MedKoo Cat#: 598950 | Name: Lipoamide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lipoamide is an Indirect Antioxidant.

Chemical Structure

Lipoamide
CAS#940-69-2

Theoretical Analysis

MedKoo Cat#: 598950

Name: Lipoamide

CAS#: 940-69-2

Chemical Formula: C8H15NOS2

Exact Mass: 205.0595

Molecular Weight: 205.33

Elemental Analysis: C, 46.80; H, 7.36; N, 6.82; O, 7.79; S, 31.23

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 650.00 2 Weeks
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Synonym
Lipoamide; Lipoacin; NSC 90787; NSC-90787; NSC90787; Thioctamide; Thioctic acid amide;
IUPAC/Chemical Name
5-(1,2-dithiolan-3-yl)pentanamide
InChi Key
FCCDDURTIIUXBY-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)
SMILES Code
O=C(N)CCCCC1SSCC1
Appearance
Solid powder
Purity
>97% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Lipoamide ((±)-α-Lipoamide) is a monocarboxylic acid amide resulting from the formal condensation of the carboxy group of lipoic acid with ammonia.
In vitro activity:
Exposure of 3T3-L1 cells to lipoamide or LA (α-lipoic acid) for 24 h increased the number and mitochondrial mass per cell. Lipoamide dose-dependently stimulated expression of endothelial nitric oxide synthase (eNOS) and formation of cGMP. Reference: Br J Pharmacol. 2011 Mar;162(5):1213-24. https://pubmed.ncbi.nlm.nih.gov/21108628/
In vivo activity:
9-week-old db/db mice were treated with ALM (alpha lipoamide) (50 mg·kg-1·d-1, i.g) for 8 weeks. ALM administration did not affect blood glucose levels in db/db mice, but restored renal function and significantly improved fibrosis of kidneys. This study demonstrated that ALM administration significantly ameliorated mitochondrial dysfunction and tubulointerstitial fibrotic lesions, along with increased expression of CDX2 and CFTR and decreased expression of β-catenin and Snail in kidneys of db/db mice. Reference: Acta Pharmacol Sin. 2022 Nov 8. https://pubmed.ncbi.nlm.nih.gov/36347997/
Solvent mg/mL mM comments
Solubility
DMSO 35.3 171.74
Ethanol 4.1 20.02
Water 0.7 3.26
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 205.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hou Y, Li X, Peng S, Yao J, Bai F, Fang J. Lipoamide Ameliorates Oxidative Stress via Induction of Nrf2/ARE Signaling Pathway in PC12 Cells. J Agric Food Chem. 2019 Jul 24;67(29):8227-8234. doi: 10.1021/acs.jafc.9b02680. Epub 2019 Jul 12. PMID: 31299148. 2. Shen W, Hao J, Feng Z, Tian C, Chen W, Packer L, Shi X, Zang W, Liu J. Lipoamide or lipoic acid stimulates mitochondrial biogenesis in 3T3-L1 adipocytes via the endothelial NO synthase-cGMP-protein kinase G signalling pathway. Br J Pharmacol. 2011 Mar;162(5):1213-24. doi: 10.1111/j.1476-5381.2010.01134.x. PMID: 21108628; PMCID: PMC3051392. 3. Zhang HF, Liu HM, Xiang JY, Zhou XC, Wang D, Chen RY, Tan WL, Liang LQ, Liu LL, Shi MJ, Zhang F, Xiao Y, Zhou YX, Zhang T, Tang L, Guo B, Wang YY. Alpha lipoamide inhibits diabetic kidney fibrosis via improving mitochondrial function and regulating RXRα expression and activation. Acta Pharmacol Sin. 2022 Nov 8. doi: 10.1038/s41401-022-00997-1. Epub ahead of print. PMID: 36347997. 4. Zhang Y, Zhou R, Qu Y, Shu M, Guo S, Bai Z. Lipoamide Inhibits NF1 Deficiency-induced Epithelial-Mesenchymal Transition in Murine Schwann Cells. Arch Med Res. 2017 Aug;48(6):498-505. doi: 10.1016/j.arcmed.2017.11.014. Epub 2017 Dec 1. PMID: 29198560.
In vitro protocol:
1. Hou Y, Li X, Peng S, Yao J, Bai F, Fang J. Lipoamide Ameliorates Oxidative Stress via Induction of Nrf2/ARE Signaling Pathway in PC12 Cells. J Agric Food Chem. 2019 Jul 24;67(29):8227-8234. doi: 10.1021/acs.jafc.9b02680. Epub 2019 Jul 12. PMID: 31299148. 2. Shen W, Hao J, Feng Z, Tian C, Chen W, Packer L, Shi X, Zang W, Liu J. Lipoamide or lipoic acid stimulates mitochondrial biogenesis in 3T3-L1 adipocytes via the endothelial NO synthase-cGMP-protein kinase G signalling pathway. Br J Pharmacol. 2011 Mar;162(5):1213-24. doi: 10.1111/j.1476-5381.2010.01134.x. PMID: 21108628; PMCID: PMC3051392.
In vivo protocol:
1. Zhang HF, Liu HM, Xiang JY, Zhou XC, Wang D, Chen RY, Tan WL, Liang LQ, Liu LL, Shi MJ, Zhang F, Xiao Y, Zhou YX, Zhang T, Tang L, Guo B, Wang YY. Alpha lipoamide inhibits diabetic kidney fibrosis via improving mitochondrial function and regulating RXRα expression and activation. Acta Pharmacol Sin. 2022 Nov 8. doi: 10.1038/s41401-022-00997-1. Epub ahead of print. PMID: 36347997. 2. Zhang Y, Zhou R, Qu Y, Shu M, Guo S, Bai Z. Lipoamide Inhibits NF1 Deficiency-induced Epithelial-Mesenchymal Transition in Murine Schwann Cells. Arch Med Res. 2017 Aug;48(6):498-505. doi: 10.1016/j.arcmed.2017.11.014. Epub 2017 Dec 1. PMID: 29198560.
1: Bryk R, Arango N, Maksymiuk C, Balakrishnan A, Wu YT, Wong CH, Masquelin T, Hipskind P, Lima CD, Nathan C. Lipoamide channel-binding sulfonamides selectively inhibit mycobacterial lipoamide dehydrogenase. Biochemistry. 2013 Dec 23;52(51):9375-84. doi: 10.1021/bi401077f. Epub 2013 Nov 26. PubMed PMID: 24251446; PubMed Central PMCID: PMC3894633. 2: Zhao L, Liu Z, Jia H, Feng Z, Liu J, Li X. Lipoamide Acts as an Indirect Antioxidant by Simultaneously Stimulating Mitochondrial Biogenesis and Phase II Antioxidant Enzyme Systems in ARPE-19 Cells. PLoS One. 2015 Jun 1;10(6):e0128502. doi: 10.1371/journal.pone.0128502. eCollection 2015. PubMed PMID: 26030919; PubMed Central PMCID: PMC4452644. 3: Chen W, Taylor NL, Chi Y, Millar AH, Lambers H, Finnegan PM. The metabolic acclimation of Arabidopsis thaliana to arsenate is sensitized by the loss of mitochondrial LIPOAMIDE DEHYDROGENASE2, a key enzyme in oxidative metabolism. Plant Cell Environ. 2014 Mar;37(3):684-95. doi: 10.1111/pce.12187. Epub 2013 Nov 11. PubMed PMID: 23961884. 4: Shen W, Hao J, Feng Z, Tian C, Chen W, Packer L, Shi X, Zang W, Liu J. Lipoamide or lipoic acid stimulates mitochondrial biogenesis in 3T3-L1 adipocytes via the endothelial NO synthase-cGMP-protein kinase G signalling pathway. Br J Pharmacol. 2011 Mar;162(5):1213-24. doi: 10.1111/j.1476-5381.2010.01134.x. PubMed PMID: 21108628; PubMed Central PMCID: PMC3051392. 5: Folda A, Citta A, Scutari G, Bindoli A, Rigobello MP. Contrasting effects of selenite and tellurite on lipoamide dehydrogenase activity suggest a different biological behaviour of the two chalcogens. Arch Biochem Biophys. 2012 Jan 1;517(1):30-6. doi: 10.1016/j.abb.2011.11.009. Epub 2011 Nov 15. PubMed PMID: 22100759. 6: Wu Z, Soulages JL, Joshi BD, Daniel SM, Hager ZJ, Arrese EL. TGL-mediated lipolysis in Manduca sexta fat body: possible roles for lipoamide-dehydrogenase (LipDH) and high-density lipophorin (HDLp). Insect Biochem Mol Biol. 2014 Feb;45:58-68. doi: 10.1016/j.ibmb.2013.12.001. Epub 2013 Dec 12. PubMed PMID: 24333838; PubMed Central PMCID: PMC3932539. 7: Neuburger M, Polidori AM, Piètre E, Faure M, Jourdain A, Bourguignon J, Pucci B, Douce R. Interaction between the lipoamide-containing H-protein and the lipoamide dehydrogenase (L-protein) of the glycine decarboxylase multienzyme system. 1. Biochemical studies. Eur J Biochem. 2000 May;267(10):2882-9. PubMed PMID: 10806385. 8: Mathias RA, Greco TM, Oberstein A, Budayeva HG, Chakrabarti R, Rowland EA, Kang Y, Shenk T, Cristea IM. Sirtuin 4 is a lipoamidase regulating pyruvate dehydrogenase complex activity. Cell. 2014 Dec 18;159(7):1615-25. doi: 10.1016/j.cell.2014.11.046. PubMed PMID: 25525879; PubMed Central PMCID: PMC4344121. 9: Thijssen HH, Janssen YP, Vervoort LT. Microsomal lipoamide reductase provides vitamin K epoxide reductase with reducing equivalents. Biochem J. 1994 Jan 15;297 ( Pt 2):277-80. PubMed PMID: 8297331; PubMed Central PMCID: PMC1137825. 10: Onder O, Yoon H, Naumann B, Hippler M, Dancis A, Daldal F. Modifications of the lipoamide-containing mitochondrial subproteome in a yeast mutant defective in cysteine desulfurase. Mol Cell Proteomics. 2006 Aug;5(8):1426-36. Epub 2006 May 8. PubMed PMID: 16684766. 11: Faure M, Bourguignon J, Neuburger M, MacHerel D, Sieker L, Ober R, Kahn R, Cohen-Addad C, Douce R. Interaction between the lipoamide-containing H-protein and the lipoamide dehydrogenase (L-protein) of the glycine decarboxylase multienzyme system 2. Crystal structures of H- and L-proteins. Eur J Biochem. 2000 May;267(10):2890-8. Erratum in: Eur J Biochem 2000 Jun;267(12):3914. PubMed PMID: 10806386. 12: Bisby RH, Parker AW. Antioxidant reactions of dihydrolipoic acid and lipoamide with triplet duroquinone. Biochem Biophys Res Commun. 1998 Mar 6;244(1):263-7. Erratum in: Biochem Biophys Res Commun 1998 Aug 10;249(1):297. PubMed PMID: 9514912. 13: Bryk R, Arango N, Venugopal A, Warren JD, Park YH, Patel MS, Lima CD, Nathan C. Triazaspirodimethoxybenzoyls as selective inhibitors of mycobacterial lipoamide dehydrogenase . Biochemistry. 2010 Mar 2;49(8):1616-27. doi: 10.1021/bi9016186. PubMed PMID: 20078138; PubMed Central PMCID: PMC2827632. 14: Sumegi B, Butwell NB, Malloy CR, Sherry AD. Lipoamide influences substrate selection in post-ischaemic perfused rat hearts. Biochem J. 1994 Jan 1;297 ( Pt 1):109-13. PubMed PMID: 7904156; PubMed Central PMCID: PMC1137798. 15: Arnér ES, Nordberg J, Holmgren A. Efficient reduction of lipoamide and lipoic acid by mammalian thioredoxin reductase. Biochem Biophys Res Commun. 1996 Aug 5;225(1):268-74. PubMed PMID: 8769129. 16: Zhou B, Wen M, Lin X, Chen YH, Gou Y, Li Y, Zhang Y, Li HW, Tang L. Alpha Lipoamide Ameliorates Motor Deficits and Mitochondrial Dynamics in the Parkinson's Disease Model Induced by 6-Hydroxydopamine. Neurotox Res. 2018 May;33(4):759-767. doi: 10.1007/s12640-017-9819-5. Epub 2017 Oct 10. PubMed PMID: 29019159. 17: Matuda S, Saheki T. Immunochemical comparison of lipoamide dehydrogenases from various sources and reactivity of various lipoamide dehydrogenases with rat heart pyruvate dehydrogenase-subcomplex. Biochem Biophys Res Commun. 1985 Jun 14;129(2):479-84. PubMed PMID: 3893428. 18: Self WT, Tsai L, Stadtman TC. Synthesis and characterization of selenotrisulfide-derivatives of lipoic acid and lipoamide. Proc Natl Acad Sci U S A. 2000 Nov 7;97(23):12481-6. PubMed PMID: 11050172; PubMed Central PMCID: PMC18789. 19: Szabados E, Fischer GM, Gallyas F Jr, Kispal G, Sumegi B. Enhanced ADP-ribosylation and its diminution by lipoamide after ischemia-reperfusion in perfused rat heart. Free Radic Biol Med. 1999 Nov;27(9-10):1103-13. PubMed PMID: 10569643. 20: Youn H, Kwak J, Youn HD, Hah YC, Kang SO. Lipoamide dehydrogenase from streptomyces seoulensis: biochemical and genetic properties. Biochim Biophys Acta. 1998 Nov 10;1388(2):405-18. PubMed PMID: 9858775.