 |
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| Anmerkung: |
© Springer-Verlag Berlin Heidelberg 2015 |
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| Übergeordnetes Werk: |
Enthalten in: Environmental science and pollution research - Springer Berlin Heidelberg, 1994, 23(2015), 3 vom: 14. Juli, Seite 2119-2127 |
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| Übergeordnetes Werk: |
volume:23 ; year:2015 ; number:3 ; day:14 ; month:07 ; pages:2119-2127 |
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| DOI / URN: |
10.1007/s11356-015-4886-8 |
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| 245 | 1 | 0 | |a Mechanistic insights into the specificity of human cytosolic sulfotransferase 2A1 (hSULT2A1) for hydroxylated polychlorinated biphenyls through the use of fluoro-tagged probes |
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| 520 | |a Abstract Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR) studies are performed with many distinct compounds. Based on the chemical properties of the tested compounds, complex relationships can be established so that models can be developed to predict toxicity of novel compounds. In this study, the use of fluorinated analogues as supplemental QSAR compounds was investigated. Substituting fluorine induces changes in electronic and steric properties of the substrate without substantially changing the chemical backbone of the substrate. In vitro assays were performed using purified human cytosolic sulfotransferase hSULT2A1 as a model enzyme. A mono-hydroxylated polychlorinated biphenyl (4-OH PCB 14) and its four possible mono-fluoro analogues were used as test compounds. Remarkable similarities were found between this approach and previously published QSAR studies for hSULT2A1. Both studies implicate the importance of dipole moment and dihedral angle as being important to PCB structure in respect to being substrates for hSULT2A1. We conclude that mono-fluorinated analogues of a target substrate can be a useful tool to study the structure activity relationships for enzyme specificity. | ||
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| 650 | 4 | |a Polychlorinated biphenyls | |
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10.1007/s11356-015-4886-8 doi (DE-627)OLC2040457739 (DE-He213)s11356-015-4886-8-p DE-627 ger DE-627 rakwb eng 570 360 333.7 VZ 690 333.7 540 VZ BIODIV DE-30 fid Ekuase, E. J. verfasserin aut Mechanistic insights into the specificity of human cytosolic sulfotransferase 2A1 (hSULT2A1) for hydroxylated polychlorinated biphenyls through the use of fluoro-tagged probes 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © Springer-Verlag Berlin Heidelberg 2015 Abstract Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR) studies are performed with many distinct compounds. Based on the chemical properties of the tested compounds, complex relationships can be established so that models can be developed to predict toxicity of novel compounds. In this study, the use of fluorinated analogues as supplemental QSAR compounds was investigated. Substituting fluorine induces changes in electronic and steric properties of the substrate without substantially changing the chemical backbone of the substrate. In vitro assays were performed using purified human cytosolic sulfotransferase hSULT2A1 as a model enzyme. A mono-hydroxylated polychlorinated biphenyl (4-OH PCB 14) and its four possible mono-fluoro analogues were used as test compounds. Remarkable similarities were found between this approach and previously published QSAR studies for hSULT2A1. Both studies implicate the importance of dipole moment and dihedral angle as being important to PCB structure in respect to being substrates for hSULT2A1. We conclude that mono-fluorinated analogues of a target substrate can be a useful tool to study the structure activity relationships for enzyme specificity. F-tagged probes QSAR hSULT2A1 Polychlorinated biphenyls Hydroxylated polychlorinated biphenyls Sulfotransferase Computational chemistry 4-Hydroxy-3,5-dichlorobiphenyl van ‘t Erve, T. J. aut Rahaman, A. aut Robertson, L. W. aut Duffel, M. W. aut Luthe, G. aut Enthalten in Environmental science and pollution research Springer Berlin Heidelberg, 1994 23(2015), 3 vom: 14. Juli, Seite 2119-2127 (DE-627)171335805 (DE-600)1178791-0 (DE-576)038875101 0944-1344 nnns volume:23 year:2015 number:3 day:14 month:07 pages:2119-2127 https://doi.org/10.1007/s11356-015-4886-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC FID-BIODIV SSG-OLC-UMW SSG-OLC-ARC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-FOR SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_252 GBV_ILN_267 GBV_ILN_370 GBV_ILN_2018 GBV_ILN_2057 GBV_ILN_4012 GBV_ILN_4046 GBV_ILN_4219 GBV_ILN_4266 GBV_ILN_4277 AR 23 2015 3 14 07 2119-2127 |
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10.1007/s11356-015-4886-8 doi (DE-627)OLC2040457739 (DE-He213)s11356-015-4886-8-p DE-627 ger DE-627 rakwb eng 570 360 333.7 VZ 690 333.7 540 VZ BIODIV DE-30 fid Ekuase, E. J. verfasserin aut Mechanistic insights into the specificity of human cytosolic sulfotransferase 2A1 (hSULT2A1) for hydroxylated polychlorinated biphenyls through the use of fluoro-tagged probes 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © Springer-Verlag Berlin Heidelberg 2015 Abstract Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR) studies are performed with many distinct compounds. Based on the chemical properties of the tested compounds, complex relationships can be established so that models can be developed to predict toxicity of novel compounds. In this study, the use of fluorinated analogues as supplemental QSAR compounds was investigated. Substituting fluorine induces changes in electronic and steric properties of the substrate without substantially changing the chemical backbone of the substrate. In vitro assays were performed using purified human cytosolic sulfotransferase hSULT2A1 as a model enzyme. A mono-hydroxylated polychlorinated biphenyl (4-OH PCB 14) and its four possible mono-fluoro analogues were used as test compounds. Remarkable similarities were found between this approach and previously published QSAR studies for hSULT2A1. Both studies implicate the importance of dipole moment and dihedral angle as being important to PCB structure in respect to being substrates for hSULT2A1. We conclude that mono-fluorinated analogues of a target substrate can be a useful tool to study the structure activity relationships for enzyme specificity. F-tagged probes QSAR hSULT2A1 Polychlorinated biphenyls Hydroxylated polychlorinated biphenyls Sulfotransferase Computational chemistry 4-Hydroxy-3,5-dichlorobiphenyl van ‘t Erve, T. J. aut Rahaman, A. aut Robertson, L. W. aut Duffel, M. W. aut Luthe, G. aut Enthalten in Environmental science and pollution research Springer Berlin Heidelberg, 1994 23(2015), 3 vom: 14. Juli, Seite 2119-2127 (DE-627)171335805 (DE-600)1178791-0 (DE-576)038875101 0944-1344 nnns volume:23 year:2015 number:3 day:14 month:07 pages:2119-2127 https://doi.org/10.1007/s11356-015-4886-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC FID-BIODIV SSG-OLC-UMW SSG-OLC-ARC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-FOR SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_252 GBV_ILN_267 GBV_ILN_370 GBV_ILN_2018 GBV_ILN_2057 GBV_ILN_4012 GBV_ILN_4046 GBV_ILN_4219 GBV_ILN_4266 GBV_ILN_4277 AR 23 2015 3 14 07 2119-2127 |
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mechanistic insights into the specificity of human cytosolic sulfotransferase 2a1 (hsult2a1) for hydroxylated polychlorinated biphenyls through the use of fluoro-tagged probes |
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Mechanistic insights into the specificity of human cytosolic sulfotransferase 2A1 (hSULT2A1) for hydroxylated polychlorinated biphenyls through the use of fluoro-tagged probes |
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Abstract Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR) studies are performed with many distinct compounds. Based on the chemical properties of the tested compounds, complex relationships can be established so that models can be developed to predict toxicity of novel compounds. In this study, the use of fluorinated analogues as supplemental QSAR compounds was investigated. Substituting fluorine induces changes in electronic and steric properties of the substrate without substantially changing the chemical backbone of the substrate. In vitro assays were performed using purified human cytosolic sulfotransferase hSULT2A1 as a model enzyme. A mono-hydroxylated polychlorinated biphenyl (4-OH PCB 14) and its four possible mono-fluoro analogues were used as test compounds. Remarkable similarities were found between this approach and previously published QSAR studies for hSULT2A1. Both studies implicate the importance of dipole moment and dihedral angle as being important to PCB structure in respect to being substrates for hSULT2A1. We conclude that mono-fluorinated analogues of a target substrate can be a useful tool to study the structure activity relationships for enzyme specificity. © Springer-Verlag Berlin Heidelberg 2015 |
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Abstract Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR) studies are performed with many distinct compounds. Based on the chemical properties of the tested compounds, complex relationships can be established so that models can be developed to predict toxicity of novel compounds. In this study, the use of fluorinated analogues as supplemental QSAR compounds was investigated. Substituting fluorine induces changes in electronic and steric properties of the substrate without substantially changing the chemical backbone of the substrate. In vitro assays were performed using purified human cytosolic sulfotransferase hSULT2A1 as a model enzyme. A mono-hydroxylated polychlorinated biphenyl (4-OH PCB 14) and its four possible mono-fluoro analogues were used as test compounds. Remarkable similarities were found between this approach and previously published QSAR studies for hSULT2A1. Both studies implicate the importance of dipole moment and dihedral angle as being important to PCB structure in respect to being substrates for hSULT2A1. We conclude that mono-fluorinated analogues of a target substrate can be a useful tool to study the structure activity relationships for enzyme specificity. © Springer-Verlag Berlin Heidelberg 2015 |
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Abstract Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR) studies are performed with many distinct compounds. Based on the chemical properties of the tested compounds, complex relationships can be established so that models can be developed to predict toxicity of novel compounds. In this study, the use of fluorinated analogues as supplemental QSAR compounds was investigated. Substituting fluorine induces changes in electronic and steric properties of the substrate without substantially changing the chemical backbone of the substrate. In vitro assays were performed using purified human cytosolic sulfotransferase hSULT2A1 as a model enzyme. A mono-hydroxylated polychlorinated biphenyl (4-OH PCB 14) and its four possible mono-fluoro analogues were used as test compounds. Remarkable similarities were found between this approach and previously published QSAR studies for hSULT2A1. Both studies implicate the importance of dipole moment and dihedral angle as being important to PCB structure in respect to being substrates for hSULT2A1. We conclude that mono-fluorinated analogues of a target substrate can be a useful tool to study the structure activity relationships for enzyme specificity. © Springer-Verlag Berlin Heidelberg 2015 |
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