Dihydrolipoic acid (BioDeep_00001873844)

Main id: BioDeep_00000003942

 

PANOMIX_OTCML-2023


代谢物信息卡片


Dihydrolipoic acid

化学式: C8H16O2S2 (208.0592)
中文名称: 二氢硫辛酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(CCC(=O)O)CC(CCS)S
InChI: InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)

描述信息

A thio-fatty acid that is reduced form of lipoic acid. A potent antioxidant shown to directly destroy superoxide, hydroperoxy and hydroxyl radicals; also has neuroprotective and anti-tumour effects.
D020011 - Protective Agents > D000975 - Antioxidants

同义名列表

2 个代谢物同义名

Dihydrolipoic acid; Dihydrolipoate



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 11 AKT1, ALB, CASP3, CAT, MAPK8, MPST, NFE2L2, NLRP3, TXN, TYR, XDH
Peripheral membrane protein 1 HSD17B6
Nucleus 9 AKT1, ALB, CASP3, JUND, MAPK8, MPO, NFE2L2, NLRP3, TXN
cytosol 11 AKT1, ALB, CASP3, CAT, GSR, MAPK8, MB, NFE2L2, NLRP3, TXN, XDH
centrosome 2 ALB, NFE2L2
nucleoplasm 7 AKT1, CASP3, JUND, MAPK8, MPO, NFE2L2, TXN
RNA polymerase II transcription regulator complex 2 JUND, NFE2L2
Cell membrane 2 AKT1, TNF
lamellipodium 1 AKT1
Early endosome membrane 1 HSD17B6
Golgi apparatus membrane 1 NLRP3
Synapse 2 MAPK8, MPST
cell cortex 1 AKT1
cell surface 1 TNF
glutamatergic synapse 2 AKT1, CASP3
Golgi apparatus 2 ALB, NFE2L2
Golgi membrane 2 INS, NLRP3
neuronal cell body 2 CASP3, TNF
postsynapse 1 AKT1
Cytoplasm, cytosol 2 NFE2L2, NLRP3
Lysosome 2 MPO, TYR
plasma membrane 4 AKT1, F2, NFE2L2, TNF
Membrane 3 AKT1, CAT, NLRP3
axon 1 MAPK8
extracellular exosome 8 ALB, CAT, F2, GSR, MB, MPO, MPST, TXN
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 ALB, HSD17B6, NLRP3
extracellular space 7 ALB, F2, INS, MPO, TNF, TST, XDH
perinuclear region of cytoplasm 1 TYR
mitochondrion 5 CAT, GSR, MPST, NLRP3, TST
protein-containing complex 3 AKT1, ALB, CAT
intracellular membrane-bounded organelle 4 CAT, HSD17B6, MPO, TYR
Microsome membrane 1 HSD17B6
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TYR
Secreted 5 ALB, F2, INS, NLRP3, TXN
extracellular region 8 ALB, CAT, F2, INS, MPO, NLRP3, TNF, TXN
Mitochondrion matrix 1 TST
mitochondrial matrix 4 CAT, GSR, MPST, TST
anchoring junction 1 ALB
transcription regulator complex 1 JUND
external side of plasma membrane 2 GSR, TNF
microtubule cytoskeleton 1 AKT1
Melanosome membrane 1 TYR
sarcoplasm 1 MB
cell-cell junction 1 AKT1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Membrane raft 1 TNF
focal adhesion 1 CAT
spindle 1 AKT1
Peroxisome 2 CAT, XDH
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 F2
secretory granule 1 MPO
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
neuron projection 1 MPST
ciliary basal body 2 AKT1, ALB
chromatin 2 JUND, NFE2L2
mediator complex 1 NFE2L2
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 2 ALB, F2
Endomembrane system 1 NLRP3
endosome lumen 1 INS
microtubule organizing center 1 NLRP3
Melanosome 1 TYR
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 3 ALB, F2, INS
transcription repressor complex 1 JUND
platelet alpha granule lumen 1 ALB
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
phagocytic vesicle lumen 1 MPO
Synapse, synaptosome 1 MPST
protein-DNA complex 1 NFE2L2
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Cytoplasm, sarcoplasm 1 MB
catalase complex 1 CAT
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Hsueh-Hsiao Wang, Cheng-An J Lin, Ya-Ming Tseng, Hsin-I Lee, Yi-Nan Lee, Hung-I Yeh, Po-Sheng Yang, Hsien-Yu Peng, Yih-Jer Wu. Dihydrolipoic acid-coated gold nanocluster bioactivity against senescence and inflammation through the mitochondria-mediated JNK/AP-1 pathway. Nanomedicine : nanotechnology, biology, and medicine. 2021 08; 36(?):102427. doi: 10.1016/j.nano.2021.102427. [PMID: 34174418]
  • Woody Perng, Goutam Palui, Wentao Wang, Hedi Mattoussi. Elucidating the Role of Surface Coating in the Promotion or Prevention of Protein Corona around Quantum Dots. Bioconjugate chemistry. 2019 09; 30(9):2469-2480. doi: 10.1021/acs.bioconjchem.9b00549. [PMID: 31448900]
  • Diego Bouzas-Ramos, Marta García-Cortes, Alfredo Sanz-Medel, Jorge Ruiz Encinar, José M Costa-Fernández. Assessment of the removal of side nanoparticulated populations generated during one-pot synthesis by asymmetric flow field-flow fractionation coupled to elemental mass spectrometry. Journal of chromatography. A. 2017 Oct; 1519(?):156-161. doi: 10.1016/j.chroma.2017.08.068. [PMID: 28888679]
  • Zhong-Wei Zhang, Sha Luo, Gong-Chang Zhang, Ling-Yang Feng, Chong Zheng, Yang-Hong Zhou, Jun-Bo Du, Ming Yuan, Yang-Er Chen, Chang-Quan Wang, Wen-Juan Liu, Xiao-Chao Xu, Yong Hu, Su-Lan Bai, Dong-Dong Kong, Shu Yuan, Yi-Kun He. Nitric oxide induces monosaccharide accumulation through enzyme S-nitrosylation. Plant, cell & environment. 2017 Sep; 40(9):1834-1848. doi: 10.1111/pce.12989. [PMID: 28556250]
  • Matías Regiart, Martin A Fernández-Baldo, Jhonny Villarroel-Rocha, Germán A Messina, Franco A Bertolino, Karim Sapag, Aaron T Timperman, Julio Raba. Microfluidic immunosensor based on mesoporous silica platform and CMK-3/poly-acrylamide-co-methacrylate of dihydrolipoic acid modified gold electrode for cancer biomarker detection. Analytica chimica acta. 2017 Apr; 963(?):83-92. doi: 10.1016/j.aca.2017.01.029. [PMID: 28335979]
  • Anna Bilska-Wilkosz, Małgorzata Iciek, Danuta Kowalczyk-Pachel, Magdalena Górny, Maria Sokołowska-Jeżewicz, Lidia Włodek. Lipoic Acid as a Possible Pharmacological Source of Hydrogen Sulfide/Sulfane Sulfur. Molecules (Basel, Switzerland). 2017 Mar; 22(3):. doi: 10.3390/molecules22030388. [PMID: 28257119]
  • Mengna Xia, Anjeza Erickson, Xiaohua Yi, Régis Moreau. Mapping the response of human fibroblast growth factor 21 (FGF21) promoter to serum availability and lipoic acid in HepG2 hepatoma cells. Biochimica et biophysica acta. 2016 Mar; 1860(3):498-507. doi: 10.1016/j.bbagen.2015.12.004. [PMID: 26691139]
  • Muhammad Imran Khan, Zafar Iqbal, Abad Khan. Simultaneous determination of the endogenous free α-lipoic acid and dihydrolipoic acid in human plasma and erythrocytes by RP-HPLC coupled with electrochemical detector. Methods in molecular biology (Clifton, N.J.). 2015; 1208(?):345-60. doi: 10.1007/978-1-4939-1441-8_25. [PMID: 25323519]
  • Chaofu Ke, Yan Hou, Haiyu Zhang, Kai Yang, Jingtao Wang, Bing Guo, Fan Zhang, Hailong Li, Xiaohua Zhou, Ying Li, Kang Li. Plasma Metabolic Profiles in Women are Menopause Dependent. PloS one. 2015; 10(11):e0141743. doi: 10.1371/journal.pone.0141743. [PMID: 26580805]
  • Pei-Suen Tsou, Beatrix Balogh, Adam J Pinney, George Zakhem, Ann Lozier, M Asif Amin, William A Stinson, Elena Schiopu, Dinesh Khanna, David A Fox, Alisa E Koch. Lipoic acid plays a role in scleroderma: insights obtained from scleroderma dermal fibroblasts. Arthritis research & therapy. 2014; 16(5):411. doi: 10.1186/s13075-014-0411-6. [PMID: 25123250]
  • Valérie Gautier, Hai-Tuong Le, Abderrahim Malki, Nadia Messaoudi, Teresa Caldas, Fatoum Kthiri, Ahmed Landoulsi, Gilbert Richarme. YajL, the prokaryotic homolog of the Parkinsonism-associated protein DJ-1, protects cells against protein sulfenylation. Journal of molecular biology. 2012 Aug; 421(4-5):662-70. doi: 10.1016/j.jmb.2012.01.047. [PMID: 22321799]
  • Xiaofang Qiu, Caiyan Lei, Lili Huang, Xing Li, He Hao, Zhigao Du, Hong Wang, Hechun Ye, Ludger Beerhues, Benye Liu. Endogenous hydrogen peroxide is a key factor in the yeast extract-induced activation of biphenyl biosynthesis in cell cultures of Sorbus aucuparia. Planta. 2012 Jan; 235(1):217-23. doi: 10.1007/s00425-011-1545-2. [PMID: 22086110]
  • XiaoXiao Huang, YiJuan Long, HaiJie Zhang, QinLong Wang, Rui Zhu, HuZhi Zheng. Gold nanoparticles as a probe for prion determination via resonance light scattering method. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2012; 28(5):475-9. doi: 10.2116/analsci.28.475. [PMID: 22687927]
  • Patrick M Finnegan, Weihua Chen. Arsenic toxicity: the effects on plant metabolism. Frontiers in physiology. 2012; 3(?):182. doi: 10.3389/fphys.2012.00182. [PMID: 22685440]
  • Ramar Perumal Samy, Ponnampalam Gopalakrishnakone, Vincent Tk Chow. Therapeutic application of natural inhibitors against snake venom phospholipase A(2). Bioinformation. 2012; 8(1):48-57. doi: 10.6026/97320630008048. [PMID: 22359435]
  • Zheng-Jiang Zhu, Yi-Cheun Yeh, Rui Tang, Bo Yan, Joshua Tamayo, Richard W Vachet, Vincent M Rotello. Stability of quantum dots in live cells. Nature chemistry. 2011 Oct; 3(12):963-8. doi: 10.1038/nchem.1177. [PMID: 22109277]
  • Marie Vancová, Miroslav Slouf, Jan Langhans, Eva Pavlová, Jana Nebesářová. Application of colloidal palladium nanoparticles for labeling in electron microscopy. Microscopy and microanalysis : the official journal of Microscopy Society of America, Microbeam Analysis Society, Microscopical Society of Canada. 2011 Oct; 17(5):810-6. doi: 10.1017/s1431927611000547. [PMID: 21902867]
  • Abad Khan, Zafar Iqbal, David G Watson, Amirzada Khan, Inamullah Khan, Naveed Muhammad, Salar Muhammad, Hashmat Ara Nasib, Naveed Iqbal, Faiz-Ur-Rehman, Muhammad Kashif. Simultaneous determination of lipoic acid (LA) and dihydrolipoic acid (DHLA) in human plasma using high-performance liquid chromatography coupled with electrochemical detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Jun; 879(20):1725-31. doi: 10.1016/j.jchromb.2011.04.017. [PMID: 21550862]
  • Gun-Dong Kim, Tae-Ho Kim, An-Hee Jang, Hyun-Jong Ahn, Yong Seek Park, Cheung-Seog Park. α-Lipoic acid suppresses the development of DNFB-induced atopic dermatitis-like symptoms in NC/Nga mice. Experimental dermatology. 2011 Feb; 20(2):97-101. doi: 10.1111/j.1600-0625.2010.01165.x. [PMID: 21166725]
  • Frank Morgner, Stefan Stufler, Daniel Geissler, Igor L Medintz, W Russ Algar, Kimihiro Susumu, Michael H Stewart, Juan B Blanco-Canosa, Philip E Dawson, Niko Hildebrandt. Terbium to quantum dot FRET bioconjugates for clinical diagnostics: influence of human plasma on optical and assembly properties. Sensors (Basel, Switzerland). 2011; 11(10):9667-84. doi: 10.3390/s111009667. [PMID: 22163719]
  • Peng Chen, Qiu-Gang Ma, Cheng Ji, Jian-Yun Zhang, Li-Hong Zhao, Yong Zhang, Yong-Ze Jie. Dietary lipoic acid influences antioxidant capability and oxidative status of broilers. International journal of molecular sciences. 2011; 12(12):8476-88. doi: 10.3390/ijms12128476. [PMID: 22272085]
  • Cimen Karasu. Glycoxidative stress and cardiovascular complications in experimentally-induced diabetes: effects of antioxidant treatment. The open cardiovascular medicine journal. 2010 Nov; 4(?):240-56. doi: 10.2174/1874192401004010240. [PMID: 21270942]
  • Trajce Stafilov, Milihate Aliu, Robert Sajn. Arsenic in surface soils affected by mining and metallurgical processing in K. Mitrovica region, Kosovo. International journal of environmental research and public health. 2010 11; 7(11):4050-61. doi: 10.3390/ijerph7114050. [PMID: 21139876]
  • Charles H Vannoy, Roger M Leblanc. Effects of DHLA-capped CdSe/ZnS quantum dots on the fibrillation of human serum albumin. The journal of physical chemistry. B. 2010 Aug; 114(33):10881-8. doi: 10.1021/jp1045904. [PMID: 20681557]
  • Chong-Kuei Lii, Kai-Li Liu, Yi-Ping Cheng, Ai-Hsuan Lin, Haw-Wen Chen, Chia-Wen Tsai. Sulforaphane and alpha-lipoic acid upregulate the expression of the pi class of glutathione S-transferase through c-jun and Nrf2 activation. The Journal of nutrition. 2010 May; 140(5):885-92. doi: 10.3945/jn.110.121418. [PMID: 20237067]
  • Pinar Atukeren, Seval Aydin, Ezel Uslu, M Koray Gumustas, Ufuk Cakatay. Redox homeostasis of albumin in relation to alpha-lipoic acid and dihydrolipoic acid. Oxidative medicine and cellular longevity. 2010 May; 3(3):206-13. doi: 10.4161/oxim.3.3.11786. [PMID: 20716945]
  • Raghu G Nath, Mona Y Wu, Armaghan Emami, Fung-Lung Chung. Effects of epigallocatechin gallate, L-ascorbic acid, alpha-tocopherol, and dihydrolipoic acid on the formation of deoxyguanosine adducts derived from lipid peroxidation. Nutrition and cancer. 2010; 62(5):622-9. doi: 10.1080/01635580903532424. [PMID: 20574923]
  • Atef M Al-Attar. Physiological and histopathological investigations on the effects of alpha-lipoic acid in rats exposed to malathion. Journal of biomedicine & biotechnology. 2010; 2010(?):203503. doi: 10.1155/2010/203503. [PMID: 20454535]
  • M G Carbonelli, L Di Renzo, M Bigioni, N Di Daniele, A De Lorenzo, M A Fusco. Alpha-lipoic acid supplementation: a tool for obesity therapy?. Current pharmaceutical design. 2010; 16(7):840-6. doi: 10.2174/138161210790883589. [PMID: 20388095]
  • Mario Menschikowski, Albert Hagelgans, Graeme Eisenhofer, Gabriele Siegert. Regulation of endothelial protein C receptor shedding by cytokines is mediated through differential activation of MAP kinase signaling pathways. Experimental cell research. 2009 Sep; 315(15):2673-82. doi: 10.1016/j.yexcr.2009.05.015. [PMID: 19467228]
  • Santhrani Thaakur, G Himabindhu. Effect of alpha lipoic acid on the tardive dyskinesia and oxidative stress induced by haloperidol in rats. Journal of neural transmission (Vienna, Austria : 1996). 2009 Jul; 116(7):807-14. doi: 10.1007/s00702-009-0232-y. [PMID: 19444377]
  • Anna Goraca, Katarzyna Asłanowicz-Antkowiak. Prophylaxis with alpha-lipoic acid against lipopolysaccharide-induced brain injury in rats. Archivum immunologiae et therapiae experimentalis. 2009 Mar; 57(2):141-6. doi: 10.1007/s00005-009-0015-z. [PMID: 19333732]
  • Magdalena Dudek, Marek Bednarski, Anna Bilska, Małgorzata Iciek, Maria Sokołowska-Jezewicz, Barbara Filipek, Lidia Włodek. The role of lipoic acid in prevention of nitroglycerin tolerance. European journal of pharmacology. 2008 Sep; 591(1-3):203-10. doi: 10.1016/j.ejphar.2008.06.073. [PMID: 18616939]
  • Zulkhairi Amom, Zaiton Zakaria, Jamaluddin Mohamed, Azrina Azlan, Hasnah Bahari, Mohd Taufik Hidayat Baharuldin, Mohd Aris Moklas, Khairul Osman, Zanariyah Asmawi, Mohd Kamal Nik Hassan. Lipid lowering effect of antioxidant alpha-lipoic Acid in experimental atherosclerosis. Journal of clinical biochemistry and nutrition. 2008 Sep; 43(2):88-94. doi: 10.3164/jcbn.2008051. [PMID: 18818758]
  • Emma E Lees, Menachem J Gunzburg, Tich-Lam Nguyen, Geoffrey J Howlett, Julie Rothacker, Edouard C Nice, Andrew H A Clayton, Paul Mulvaney. Experimental determination of quantum dot size distributions, ligand packing densities, and bioconjugation using analytical ultracentrifugation. Nano letters. 2008 Sep; 8(9):2883-90. doi: 10.1021/nl801629f. [PMID: 18665653]
  • Matteo Beretta, Karl Gruber, Alexander Kollau, Michael Russwurm, Doris Koesling, Walter Goessler, Wing Ming Keung, Kurt Schmidt, Bernd Mayer. Bioactivation of nitroglycerin by purified mitochondrial and cytosolic aldehyde dehydrogenases. The Journal of biological chemistry. 2008 Jun; 283(26):17873-80. doi: 10.1074/jbc.m801182200. [PMID: 18450747]
  • S Ghibu, C Richard, S Delemasure, C Vergely, C Mogosan, A Muresan. [An endogenous dithiol with antioxidant properties: alpha-lipoic acid, potential uses in cardiovascular diseases]. Annales de cardiologie et d'angeiologie. 2008 Jun; 57(3):161-5. doi: 10.1016/j.ancard.2008.02.018. [PMID: 18571145]
  • Anna Bilska, Magdalena Dudek, Małgorzata Iciek, Inga Kwiecień, Maria Sokołowska-Jezewicz, Barbara Filipek, Lidia Włodek. Biological actions of lipoic acid associated with sulfane sulfur metabolism. Pharmacological reports : PR. 2008 Mar; 60(2):225-32. doi: . [PMID: 18443384]
  • Andrew J Percy, Jürgen Gailer. Methylated trivalent arsenic-glutathione complexes are more stable than their arsenite analog. Bioinorganic chemistry and applications. 2008; ?(?):539082. doi: 10.1155/2008/539082. [PMID: 18509491]
  • Yevgeniya I Shurubor, Wayne R Matson, Walter C Willett, Susan E Hankinson, Bruce S Kristal. Biological variability dominates and influences analytical variance in HPLC-ECD studies of the human plasma metabolome. BMC clinical pathology. 2007 Nov; 7(?):9. doi: 10.1186/1472-6890-7-9. [PMID: 17997839]
  • Victor Paromov, Zacharias Suntres, Milton Smith, William L Stone. Sulfur mustard toxicity following dermal exposure: role of oxidative stress, and antioxidant therapy. Journal of burns and wounds. 2007 Oct; 7(?):e7. doi: ". [PMID: 18091984]
  • Lina Holmquist, Grant Stuchbury, Katrin Berbaum, Sonja Muscat, Simon Young, Klaus Hager, Jürgen Engel, Gerald Münch. Lipoic acid as a novel treatment for Alzheimer's disease and related dementias. Pharmacology & therapeutics. 2007 Jan; 113(1):154-64. doi: 10.1016/j.pharmthera.2006.07.001. [PMID: 16989905]
  • Noor Mohamed Jameel, Mysore A Shekhar, Bannikuppe S Vishwanath. Alpha-lipoic acid: an inhibitor of secretory phospholipase A2 with anti-inflammatory activity. Life sciences. 2006 Dec; 80(2):146-53. doi: 10.1016/j.lfs.2006.08.032. [PMID: 17011589]
  • Detcho A Stoyanovsky, Yulia Y Tyurina, Vladimir A Tyurin, Deepthi Anand, Dhara N Mandavia, David Gius, Juliana Ivanova, Bruce Pitt, Timothy R Billiar, Valerian E Kagan. Thioredoxin and lipoic acid catalyze the denitrosation of low molecular weight and protein S-nitrosothiols. Journal of the American Chemical Society. 2005 Nov; 127(45):15815-23. doi: 10.1021/ja0529135. [PMID: 16277524]
  • Maria Mercedes Meza, Lizhi Yu, Yelitza Y Rodriguez, Mischa Guild, David Thompson, A Jay Gandolfi, Walter T Klimecki. Developmentally restricted genetic determinants of human arsenic metabolism: association between urinary methylated arsenic and CYT19 polymorphisms in children. Environmental health perspectives. 2005 Jun; 113(6):775-81. doi: 10.1289/ehp.7780. [PMID: 15929903]
  • Olga L Valenzuela, Victor H Borja-Aburto, Gonzalo G Garcia-Vargas, Martha B Cruz-Gonzalez, Eliud A Garcia-Montalvo, Emma S Calderon-Aranda, Luz M Del Razo. Urinary trivalent methylated arsenic species in a population chronically exposed to inorganic arsenic. Environmental health perspectives. 2005 Mar; 113(3):250-4. doi: 10.1289/ehp.7519. [PMID: 15743710]
  • Ana S Hill, Quinton R Rogers, Sharron L O'Neill, Mary M Christopher. Effects of dietary antioxidant supplementation before and after oral acetaminophen challenge in cats. American journal of veterinary research. 2005 Feb; 66(2):196-204. doi: 10.2460/ajvr.2005.66.196. [PMID: 15757115]
  • Dominika Malińska, Katarzyna Winiarska. [Lipoic acid: characteristics and therapeutic application]. Postepy higieny i medycyny doswiadczalnej (Online). 2005; 59(?):535-43. doi: . [PMID: 16407792]
  • M A Yorek, L J Coppey, J S Gellett, E P Davidson, D D Lund. Effect of fidarestat and alpha-lipoic acid on diabetes-induced epineurial arteriole vascular dysfunction. Experimental diabesity research. 2004 Apr; 5(2):123-35. doi: 10.1080/15438600490277824. [PMID: 15203883]
  • A S Hill, J A Werner, Q R Rogers, S L O'Neill, M M Christopher. Lipoic acid is 10 times more toxic in cats than reported in humans, dogs or rats. Journal of animal physiology and animal nutrition. 2004 Apr; 88(3-4):150-6. doi: 10.1111/j.1439-0396.2003.00472.x. [PMID: 15059240]
  • Domenico Lapenna, Giuliano Ciofani, Sante Donato Pierdomenico, Maria Adele Giamberardino, Franco Cuccurullo. Dihydrolipoic acid inhibits 15-lipoxygenase-dependent lipid peroxidation. Free radical biology & medicine. 2003 Nov; 35(10):1203-9. doi: 10.1016/s0891-5849(03)00508-2. [PMID: 14607519]
  • Michael D Coleman, Sandra Fernandes, Leena Khanderia. A preliminary evaluation of a novel method to monitor a triple antioxidant combination (vitamins E, C and α-lipoic acid) in diabetic volunteers using in vitro methaemoglobin formation. Environmental toxicology and pharmacology. 2003 Jun; 14(1-2):69-75. doi: 10.1016/s1382-6689(03)00027-9. [PMID: 21782664]
  • Walter Riedel, Uwe Lang, Ulrich Oetjen, Ulrike Schlapp, Masaaki Shibata. Inhibition of oxygen radical formation by methylene blue, aspirin, or alpha-lipoic acid, prevents bacterial-lipopolysaccharide-induced fever. Molecular and cellular biochemistry. 2003 May; 247(1-2):83-94. doi: 10.1023/a:1024142400835. [PMID: 12841635]
  • Michael L Koenig, James L Meyerhoff. In vitro neuroprotection against oxidative stress by pre-treatment with a combination of dihydrolipoic acid and phenyl-butyl nitrones. Neurotoxicity research. 2003; 5(4):265-72. doi: 10.1007/bf03033384. [PMID: 12835118]
  • C B Lin, L Babiarz, F Liebel, E Roydon Price, M Kizoulis, G J Gendimenico, D E Fisher, M Seiberg. Modulation of microphthalmia-associated transcription factor gene expression alters skin pigmentation. The Journal of investigative dermatology. 2002 Dec; 119(6):1330-40. doi: 10.1046/j.1523-1747.2002.19615.x. [PMID: 12485436]
  • Alexander B Sigalov, Lawrence J Stern. Dihydrolipoic acid as an effective cofactor for peptide methionine sulfoxide reductase in enzymatic repair of oxidative damage to both lipid-free and lipid-bound apolipoprotein a-I. Antioxidants & redox signaling. 2002 Jun; 4(3):553-7. doi: 10.1089/15230860260196353. [PMID: 12215223]
  • Yildiz Dinçer, Ayşegül Telci, Refik Kayali, Ilker A Yilmaz, Ufuk Cakatay, Tülay Akçay. Effect of alpha-lipoic acid on lipid peroxidation and anti-oxidant enzyme activities in diabetic rats. Clinical and experimental pharmacology & physiology. 2002 Apr; 29(4):281-4. doi: 10.1046/j.1440-1681.2002.03642.x. [PMID: 11985536]
  • L Packer, K Kraemer, G Rimbach. Molecular aspects of lipoic acid in the prevention of diabetes complications. Nutrition (Burbank, Los Angeles County, Calif.). 2001 Oct; 17(10):888-95. doi: 10.1016/s0899-9007(01)00658-x. [PMID: 11684397]
  • J S Coombes, S K Powers, B Rowell, K L Hamilton, S L Dodd, R A Shanely, C K Sen, L Packer. Effects of vitamin E and alpha-lipoic acid on skeletal muscle contractile properties. Journal of applied physiology (Bethesda, Md. : 1985). 2001 Apr; 90(4):1424-30. doi: 10.1152/jappl.2001.90.4.1424. [PMID: 11247943]
  • A Zulkhairi, Z Zaiton, O Khairul, A Zanariyah, M Jamaluddin. The effect of ∞-lipoic Acid in blood lipid levels and malondialdehyde in atherosclerotic-induced new zealand white rabbit. The Malaysian journal of medical sciences : MJMS. 2001 Jan; 8(1):46-52. doi: ". [PMID: 22973156]
  • M Podda, T M Zollner, M Grundmann-Kollmann, J J Thiele, L Packer, R Kaufmann. Activity of alpha-lipoic acid in the protection against oxidative stress in skin. Current problems in dermatology. 2001; 29(?):43-51. doi: 10.1159/000060652. [PMID: 11225200]
  • A I Haj-Yehia, P Assaf, T Nassar, J Katzhendler. Determination of lipoic acid and dihydrolipoic acid in human plasma and urine by high-performance liquid chromatography with fluorimetric detection. Journal of chromatography. A. 2000 Feb; 870(1-2):381-8. doi: 10.1016/s0021-9673(99)00857-2. [PMID: 10722093]
  • D Schneider, E F Elstner. Coenzyme Q10, vitamin E, and dihydrothioctic acid cooperatively prevent diene conjugation in isolated low-density lipoprotein. Antioxidants & redox signaling. 2000; 2(2):327-33. doi: 10.1089/ars.2000.2.2-327. [PMID: 11229536]
  • E Szabados, G M Fischer, F Gallyas, G Kispal, B Sumegi. Enhanced ADP-ribosylation and its diminution by lipoamide after ischemia-reperfusion in perfused rat heart. Free radical biology & medicine. 1999 Nov; 27(9-10):1103-13. doi: 10.1016/s0891-5849(99)00151-3. [PMID: 10569643]
  • J P Fabisiak, L L Pearce, G G Borisenko, Y Y Tyhurina, V A Tyurin, J Razzack, J S Lazo, B R Pitt, V E Kagan. Bifunctional anti/prooxidant potential of metallothionenin: redox signaling of copper binding and release. Antioxidants & redox signaling. 1999; 1(3):349-64. doi: 10.1089/ars.1999.1.3-349. [PMID: 11229446]
  • J K Lodge, M G Traber, L Packer. Thiol chelation of Cu2+ by dihydrolipoic acid prevents human low density lipoprotein peroxidation. Free radical biology & medicine. 1998 Aug; 25(3):287-97. doi: 10.1016/s0891-5849(98)00048-3. [PMID: 9680174]
  • H Nohl, L Gille. Evaluation of the antioxidant capacity of ubiquinol and dihydrolipoic acid. Zeitschrift fur Naturforschung. C, Journal of biosciences. 1998 Mar; 53(3-4):250-3. doi: 10.1515/znc-1998-3-415. [PMID: 9618938]
  • W Witt, B Rüstow. Determination of lipoic acid by precolumn derivatization with monobromobimane and reversed-phase high-performance liquid chromatography. Journal of chromatography. B, Biomedical sciences and applications. 1998 Jan; 705(1):127-31. doi: 10.1016/s0378-4347(97)00488-x. [PMID: 9498679]
  • J Teichert, R Preiss. High-performance liquid chromatography methods for determination of lipoic and dihydrolipoic acid in human plasma. Methods in enzymology. 1997; 279(?):159-66. doi: 10.1016/s0076-6879(97)79019-0. [PMID: 9211267]
  • H Nohl, L Gille, K Staniek. Endogenous and exogenous regulation of redox-properties of coenzyme Q. Molecular aspects of medicine. 1997; 18 Suppl(?):S33-40. doi: 10.1016/s0098-2997(97)00020-4. [PMID: 9266504]
  • S Matsugo, D Han, H J Tritschler, L Packer. Decomposition of alpha-lipoic acid derivatives by photoirradiation-formation of dihydrolipoic acid from alpha-lipoic acid-. Biochemistry and molecular biology international. 1996 Feb; 38(1):51-9. doi: NULL. [PMID: 8932519]
  • S Matsugo, L J Yan, D Han, H J Tritschler, L Packer. Elucidation of antioxidant activity of dihydrolipoic acid toward hydroxyl radical using a novel hydroxyl radical generator NP-III. Biochemistry and molecular biology international. 1995 Oct; 37(2):375-83. doi: . [PMID: 8673022]
  • C Chen, G Loo. Inhibition of lecithin: cholesterol acyltransferase activity in human blood plasma by cigarette smoke extract and reactive aldehydes. Journal of biochemical toxicology. 1995 Jun; 10(3):121-8. doi: 10.1002/jbt.2570100302. [PMID: 7473602]
  • D A Stoyanovsky, R Goldman, R M Darrow, D T Organisciak, V E Kagan. Endogenous ascorbate regenerates vitamin E in the retina directly and in combination with exogenous dihydrolipoic acid. Current eye research. 1995 Mar; 14(3):181-9. doi: 10.3109/02713689509033513. [PMID: 7796601]
  • A van der Vliet, C E Cross, B Halliwell, C A O'Neill. Plasma protein sulfhydryl oxidation: effect of low molecular weight thiols. Methods in enzymology. 1995; 251(?):448-55. doi: 10.1016/0076-6879(95)51148-2. [PMID: 7651226]
  • M Podda, H J Tritschler, H Ulrich, L Packer. Alpha-lipoic acid supplementation prevents symptoms of vitamin E deficiency. Biochemical and biophysical research communications. 1994 Oct; 204(1):98-104. doi: 10.1006/bbrc.1994.2431. [PMID: 7945398]
  • C A O'Neill, B Halliwell, A van der Vliet, P A Davis, L Packer, H Tritschler, W J Strohman, T Rieland, C E Cross, A Z Reznick. Aldehyde-induced protein modifications in human plasma: protection by glutathione and dihydrolipoic acid. The Journal of laboratory and clinical medicine. 1994 Sep; 124(3):359-70. doi: . [PMID: 8083579]
  • V Schepkin, T Kawabata, L Packer. NMR study of lipoic acid binding to bovine serum albumin. Biochemistry and molecular biology international. 1994 Aug; 33(5):879-86. doi: . [PMID: 7987256]
  • S Legastelois, V Thomas, G Quash, M P Métais, J Tebib, A Moreira, J C Monier. Naturally occurring antibodies reacting with lipoic acid: screening method, characterization and biochemical interest. Journal of immunological methods. 1994 May; 171(1):111-9. doi: 10.1016/0022-1759(94)90234-8. [PMID: 8176232]
  • M Mizuno, L Packer. Effects of alpha-lipoic acid and dihydrolipoic acid on expression of proto-oncogene c-fos. Biochemical and biophysical research communications. 1994 Apr; 200(2):1136-42. doi: 10.1006/bbrc.1994.1569. [PMID: 8179594]
  • T Kawabata, S C Yap, L Packer. The short-chain homologue of dihydrolipoic acid, tetranordihydrolipoate, protects against iron-induced lipid peroxidation in the aqueous phase. Biochemical and biophysical research communications. 1994 Feb; 199(1):361-7. doi: 10.1006/bbrc.1994.1237. [PMID: 8123035]
  • B C Scott, O I Aruoma, P J Evans, C O'Neill, A Van der Vliet, C E Cross, H Tritschler, B Halliwell. Lipoic and dihydrolipoic acids as antioxidants. A critical evaluation. Free radical research. 1994 Feb; 20(2):119-33. doi: 10.3109/10715769409147509. [PMID: 7516789]
  • B Scheer, G Zimmer. Dihydrolipoic acid prevents hypoxic/reoxygenation and peroxidative damage in rat heart mitochondria. Archives of biochemistry and biophysics. 1993 May; 302(2):385-90. doi: 10.1006/abbi.1993.1228. [PMID: 8387744]
  • Y J Suzuki, M Tsuchiya, L Packer. Antioxidant activities of dihydrolipoic acid and its structural homologues. Free radical research communications. 1993; 18(2):115-22. doi: 10.3109/10715769309147348. [PMID: 8386684]
  • M E Murphy, H Scholich, H Sies. Protection by glutathione and other thiol compounds against the loss of protein thiols and tocopherol homologs during microsomal lipid peroxidation. European journal of biochemistry. 1992 Nov; 210(1):139-46. doi: 10.1111/j.1432-1033.1992.tb17401.x. [PMID: 1446667]
  • J Teichert, R Preiss. HPLC-methods for determination of lipoic acid and its reduced form in human plasma. International journal of clinical pharmacology, therapy, and toxicology. 1992 Nov; 30(11):511-2. doi: NULL. [PMID: 1490813]
  • V E Kagan, A Shvedova, E Serbinova, S Khan, C Swanson, R Powell, L Packer. Dihydrolipoic acid--a universal antioxidant both in the membrane and in the aqueous phase. Reduction of peroxyl, ascorbyl and chromanoxyl radicals. Biochemical pharmacology. 1992 Oct; 44(8):1637-49. doi: 10.1016/0006-2952(92)90482-x. [PMID: 1417985]
  • V E Kagan, E A Serbinova, T Forte, G Scita, L Packer. Recycling of vitamin E in human low density lipoproteins. Journal of lipid research. 1992 Mar; 33(3):385-97. doi: 10.1016/s0022-2275(20)41529-9. [PMID: 1314881]
  • J H Prehn, C Karkoutly, J Nuglisch, B Peruche, J Krieglstein. Dihydrolipoate reduces neuronal injury after cerebral ischemia. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism. 1992 Jan; 12(1):78-87. doi: 10.1038/jcbfm.1992.10. [PMID: 1345759]
  • V Kagan, E Witt, R Goldman, G Scita, L Packer. Ultraviolet light-induced generation of vitamin E radicals and their recycling. A possible photosensitizing effect of vitamin E in skin. Free radical research communications. 1992; 16(1):51-64. doi: 10.3109/10715769209049159. [PMID: 1325398]
  • Y J Suzuki, M Tsuchiya, L Packer. Thioctic acid and dihydrolipoic acid are novel antioxidants which interact with reactive oxygen species. Free radical research communications. 1991; 15(5):255-63. doi: 10.3109/10715769109105221. [PMID: 1666623]
  • V E Kagan, H J Freisleben, M Tsuchiya, T Forte, L Packer. Generation of probucol radicals and their reduction by ascorbate and dihydrolipoic acid in human low density lipoproteins. Free radical research communications. 1991; 15(5):265-76. doi: 10.3109/10715769109105222. [PMID: 1666624]
  • L Müller, H Menzel. Studies on the efficacy of lipoate and dihydrolipoate in the alteration of cadmium2+ toxicity in isolated hepatocytes. Biochimica et biophysica acta. 1990 May; 1052(3):386-91. doi: 10.1016/0167-4889(90)90147-6. [PMID: 2112957]
  • H Scholich, M E Murphy, H Sies. Antioxidant activity of dihydrolipoate against microsomal lipid peroxidation and its dependence on alpha-tocopherol. Biochimica et biophysica acta. 1989 Feb; 1001(3):256-61. doi: 10.1016/0005-2760(89)90108-2. [PMID: 2492825]
  • J Bourguignon, M Neuburger, R Douce. Resolution and characterization of the glycine-cleavage reaction in pea leaf mitochondria. Properties of the forward reaction catalysed by glycine decarboxylase and serine hydroxymethyltransferase. The Biochemical journal. 1988 Oct; 255(1):169-78. doi: 10.1042/bj2550169. [PMID: 3143355]