A quinone with diverse biological activities
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Pyrroloquinoline quinone

Item No. 20681

Technical Information
Formal Name
4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
CAS Number
72909-34-3
Synonyms
  • PQQ
Molecular Formula
C14H6N2O8
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 1 mg/mlDMSO: 2 mg/mlEthanol: 0.1 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
251, 371 nm
SMILES
O=C(O)C1=C(C(NC(C(O)=O)=C2)=C2C(C3=O)=O)C3=NC(C(O)=O)=C1
InChi Code
InChI=1S/C14H6N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)
InChi Key
MMXZSJMASHPLLR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Pyrroloquinoline quinone (PQQ) is a quinone and redox enzyme cofactor that has been found in a variety of bacteria and has diverse biological activities.1,2,3,4,5 It inhibits fibril formation by the amyloid proteins amyloid-β (1-42) (Aβ42) and mouse prion protein when used at a concentrations of 100 and 300 μM.1 PQQ stimulates cell proliferation, reduces glutamate-induced production of reactive oxygen species (ROS), necrosis, and caspase-3 activity, and increases activity of superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX) in neural stem and progenitor cells.2 It inhibits LPS-induced production of nitric oxide (NO) and prostaglandin E2 (PGE2) and suppresses LPS-induced expression of the pro-inflammatory mediators iNOS, COX-2, TNF-α, IL-1β, IL-6, MCP-1, and MIP-1α in primary microglia.6 In vivo, PQQ (3 and 10 mg/kg) reduces Iba-1 expression, a marker of microglial activation, in the cerebral cortex and hippocampal dentate gyrus in mice. PQQ decreases the number of hepatic cells positive for α-smooth muscle actin (α-SMA) and reduces collagen deposition and hepatic hydroxyproline levels in a mouse model of liver fibrosis.4 It also decreases serum glucose and total cholesterol levels, increases brain SOD, CAT, and GPX activities, and decreases brain lipid hydroperoxide levels in mice with diabetes induced by streptozotocin (Item No. 13104).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, J., Kobayashi, M., Fukuda, M., et alPyrroloquinoline quinone inhibits the fibrillation of amyloid proteins. Prion 4(1), 26-31 (2010).

    2. Guan, S., Xu, J., Guo, Y., et alPyrroloquinoline quinone against glutamate-induced neurotoxicity in cultured neural stem and progenitor cells. Int. J. Dev. Neurosci. 42, 37-45 (2015).

    3. Yang, C., Yu, L., Kong, L., et alPyrroloquinoline quinone (PQQ) inhibits lipopolysaccharide induced inflammation in part via downregulated NF-κB and p38/JNK activation in microglial and attenuates microglia activation in lipopolysaccharide treatment mice. PLoS One 9(10), e109502 (2014).

    4. Jia, D., Duan, F., Peng, P., et alPyrroloquinoline-quinone suppresses liver fibrogenesis in mice. PLoS One 10(3), e0121939 (2015).

    5. Kumar, N., and Kar, A. Pyrroloquinoline quinone ameliorates oxidative stress and lipid peroxidation in the brain of streptozotocin-induced diabetic mice. Can. J. Physiol. Pharmacol. 93(1), 71-79 (2015).

    6. Yang, Y., Kuwano, T., Lagor, W.R., et alLipidomic analyses of female mice lacking hepatic lipase and endothelial lipase indicate selective modulation of plasma lipid species. Lipids 49(6), 505-515 (2014).