Novel glycosyl prodrug of RXP03 as MMP-11 prodrug: design, synthesis and virtual screening

Moaz M. Abdou; Ferenc Ötvös; Dewen Dong; Magdalini Matziari

doi:10.1186/s13065-023-01075-1

Novel glycosyl prodrug of RXP03 as MMP-11 prodrug: design, synthesis and virtual screening

Moaz M. Abdou^*, Ferenc Ötvös, Dewen Dong, Magdalini Matziari

^*Corresponding author for this work

Department of Chemistry and Materials Science

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

1 Citation (Scopus)

Abstract

Like most phosphinic acids, the potent and selective RXP03 inhibitor of different MMPs exhibited moderate absorption and low bioavailability, which impaired its use. In an unprecedented attempt, we present an interesting synthetic approach to a new class of phosphinate prodrug, glycosyl ester of RXP03, to provide a potentially improved blood–brain barrier (BBB) behavior compared to the former lead compound RXP03. To validate this speculation, a predictive study for permeability enhancer of glycosyl ester of RXP03 showed encouraging insights to improve drug delivery across biological barriers.

Original language	English
Article number	167
Journal	BMC Chemistry
Volume	17
Issue number	1
DOIs	https://doi.org/10.1186/s13065-023-01075-1
Publication status	Published - Dec 2023

Keywords

Matrix metalloproteases
Molecular docking
Permeability enhancer
Phosphinic ester
Prodrug
RXP03

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10.1186/s13065-023-01075-1

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abstract = "Like most phosphinic acids, the potent and selective RXP03 inhibitor of different MMPs exhibited moderate absorption and low bioavailability, which impaired its use. In an unprecedented attempt, we present an interesting synthetic approach to a new class of phosphinate prodrug, glycosyl ester of RXP03, to provide a potentially improved blood–brain barrier (BBB) behavior compared to the former lead compound RXP03. To validate this speculation, a predictive study for permeability enhancer of glycosyl ester of RXP03 showed encouraging insights to improve drug delivery across biological barriers.",

keywords = "Matrix metalloproteases, Molecular docking, Permeability enhancer, Phosphinic ester, Prodrug, RXP03",

author = "Abdou, {Moaz M.} and Ferenc {\"O}tv{\"o}s and Dewen Dong and Magdalini Matziari",

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T2 - design, synthesis and virtual screening

AU - Abdou, Moaz M.

AU - Ötvös, Ferenc

AU - Dong, Dewen

AU - Matziari, Magdalini

PY - 2023/12

Y1 - 2023/12

N2 - Like most phosphinic acids, the potent and selective RXP03 inhibitor of different MMPs exhibited moderate absorption and low bioavailability, which impaired its use. In an unprecedented attempt, we present an interesting synthetic approach to a new class of phosphinate prodrug, glycosyl ester of RXP03, to provide a potentially improved blood–brain barrier (BBB) behavior compared to the former lead compound RXP03. To validate this speculation, a predictive study for permeability enhancer of glycosyl ester of RXP03 showed encouraging insights to improve drug delivery across biological barriers.

AB - Like most phosphinic acids, the potent and selective RXP03 inhibitor of different MMPs exhibited moderate absorption and low bioavailability, which impaired its use. In an unprecedented attempt, we present an interesting synthetic approach to a new class of phosphinate prodrug, glycosyl ester of RXP03, to provide a potentially improved blood–brain barrier (BBB) behavior compared to the former lead compound RXP03. To validate this speculation, a predictive study for permeability enhancer of glycosyl ester of RXP03 showed encouraging insights to improve drug delivery across biological barriers.

KW - Matrix metalloproteases

KW - Molecular docking

KW - Permeability enhancer

KW - Phosphinic ester

KW - Prodrug

KW - RXP03

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DO - 10.1186/s13065-023-01075-1

M3 - Article

AN - SCOPUS:85178119541

SN - 2661-801X

VL - 17

JO - BMC Chemistry

JF - BMC Chemistry

IS - 1

M1 - 167

ER -

Novel glycosyl prodrug of RXP03 as MMP-11 prodrug: design, synthesis and virtual screening

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Keywords

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