An Optimized Pyrimidinol Multifunctional Radical Quencher
A series of aza analogues (4–9) of the experimental neuroprotective drug idebenone (1) have been prepared and evaluated for their ability to attenuate oxidative stress induced by glutathione depletion and to compensate for the decrease in oxidative phosphorylation efficiency in cultured Friedreich’s...
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| Published in | ACS medicinal chemistry letters Vol. 4; no. 8; pp. 724 - 729 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
08.08.2013
Amer Chemical Soc |
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| Abstract | A series of aza analogues (4–9) of the experimental neuroprotective drug idebenone (1) have been prepared and evaluated for their ability to attenuate oxidative stress induced by glutathione depletion and to compensate for the decrease in oxidative phosphorylation efficiency in cultured Friedreich’s ataxia (FRDA) fibroblasts and lymphocytes and also coenzyme Q10-deficient lymphocytes. Modification of the redox core of the previously reported 3 improved its antioxidant and cytoprotective properties. Compounds 4–9, having the same redox core, exhibited a range of antioxidant activities, reflecting side chain differences. Compounds having side chains extending 14–16 atoms from the pyrimidinol ring (6, 7, and 9) were potent antioxidants. They were superior to idebenone and more active than 3, 4, 5, and 8. Optimized analogue 7 and its acetate (7a) are of interest in defining potential therapeutic agents capable of blocking oxidative stress, maintaining mitochondrial membrane integrity, and augmenting ATP levels. Compounds with such properties may find utility in treating mitochondrial and neurodegenerative diseases such as FRDA and Alzheimer’s disease. |
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| AbstractList | A series
of aza analogues (
4
–
9
) of the experimental
neuroprotective drug idebenone (
1
) have been prepared
and evaluated for their ability to attenuate oxidative stress induced
by glutathione depletion and to compensate for the decrease in oxidative
phosphorylation efficiency in cultured Friedreich’s ataxia
(FRDA) fibroblasts and lymphocytes and also coenzyme Q
10
-deficient lymphocytes. Modification of the redox core of the previously
reported
3
improved its antioxidant and cytoprotective
properties. Compounds
4
–
9
, having
the same redox core, exhibited a range of antioxidant activities,
reflecting side chain differences. Compounds having side chains extending
14–16 atoms from the pyrimidinol ring (
6
,
7
, and
9
) were potent antioxidants. They were
superior to idebenone and more active than
3
,
4
,
5
, and
8
. Optimized analogue
7
and its acetate (
7a
) are of interest in defining potential
therapeutic agents capable of blocking oxidative stress, maintaining
mitochondrial membrane integrity, and augmenting ATP levels. Compounds
with such properties may find utility in treating mitochondrial and
neurodegenerative diseases such as FRDA and Alzheimer’s disease. A series of aza analogues (4-9) of the experimental neuroprotective drug idebenone (1) have been prepared and evaluated for their ability to attenuate oxidative stress induced by glutathione depletion and to compensate for the decrease in oxidative phosphorylation efficiency in cultured Friedreich's ataxia (FRDA) fibroblasts and lymphocytes and also coenzyme Q(10)-deficient lymphocytes. Modification of the redox core of the previously reported 3 improved its antioxidant and cytoprotective properties. Compounds 4-9, having the same redox core, exhibited a range of antioxidant activities, reflecting side chain differences. Compounds having side chains extending 14-16 atoms from the pyrimidinol ring (6, 7, and 9) were potent antioxidants. They were superior to idebenone and more active than 3, 4, 5, and 8. Optimized analogue 7 and its acetate (7a) are of interest in defining potential therapeutic agents capable of blocking oxidative stress, maintaining mitochondrial membrane integrity, and augmenting ATP levels. Compounds with such properties may find utility in treating mitochondrial and neurodegenerative diseases such as FRDA and Alzheimer's disease. A series of aza analogues (4–9) of the experimental neuroprotective drug idebenone (1) have been prepared and evaluated for their ability to attenuate oxidative stress induced by glutathione depletion and to compensate for the decrease in oxidative phosphorylation efficiency in cultured Friedreich’s ataxia (FRDA) fibroblasts and lymphocytes and also coenzyme Q10-deficient lymphocytes. Modification of the redox core of the previously reported 3 improved its antioxidant and cytoprotective properties. Compounds 4–9, having the same redox core, exhibited a range of antioxidant activities, reflecting side chain differences. Compounds having side chains extending 14–16 atoms from the pyrimidinol ring (6, 7, and 9) were potent antioxidants. They were superior to idebenone and more active than 3, 4, 5, and 8. Optimized analogue 7 and its acetate (7a) are of interest in defining potential therapeutic agents capable of blocking oxidative stress, maintaining mitochondrial membrane integrity, and augmenting ATP levels. Compounds with such properties may find utility in treating mitochondrial and neurodegenerative diseases such as FRDA and Alzheimer’s disease. |
| Author | Roy, Basab Khdour, Omar M Hecht, Sidney M Arce, Pablo M |
| AuthorAffiliation | Arizona State University |
| AuthorAffiliation_xml | – name: Arizona State University |
| Author_xml | – sequence: 1 givenname: Omar M surname: Khdour fullname: Khdour, Omar M – sequence: 2 givenname: Pablo M surname: Arce fullname: Arce, Pablo M – sequence: 3 givenname: Basab surname: Roy fullname: Roy, Basab – sequence: 4 givenname: Sidney M surname: Hecht fullname: Hecht, Sidney M email: sid.hecht@asu.edu |
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| CitedBy_id | crossref_primary_10_1016_j_jalz_2017_12_005 crossref_primary_10_4155_fmc_2018_0481 crossref_primary_10_1016_j_bmc_2017_08_021 crossref_primary_10_1016_j_bmc_2014_06_040 crossref_primary_10_3390_nano8020087 crossref_primary_10_1016_j_bmc_2018_05_005 crossref_primary_10_1021_cr500226n crossref_primary_10_1177_08853282221111656 crossref_primary_10_1016_j_bmc_2016_08_039 crossref_primary_10_1016_j_bmc_2017_01_030 crossref_primary_10_1021_cn500323q |
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| Keywords | electron transport chain Mitochondrial dysfunction cytoprotection lipid peroxidation adenosine triphosphate OXIDATIVE STRESS VITAMIN-E REACTIVE OXYGEN ANTIOXIDANTS ANALOGS IDEBENONE ATAXIA |
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| Title | An Optimized Pyrimidinol Multifunctional Radical Quencher |
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