A novel anti-oxidant and anti-cancer strategy: a peptoid anti-inflammatory drug conjugate with SOD mimic activity

M.A. Bailey; Matthew Ingram; D.P. Naughton

doi:10.1016/j.bbrc.2004.03.162

A novel anti-oxidant and anti-cancer strategy: a peptoid anti-inflammatory drug conjugate with SOD mimic activity

M.A. Bailey, Matthew Ingram, D.P. Naughton

University of Brighton

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

Abstract

Activation of reactive oxygen and nitrogen species (RONS) by redox-active metal ions has been proposed to contribute to oxidative damage in inflamed tissues. Here, we report a dual-function anti-oxidant conjugate comprising an anti-inflammatory agent (5-aminosalicylic acid) and a chelator with potential as a superoxide dismutase mimic. The conjugate ethylenediaminetetraacetic acid bis-(5-aminosalicylic acid methyl ester) [EBAME] chelates Cu(II) ions in a 1:1 ratio, as assessed spectrophotometrically using Job’s method. Superoxide dismutase (SOD) activity was determined for the Mn(II)-conjugate as 0.758 ± 0.130 U at a concentration of 0.99 μM. In inflamed tissues, peptidase mediated release of active 5-ASA would also release the EDTA chelator which has significant SOD mimic activity when complexed to Cu(II) ions. Thus, EBAME has potential as a dual-function anti-inflammatory agent with reduced gastric irritability.

Original language	English
Pages (from-to)	1155-1158
Number of pages	4
Journal	Biochemical and biophysical research communications
Volume	317
Issue number	4
DOIs	https://doi.org/10.1016/j.bbrc.2004.03.162
Publication status	Published - May 2004

Keywords

Superoxide dismutase mimic
5-Aminosalicylic acid
Ethylenediaminetetraacetic acid
Metal ions
Inflammation

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http://www.sciencedirect.com/science/article/pii/S0006291X04006631Licence: Unspecified

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title = "A novel anti-oxidant and anti-cancer strategy: a peptoid anti-inflammatory drug conjugate with SOD mimic activity",

abstract = "Activation of reactive oxygen and nitrogen species (RONS) by redox-active metal ions has been proposed to contribute to oxidative damage in inflamed tissues. Here, we report a dual-function anti-oxidant conjugate comprising an anti-inflammatory agent (5-aminosalicylic acid) and a chelator with potential as a superoxide dismutase mimic. The conjugate ethylenediaminetetraacetic acid bis-(5-aminosalicylic acid methyl ester) [EBAME] chelates Cu(II) ions in a 1:1 ratio, as assessed spectrophotometrically using Job{\textquoteright}s method. Superoxide dismutase (SOD) activity was determined for the Mn(II)-conjugate as 0.758 ± 0.130 U at a concentration of 0.99 μM. In inflamed tissues, peptidase mediated release of active 5-ASA would also release the EDTA chelator which has significant SOD mimic activity when complexed to Cu(II) ions. Thus, EBAME has potential as a dual-function anti-inflammatory agent with reduced gastric irritability.",

keywords = "Superoxide dismutase mimic, 5-Aminosalicylic acid, Ethylenediaminetetraacetic acid, Metal ions, Inflammation",

author = "M.A. Bailey and Matthew Ingram and D.P. Naughton",

year = "2004",

month = may,

doi = "10.1016/j.bbrc.2004.03.162",

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AU - Bailey, M.A.

AU - Ingram, Matthew

AU - Naughton, D.P.

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Y1 - 2004/5

N2 - Activation of reactive oxygen and nitrogen species (RONS) by redox-active metal ions has been proposed to contribute to oxidative damage in inflamed tissues. Here, we report a dual-function anti-oxidant conjugate comprising an anti-inflammatory agent (5-aminosalicylic acid) and a chelator with potential as a superoxide dismutase mimic. The conjugate ethylenediaminetetraacetic acid bis-(5-aminosalicylic acid methyl ester) [EBAME] chelates Cu(II) ions in a 1:1 ratio, as assessed spectrophotometrically using Job’s method. Superoxide dismutase (SOD) activity was determined for the Mn(II)-conjugate as 0.758 ± 0.130 U at a concentration of 0.99 μM. In inflamed tissues, peptidase mediated release of active 5-ASA would also release the EDTA chelator which has significant SOD mimic activity when complexed to Cu(II) ions. Thus, EBAME has potential as a dual-function anti-inflammatory agent with reduced gastric irritability.

AB - Activation of reactive oxygen and nitrogen species (RONS) by redox-active metal ions has been proposed to contribute to oxidative damage in inflamed tissues. Here, we report a dual-function anti-oxidant conjugate comprising an anti-inflammatory agent (5-aminosalicylic acid) and a chelator with potential as a superoxide dismutase mimic. The conjugate ethylenediaminetetraacetic acid bis-(5-aminosalicylic acid methyl ester) [EBAME] chelates Cu(II) ions in a 1:1 ratio, as assessed spectrophotometrically using Job’s method. Superoxide dismutase (SOD) activity was determined for the Mn(II)-conjugate as 0.758 ± 0.130 U at a concentration of 0.99 μM. In inflamed tissues, peptidase mediated release of active 5-ASA would also release the EDTA chelator which has significant SOD mimic activity when complexed to Cu(II) ions. Thus, EBAME has potential as a dual-function anti-inflammatory agent with reduced gastric irritability.

KW - Superoxide dismutase mimic

KW - 5-Aminosalicylic acid

KW - Ethylenediaminetetraacetic acid

KW - Metal ions

KW - Inflammation

U2 - 10.1016/j.bbrc.2004.03.162

DO - 10.1016/j.bbrc.2004.03.162

M3 - Article

SN - 0006-291X

VL - 317

SP - 1155

EP - 1158

JO - Biochemical and biophysical research communications

JF - Biochemical and biophysical research communications

IS - 4

ER -

A novel anti-oxidant and anti-cancer strategy: a peptoid anti-inflammatory drug conjugate with SOD mimic activity

Abstract

Keywords

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