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Merck

D7783

Sigma-Aldrich

Methoxatin

≥95.0% (HPLC)

Synonym(e):

4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]chinolin-2,7,9-tricarbonsäure, PQQ, PyrroloQuinolineQuinone Derivat

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About This Item

Empirische Formel (Hill-System):
C14H6N2O8
CAS-Nummer:
Molekulargewicht:
330.21
Beilstein:
3596812
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.79

Biologische Quelle

synthetic

Assay

≥95.0% (HPLC)

Form

powder

Methode(n)

HPLC: suitable

Farbe

red to deep red

Lagertemp.

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)

InChIKey

MMXZSJMASHPLLR-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


Analysenzertifikate (COA)

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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

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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