Page last updated: 2024-11-12

ageladine a

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

Description

Ageladine A: an antiangiogenic matrixmetalloproteinase inhibitor from the marine sponge Agelas nakamurai; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ageladine A : An imidazopyridine that is 1H-imidazo[4,5-c]pyridin-2-amine substituted by a 4,5-dibromo-1H-pyrrol-2-yl group at position 4. It is an alkaloid isolated from a marine sponge Agelas nakamurai and acts as an inhibitor of the matrix metalloproteinases, the key enzymes involved in tumour growth, migration, angiogenesis, invasion and metastasis. [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 CID10089677
CHEMBL ID230806
CHEBI ID65373
SCHEMBL ID12563004
MeSH IDM0461836

Synonyms (12)

Synonym
chebi:65373 ,
CHEMBL230806 ,
ageladine a
bdbm50215926
4-(4,5-dibromo-1h-pyrrol-2-yl)-1h-imidazo[4,5-c]pyridin-2-amine
SCHEMBL12563004
ageladine a, tfa
643020-13-7
Q27133816
EX-A5061
4-(4,5-dibromo-1h-pyrrol-2-yl)-3h-imidazo[4,5-c]pyridin-2-amine
(4-(4,5-dibromo-1h-pyrrol-2-yl)-1h-imidazo[4,5-c]-pyridin-2-amine), tfa

Research Excerpts

Overview

Ageladine A is a marine natural product that can be used to fluorescently stain living tissues and cells.

ExcerptReferenceRelevance
"Ageladine A is a marine natural product that can be used to fluorescently stain living tissues and cells. "( Tracking of fast moving neuronal vesicles with ageladine A.
Bickmeyer, U; Heine, M; Karuso, P; Köck, M; Münd, D; Podbielski, I, 2010
)
2.06
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
matrix metalloproteinase inhibitornull
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
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 (5)

ClassDescription
imidazopyridine
pyrrolesAn azole that includes only one N atom and no other heteroatom as a part of the aromatic skeleton.
organobromine compoundA compound containing at least one carbon-bromine bond.
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
aromatic amineAn amino compound in which the amino group is linked directly to an aromatic system.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Casein kinase I isoform alphaSus scrofa (pig)IC50 (µMol)50.00001.20001.20001.2000AID693134
72 kDa type IV collagenaseHomo sapiens (human)IC50 (µMol)1.70000.00001.284810.0000AID452441
Serine/threonine-protein kinase pim-1Homo sapiens (human)IC50 (µMol)10.00000.00040.887110.0000AID693136
Macrophage metalloelastaseHomo sapiens (human)IC50 (µMol)3.66000.00022.721710.0000AID1245161; AID291765; AID449027
Dual specificity tyrosine-phosphorylation-regulated kinase 1ARattus norvegicus (Norway rat)IC50 (µMol)30.00000.01000.57412.8000AID693108
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (76)

Processvia Protein(s)Taxonomy
angiogenesis72 kDa type IV collagenaseHomo sapiens (human)
ovarian follicle development72 kDa type IV collagenaseHomo sapiens (human)
ovulation from ovarian follicle72 kDa type IV collagenaseHomo sapiens (human)
luteinization72 kDa type IV collagenaseHomo sapiens (human)
blood vessel maturation72 kDa type IV collagenaseHomo sapiens (human)
intramembranous ossification72 kDa type IV collagenaseHomo sapiens (human)
proteolysis72 kDa type IV collagenaseHomo sapiens (human)
negative regulation of cell adhesion72 kDa type IV collagenaseHomo sapiens (human)
heart development72 kDa type IV collagenaseHomo sapiens (human)
embryo implantation72 kDa type IV collagenaseHomo sapiens (human)
parturition72 kDa type IV collagenaseHomo sapiens (human)
response to xenobiotic stimulus72 kDa type IV collagenaseHomo sapiens (human)
response to mechanical stimulus72 kDa type IV collagenaseHomo sapiens (human)
peripheral nervous system axon regeneration72 kDa type IV collagenaseHomo sapiens (human)
response to activity72 kDa type IV collagenaseHomo sapiens (human)
protein metabolic process72 kDa type IV collagenaseHomo sapiens (human)
extracellular matrix disassembly72 kDa type IV collagenaseHomo sapiens (human)
protein catabolic process72 kDa type IV collagenaseHomo sapiens (human)
positive regulation of cell migration72 kDa type IV collagenaseHomo sapiens (human)
collagen catabolic process72 kDa type IV collagenaseHomo sapiens (human)
response to retinoic acid72 kDa type IV collagenaseHomo sapiens (human)
cellular response to reactive oxygen species72 kDa type IV collagenaseHomo sapiens (human)
response to nicotine72 kDa type IV collagenaseHomo sapiens (human)
endodermal cell differentiation72 kDa type IV collagenaseHomo sapiens (human)
response to hydrogen peroxide72 kDa type IV collagenaseHomo sapiens (human)
response to estrogen72 kDa type IV collagenaseHomo sapiens (human)
negative regulation of vasoconstriction72 kDa type IV collagenaseHomo sapiens (human)
ephrin receptor signaling pathway72 kDa type IV collagenaseHomo sapiens (human)
macrophage chemotaxis72 kDa type IV collagenaseHomo sapiens (human)
response to electrical stimulus72 kDa type IV collagenaseHomo sapiens (human)
response to hyperoxia72 kDa type IV collagenaseHomo sapiens (human)
face morphogenesis72 kDa type IV collagenaseHomo sapiens (human)
bone trabecula formation72 kDa type IV collagenaseHomo sapiens (human)
prostate gland epithelium morphogenesis72 kDa type IV collagenaseHomo sapiens (human)
cellular response to amino acid stimulus72 kDa type IV collagenaseHomo sapiens (human)
cellular response to interleukin-172 kDa type IV collagenaseHomo sapiens (human)
cellular response to estradiol stimulus72 kDa type IV collagenaseHomo sapiens (human)
cellular response to UV-A72 kDa type IV collagenaseHomo sapiens (human)
cellular response to fluid shear stress72 kDa type IV collagenaseHomo sapiens (human)
positive regulation of oxidative stress-induced neuron intrinsic apoptotic signaling pathway72 kDa type IV collagenaseHomo sapiens (human)
response to amyloid-beta72 kDa type IV collagenaseHomo sapiens (human)
positive regulation of vascular associated smooth muscle cell proliferation72 kDa type IV collagenaseHomo sapiens (human)
extracellular matrix organization72 kDa type IV collagenaseHomo sapiens (human)
response to hypoxia72 kDa type IV collagenaseHomo sapiens (human)
tissue remodeling72 kDa type IV collagenaseHomo sapiens (human)
protein phosphorylationSerine/threonine-protein kinase pim-1Homo sapiens (human)
apoptotic processSerine/threonine-protein kinase pim-1Homo sapiens (human)
regulation of transmembrane transporter activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
negative regulation of apoptotic processSerine/threonine-protein kinase pim-1Homo sapiens (human)
negative regulation of DNA-binding transcription factor activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
negative regulation of innate immune responseSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of DNA-templated transcriptionSerine/threonine-protein kinase pim-1Homo sapiens (human)
protein autophosphorylationSerine/threonine-protein kinase pim-1Homo sapiens (human)
protein stabilizationSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of cardiac muscle cell proliferationSerine/threonine-protein kinase pim-1Homo sapiens (human)
vitamin D receptor signaling pathwaySerine/threonine-protein kinase pim-1Homo sapiens (human)
cellular response to type II interferonSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of brown fat cell differentiationSerine/threonine-protein kinase pim-1Homo sapiens (human)
regulation of hematopoietic stem cell proliferationSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of TORC1 signalingSerine/threonine-protein kinase pim-1Homo sapiens (human)
positive regulation of cardioblast proliferationSerine/threonine-protein kinase pim-1Homo sapiens (human)
cellular detoxificationSerine/threonine-protein kinase pim-1Homo sapiens (human)
negative regulation of transcription by RNA polymerase IIMacrophage metalloelastaseHomo sapiens (human)
proteolysisMacrophage metalloelastaseHomo sapiens (human)
protein import into nucleusMacrophage metalloelastaseHomo sapiens (human)
extracellular matrix disassemblyMacrophage metalloelastaseHomo sapiens (human)
collagen catabolic processMacrophage metalloelastaseHomo sapiens (human)
positive regulation of interferon-alpha productionMacrophage metalloelastaseHomo sapiens (human)
wound healing, spreading of epidermal cellsMacrophage metalloelastaseHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIMacrophage metalloelastaseHomo sapiens (human)
lung alveolus developmentMacrophage metalloelastaseHomo sapiens (human)
regulation of defense response to virus by hostMacrophage metalloelastaseHomo sapiens (human)
positive regulation of epithelial cell proliferation involved in wound healingMacrophage metalloelastaseHomo sapiens (human)
elastin catabolic processMacrophage metalloelastaseHomo sapiens (human)
negative regulation of type I interferon-mediated signaling pathwayMacrophage metalloelastaseHomo sapiens (human)
positive regulation of type I interferon-mediated signaling pathwayMacrophage metalloelastaseHomo sapiens (human)
bronchiole developmentMacrophage metalloelastaseHomo sapiens (human)
cellular response to virusMacrophage metalloelastaseHomo sapiens (human)
response to amyloid-betaMacrophage metalloelastaseHomo sapiens (human)
negative regulation of endothelial cell-matrix adhesion via fibronectinMacrophage metalloelastaseHomo sapiens (human)
extracellular matrix organizationMacrophage metalloelastaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
fibronectin binding72 kDa type IV collagenaseHomo sapiens (human)
endopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
metalloendopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
serine-type endopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
protein binding72 kDa type IV collagenaseHomo sapiens (human)
metallopeptidase activity72 kDa type IV collagenaseHomo sapiens (human)
zinc ion binding72 kDa type IV collagenaseHomo sapiens (human)
protein serine/threonine kinase activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
protein bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
ATP bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
transcription factor bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
manganese ion bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
ribosomal small subunit bindingSerine/threonine-protein kinase pim-1Homo sapiens (human)
protein serine kinase activitySerine/threonine-protein kinase pim-1Homo sapiens (human)
core promoter sequence-specific DNA bindingMacrophage metalloelastaseHomo sapiens (human)
endopeptidase activityMacrophage metalloelastaseHomo sapiens (human)
metalloendopeptidase activityMacrophage metalloelastaseHomo sapiens (human)
serine-type endopeptidase activityMacrophage metalloelastaseHomo sapiens (human)
calcium ion bindingMacrophage metalloelastaseHomo sapiens (human)
collagen bindingMacrophage metalloelastaseHomo sapiens (human)
zinc ion bindingMacrophage metalloelastaseHomo sapiens (human)
sequence-specific DNA bindingMacrophage metalloelastaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
collagen-containing extracellular matrix72 kDa type IV collagenaseHomo sapiens (human)
extracellular region72 kDa type IV collagenaseHomo sapiens (human)
extracellular space72 kDa type IV collagenaseHomo sapiens (human)
nucleus72 kDa type IV collagenaseHomo sapiens (human)
mitochondrion72 kDa type IV collagenaseHomo sapiens (human)
plasma membrane72 kDa type IV collagenaseHomo sapiens (human)
sarcomere72 kDa type IV collagenaseHomo sapiens (human)
collagen-containing extracellular matrix72 kDa type IV collagenaseHomo sapiens (human)
extracellular space72 kDa type IV collagenaseHomo sapiens (human)
nucleusSerine/threonine-protein kinase pim-1Homo sapiens (human)
nucleoplasmSerine/threonine-protein kinase pim-1Homo sapiens (human)
nucleolusSerine/threonine-protein kinase pim-1Homo sapiens (human)
cytoplasmSerine/threonine-protein kinase pim-1Homo sapiens (human)
cytosolSerine/threonine-protein kinase pim-1Homo sapiens (human)
plasma membraneSerine/threonine-protein kinase pim-1Homo sapiens (human)
cytoplasmSerine/threonine-protein kinase pim-1Homo sapiens (human)
extracellular regionMacrophage metalloelastaseHomo sapiens (human)
extracellular spaceMacrophage metalloelastaseHomo sapiens (human)
nucleusMacrophage metalloelastaseHomo sapiens (human)
cytoplasmMacrophage metalloelastaseHomo sapiens (human)
extracellular matrixMacrophage metalloelastaseHomo sapiens (human)
extracellular spaceMacrophage metalloelastaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID693131Inhibition of starfish oocytes CDK1/cyclin B using [gamma-32P] ATP at 100 uM after 30 mins by scintillation counting2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693091Antiangiogenic activity in Fischer rat aorta fragments assessed as vessel outgrowth at 100 ug/mL after 5 days2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693105Binding affinity to DYRK1A assessed as ATP binding remaining at 10 uM2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693106Binding affinity to DYRK2 assessed as ATP binding remaining at 10 uM2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693081Inhibition of MMP82011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693138Inhibition of GSK3 at 100 uM2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693079Inhibition of MMP12011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693133Inhibition of human recombinant CDK5/p25 using [gamma-32P] ATP at 100 uM after 30 mins by scintillation counting2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693134Inhibition of porcine brain CK1 using RRKHAAIGpSAYSITA as substrate2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693082Inhibition of MMP92011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693136Inhibition of human recombinant PIM1 using [gamma-32P] ATP after 30 mins by scintillation counting2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693087Inhibition of MMP14 using MOCAc-Pro-Leu-Gly-Leu-A2pr(Dnp)-Ala-Arg- NH2 as substrate preincubated for 10 mins measured after 3 hrs by fluorescence assay2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693102Antiangiogenic activity in Fischer rat aorta fragments assessed as vessel outgrowth at 1 ug/mL after 5 days2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693107Binding affinity to JH domain of TYK2 assessed as ATP binding remaining at 10 uM2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693100Growth inhibition of human NCI60 cells at 10 uM2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693101Antiangiogenic activity in Fischer rat aorta fragments assessed as vessel outgrowth at 10 ug/mL after 5 days2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693103Antiangiogenic activity in Fischer rat aorta fragments assessed as vessel outgrowth at 0.1 ug/mL after 5 days2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID449027Inhibition of human MMP12 catalytic domain2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Synthesis of novel ageladine A analogs showing more potent matrix metalloproteinase (MMP)-12 inhibitory activity than the natural product.
AID693084Inhibition of MMP132011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID291765Inhibition of MMP122007Bioorganic & medicinal chemistry letters, Aug-15, Volume: 17, Issue:16
Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs.
AID693083Inhibition of MMP122011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693080Inhibition of MMP22011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693108Inhibition of rat recombinant GST-fused DYRK1A expressed in Escherichia coli using [gamma-32P] ATP after 30 mins by scintillation counting2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID1245161Inhibition of MMP12 (unknown origin)2015Bioorganic & medicinal chemistry, Sep-15, Volume: 23, Issue:18
Imidazopyridines as a source of biological activity and their pharmacological potentials-Infrared and Raman spectroscopic evidence of their content in pharmaceuticals and plant materials.
AID452441Inhibition of MMP22010Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1
Synthesis and anticancer activities of ageladine A and structural analogs.
AID693085Inhibition of human recombinant MMP2 using MOCAc-Pro-Leu-Gly-Leu-A2pr(Dnp)-Ala-Arg- NH2 as substrate preincubated for 10 mins measured after 3 hrs by fluorescence assay2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693109Binding affinity to YSK4 assessed as ATP binding remaining at 10 uM2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
AID693104Antiangiogenic activity in Fischer rat aorta fragments assessed as vessel outgrowth after 5 days2011Journal of medicinal chemistry, Apr-14, Volume: 54, Issue:7
A one-pot synthesis and biological activity of ageladine A and analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's8 (34.78)29.6817
2010's13 (56.52)24.3611
2020's2 (8.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.04

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 Index19.04 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.04)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (8.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (91.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]