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D7783 Sigma

Pyrroloquinoline quinone

≥95.0% (HPLC)

Synonym: 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, Methoxatin, PQQ

  • CAS Number 72909-34-3

  • Empirical Formula (Hill Notation) C14H6N2O8

  • Molecular Weight 330.21

  •  Beilstein Registry Number 3596812

  •  MDL number MFCD00043125

  •  PubChem Substance ID 24894162

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Properties

Related Categories Biochemicals and Reagents, Cofactors, Enzymes, Inhibitors, and Substrates, Oxidation-Reduction
assay   ≥95.0% (HPLC)
storage temp.   2-8°C

Description

Biochem/physiol Actions

PQQ is present in nanomolar quantities in most foods and in most animal tissuse. It promotes growth, mitochondrial function, and development in vivo and stimulates cell proliferation and viability in culture. It is a potent antioxidant that scavenges superoxide and peroxinitrite. It is neuroprotectant against 6-hydroxydopamine-induced and hypoxia/ischemia-induced neurotoxicity. PQQ conjugates to α-synuclein in vitro, inhibiting the formation of amyloid fibrils.

General description

Novel o-quinone coenzyme found in bacterial dehydrogenases and oxidases.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D7783.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Quinoproteins, enzymes with pyrrolo-quinoline quinone as cofactor. Duine, J.A. Annu. Rev. Biochem. 58, 403-426, (1989)

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Simple and Sensitive Method for Pyrroloquinoline Quinone (PQQ) Analysis in Various Foods Using Liquid Chromatography/Electrospray-Ionization Tandem Mass Spectrometry. Noji, N., et al. J. Agric. Food Chem. 55, 7258-7263, (2007)

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Activation of Ras signaling pathways by pyrroloquinoline quinone in NIH3T3 mouse fibroblasts. Kumazawa, T., et al. Int. J. Mol. Med. 19, 765-770, (2007)

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Pyrroloquinoline quinone is a potent neuroprotective nutrient against 6-hydroxydopamine-induced neurotoxicity. Hara, H., et al. Neurochem. Res. 32, 489-495, (2007)

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Pyrroloquinoline quinone (PQQ) prevents fibril formation of α-synuclein. Kobayashi, M., et al. Biochem. Biophys. Res. Commun. 349, 1139-1144, (2006)

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Neuroprotection by pyrroloquinoline quinone (PQQ) in reversible middle cerebral artery occlusion in the adult rat. Zhang, Y., et al. Brain Res. 1094, 200-2006, (2006)

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Pyrroloquinoline quinone modulates mitochondrial quantity and function in mice. Stites, T., et al. J. Nutr. 136, 390-396, (2006)

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The PQQ story. Duine, J.A. J. Biosci. Bioeng. 88, 231-236, (1999)

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Pyrroloquinoline quinone nutritional status alters lysine metabolism and modulates mitochondrial DNA content in the mouse and rat. Bauerly, K.A., et al. Biochim. Biophys. Acta 1760, 1741-1748, (2006)

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Quinoproteins: enzymes containing the quinonoid cofactor pyrroloquinoline quinone, topaquinone or tryptophan-tryptophan quinone. Duine JA Eur. J. Biochem. 200(2), 271-84, (1991)

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Pyrroloquinoline quinone modulates the kinetic parameters of the mammalian selenoprotein thioredoxin reductase 1 and is an inhibitor of glutathione reductase. Xu J and Arnér ES Biochem. Pharmacol. 83(6), 815-20, (2012)

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Pyrroloquinoline quinone: a novel cofactor. Duine JA and Jongejan JA Vitam. Horm. 45, 223-62, (1989)

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The cofactor pyrroloquinoline quinone. Duine JA, van der Meer RA, and Groen BW Annu. Rev. Nutr. 10, 297-318, (1990)

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[Pyrroloquinoline quinone and its physiological effects]. Liu JP and Zhao YF Sheng Li Ke Xue Jin Zhan 27(2), 170-2, (1996)

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Pyrroloquinoline quinone: a new redox cofactor in eukaryotic enzymes. Hartmann C and Klinman JP Biofactors 1(1), 41-9, (1988)

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[Study of chemical kinetics between pyrroloquinoline quinine and D-serine in body by ion-pair liquid chromatography]. Zhou X, Qin X, Zhang J, et al. Se Pu 30(2), 196-200, (2012)

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[Effects of pyrroloquinoline quinone on proliferation and expression of c-fos, c-jun, CREB and PCNA in cultured Schwann cells]. Li HH, He B, Peng H, et al. Zhonghua Zheng Xing Wai Ke Za Zhi 27(4), 298-303, (2011)

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[Discovery and recent development of a novel coenzyme pyrroloquinoline quinone (PQQ)]. Matsushita K and Adachi O Seikagaku. 63(3), 218-21, (1991)

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Biochemistry and physiology of pyrroloquinoline quinone and quinoprotein dehydrogenases. Adachi O, Matsushita K, and Ameyama M J. Nutr. Sci. Vitaminol. Spec No, 224-7, (1992)

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Potential physiological importance of pyrroloquinoline quinone. Rucker R, Chowanadisai W, and Nakano M Altern. Med. Rev. 14(3), 268-77, (2009)

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The role of phenolics, conjugated linoleic acid, carnosine, and pyrroloquinoline quinone as nonessential dietary antioxidants. Decker EA Nutr. Rev. 53(3), 49-58, (1995)

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Pyrroloquinoline quinone (PQQ) from methanol dehydrogenase and tryptophan tryptophylquinone (TTQ) from methylamine dehydrogenase. Davidson VL Adv. Protein Chem. 58, 95-140, (2001)

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Structural requirements of pyrroloquinoline quinone dependent enzymatic reactions. Oubrie A and Dijkstra BW Protein Sci. 9(7), 1265-73, (2000)

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Influence of adding pyrroloquinoline quinone to parenteral nutrition on gut-associated lymphoid tissue. Omata J, Fukatsu K, Murakoshi S, et al. J. Parenter. Enteral Nutr. 35(5), 616-24, (2011)

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Pyrroloquinoline-quinone and its versatile roles in biological processes. Misra HS, Rajpurohit YS, and Khairnar NP J. Biosci. 37(2), 313-25, (2012)

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Differently substituted sulfonated polyanilines: the role of polymer compositions in electron transfer with pyrroloquinoline quinone-dependent glucose dehydrogenase. Sarauli D, Xu C, Dietzel B, et al. Acta Biomater. 9(9), 8290-8, (2013)

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Pyrroloquinoline quinone (PQQ) and quinoprotein enzymes. Anthony C Antioxid. Redox Signal. 3(5), 757-74, (2001)

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The neuroprotective action of pyrroloquinoline quinone against glutamate-induced apoptosis in hippocampal neurons is mediated through the activation of PI3K/Akt pathway. Zhang Q, Shen M, Ding M, et al. Toxicol. Appl. Pharmacol. 252, 62-72, (2011)

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Coupling of pyrroloquinoline quinone dependent glucose dehydrogenase to (cytochrome c/DNA)-multilayer systems on electrodes. Wettstein Ch, Möhwald H, and Lisdat F Bioelectrochemistry 88, 97-102, (2012)

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Pyrroloquinoline quinone: a novel vitamin? Bishop A, Gallop PM, and Karnovsky ML Nutr. Rev. 56(10), 287-93, (1998)

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Pyrroloquinoline quinone stimulates epithelial cell proliferation by activating epidermal growth factor receptor through redox cycling. Kimura K, Takada M, Ishii T, et al. Free Radic. Biol. Med. 53(6), 1239-51, (2012)

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Physiologic importance of pyrroloquinoline quinone. Smidt CR, Steinberg FM, and Rucker RB Proc. Soc. Exp. Biol. Med. 197(1), 19-26, (1991)

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Kinetic study of the quenching reaction of singlet oxygen by Pyrroloquinolinequinol (PQQH(2), a reduced form of Pyrroloquinolinequinone) in micellar solution. Mukai K, Ouchi A, and Nakano M J. Agric. Food Chem. 59(5), 1705-12, (2011)

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High-temperature sorbose fermentation with thermotolerant Gluconobacter frateurii CHM43 and its mutant strain adapted to higher temperature. Hattori H, Yakushi T, Matsutani M, et al. Appl. Microbiol. Biotechnol. 95(6), 1531-40, (2012)

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Uranium exerts acute toxicity by binding to pyrroloquinoline quinone cofactor. VanEngelen MR, Szilagyi RK, Gerlach R, et al. Environ. Sci. Technol. 45(3), 937-42, (2011)

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Distribution and properties of the genes encoding the biosynthesis of the bacterial cofactor, pyrroloquinoline quinone. Shen YQ, Bonnot F, Imsand EM, et al. Biochemistry 51(11), 2265-75, (2012)

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Altering pyrroloquinoline quinone nutritional status modulates mitochondrial, lipid, and energy metabolism in rats. Bauerly K, Harris C, Chowanadisai W, et al. PLoS ONE 6(7), e21779, (2011)

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Biochemical and physiological functions of pyrroloquinoline quinone. Ameyama M, Matsushita K, Shinagawa E, et al. Vitam. Horm. 46, 229-70, (1991)

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The pyrroloquinoline quinone (PQQ) coenzymes: a case of mistaken identity. Harris ED Nutr. Rev. 50(9), 263-7, (1992)

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Effect of pyrroloquinoline quinone on neuropathic pain following chronic constriction injury of the sciatic nerve in rats. Gong D, Geng C, Jiang L, et al. Eur. J. Pharmacol. 697(1-3), 53-8, (2012)

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The neuroprotective effect of pyrroloquinoline quinone on traumatic brain injury. Zhang L, Liu J, Cheng C, et al. J. Neurotrauma 29(5), 851-64, (2012)

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Pyrroloquinoline quinone, a novel protein tyrosine phosphatase 1B inhibitor, activates insulin signaling in C2C12 myotubes and improves impaired glucose tolerance in diabetic KK-A(y) mice. Takada M, Sumi M, Maeda A, et al. Biochem. Biophys. Res. Commun. 428(2), 315-20, (2012)

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Characterization of a protein-generated O₂ binding pocket in PqqC, a cofactorless oxidase catalyzing the final step in PQQ production. RoseFigura JM, Puehringer S, Schwarzenbacher R, et al. Biochemistry 50(9), 1556-66, (2011)

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Pyrroloquinoline quinone and molecules mimicking its functional domains. Modulators of connective tissue formation? Hanauske-Abel HM, Tschank G, Günzler V, et al. FEBS Lett. 214(2), 236-43, (1987)

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Inhibition of receptor activator of nuclear factor-κB ligand (RANKL)-induced osteoclast formation by pyrroloquinoline quinine (PQQ). Odkhuu E, Koide N, Haque A, et al. Immunol. Lett. 142(1-2), 34-40, (2012)

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Identification of Pantoea ananatis gene encoding membrane pyrroloquinoline quinone (PQQ)-dependent glucose dehydrogenase and pqqABCDEF operon essential for PQQ biosynthesis. Andreeva IG, Golubeva LI, Kuvaeva TM, et al. FEMS Microbiol. Lett. 318(1), 55-60, (2011)

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The pyrroloquinoline quinone (PQQ)-containing quinoprotein dehydrogenases. Anthony C Biochem. Soc. Trans. 26(3), 413-7, (1998)

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Absorbance-based assay for membrane disruption by antimicrobial peptides and synthetic copolymers using pyrroloquinoline quinone-loaded liposomes. Zimmerman LB, Worley BV, et al. Anal. Biochem. 411, 194-199, (2011)

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The enzymatic reaction-induced configuration change of the prosthetic group PQQ of methanol dehydrogenase. Li J, Gan JH, Mathews FS, Xia ZX. Biochem. Biophys. Res. Commun. 406-, 621-626, (2011)

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The active (ADHa) and inactive (ADHi) forms of the PQQ-alcohol dehydrogenase from Gluconacetobacter diazotrophicus differ in their respective oligomeric structures and redox state of their corresponding prosthetic groups. Gómez-Manzo S, González-Valdez AA, Oria-Hernández J, et al. FEMS Microbiol. Lett. 328(2), 106-13, (2012)

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Pyrroloquinoline quinone rescues hippocampal neurons from glutamate-induced cell death through activation of Nrf2 and up-regulation of antioxidant genes. Zhang Q, Ding M, Gao XR, et al. Genet. Mol. Res. 11(3), 2652-64, (2012)

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Mycobacterium smegmatis genomic characteristics associated with its saprophyte lifestyle. Long Q, Zhou Q, Ji L, et al. J. Cell. Biochem. 113(10), 3051-5, (2012)

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A novel molecular marker for studying phylogeny and diversity of phosphate-solubilizing pseudomonads: the pyrroloquinoline quinone biosynthetic gene pqqC. Meyer JB, Frapolli M, Keel C, et al. Appl. Environ. Microbiol. 77(20), 7345-54, (2011)

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