Page last updated: 2024-10-15

quininib

Description

quininib: has antiangiogenic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

quininib : A styrylquinoline that is trans-2-styrylquinoline in which the the phenyl group has been substituted at position 2 by a hydroxy group. It is an anti-angiogenic compound that exerts a dose-dependent antagonism of the cysteinyl leukotriene pathway, preferentially antagonising cysteinyl leukotriene receptor 1. The major species at pH 7.3 [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 CID135411330
CHEMBL ID127545
CHEBI ID133170
SCHEMBL ID10325190

Synonyms (25)

Synonym
1379458-56-6
2-[(e)-2-(quinolin-2-yl)vinyl]phenol
CHEBI:133170
quininib
CHEMBL127545 ,
2-(2-(quinolin-2-yl)vinyl)phenol
2-(2-quinolin-2-yl-vinyl)-phenol
bdbm50001270
(6e)-6-[(2e)-2-(1h-quinolin-2-ylidene)ethylidene]cyclohexa-2,4-dien-1-one
2-[(e)-2-(quinolin-2-yl)ethenyl]phenol
AKOS005697868
AKOS015955311
(e)-2-(2-(quinolin-2-yl)vinyl)phenol
F0863-0555
143816-42-6
AB00094585-01
cambridge id 5719593
SCHEMBL10325190
quininib, >=98% (hplc)
2-[(1e)-2-(2-quinolinyl)ethenyl]-phenol
4838-66-8
2-[(e)-2-quinolin-2-ylethenyl]phenol
CS-0068377
HY-119442
2-[(1e)-2-(quinolin-2-yl)ethenyl]phenol

Research Excerpts

Overview

The quininib series is a novel collection of small-molecule drugs with antiangiogenic, antivascular permeability, anti-inflammatory, and antiproliferative activity.

ExcerptReference
"The quininib series is a novel collection of small-molecule drugs with antiangiogenic, antivascular permeability, anti-inflammatory, and antiproliferative activity. "( Discovery and Development of the Quininib Series of Ocular Drugs.
Alvarez, Y; Kennedy, B; Mahon, N; O'Brien, J; Reynolds, A; Slater, K,
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
angiogenesis inhibitorAn agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
[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 (2)

ClassDescription
styrylquinoline
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[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]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NeprilysinHomo sapiens (human)IC50 (µMol)100.00000.00020.54226.7000AID404720
Endothelin-converting enzyme 2Homo sapiens (human)IC50 (µMol)6.42006.42006.42006.4200AID404719
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
kidney developmentNeprilysinHomo sapiens (human)
placenta developmentNeprilysinHomo sapiens (human)
proteolysisNeprilysinHomo sapiens (human)
peptide metabolic processNeprilysinHomo sapiens (human)
learning or memoryNeprilysinHomo sapiens (human)
substance P catabolic processNeprilysinHomo sapiens (human)
bradykinin catabolic processNeprilysinHomo sapiens (human)
sensory perception of painNeprilysinHomo sapiens (human)
protein catabolic processNeprilysinHomo sapiens (human)
lung developmentNeprilysinHomo sapiens (human)
hormone catabolic processNeprilysinHomo sapiens (human)
response to estrogenNeprilysinHomo sapiens (human)
creatinine metabolic processNeprilysinHomo sapiens (human)
amyloid-beta metabolic processNeprilysinHomo sapiens (human)
positive regulation of neurogenesisNeprilysinHomo sapiens (human)
neuropeptide processingNeprilysinHomo sapiens (human)
cellular response to cytokine stimulusNeprilysinHomo sapiens (human)
cellular response to UV-ANeprilysinHomo sapiens (human)
cellular response to UV-BNeprilysinHomo sapiens (human)
replicative senescenceNeprilysinHomo sapiens (human)
amyloid-beta clearanceNeprilysinHomo sapiens (human)
amyloid-beta clearance by cellular catabolic processNeprilysinHomo sapiens (human)
positive regulation of long-term synaptic potentiationNeprilysinHomo sapiens (human)
protein processingNeprilysinHomo sapiens (human)
G protein-coupled receptor signaling pathwayEndothelin-converting enzyme 2Homo sapiens (human)
cell-cell signalingEndothelin-converting enzyme 2Homo sapiens (human)
peptide hormone processingEndothelin-converting enzyme 2Homo sapiens (human)
methylationEndothelin-converting enzyme 2Homo sapiens (human)
protein processingEndothelin-converting enzyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
phosphatidylserine bindingNeprilysinHomo sapiens (human)
endopeptidase activityNeprilysinHomo sapiens (human)
metalloendopeptidase activityNeprilysinHomo sapiens (human)
protein bindingNeprilysinHomo sapiens (human)
exopeptidase activityNeprilysinHomo sapiens (human)
zinc ion bindingNeprilysinHomo sapiens (human)
peptide bindingNeprilysinHomo sapiens (human)
protein homodimerization activityNeprilysinHomo sapiens (human)
oligopeptidase activityNeprilysinHomo sapiens (human)
cardiolipin bindingNeprilysinHomo sapiens (human)
metalloendopeptidase activityEndothelin-converting enzyme 2Homo sapiens (human)
methyltransferase activityEndothelin-converting enzyme 2Homo sapiens (human)
metal ion bindingEndothelin-converting enzyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (22)

Processvia Protein(s)Taxonomy
cytoplasmNeprilysinHomo sapiens (human)
early endosomeNeprilysinHomo sapiens (human)
trans-Golgi networkNeprilysinHomo sapiens (human)
plasma membraneNeprilysinHomo sapiens (human)
brush borderNeprilysinHomo sapiens (human)
focal adhesionNeprilysinHomo sapiens (human)
synaptic vesicleNeprilysinHomo sapiens (human)
cell surfaceNeprilysinHomo sapiens (human)
membraneNeprilysinHomo sapiens (human)
axonNeprilysinHomo sapiens (human)
dendriteNeprilysinHomo sapiens (human)
secretory granule membraneNeprilysinHomo sapiens (human)
cytoplasmic vesicleNeprilysinHomo sapiens (human)
neuronal cell bodyNeprilysinHomo sapiens (human)
neuron projection terminusNeprilysinHomo sapiens (human)
membrane raftNeprilysinHomo sapiens (human)
synapseNeprilysinHomo sapiens (human)
extracellular exosomeNeprilysinHomo sapiens (human)
presynapseNeprilysinHomo sapiens (human)
plasma membraneNeprilysinHomo sapiens (human)
Golgi membraneEndothelin-converting enzyme 2Homo sapiens (human)
transport vesicle membraneEndothelin-converting enzyme 2Homo sapiens (human)
cytoplasmic vesicle membraneEndothelin-converting enzyme 2Homo sapiens (human)
plasma membraneEndothelin-converting enzyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID717782Antimicrobial activity against methicillin-resistant Staphylococcus aureus H 5996/08 after 48 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717781Antimicrobial activity against Staphylococcus epidermidis H 6966/08 after 24 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717783Antimicrobial activity against methicillin-resistant Staphylococcus aureus H 5996/08 after 24 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717788Antimicrobial activity against Absidia corymbifera 272 after 24 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717900Antimicrobial activity against Candida glabrata 20/I after 24 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717785Antimicrobial activity against Staphylococcus aureus CCM 4516/08 after 24 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID404719Reduction of recombinant ECE2 activity measured by McaBk2 fluorescent substrate hydrolysis2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Homology modeling and site-directed mutagenesis to identify selective inhibitors of endothelin-converting enzyme-2.
AID717787Antimicrobial activity against Trichophyton mentagrophytes 445 after 72 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717779Lipophilicity, log P of compound by RP-HPLC analysis2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717902Antimicrobial activity against Candida tropicalis 156 after 24 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717789Antimicrobial activity against Aspergillus fumigatus 231 after 24 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717903Antimicrobial activity against Candida albicans ATCC 44859 after 24 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID404718Reduction of recombinant ECE2 activity measured by McaBk2 fluorescent substrate hydrolysis at 10 uM2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Homology modeling and site-directed mutagenesis to identify selective inhibitors of endothelin-converting enzyme-2.
AID79872In vitro inhibition of [3H]LTD4 binding to guinea pig lung membranes.1992Journal of medicinal chemistry, Oct-16, Volume: 35, Issue:21
Development of a novel series of styrylquinoline compounds as high-affinity leukotriene D4 receptor antagonists: synthetic and structure-activity studies leading to the discovery of (+-)-3-[[[3-[2-(7-chloro-2-quinolinyl)-(E)-ethenyl]phenyl][[3- (dimethyla
AID717901Antimicrobial activity against Candida krusei ATCC 6258 after 24 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717780Antimicrobial activity against Staphylococcus epidermidis H 6966/08 after 48 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID404720Inhibition of Neprilysin2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Homology modeling and site-directed mutagenesis to identify selective inhibitors of endothelin-converting enzyme-2.
AID717790Antimicrobial activity against Trichosporon beigelii 1188 after 24 hrs by broth microdilution test2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID717784Antimicrobial activity against Staphylococcus aureus CCM 4516/08 after 48 hrs by broth microdilution method2012Bioorganic & medicinal chemistry, Dec-15, Volume: 20, Issue:24
Contribution to investigation of antimicrobial activity of styrylquinolines.
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (8.33)18.2507
2000's1 (8.33)29.6817
2010's8 (66.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]