Pyrroloquinoline quinone

Pyrroloquinoline quinone

Identifiers
CAS Number	72909-34-3 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:18315 Y
ChemSpider	997 Y
KEGG	C00113 Y
MeSH	PQQ+Cofactor
PubChem	1024
UNII	47819QGH5L N
InChI 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) Y Key: MMXZSJMASHPLLR-UHFFFAOYSA-N Y InChI=1/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) Key: MMXZSJMASHPLLR-UHFFFAOYAP
SMILES c1c2c([nH]c1C(=O)O)-c3c(cc(nc3C(=O)C2=O)C(=O)O)C(=O)O
Properties
Chemical formula	C14H6N2O8
Molar mass	330.21 g·mol−1
Density	1.963 g/cm3
Hazards
Flash point	569.8 °C (1,057.6 °F; 842.9 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Pyrroloquinoline quinone (PQQ) is redox cofactor. It is found in soil and foods such as kiwifruit, as well as human breast milk. Enzymes containing PQQ are called quinoproteins. Glucose dehydrogenase, one of the quinoproteins, is used as a glucose sensor. PQQ stimulates growth in bacteria and displays antioxidant and neuroprotective effects.

It was discovered by J.G. Hauge as the third redox cofactor after nicotinamide and flavin in bacteria (although he hypothesised that it was naphthoquinone). Anthony and Zatman also found the unknown redox cofactor in alcohol dehydrogenase. In 1979, Salisbury and colleagues as well as Duine and colleagues extracted this prosthetic group from methanol dehydrogenase of methylotrophs and identified its molecular structure. Adachi and colleagues discovered that PQQ was also found in Acetobacter.

A 2010 study revealed that PQQ’s critical role in growth and development stems from its unique ability to activate cell signaling pathways directly involved in cellular energy metabolism, development and function. The study demonstrated that PQQ protects mouse hepatocyte from oxidative stress and promotes the spontaneous generation of new mitochondria within aging cells, a process known as mitochondrial biogenesis.

PQQ’s influence over cell signaling pathways is involved in the generation of new mitochondria. Three mouse proteins that are activated by PQQ cause cells to undergo spontaneous mitochondrial biogenesis: peroxisome proliferator-activated receptor gamma coactivator 1-alpha, cAMP response element-binding protein and the DJ-1 protein.