Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity

Marilena Tauro; Antonio Laghezza; Fulvio Loiodice; Luca Piemontese; Alessia Caradonna; Davide Capelli; Roberta Montanari; Giorgio Pochetti; Antonella Di Pizio; Mariangela Agamennone; Cristina Campestre; Paolo Tortorella

doi:10.1080/14756366.2016.1217853

Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity

Marilena Tauro (First Author), Antonio Laghezza (Co-Author), Fulvio Loiodice (Co-Author), Luca Piemontese (Co-Author), Alessia Caradonna (Co-Author), Davide Capelli (Co-Author), Roberta Montanari (Co-Author), Giorgio Pochetti (Co-Author), Antonella Di Pizio (Co-Author), Mariangela Agamennone (Co-Author), Cristina Campestre (Co-Author), Paolo Tortorella^* (Last Author)

^*Corresponding author for this work

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

30 Scopus citations

Abstract

New catechol-containing chemical entities have been investigated as matrix metalloproteinase inhibitors as well as antioxidant molecules. The combination of the two properties could represent a useful feature due to the potential application in all the pathological processes characterized by increased proteolytic activity and radical oxygen species (ROS) production, such as inflammation and photoaging. A series of catechol-based molecules were synthesized and tested for both proteolytic and oxidative inhibitory activity, and the detailed binding mode was assessed by crystal structure determination of the complex between a catechol derivative and the matrix metalloproteinase-8. Surprisingly, X-ray structure reveals that the catechol oxygens do not coordinates the zinc atom.

Original language	English
Pages (from-to)	25-37
Number of pages	13
Journal	Journal of Enzyme Inhibition and Medicinal Chemistry
Volume	31
DOIs	https://doi.org/10.1080/14756366.2016.1217853
State	Published - 4 Nov 2016
Externally published	Yes

Keywords

Antioxidants
X-ray crystallography
inhibitors
metalloenzymes
structure–activity relationships

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10.1080/14756366.2016.1217853

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Tauro, M., Laghezza, A., Loiodice, F., Piemontese, L., Caradonna, A., Capelli, D., Montanari, R., Pochetti, G., Di Pizio, A., Agamennone, M., Campestre, C., & Tortorella, P. (2016). Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity. Journal of Enzyme Inhibition and Medicinal Chemistry, 31, 25-37. https://doi.org/10.1080/14756366.2016.1217853

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title = "Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity",

abstract = "New catechol-containing chemical entities have been investigated as matrix metalloproteinase inhibitors as well as antioxidant molecules. The combination of the two properties could represent a useful feature due to the potential application in all the pathological processes characterized by increased proteolytic activity and radical oxygen species (ROS) production, such as inflammation and photoaging. A series of catechol-based molecules were synthesized and tested for both proteolytic and oxidative inhibitory activity, and the detailed binding mode was assessed by crystal structure determination of the complex between a catechol derivative and the matrix metalloproteinase-8. Surprisingly, X-ray structure reveals that the catechol oxygens do not coordinates the zinc atom.",

keywords = "Antioxidants, X-ray crystallography, inhibitors, metalloenzymes, structure–activity relationships",

author = "Marilena Tauro and Antonio Laghezza and Fulvio Loiodice and Luca Piemontese and Alessia Caradonna and Davide Capelli and Roberta Montanari and Giorgio Pochetti and \{Di Pizio\}, Antonella and Mariangela Agamennone and Cristina Campestre and Paolo Tortorella",

note = "Publisher Copyright: {\textcopyright} 2016 Informa UK Limited, trading as Taylor \& Francis Group.",

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month = nov,

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doi = "10.1080/14756366.2016.1217853",

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Tauro, M, Laghezza, A, Loiodice, F, Piemontese, L, Caradonna, A, Capelli, D, Montanari, R, Pochetti, G, Di Pizio, A, Agamennone, M, Campestre, C & Tortorella, P 2016, 'Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity', Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 31, pp. 25-37. https://doi.org/10.1080/14756366.2016.1217853

TY - JOUR

T1 - Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity

AU - Tauro, Marilena

AU - Laghezza, Antonio

AU - Loiodice, Fulvio

AU - Piemontese, Luca

AU - Caradonna, Alessia

AU - Capelli, Davide

AU - Montanari, Roberta

AU - Pochetti, Giorgio

AU - Di Pizio, Antonella

AU - Agamennone, Mariangela

AU - Campestre, Cristina

AU - Tortorella, Paolo

PY - 2016/11/4

Y1 - 2016/11/4

N2 - New catechol-containing chemical entities have been investigated as matrix metalloproteinase inhibitors as well as antioxidant molecules. The combination of the two properties could represent a useful feature due to the potential application in all the pathological processes characterized by increased proteolytic activity and radical oxygen species (ROS) production, such as inflammation and photoaging. A series of catechol-based molecules were synthesized and tested for both proteolytic and oxidative inhibitory activity, and the detailed binding mode was assessed by crystal structure determination of the complex between a catechol derivative and the matrix metalloproteinase-8. Surprisingly, X-ray structure reveals that the catechol oxygens do not coordinates the zinc atom.

AB - New catechol-containing chemical entities have been investigated as matrix metalloproteinase inhibitors as well as antioxidant molecules. The combination of the two properties could represent a useful feature due to the potential application in all the pathological processes characterized by increased proteolytic activity and radical oxygen species (ROS) production, such as inflammation and photoaging. A series of catechol-based molecules were synthesized and tested for both proteolytic and oxidative inhibitory activity, and the detailed binding mode was assessed by crystal structure determination of the complex between a catechol derivative and the matrix metalloproteinase-8. Surprisingly, X-ray structure reveals that the catechol oxygens do not coordinates the zinc atom.

KW - Antioxidants

KW - X-ray crystallography

KW - inhibitors

KW - metalloenzymes

KW - structure–activity relationships

UR - https://www.scopus.com/pages/publications/84983339571

U2 - 10.1080/14756366.2016.1217853

DO - 10.1080/14756366.2016.1217853

M3 - Article

C2 - 27556138

AN - SCOPUS:84983339571

SN - 1475-6366

VL - 31

SP - 25

EP - 37

JO - Journal of Enzyme Inhibition and Medicinal Chemistry

JF - Journal of Enzyme Inhibition and Medicinal Chemistry

ER -

Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity

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Keywords

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