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D7783

Sigma-Aldrich

Pyrroloquinoline quinone

≥95.0% (HPLC)

Sinônimo(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

Fórmula empírica (Notação de Hill):
C14H6N2O8
Número CAS:
Peso molecular:
330.21
Beilstein:
3596812
Número MDL:
Código UNSPSC:
12352106
ID de substância PubChem:
NACRES:
NA.79

fonte biológica

synthetic

Nível de qualidade

Ensaio

≥95.0% (HPLC)

forma

powder

técnica(s)

HPLC: suitable

cor

red to deep red

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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)

chave InChI

MMXZSJMASHPLLR-UHFFFAOYSA-N

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Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

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Os clientes também visualizaram

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)
Crystal structure of PqqB from Pseudomonas putida at 2.2
Metlitzky M, et al.
Journal of biophysical chemistry, 3(02), 206-206 (2012)
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)
Pyrroloquinoline quinone (PQQ) from methanol dehydrogenase and tryptophan tryptophylquinone (TTQ) from methylamine dehydrogenase.
V L Davidson
Advances in protein chemistry, 58, 95-140 (2001-10-23)
J A Duine
European journal of biochemistry, 200(2), 271-284 (1991-09-01)
The presently best known and largest group of quinoproteins consists of enzymes using the cofactor 2,7,9-tricarboxy-1H-pyrrolo[2,3-f]quinoline- 4,5-dione (PQQ), a compound having a pyrrole ring fused to a quinoline ring with an o-quinone group in it. Representatives of this group are

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