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D7783

Sigma-Aldrich

Pyrroloquinoline quinone

≥95.0% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C14H6N2O8
CAS Number:
Molecular Weight:
330.21
Beilstein/REAXYS Number:
3596812
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.79
Pricing and availability is not currently available.

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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General description

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.[1]

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[2]
  • as a standard in fluorescence analysis[3]
  • to test its efficiency in suppressing restrained oxidative stress and hepatic fibrogenesis in mouse models[4]

Biochem/physiol Actions

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.[5] PQQ is used as a potential therapeutic to treat liver fibrosis.[4]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
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)
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 (PQQ) from methanol dehydrogenase and tryptophan tryptophylquinone (TTQ) from methylamine dehydrogenase.
V L Davidson
Advances in protein chemistry, 58, 95-140 (2001-10-23)
Jiro Omata et al.
JPEN. Journal of parenteral and enteral nutrition, 35(5), 616-624 (2011-04-22)
Experimental intravenous (IV) parenteral nutrition (PN) diminishes gut-associated lymphoid tissue (GALT) cell number and function. PN solution cannot maintain GALT at the same level as a normal diet, even when delivered intragastrically (IG). Previous studies demonstrated pyrroloquinoline quinone (PQQ)-deficient mice

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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