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D7783

Sigma-Aldrich

Pyrroloquinoline quinone

≥95.0% (HPLC)

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

biological source

synthetic

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

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1 of 4

This Item
O087780198SML0775
vibrant-m

D7783

Pyrroloquinoline quinone

vibrant-m

O0877

Oxolinic acid

vibrant-m

80198

Methoxatin disodium salt

vibrant-m

SML0775

PZ-II-029

biological source

synthetic

biological source

-

biological source

fermentation/recombinant

biological source

-

assay

≥95.0% (HPLC)

assay

-

assay

≥97.0% (HPLC)

assay

≥98% (HPLC)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

form

powder

form

-

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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
Pyrroloquinoline quinone: a novel cofactor.
J A Duine et al.
Vitamins and hormones, 45, 223-262 (1989-01-01)
H S Misra et al.
Journal of biosciences, 37(2), 313-325 (2012-05-15)
Pyrroloquinoline-quinine (PQQ) was initially characterized as a redox cofactor for membrane-bound dehydrogenases in the bacterial system. Subsequently, PQQ was shown to be an antioxidant protecting the living cells from oxidative damage in vivo and the biomolecules from artificially produced reaction

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