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Principaux documents

D7783

Sigma-Aldrich

Pyrroloquinoline quinone

≥95.0% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C14H6N2O8
Numéro CAS:
Poids moléculaire :
330.21
Beilstein:
3596812
Numéro MDL:
Code UNSPSC :
12352106
ID de substance PubChem :
Nomenclature NACRES :
NA.79

Source biologique

synthetic

Niveau de qualité

Essai

≥95.0% (HPLC)

Forme

powder

Technique(s)

HPLC: suitable

Couleur

red to deep red

Température de stockage

2-8°C

Chaîne 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)

Clé InChI

MMXZSJMASHPLLR-UHFFFAOYSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.
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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Consulter la Bibliothèque de documents

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)
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
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)

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