SALMON: Solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy

Christian Ludwig; Paul J.A. Michiels; Xiaoqiu Wu; Kathryn L. Kavanagh; Ewa Pilka; Anna Jansson; Udo Oppermann; Ulrich L. Günther

doi:10.1021/jm701020f

SALMON: Solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy

Christian Ludwig^*, Paul J.A. Michiels, Xiaoqiu Wu, Kathryn L. Kavanagh, Ewa Pilka, Anna Jansson, Udo Oppermann, Ulrich L. Günther

^*Corresponding author for this work

Institute of Chemistry and Metabolomics

65 Citations (Scopus)

Abstract

Quinone oxidoreductase 2 (NQO2) binds the prodrug tretazicar (also known as CB1954, 5-(aziridin-1-yl)-2,4-dinitrobenzamide), which exhibits a profound antitumor effect in human cancers when administered together with caricotamide. X-ray structure determination allowed for two possible orientations of the ligand. Here we describe a new NMR method, SALMON (solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy), based on waterLOGSY to determine the orientation of a ligand bound to a protein by mapping its solvent accessibility, which was used to unambiguously determine the orientation of CB1954 in NQO2.

Original language	English
Journal	Journal of Medicinal Chemistry
Volume	51
Issue number	1
Pages (from-to)	1-3
Number of pages	3
ISSN	0022-2623
DOIs	https://doi.org/10.1021/jm701020f
Publication status	Published - 10.01.2008

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Academic Focus: Center for Infection and Inflammation Research (ZIEL)

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title = "SALMON: Solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy",

abstract = "Quinone oxidoreductase 2 (NQO2) binds the prodrug tretazicar (also known as CB1954, 5-(aziridin-1-yl)-2,4-dinitrobenzamide), which exhibits a profound antitumor effect in human cancers when administered together with caricotamide. X-ray structure determination allowed for two possible orientations of the ligand. Here we describe a new NMR method, SALMON (solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy), based on waterLOGSY to determine the orientation of a ligand bound to a protein by mapping its solvent accessibility, which was used to unambiguously determine the orientation of CB1954 in NQO2.",

author = "Christian Ludwig and Michiels, \{Paul J.A.\} and Xiaoqiu Wu and Kavanagh, \{Kathryn L.\} and Ewa Pilka and Anna Jansson and Udo Oppermann and G{\"u}nther, \{Ulrich L.\}",

year = "2008",

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T1 - SALMON: Solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy

AU - Ludwig, Christian

AU - Michiels, Paul J.A.

AU - Wu, Xiaoqiu

AU - Kavanagh, Kathryn L.

AU - Pilka, Ewa

AU - Jansson, Anna

AU - Oppermann, Udo

AU - Günther, Ulrich L.

PY - 2008/1/10

Y1 - 2008/1/10

N2 - Quinone oxidoreductase 2 (NQO2) binds the prodrug tretazicar (also known as CB1954, 5-(aziridin-1-yl)-2,4-dinitrobenzamide), which exhibits a profound antitumor effect in human cancers when administered together with caricotamide. X-ray structure determination allowed for two possible orientations of the ligand. Here we describe a new NMR method, SALMON (solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy), based on waterLOGSY to determine the orientation of a ligand bound to a protein by mapping its solvent accessibility, which was used to unambiguously determine the orientation of CB1954 in NQO2.

AB - Quinone oxidoreductase 2 (NQO2) binds the prodrug tretazicar (also known as CB1954, 5-(aziridin-1-yl)-2,4-dinitrobenzamide), which exhibits a profound antitumor effect in human cancers when administered together with caricotamide. X-ray structure determination allowed for two possible orientations of the ligand. Here we describe a new NMR method, SALMON (solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy), based on waterLOGSY to determine the orientation of a ligand bound to a protein by mapping its solvent accessibility, which was used to unambiguously determine the orientation of CB1954 in NQO2.

UR - https://www.scopus.com/pages/publications/37849034596

U2 - 10.1021/jm701020f

DO - 10.1021/jm701020f

M3 - Journal articles

C2 - 18062662

AN - SCOPUS:37849034596

SN - 0022-2623

VL - 51

SP - 1

EP - 3

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 1

ER -

SALMON: Solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy

Abstract

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