D7783

Sigma-Aldrich

Pyrroloquinoline quinone

≥95.0% (HPLC)

Synonym(s):
Methoxatin, PQQ, 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
Empirical Formula (Hill Notation):
C14H6N2O8
CAS Number:
Molecular Weight:
330.21
Beilstein/REAXYS Number:
3596812
MDL number:
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic

assay

≥95.0% (HPLC)

form

powder

application(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

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General description

Pyrroloquinoline Quinone (PQQ), also referred as methoxatin, is a water soluble orthoquinone molecule with redox-cycling ability.
Novel o-quinone coenzyme found in bacterial dehydrogenases and oxidases.

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.

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.

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Nanocurcumin--pyrroloquinoline formulation prevents hypertrophy--induced pathological damage by relieving mitochondrial stress in cardiomyocytes under hypoxic conditions
Nehra S, et al.
Experimental & Molecular Medicine, 49(12), e404-e404 (2017)
Crystal structure of PqqB from Pseudomonas putida at 2.2
Metlitzky M, et al.
Journal of biophysical chemistry, 3(02), 206-206 (2012)
The life history of pyrroloquinoline quinone (PQQ): a versatile molecule with novel impacts on living systems
Naveed M, et al.
Molecular Biology, 1(10), 29-46 (2016)
E A Decker
Nutrition reviews, 53(3), 49-58 (1995-03-01)
Oxidative reactions have been implicated in the development of numerous diseases including atherosclerosis and cancer. Oxidation of lipids, proteins, and nucleic acids can result in loss of membrane integrity and function, inactivation of enzymes, modification of lipoproteins, and chemical alteration...
The cofactor pyrroloquinoline quinone.
J A Duine et al.
Annual review of nutrition, 10, 297-318 (1990-01-01)

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