Page last updated: 2024-12-11

variolin b

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

Description

variolin B: from Antartic sponge, Kirkpatrickia variolosa; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9817550
CHEMBL ID380500
SCHEMBL ID13175404
MeSH IDM0450818

Synonyms (8)

Synonym
variolin b
DB08694
CHEMBL380500
bdbm50398327
9-amino-5-(2-aminopyrimidin-4-yl)pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol
SCHEMBL13175404
13-amino-8-(2-aminopyrimidin-4-yl)-1,3,12-triazatricyclo[7.4.0.02,7]trideca-2(7),4,8,10,12-pentaen-6-one
Q27097881

Research Excerpts

Overview

Variolin B (VAR-B) is a natural product isolated from the sponge Kirkpatrickia variolosa, found in Antarctica. It showed promising anti-cancer activity soon after its isolation.

ExcerptReferenceRelevance
"Variolin B is a rare marine alkaloid that showed promising anti-cancer activity soon after its isolation. "( Intercalative DNA binding of the marine anticancer drug variolin B.
Albericio, F; Álvarez, M; Arribas-Bosacoma, R; Aymamí, J; Canals, A; Coll, M, 2017
)
2.14
"Variolin B (VAR-B) is a natural product isolated from the sponge Kirkpatrickia variolosa, found in Antarctica. "( Variolin B and its derivate deoxy-variolin B: new marine natural compounds with cyclin-dependent kinase inhibitor activity.
Bailly, C; Cuevas, C; D'Incalci, M; Damia, G; Di Francesco, AM; Erba, E; Fernandez Sousa-Faro, JM; Riccardi, R; Simone, M; Vikhanskaya, F, 2005
)
3.21
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Endothelial PAS domain-containing protein 1Homo sapiens (human)EC50 (µMol)0.70000.02000.93303.3000AID707849
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
response to hypoxiaEndothelial PAS domain-containing protein 1Homo sapiens (human)
angiogenesisEndothelial PAS domain-containing protein 1Homo sapiens (human)
embryonic placenta developmentEndothelial PAS domain-containing protein 1Homo sapiens (human)
blood vessel remodelingEndothelial PAS domain-containing protein 1Homo sapiens (human)
regulation of heart rateEndothelial PAS domain-containing protein 1Homo sapiens (human)
epithelial cell maturationEndothelial PAS domain-containing protein 1Homo sapiens (human)
response to oxidative stressEndothelial PAS domain-containing protein 1Homo sapiens (human)
mitochondrion organizationEndothelial PAS domain-containing protein 1Homo sapiens (human)
signal transductionEndothelial PAS domain-containing protein 1Homo sapiens (human)
visual perceptionEndothelial PAS domain-containing protein 1Homo sapiens (human)
erythrocyte differentiationEndothelial PAS domain-containing protein 1Homo sapiens (human)
lung developmentEndothelial PAS domain-containing protein 1Homo sapiens (human)
norepinephrine metabolic processEndothelial PAS domain-containing protein 1Homo sapiens (human)
mRNA transcription by RNA polymerase IIEndothelial PAS domain-containing protein 1Homo sapiens (human)
surfactant homeostasisEndothelial PAS domain-containing protein 1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIEndothelial PAS domain-containing protein 1Homo sapiens (human)
myoblast fate commitmentEndothelial PAS domain-containing protein 1Homo sapiens (human)
multicellular organismal-level iron ion homeostasisEndothelial PAS domain-containing protein 1Homo sapiens (human)
cellular response to hypoxiaEndothelial PAS domain-containing protein 1Homo sapiens (human)
positive regulation of cold-induced thermogenesisEndothelial PAS domain-containing protein 1Homo sapiens (human)
regulation of protein neddylationEndothelial PAS domain-containing protein 1Homo sapiens (human)
regulation of transcription by RNA polymerase IIEndothelial PAS domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
sequence-specific DNA bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEndothelial PAS domain-containing protein 1Homo sapiens (human)
transcription coactivator bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificEndothelial PAS domain-containing protein 1Homo sapiens (human)
protein bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
protein heterodimerization activityEndothelial PAS domain-containing protein 1Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
nucleoplasmEndothelial PAS domain-containing protein 1Homo sapiens (human)
cytosolEndothelial PAS domain-containing protein 1Homo sapiens (human)
nuclear speckEndothelial PAS domain-containing protein 1Homo sapiens (human)
chromatinEndothelial PAS domain-containing protein 1Homo sapiens (human)
transcription regulator complexEndothelial PAS domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (42)

Assay IDTitleYearJournalArticle
AID707624Inhibition of HIF2alpha in human RCC4 cells coexpressing HIF1alpha assessed as reduction in GLUT1 mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260403Inhibition of growth against DU145 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID707640Inhibition of HIF2alpha in human 786-0 cells assessed as reduction in TGFalpha mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260415Inhibition of growth against LoVo cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID707423Downregulation of HIF2alpha mRNA expression in human SK-RC-28 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707431Downregulation of TGFalpha mRNA expression in human SK-RC-28 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707437Downregulation of HIF2alpha mRNA expression in human RCC4 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707637Inhibition of HIF2alpha in human 786-0 cells assessed as reduction in GLUT1 mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707635Inhibition of HIF2alpha in human 786-0 cells assessed as reduction in CCND1 mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707439Downregulation of HIF1alpha mRNA expression in human RCC4 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260406Inhibition of growth against IGROV cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID707682Cytotoxicity against human SK-RC-28 cells expressing HIF1alpha after 2 days by XTT assay2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707627Inhibition of HIF1alpha in human RCC4 cells coexpressing HIF2alpha assessed as decrease in carbonic anhydrase 9 mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707849Inhibition of HIF2alpha in human 786-0 cells expressing truncated HIF1alpha assessed as reduction in luciferase activity after 24 hrs by reporter gene assay2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707630Downregulation of HIF2alpha mRNA expression in human 786-0 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707436Inhibition of HIF1alpha in human SK-RC-28 cells assessed as reduction in carbonic anhydrase 9 expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707428Downregulation of GLUT1 mRNA expression in human SK-RC-28 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707441Inhibition of HIF1alpha/2alpha in human RCC4 cells assessed as reduction in VEGFA mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707631Downregulation of HIF1alpha mRNA expression in human 786-0 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260416Inhibition of growth against LoVo-Dox cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID707621Inhibition of HIF2alpha in human RCC4 cells coexpressing HIF1alpha assessed as reduction in CCND1 mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260409Inhibition of growth against MEL28 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260405Inhibition of growth against SKOV3 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260412Inhibition of growth against K562 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID707625Inhibition of HIF2alpha in human RCC4 cells coexpressing HIF1alpha assessed as reduction in TGFalpha mRNA expression at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707848Inhibition of HIF-mediated VEGFA protein expression in serum deprived human 786-0 cells at 1 uM after 48 hrs relative to control2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260411Inhibition of growth against A549 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260407Inhibition of growth against IGROV-ET cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260417Inhibition of growth against HeLa cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID707841Cytotoxicity against human RCC4 cells expressing HIF2alpha and HIF1alpha after 2 days by XTT assay2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707641Down regulation of carbonic anhydrase 9 expression in human 786-0 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707425Downregulation of HIF1alpha mRNA expression in human SK-RC-28 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707842Cytotoxicity against human 786-0 cells expressing HIF2alpha after 2 days by XTT assay2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707427Downregulation of CCND1 mRNA expression in human SK-RC-28 cells at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID707634Inhibition of HIF2alpha in human 786-0 cells assessed as reduction in VEGFA at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260414Inhibition of growth against HT29 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260408Inhibition of growth against SKBR3 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260410Inhibition of growth against HMEC1 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID707433Inhibition of HIF1alpha in human SK-RC-28 cells assessed as reduction in VEGFA at 1 uM after 48 hrs by RT-PCR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Inhibition of hypoxia inducible factor-2 transcription: isolation of active modulators from marine sponges.
AID260418Inhibition of growth against HeLa-Apl cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260413Inhibition of growth against PANC1 cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
AID260404Inhibition of growth against LnCAP cells after 72 hrs exposure2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
Synthesis and cytotoxic evaluation of new derivatives of the marine alkaloid variolin B.
[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's0 (0.00)18.2507
2000's8 (66.67)29.6817
2010's4 (33.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.44

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 Index19.44 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]