Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors.

Christopher Öberg; Hakon Leffler; Ulf Nilsson

doi:10.1021/jm701266y

Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors.

Christopher Öberg, Hakon Leffler, Ulf Nilsson

Research output: Contribution to journal › Article › peer-review

Abstract

Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta- d-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide and O2 anionic substituents in that the benzamide stacked face-to-face and the anionic O2 substituent ion-paired with the guanidinium moiety.

Original language	English
Pages (from-to)	2297-2301
Journal	Journal of Medicinal Chemistry
Volume	51
Issue number	7
DOIs	https://doi.org/10.1021/jm701266y
Publication status	Published - 2008

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)

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Medicinal Chemistry

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10.1021/jm701266y

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title = "Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors.",

abstract = "Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta- d-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide and O2 anionic substituents in that the benzamide stacked face-to-face and the anionic O2 substituent ion-paired with the guanidinium moiety.",

author = "Christopher {\"O}berg and Hakon Leffler and Ulf Nilsson",

note = "The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)",

year = "2008",

doi = "10.1021/jm701266y",

language = "English",

volume = "51",

pages = "2297--2301",

journal = "Journal of Medicinal Chemistry",

issn = "1520-4804",

publisher = "The American Chemical Society (ACS)",

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TY - JOUR

T1 - Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors.

AU - Öberg, Christopher

AU - Leffler, Hakon

AU - Nilsson, Ulf

N1 - The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)

PY - 2008

Y1 - 2008

N2 - Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta- d-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide and O2 anionic substituents in that the benzamide stacked face-to-face and the anionic O2 substituent ion-paired with the guanidinium moiety.

AB - Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta- d-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide and O2 anionic substituents in that the benzamide stacked face-to-face and the anionic O2 substituent ion-paired with the guanidinium moiety.

U2 - 10.1021/jm701266y

DO - 10.1021/jm701266y

M3 - Article

SN - 1520-4804

VL - 51

SP - 2297

EP - 2301

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 7

ER -

Arginine Binding Motifs: Design and Synthesis of Galactose-Derived Arginine Tweezers as Galectin-3 Inhibitors.

Abstract

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