Features of Idebenone and Related Short-Chain Quinones that Rescue ATP Levels under Conditions of Impaired Mitochondrial Complex I
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{"title"=>"Features of idebenone and related short-chain quinones that rescue ATP levels under conditions of impaired mitochondrial complex I", "type"=>"journal", "authors"=>[{"first_name"=>"Michael", "last_name"=>"Erb", "scopus_author_id"=>"57196563244"}, {"first_name"=>"Barbara", "last_name"=>"Hoffmann-Enger", "scopus_author_id"=>"28367666900"}, {"first_name"=>"Holger", "last_name"=>"Deppe", "scopus_author_id"=>"9942969900"}, {"first_name"=>"Michael", "last_name"=>"Soeberdt", "scopus_author_id"=>"6507420890"}, {"first_name"=>"Roman H.", "last_name"=>"Haefeli", "scopus_author_id"=>"46960953800"}, {"first_name"=>"Christian", "last_name"=>"Rummey", "scopus_author_id"=>"6602786187"}, {"first_name"=>"Achim", "last_name"=>"Feurer", "scopus_author_id"=>"6507406051"}, {"first_name"=>"Nuri", "last_name"=>"Gueven", "scopus_author_id"=>"6603624676"}], "year"=>2012, "source"=>"PLoS ONE", "identifiers"=>{"sgr"=>"84860477515", "doi"=>"10.1371/journal.pone.0036153", "pui"=>"364720932", "pmid"=>"22558363", "scopus"=>"2-s2.0-84860477515", "issn"=>"19326203"}, "id"=>"4e0b1379-9ec4-3850-b5f7-ee1379ba20d9", "abstract"=>"Short-chain quinones have been investigated as therapeutic molecules due to their ability to modulate cellular redox reactions, mitochondrial electron transfer and oxidative stress, which are pathologically altered in many mitochondrial and neuromuscular disorders. Recently, we and others described that certain short-chain quinones are able to bypass a deficiency in complex I by shuttling electrons directly from the cytoplasm to complex III of the mitochondrial respiratory chain to produce ATP. Although this energy rescue activity is highly interesting for the therapy of disorders associated with complex I dysfunction, no structure-activity-relationship has been reported for short-chain quinones so far. Using a panel of 70 quinones, we observed that the capacity for this cellular energy rescue as well as their effect on lipid peroxidation was influenced more by the physicochemical properties (in particular logD) of the whole molecule than the quinone moiety itself. Thus, the observed correlations allow us to explain the differential biological activities and therapeutic potential of short-chain quinones for the therapy of disorders associated with mitochondrial complex I dysfunction and/or oxidative stress.", "link"=>"http://www.mendeley.com/research/features-idebenone-related-shortchain-quinones-rescue-atp-levels-under-conditions-impaired-mitochond", "reader_count"=>32, "reader_count_by_academic_status"=>{"Researcher"=>9, "Student > Doctoral Student"=>3, "Student > Ph. D. Student"=>11, "Other"=>4, "Student > Bachelor"=>3, "Professor"=>1, "Student > Master"=>1}, "reader_count_by_user_role"=>{"Researcher"=>9, "Student > Doctoral Student"=>3, "Student > Ph. D. Student"=>11, "Other"=>4, "Student > Bachelor"=>3, "Professor"=>1, "Student > Master"=>1}, "reader_count_by_subject_area"=>{"Biochemistry, Genetics and Molecular Biology"=>6, "Agricultural and Biological Sciences"=>12, "Medicine and Dentistry"=>4, "Neuroscience"=>1, "Pharmacology, Toxicology and Pharmaceutical Science"=>3, "Chemistry"=>6}, "reader_count_by_subdiscipline"=>{"Medicine and Dentistry"=>{"Medicine and Dentistry"=>4}, "Neuroscience"=>{"Neuroscience"=>1}, "Chemistry"=>{"Chemistry"=>6}, "Agricultural and Biological Sciences"=>{"Agricultural and Biological Sciences"=>12}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>6}, "Pharmacology, Toxicology and Pharmaceutical Science"=>{"Pharmacology, Toxicology and Pharmaceutical Science"=>3}}, "reader_count_by_country"=>{"United States"=>2, "United Kingdom"=>1}, "group_count"=>4}

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/645907"], "description"=>"<p>(A) ATP rescue by 4 different quinones was determined in rotenone-treated rat myoblasts (L6). ATP rescue is defined as the percentage of quinone-induced increase in ATP levels in the presence of rotenone, relative to the ATP reduction by rotenone alone. Bars represent the mean of 3 wells, error bars represent standard deviation. (B) ATP rescue by different quinones is not cell type- or species-dependent. ATP rescue by 70 quinones was determined in primary human myoblasts (9Te), rat myoblasts (L6) and human immortalized hepatic cells (HepG2). Correlation of values derived from rat myoblasts (L6) and human myoblasts (9Te), are shown (R<sup>2</sup> = 0.8434). Similar results were obtained for rat myoblasts (L6) vs. human immortalized hepatic cells (HepG2) as well as human myoblasts (9Te) vs. human immortalized hepatic cells (HepG2) (<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s001\" target=\"_blank\">Figure S1</a>). For reasons of clarity, error bars were omitted from (B) but standard deviation (SD) values can be found in Supplementary <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s005\" target=\"_blank\">Table S2</a> which lists all results.</p>", "links"=>[], "tags"=>["atp", "rotenone"], "article_id"=>316393, "categories"=>["Physiology", "Biochemistry", "Chemistry", "Pharmacology"], "users"=>["Michael Erb", "Barbara Hoffmann-Enger", "Holger Deppe", "Michael Soeberdt", "Roman H. Haefeli", "Christian Rummey", "Achim Feurer", "Nuri Gueven"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0036153.g001", "stats"=>{"downloads"=>1, "page_views"=>14, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Efficacy_of_ATP_rescue_in_the_presence_of_rotenone_by_different_quinones_/316393", "title"=>"Efficacy of ATP rescue in the presence of rotenone by different quinones.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-04-27 01:46:33"}
  • {"files"=>["https://ndownloader.figshare.com/files/646583"], "description"=>"<p>Only quinones with a logD<7 are reduced by cytoplasmic NQO1 or other reductases. Once reduced, and depending on permissive lipophilicity characteristics (27), they can shuttle electrons into the mitochondrial respiratory chain by reducing complex III or integrate into lipid membranes to prevent lipid peroxidation. However, these effects manifest only, if the compounds upon oxidation can return to the cytoplasm to be reduced again, which allows them to act in a catalytical manner. (N: no, Y: yes).</p>", "links"=>[], "tags"=>["requirements", "cytoplasmic-mitochondrial", "electron", "atp"], "article_id"=>317064, "categories"=>["Physiology", "Biochemistry", "Chemistry", "Pharmacology"], "users"=>["Michael Erb", "Barbara Hoffmann-Enger", "Holger Deppe", "Michael Soeberdt", "Roman H. Haefeli", "Christian Rummey", "Achim Feurer", "Nuri Gueven"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0036153.g005", "stats"=>{"downloads"=>1, "page_views"=>4, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Schematic_representation_of_the_requirements_for_cytoplasmic_mitochondrial_electron_transfer_and_ATP_rescue_/317064", "title"=>"Schematic representation of the requirements for cytoplasmic-mitochondrial electron transfer and ATP rescue.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-04-27 01:57:44"}
  • {"files"=>["https://ndownloader.figshare.com/files/646032"], "description"=>"<p><i>In vitro</i> reduction of 70 quinone derivatives by recombinant NQO1 was correlated to their calculated logD values. Each data point represents the mean from 2 independent experiments (see <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s004\" target=\"_blank\">Table S1</a> for details about the quinones used). For reasons of clarity, error bars were omitted from graphs but standard deviation values can be found in Supplementary <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s005\" target=\"_blank\">Table S2</a> which lists all results.</p>", "links"=>[], "tags"=>["quinones", "nqo1", "assay", "logd"], "article_id"=>316515, "categories"=>["Physiology", "Biochemistry", "Chemistry", "Pharmacology"], "users"=>["Michael Erb", "Barbara Hoffmann-Enger", "Holger Deppe", "Michael Soeberdt", "Roman H. Haefeli", "Christian Rummey", "Achim Feurer", "Nuri Gueven"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0036153.g002", "stats"=>{"downloads"=>2, "page_views"=>9, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Reduction_of_quinones_by_NQO1_in_a_cell_free_assay_system_is_dependent_on_their_logD_values_/316515", "title"=>"Reduction of quinones by NQO1 in a cell free assay system is dependent on their logD values.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-04-27 01:48:35"}
  • {"files"=>["https://ndownloader.figshare.com/files/646255"], "description"=>"<p>(A) Cellular ATP rescue capacity was correlated to the rate of reduction by recombinant NQO1 enzyme in a cell-free assay. Clear outliers (boxed compounds, red circles) are either mitochondrially targeted (#69, 70) or have logD values <2. (Compare to <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone-0036153-g003\" target=\"_blank\">Figure 3B</a>). Similarly, some compounds demonstrated good ATP rescue activity while being poorly reduced by NQO1 in vitro (boxed compounds, blue circles). Of all compounds tested, about 14% demonstrated very good (>80%) ATP rescue activity (green circles). (B) ATP rescue ability was correlated to the logD value of each compound. Data represent values for rat myoblasts (L6). Similar results were obtained for human immortalized hepatic cells (HepG2) and human myoblasts (9Te) (<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s002\" target=\"_blank\">Figure S2</a>). The data represent one typical experiment out of three experiments, which yielded similar results. The values are means ± SD, n = 3 replicate wells. Color coding of results is analogous to (A). For reasons of clarity, error bars were omitted from graphs but standard deviation values can be found in <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s005\" target=\"_blank\">Table S2</a>, which lists all results.</p>", "links"=>[], "tags"=>["atp", "quinones", "rotenone", "logd"], "article_id"=>316738, "categories"=>["Physiology", "Biochemistry", "Chemistry", "Pharmacology"], "users"=>["Michael Erb", "Barbara Hoffmann-Enger", "Holger Deppe", "Michael Soeberdt", "Roman H. Haefeli", "Christian Rummey", "Achim Feurer", "Nuri Gueven"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0036153.g003", "stats"=>{"downloads"=>1, "page_views"=>10, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Cellular_ATP_rescue_by_different_quinones_in_the_presence_of_rotenone_is_dependent_on_their_logD_value_/316738", "title"=>"Cellular ATP rescue by different quinones in the presence of rotenone is dependent on their logD value.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-04-27 01:52:18"}
  • {"files"=>["https://ndownloader.figshare.com/files/333370", "https://ndownloader.figshare.com/files/333623", "https://ndownloader.figshare.com/files/333727", "https://ndownloader.figshare.com/files/333804", "https://ndownloader.figshare.com/files/333897"], "description"=>"<div><p>Short-chain quinones have been investigated as therapeutic molecules due to their ability to modulate cellular redox reactions, mitochondrial electron transfer and oxidative stress, which are pathologically altered in many mitochondrial and neuromuscular disorders. Recently, we and others described that certain short-chain quinones are able to bypass a deficiency in complex I by shuttling electrons directly from the cytoplasm to complex III of the mitochondrial respiratory chain to produce ATP. Although this energy rescue activity is highly interesting for the therapy of disorders associated with complex I dysfunction, no structure-activity-relationship has been reported for short-chain quinones so far. Using a panel of 70 quinones, we observed that the capacity for this cellular energy rescue as well as their effect on lipid peroxidation was influenced more by the physicochemical properties (in particular logD) of the whole molecule than the quinone moiety itself. Thus, the observed correlations allow us to explain the differential biological activities and therapeutic potential of short-chain quinones for the therapy of disorders associated with mitochondrial complex I dysfunction and/or oxidative stress.</p> </div>", "links"=>[], "tags"=>["features", "idebenone", "short-chain", "quinones", "atp", "levels", "conditions", "impaired", "mitochondrial"], "article_id"=>125838, "categories"=>["Physiology", "Biochemistry", "Chemistry", "Pharmacology"], "users"=>["Michael Erb", "Barbara Hoffmann-Enger", "Holger Deppe", "Michael Soeberdt", "Roman H. Haefeli", "Christian Rummey", "Achim Feurer", "Nuri Gueven"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0036153.s001", "https://dx.doi.org/10.1371/journal.pone.0036153.s002", "https://dx.doi.org/10.1371/journal.pone.0036153.s003", "https://dx.doi.org/10.1371/journal.pone.0036153.s004", "https://dx.doi.org/10.1371/journal.pone.0036153.s005"], "stats"=>{"downloads"=>5, "page_views"=>16, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/Features_of_Idebenone_and_Related_Short_Chain_Quinones_that_Rescue_ATP_Levels_under_Conditions_of_Impaired_Mitochondrial_Complex_I/125838", "title"=>"Features of Idebenone and Related Short-Chain Quinones that Rescue ATP Levels under Conditions of Impaired Mitochondrial Complex I", "pos_in_sequence"=>0, "defined_type"=>4, "published_date"=>"2012-04-27 01:37:18"}
  • {"files"=>["https://ndownloader.figshare.com/files/646380"], "description"=>"<p>(A) Cellular levels of basal lipid peroxidation were measured using BODIPY-C<sub>11</sub> dye and correlated with the respective logD value. Response to DMSO was set to 100%. Compounds #69 and 70 represent two mitochondrially targeted idebenone molecules. The values are means ± SD, n = 3 replicate wells. (B) Lipid peroxidation values were correlated to ATP rescue efficiency of each quinone. Data represent values for L6 cells. Similar results were obtained for human immortalized hepatic cells (HepG2) and human myoblasts (9Te) (<a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s003\" target=\"_blank\">Figure S3</a>). For reasons of clarity, the highly prooxidative (>200%) compounds (# 36,44,52,63 64) and error bars were omitted from graphs but standard deviation values can be found in Supplementary <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0036153#pone.0036153.s005\" target=\"_blank\">Table S2</a>, which lists all results.</p>", "links"=>[], "tags"=>["quinones", "basal", "lipid", "peroxidation", "logd"], "article_id"=>316863, "categories"=>["Physiology", "Biochemistry", "Chemistry", "Pharmacology"], "users"=>["Michael Erb", "Barbara Hoffmann-Enger", "Holger Deppe", "Michael Soeberdt", "Roman H. Haefeli", "Christian Rummey", "Achim Feurer", "Nuri Gueven"], "doi"=>"https://dx.doi.org/10.1371/journal.pone.0036153.g004", "stats"=>{"downloads"=>2, "page_views"=>13, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_quinones_on_basal_lipid_peroxidation_is_dependent_on_their_logD_value_/316863", "title"=>"Effect of quinones on basal lipid peroxidation is dependent on their logD value.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2012-04-27 01:54:23"}

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Relative Metric

{"start_date"=>"2012-01-01T00:00:00Z", "end_date"=>"2012-12-31T00:00:00Z", "subject_areas"=>[{"subject_area"=>"/Biology and life sciences", "average_usage"=>[322, 550, 671, 773, 864, 955, 1048, 1135, 1223, 1308, 1387, 1465, 1534, 1602, 1673, 1744, 1813, 1885, 1955, 2026, 2093, 2160, 2228, 2290, 2349]}, {"subject_area"=>"/Physical sciences", "average_usage"=>[304, 506, 616, 712, 799, 879, 968, 1052, 1134, 1212, 1284, 1357, 1427, 1494, 1557, 1621, 1689, 1756, 1823, 1883, 1944, 1997, 2056, 2118, 2171]}, {"subject_area"=>"/Physical sciences/Chemistry", "average_usage"=>[302, 508, 622, 720, 804, 888, 973, 1054, 1141, 1219, 1299, 1370, 1442, 1511, 1574, 1644, 1711, 1782, 1846, 1911, 1971, 2030, 2097, 2155, 2217]}]}
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