Compounds > (1,2-bis(1,2-benzisoselenazolone-3(2h)-ketone))ethane
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(1,2-bis(1,2-benzisoselenazolone-3(2h)-ketone))ethane

Description

(1,2-bis(1,2-benzisoselenazolone-3(2H)-ketone))ethane: has antineoplastic activity; structure in first source [MeSH]

Cross-References

ID SourceID
PubMed CID10387485
CHEMBL ID2035460
SCHEMBL ID3561403
MeSH IDM0455226

Synonyms (22)

Synonym
(1,2-bis(1,2-benzisoselenazolone-3(2h)-ketone))ethane
ethaselen
us8592468, ebse14
bdbm50385303
compound eb
ethaselen-1
bbske
shuang-xi-zuo-wan-1
CHEMBL2035460 ,
SCHEMBL3561403
unii-4q2ezs1iwg
2,2'-(1,2-ethanediyl)bis(1,2-benzisoselenazol-3(2h)-one)
217798-39-5
1,2-benzisoselenazol-3(2h)-one, 2,2'-(1,2-ethanediyl)bis-
4q2ezs1iwg ,
DB15051
2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one
2,2'-(ethane-1,2-diyl)bis(benzo[d][1,2]selenazol-3(2h)-one) .
EX-A5107
HY-116749
CS-0066457
AKOS040757392

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Thioredoxin reductase 1, cytoplasmicRattus norvegicus (Norway rat)IC506.0000AID665488
Thioredoxin reductase 1, cytoplasmicHomo sapiens (human)IC505.0000AID665478
Thioredoxin reductase 3Homo sapiens (human)IC505.0000AID665478
Thioredoxin reductase 2, mitochondrialHomo sapiens (human)IC505.0000AID665478

Bioassays (25)

Assay IDTitleYearJournalArticle
AID1406795Antiproliferative activity against human BEAS2B cells after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1275496Antiproliferative activity against human HeLa cells after 48 hrs by CCK8 assay2016Bioorganic & medicinal chemistry letters, Feb-15, Volume: 26, Issue:4
ISSN: 1464-3405		Synthesis and antiproliferative evaluation of novel 1,2,4-triazole derivatives incorporating benzisoselenazolone scaffold.
AID665490Inhibition of human glutathione reductase Sec498Cys mutant at 100 uM after 10 mins by GSSH reduction assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID1406790Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1406792Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1275495Antiproliferative activity against human SMMC7721 cells after 48 hrs by CCK8 assay2016Bioorganic & medicinal chemistry letters, Feb-15, Volume: 26, Issue:4
ISSN: 1464-3405		Synthesis and antiproliferative evaluation of novel 1,2,4-triazole derivatives incorporating benzisoselenazolone scaffold.
AID665483Inhibition of human glutathione reductase at 100 uM after 10 mins by GSSH reduction assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID665474Inhibition of TrxR1 in rat liver homogenate preincubated for 5 mins measured by DNTB assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID1406793Antiproliferative activity against human 184B5 cells after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1887896Antitumor activity against human MHCC97H cells xenografted in BALB/c mouse assessed as tumor volume at 30 mg/kg, ip administered every other day for 30 days2022European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254Structure modification and biological evaluation of indole-chalcone derivatives as anti-tumor agents through dual targeting tubulin and TrxR.
AID1406797Selectivity index, ratio of GI50 for human BEAS2B cells to GI50 for human HTB-54 cells2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1406794Antiproliferative activity against human HTB-54 cells after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1406791Antiproliferative activity against human CCRF-CEM cells after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1406789Antiproliferative activity against human HT-29 cells after 72 hrs by MTT assay2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1275497Antiproliferative activity against human A549 cells after 48 hrs by CCK8 assay2016Bioorganic & medicinal chemistry letters, Feb-15, Volume: 26, Issue:4
ISSN: 1464-3405		Synthesis and antiproliferative evaluation of novel 1,2,4-triazole derivatives incorporating benzisoselenazolone scaffold.
AID665489Inhibition of human C-terminal truncated TrxR2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID1275498Antiproliferative activity against mouse L929 cells after 48 hrs by CCK8 assay2016Bioorganic & medicinal chemistry letters, Feb-15, Volume: 26, Issue:4
ISSN: 1464-3405		Synthesis and antiproliferative evaluation of novel 1,2,4-triazole derivatives incorporating benzisoselenazolone scaffold.
AID1887892Antitumor activity against human MHCC97H cells xenografted in BALB/c mouse assessed as tumor growth inhibition at 30 mg/kg, ip administered every other day for 30 days2022European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254Structure modification and biological evaluation of indole-chalcone derivatives as anti-tumor agents through dual targeting tubulin and TrxR.
AID665478Inhibition of TrxR in human U87MG cells after 12 hrs by insulin-reducing method2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID665475Growth inhibition of human MIAPaCa2 cells after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID665477Growth inhibition of human LoVo cells after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID665476Growth inhibition of human U87MG cells after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID665488Non-competitive inhibition of rat TrxR12012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
ISSN: 1464-3391		Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy.
AID1406796Selectivity index, ratio of GI50 for human 184B5 cells to GI50 for human MCF7 cells2018European journal of medicinal chemistry, Sep-05, Volume: 157ISSN: 1768-3254Novel selenadiazole derivatives as selective antitumor and radical scavenging agents.
AID1887895Antitumor activity against human MHCC97H cells xenografted in BALB/c mouse assessed as tumor weight at 30 mg/kg, ip administered every other day for 30 days2022European journal of medicinal chemistry, Jan-05, Volume: 227ISSN: 1768-3254Structure modification and biological evaluation of indole-chalcone derivatives as anti-tumor agents through dual targeting tubulin and TrxR.

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's10 (34.48)29.6817
2010's17 (58.62)24.3611
2020's2 (6.90)2.80

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%
Other29 (100.00%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
ebselen
1
benzoselenazoleanti-inflammatory drug;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 3.5.4.1 (cytosine deaminase) inhibitor;
EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor;
enzyme mimic;
ferroptosis inhibitor;
genotoxin;
hepatoprotective agent;
neuroprotective agent;
radical scavenger		201820186.0low000010
fluorouracil
1
nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic		201620168.0low000010
vincristine
1
acetate ester;
formamides;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator		202220222.0low000001
colchicine
1
alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen		202220222.0low000001
paclitaxel
1
taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent		202220222.0low000001
etoposide
1
beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor		201820186.0low000010
demecolcine
1
alkaloid;
secondary amino compound		antineoplastic agent;
microtubule-destabilising agent		202220222.0low000001
doxorubicin hydrochloride
1
anthracycline202220222.0low000001
curcumin
1
aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger		202220222.0low000001
fosbretabulin
1
stilbenoid202220222.0low000001
fosbretabulin
1
202220222.0low000001
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
selenious acid
1
selenium oxoacid2014201410.0low000010
ebselen
1
benzoselenazoleanti-inflammatory drug;
antibacterial agent;
anticoronaviral agent;
antifungal agent;
antineoplastic agent;
antioxidant;
apoptosis inducer;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
EC 3.5.4.1 (cytosine deaminase) inhibitor;
EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor;
enzyme mimic;
ferroptosis inhibitor;
genotoxin;
hepatoprotective agent;
neuroprotective agent;
radical scavenger		201520159.0low000010
fluorouracil
2
nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic		201520168.5low000020
pyrroles
1
pyrrole;
secondary amine		201620168.0low000010
1,2,4-triazole
1
1,2,4-triazole201620168.0low000010
sodium selenite
1
inorganic sodium salt;
selenite salt		nutraceutical201720177.0low000010
triazoles
1
1,2,3-triazole201620168.0low000010
1,3,4-thiadiazole
1
thiadiazole201520159.0low000010
su 11248
1
monocarboxylic acid amide;
pyrroles		angiogenesis inhibitor;
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
immunomodulator;
neuroprotective agent;
vascular endothelial growth factor receptor antagonist		201620168.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Adenosis of Breast0
1
201620168.0low000010
Benign Neoplasms0
2
2012201510.5low000020
Body Weight0
1
2010201014.0low000100
Breast Cancer0
2
201620196.5low000020
Breast Neoplasms0
2
201620196.5low000020
Cancer of Colon0
1
2011201113.0low000010
Cancer of Liver0
2
2009201910.0low000110
Cancer of Lung0
4
201120198.8low000040
Cancer of Prostate0
2
2003200321.0low000200
Cancer of Stomach0
1
202120213.0low000001
Cancer of the Tongue0
1
2008200816.0low000100
Carcinoma, Epidermoid0
1
2008200816.0low000100
Carcinoma, Hepatocellular0
1
2009200915.0low000100
Carcinoma, Lewis Lung0
1
2006200618.0low000100
Carcinoma, Non-Small Cell Lung0
4
2010201711.0low000130
Carcinoma, Non-Small-Cell Lung1
4
2010201711.0low000130
Carcinoma, Squamous Cell0
1
2008200816.0low000100
Colonic Neoplasms0
1
2011201113.0low000010
Colorectal Cancer0
2
2011201610.5low000020
Colorectal Neoplasms0
2
2011201610.5low000020
Disease Models, Animal0
1
202120213.0low000001
Experimental Hepatoma0
1
202220222.0low000001
Fibrocystic Breast Disease0
1
201620168.0low000010
Hepatocellular Carcinoma0
1
2009200915.0low000100
Liver Neoplasms0
2
2009201910.0low000110
Lung Neoplasms0
4
201120198.8low000040
Neoplasms0
2
2012201510.5low000020
Prostatic Neoplasms0
2
2003200321.0low000200
Sensitivity and Specificity0
2
2007200816.5low000200
Stomach Neoplasms0
1
202120213.0low000001
Tongue Neoplasms0
1
2008200816.0low000100

Pharmacokinetics (1)

ArticleYear
High performance liquid chromatographic determination of 1,2-[bis(1,2-benzisoselenazolone-3(2H)-ketone)]-ethane (BBSKE), a novel organoselenium compound, in dog plasma using pre-column derivatization and its application in pharmacokinetic study.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, , Jun-01, Volume: 852, Issue:1-2		2007

Dosage (4)

ArticleYear
Synergism between thioredoxin reductase inhibitor ethaselen and sodium selenite in inhibiting proliferation and inducing death of human non-small cell lung cancer cells.
Chemico-biological interactions, , Sep-25, Volume: 275		2017
Synergistic effect of ethaselen and selenite treatment against A549 human non-small cell lung cancer cells.
Asian Pacific journal of cancer prevention : APJCP, , Volume: 15, Issue:17		2014
High performance liquid chromatographic determination of 1,2-[bis(1,2-benzisoselenazolone-3(2H)-ketone)]-ethane (BBSKE), a novel organoselenium compound, in dog plasma using pre-column derivatization and its application in pharmacokinetic study.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, , Jun-01, Volume: 852, Issue:1-2		2007
[Induction of apoptosis in prostate cancer cell line PC-3 by BBSKE, a novel organoselenium compound, and its effect in vivo].
Zhonghua yi xue za zhi, , Nov-25, Volume: 83, Issue:22		2003