Page last updated: 2024-11-04

pqq cofactor

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

PQQ Cofactor: A pyrrolo-quinoline having two adjacent keto-groups at the 4 and 5 positions and three acidic carboxyl groups. It is a coenzyme of some DEHYDROGENASES. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

pyrroloquinoline quinone : A pyrroloquinoline having oxo groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID1024
CHEMBL ID1235421
CHEBI ID18315
SCHEMBL ID37975
SCHEMBL ID21049248
MeSH IDM0091136

Synonyms (57)

Synonym
CHEMBL1235421
4,5-dioxo-4,5-dihydro-1h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
CHEBI:18315 ,
pyrroloquinoline dione
methoxatine
4,5-dioxo-1h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
pyrroloquinoline dione tricarboxylic acid
1h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
C00113
methoxatin
pyrroloquinoline quinone
coenzyme pqq
72909-34-3
pyrrolo-quinoline quinone
2,7,9-tricarboxy-1h-pyrrolo(2,3-f)quinoline-4,5-dione
pyrroloquinoline-quinone
pyrroloquinoline quinone, >=95.0% (hplc)
DB03205
pqq cofactor
AKOS015920260
pqq coenzyme
4,5-dihydro-4,5-dioxo-1h-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid
2,7,9-tricarboxypyrroloquinoline quinone
47819qgh5l ,
unii-47819qgh5l
1h-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
FT-0617182
c14h6n2o8
4,5-dioxo-1h,4h,5h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
SCHEMBL37975
MMXZSJMASHPLLR-UHFFFAOYSA-N
pyrroloquinoline quinone [who-dd]
pyrroloquinoline quinone [inci]
2,7,9-tricarboxy-4,5-dihydro-4,5-dioxo-1h-pyrrolo(2,3-f)quinoline
pyrroloquinolinedione tricarboxylic acid
pyrroloquinolinedione tricarboxylate
DTXSID3041162
mfcd00043125
4,5-dihydro-4,5-dioxo-1h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
CS-W009276
GS-6613
pyrroloquinoline quinone, >=97.0% (hplc)
methoxantin
BCP06301
pyrroloquinoline quinone/pqq
Q414583
pqq;methoxatin
4,5-dioxo-1h-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylicacid
pyrroloquinolinequinone(pqq)
pyrroloquinoline quinone (pqq)
SCHEMBL21049248
4,5-dioxo-4,5-dihydro-1h-pyrrolo-[2,3-f]quinoline-2,7,9-tricarboxylic acid
HY-100196
pyroquinoline quinone
P2781
bdbm50575553
GLXC-26180

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Methylmercury (MeHg), as a highly toxic environmental pollutant, could elicit central nervous system (CNS) damage."( Protection of pyrroloquinoline quinone against methylmercury-induced neurotoxicity via reducing oxidative stress.
Jin, L; Li, X; Sun, J; Wang, L; Xu, Y; Zhang, P, 2009
)
0.35
"Uranium as an environmental contaminant has been shown to be toxic to eukaryotes and prokaryotes; however, no specific mechanisms of uranium toxicity have been proposed so far."( Uranium exerts acute toxicity by binding to pyrroloquinoline quinone cofactor.
Apel, WA; Gerlach, R; Lee, BD; Peyton, BM; Szilagyi, RK; VanEngelen, MR, 2011
)
0.37
" The lowest observed adverse effect levels (LOAELs) of PQQ and PQQE were 10 μM and 2 μM respectively and the no observed adverse effect levels (NOAELs) were 5 μM and 1 μM respectively in mice cortical neurons."( Neurotoxicity and apoptosis induced by pyrroloquinoline quinone and its ester derivative on primary cortical neurons.
Mao, S; Peng, Y; Xu, D; Zhou, X, 2020
)
0.56

Compound-Compound Interactions

ExcerptReferenceRelevance
" In present study, three kinds of nerve guide conduits were constructed: one from cellulose/SPI hollow tube (CSC), another from CSC combined with SCs (CSSC), and the third one from CSSC combined with PQQ (CSSPC), respectively."( Construction of nerve guide conduits from cellulose/soy protein composite membranes combined with Schwann cells and pyrroloquinoline quinone for the repair of peripheral nerve defect.
Chen, Y; Gan, L; Huselstein, C; Liu, Y; Luo, L; Tian, W; Tong, Z; Wang, X, 2015
)
0.42
"The aim of study was to investigate the effects of pyrroloquinoline quinone (PQQ) combined with d-serine on the modulation of glycine sites in the brain of rats using social recognition test."( Modulation of glycine sites enhances social memory in rats using PQQ combined with d-serine.
Liu, D; Mao, S; Peng, Y; Qin, X; Zhang, R; Zhou, X, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" A senescence model was constructed as follows: HDFs (1x10(4)‑1x10(6)) were cultured in a six‑well plate in vitro and then exposed to UVA irradiation at a dosage of 9 J/cm2."( Protective effect of pyrroloquinoline quinine on ultraviolet A irradiation-induced human dermal fibroblast senescence in vitro proceeds via the anti-apoptotic sirtuin 1/nuclear factor-derived erythroid 2-related factor 2/heme oxygenase 1 pathway.
Lin, J; Shen, G; Wen, C; Zhang, C, 2015
)
0.42
" In this study, the effects of PQQ disodium salt (BioPQQ™) on serum TG and cholesterol levels in humans after 6 and 12 wk of treatment at an oral dosage of 20 mg/d were examined."( Effects of Pyrroloquinoline Quinone Disodium Salt Intake on the Serum Cholesterol Levels of Healthy Japanese Adults.
Kawasaki, Y; Nakano, M; Suzuki, N; Takara, T, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
water-soluble vitamin (role)Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.
cofactorAn organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
pyrroloquinoline cofactor
tricarboxylic acidAn oxoacid containing three carboxy groups.
orthoquinonesAny quinone in which the carbons of the two carbonyl groups in the quinone system are joined to each other by a single bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (4)

PathwayProteinsCompounds
Metabolism14961108
Amino acid and derivative metabolism250260
Metabolism of amine-derived hormones1440
Catecholamine biosynthesis418

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
G-protein coupled receptor 35Homo sapiens (human)IC50 (µMol)0.30600.03001.39804.6600AID1775482; AID1775483
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
G-protein coupled receptor 35Homo sapiens (human)EC50 (µMol)0.07100.00202.50079.8000AID1775481
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
cytoskeleton organizationG-protein coupled receptor 35Homo sapiens (human)
G protein-coupled receptor signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationG-protein coupled receptor 35Homo sapiens (human)
chemokine-mediated signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
negative regulation of voltage-gated calcium channel activityG-protein coupled receptor 35Homo sapiens (human)
negative regulation of neuronal action potentialG-protein coupled receptor 35Homo sapiens (human)
positive regulation of Rho protein signal transductionG-protein coupled receptor 35Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
C-X-C chemokine receptor activityG-protein coupled receptor 35Homo sapiens (human)
G protein-coupled receptor activityG-protein coupled receptor 35Homo sapiens (human)
C-X-C chemokine receptor activityG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneG-protein coupled receptor 35Homo sapiens (human)
plasma membraneG-protein coupled receptor 35Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1775482Agonist activity at human GPR35 receptor expressed in HT-29 cells assessed as desensitization of zaprinast-induced DMR response preincubated for 1 hr followed by zaprinast stimulation by DMR desensitization assay2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle.
AID1156936Induction of reactive oxygen species generation in human A549 cells at 200 uM after 48 hrs by MTT assay2014European journal of medicinal chemistry, Aug-18, Volume: 83Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives.
AID1156933Antiproliferative against human A549 cells after 48 hrs by MTT assay2014European journal of medicinal chemistry, Aug-18, Volume: 83Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives.
AID1156934Antiproliferative against human MCF7 cells after 48 hrs by MTT assay2014European journal of medicinal chemistry, Aug-18, Volume: 83Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives.
AID1775483Agonist activity at human GPR35 receptor expressed in HT-29 cells assessed as reduction in dynamic mass redistribution response in presence of GPR35 antagonist ML-145 by DMR assay2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle.
AID1156932Antiproliferative against human HepG2 cells after 48 hrs by MTT assay2014European journal of medicinal chemistry, Aug-18, Volume: 83Design, synthesis and antiproliferative activity of a novel class of indole-2-carboxylate derivatives.
AID1775481Agonist activity at human GPR35 receptor expressed in HT-29 cells assessed as dynamic mass redistribution response by DMR assay2021Journal of medicinal chemistry, 03-11, Volume: 64, Issue:5
Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (677)

TimeframeStudies, This Drug (%)All Drugs %
pre-199094 (13.88)18.7374
1990's169 (24.96)18.2507
2000's134 (19.79)29.6817
2010's192 (28.36)24.3611
2020's88 (13.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.59

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.59 (24.57)
Research Supply Index6.55 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index87.28 (26.88)
Search Engine Supply Index3.99 (0.95)

This Compound (31.59)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (1.16%)5.53%
Reviews79 (11.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other603 (87.39%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]