D7783
Pyrroloquinoline quinone
≥95.0% (HPLC)
Synonym(s):
4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, Methoxatin, PQQ
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About This Item
Empirical Formula (Hill Notation):
C14H6N2O8
CAS Number:
Molecular Weight:
330.21
UNSPSC Code:
12352106
NACRES:
NA.79
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3596812
biological source
synthetic
Quality Level
assay
≥95.0% (HPLC)
form
powder
technique(s)
HPLC: suitable
color
red to deep red
storage temp.
2-8°C
SMILES string
OC(=O)c1cc(C(O)=O)c-2c(n1)C(=O)C(=O)c3cc([nH]c-23)C(O)=O
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
General description
Novel o-quinone coenzyme found in bacterial dehydrogenases and oxidases.
Pyrroloquinoline Quinone (PQQ), also referred as methoxatin, is a water soluble orthoquinone molecule with redox-cycling ability.
Application
Pyrroloquinoline quinone has been used:
- as a component of nanocurcumin formulation (NCF), to study its therapeutic effect on ameliorate hypoxia-induced stress in hypertrophied cardiomyocytes
- as a standard in fluorescence analysis
- to test its efficiency in suppressing restrained oxidative stress and hepatic fibrogenesis in mouse models
Biochem/physiol Actions
Pyrroloquinoline Quinone (PQQ) plays a vital role in gluconic acid production and biosynthesis by microbes. It acts as an effective microbial growth stimulant and biological control determinant for plant pathogens. PQQ also acts as an anti-melanogenic agent and is used to treat disorders related to hyper pigmentation. It exhibits diverse role in metabolism and cell signaling pathways. PQQ is used as a potential therapeutic to treat liver fibrosis.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Crystal structure of PqqB from Pseudomonas putida at 2.2
Metlitzky M, et al.
Journal of biophysical chemistry, 3(02), 206-206 (2012)
C Anthony
Antioxidants & redox signaling, 3(5), 757-774 (2002-01-05)
This review summarises the characteristics, identification, and measurement of pyrroloquinoline quinone, the prosthetic group of bacterial quinoprotein dehydrogenases whose structures, mechanisms, and electron transport functions are described in detail. Type I alcohol dehydrogenase includes the "classic" methanol dehydrogenase; its x-ray
A Oubrie et al.
Protein science : a publication of the Protein Society, 9(7), 1265-1273 (2000-08-10)
On the basis of crystal structures of the pyrroloquinoline quinone (PQQ) dependent enzymes methanol dehydrogenase (MDH) and soluble glucose dehydrogenase (s-GDH), different catalytic mechanisms have been proposed. However, several lines of biochemical and kinetic evidence are strikingly similar for both
Global Trade Item Number
| SKU | GTIN |
|---|---|
| D7783-1MG | 04061833588895 |
| D7783-10MG | 04061833588888 |
| D7783-5MG | 04061833270530 |