Page last updated: 2024-12-07

aeroplysinin i

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

Description

aeroplysinin I: isolated from sponge Aplysina sp.; RN refers to (1S-trans)-isomer; structure given in second source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID100308
CHEMBL ID462153
CHEBI ID80925
SCHEMBL ID14267425
MeSH IDM0124633

Synonyms (37)

Synonym
aeroplysinin-1
28656-91-9
nsc-170364
aeroplysinin i
(+)-aeroplysinin i
nsc170364
2, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1s-trans)-
2, 3,5-dibromo-1,6-dihydroxy-4-methoxy-
aeroplysinin i, (+)-
aeroplysinin
nsc286160
nsc-286160
(.+-.)-aeroplysinin i
2, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, trans-(+)-
HSCI1_000046
2-[(1s,6r)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl]acetonitrile
C17099
aeroplysinin 1
(3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile
CHEMBL462153
chebi:80925 ,
(+)-aeroplysinin-1
SCHEMBL14267425
AKOS030530966
(+)--aeroplysinin-1
J-017181
2-((1s,6r)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dienyl)acetonitrile
aeroplysinin,aplysina aerophoba
Q27151425
2,4-cyclohexadiene-1-acetonitrile, 3,5-dibromo-1,6-dihydroxy-4-methoxy-, (1s,6r)-
CS-0016895
2-((1s,6r)-3,5-dibromo-1,6-dihydroxy-4-methoxycyclohexa-2,4-dien-1-yl)acetonitrile
(1s-trans)-3,5-dibromo-1,6-dihydroxy-4-methoxy-2,4-cyclohexadiene-1- acetonitrile
F82085
DTXSID60951322
HY-19827
GLXC-19142

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"2 microM (MTT assay, 2-h incubation, EAT cells), 1 was the more toxic compound."( Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
Beekman, AC; Ebel, R; Konings, AW; Koulman, A; Pedersen, JA; Pras, N; Proksch, P; van Uden, W; Woerdenbag, HJ, 1996
)
0.29
"Nephrotoxicity is the major dose-limiting adverse effect of cisplatin (CisPt) and results from CisPt-induced damage of tubular cells."( Spongean alkaloids protect rat kidney cells against cisplatin-induced cytotoxicity.
Fritz, G; Funk, F; Henninger, C; Krüger, K; Proksch, P; Thomale, J; Wätjen, W, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
[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]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID354622Cytotoxicity against human HeLaS3 cells after 2 weeks by clonogenic assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID288820Ratio of MIC for BAEC sprouting to IC50 for BAEC2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1.
AID366421Antibacterial activity against Staphylococcus aureus ATCC 6538P assessed as inhibition zone diameter after 24 hrs by agar diffusion method2008Journal of natural products, Aug, Volume: 71, Issue:8
Bioactive brominated metabolites from the red sea sponge Suberea mollis.
AID354618Cytotoxicity against mouse EN19 cells after 3 days by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354624Cytotoxicity against buthionine sulfoximine-pretreated mouse EN19 cells after 3 days by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354623Cytotoxicity against buthionine sulfoximine-pretreated mouse EN19 cells after 2 hrs by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID366422Antibacterial activity against Pseudomonas aeruginosa ATCC 9027 assessed as inhibition zone diameter after 24 hrs by agar diffusion method2008Journal of natural products, Aug, Volume: 71, Issue:8
Bioactive brominated metabolites from the red sea sponge Suberea mollis.
AID354627Dose enhancement factor, ratio of IC50 for mouse EN19 cells after 2 hrs to IC50 for buthionine sulfoximine-pretreated mouse EN19 cells after 2 hrs by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354620Cytotoxicity against human HeLaS3 cells after 4 days by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354628Dose enhancement factor, ratio of IC50 for mouse EN19 cells after 3 days to IC50 for buthionine sulfoximine-pretreated mouse EN19 cells after 3 days by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354619Cytotoxicity against human HeLaS3 cells after 2 hrs by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354625Cytotoxicity against buthionine sulfoximine-pretreated human HeLaS3 cells after 2 hrs by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354630Dose enhancement factor, ratio of IC50 for human HeLaS3 cells after 4 days to IC50 for buthionine sulfoximine-pretreated human HeLaS3 cells after 4 days by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354617Cytotoxicity against mouse EN19 cells after 2 hrs by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID1666597Induction of DNA damage in human SU8686 cells assessed as increase in gammaH2AX phosphorylation at ser193 at cytotoxic IC50 in presence of 0.3 uM doxorubicin by fluorometry method2020Bioorganic & medicinal chemistry, 02-15, Volume: 28, Issue:4
Targeting the DNA damage response (DDR) by natural compounds.
AID354629Dose enhancement factor, ratio of IC50 for human HeLaS3 cells after 2 hrs to IC50 for buthionine sulfoximine-pretreated human HeLaS3 cells after 2 hrs by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354626Cytotoxicity against buthionine sulfoximine-pretreated human HeLaS3 cells after 4 days by MTT assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID354621Cytotoxicity against mouse EN19 cells after 1 week by clonogenic assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Cytotoxicity and mode of action of aeroplysinin-1 and a related dienonefrom the sponge Aplysina aerophoba.
AID288818Cytotoxicity against BAEC after 2 days by MTT assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1.
AID288819Effect on tube formation of BAEC assessed as sprouting inhibition after 48 hrs2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1.
AID366423Antibacterial activity against Klebsiella pneumoniae ATCC 10032 assessed as inhibition zone diameter after 24 hrs by agar diffusion method2008Journal of natural products, Aug, Volume: 71, Issue:8
Bioactive brominated metabolites from the red sea sponge Suberea mollis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.00)18.7374
1990's4 (16.00)18.2507
2000's4 (16.00)29.6817
2010's13 (52.00)24.3611
2020's3 (12.00)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%
Reviews2 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]