Compounds > s-adenosyl-3-thio-1,8-diaminooctane
Page last updated: 2024-11-07

s-adenosyl-3-thio-1,8-diaminooctane

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

Description

S-adenosyl-3-thio-1,8-diaminooctane: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID100766
CHEMBL ID330673
MeSH IDM0089454

Synonyms (12)

Synonym
CHEMBL330673 ,
s-adenosyl-3-thio-1,8-diaminooctane
(2s,3s,4r,5r)-2-[[6-amino-1-(2-aminoethyl)hexyl]sulfanylmethyl]-5-(6-aminopurin-9-yl)tetrahydrofuran-3,4-diol
76426-40-9
nsc363232
adodato
2-[6-amino-1-(2-amino-ethyl)-hexylsulfanylmethyl]-5-(6-amino-purin-9-yl)-tetrahydro-furan-3,4-diol
bdbm50095450
(2r,3r,4s,5s)-2-(6-aminopurin-9-yl)-5-(1,8-diaminooctan-3-ylsulfanylmethyl)oxolane-3,4-diol
adenosine, 5'-s-(6-amino-1-(2-aminoethyl)hexyl)-5'-thio-
nsc 363232
satdao

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" We have previously reported that amyloid beta-peptide (A beta), the main constituent of senile plaques in Alzheimer's disease (AD) brain, is toxic to neurons through a free radical-dependent oxidative stress mechanism and that A beta(1--42), the principal form of A beta in AD brain, causes an increase in polyamine metabolism manifested by up-regulated polyamine uptake and increased ornithine decarboxylase (ODC) activity."( Role of spermine in amyloid beta-peptide-associated free radical-induced neurotoxicity.
Ain, KB; Butterfield, DA; Varadarajan, S; Yatin, M; Yatin, SM, 2001)		0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Spermidine synthaseHomo sapiens (human)IC50 (µMol)0.25000.25000.25000.2500AID162818
Spermine synthaseHomo sapiens (human)IC50 (µMol)0.05000.02000.03500.0500AID226564
Spermidine synthaseRattus norvegicus (Norway rat)IC50 (µMol)50.13750.05000.18330.4000AID162820; AID203869; AID203875; AID203876
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
polyamine metabolic processSpermidine synthaseHomo sapiens (human)
spermidine biosynthetic processSpermidine synthaseHomo sapiens (human)
cellular response to leukemia inhibitory factorSpermidine synthaseHomo sapiens (human)
methionine metabolic processSpermine synthaseHomo sapiens (human)
polyamine metabolic processSpermine synthaseHomo sapiens (human)
spermine biosynthetic processSpermine synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
spermidine synthase activitySpermidine synthaseHomo sapiens (human)
protein bindingSpermidine synthaseHomo sapiens (human)
identical protein bindingSpermidine synthaseHomo sapiens (human)
protein homodimerization activitySpermidine synthaseHomo sapiens (human)
spermine synthase activitySpermine synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
cytosolSpermidine synthaseHomo sapiens (human)
cytosolSpermidine synthaseHomo sapiens (human)
cytosolSpermine synthaseHomo sapiens (human)
extracellular exosomeSpermine synthaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID203869Inhibition of Spermidine aminopropyltransferase (SAPT) in rat liver.1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Synthesis and biochemical evaluation of adenosylspermidine, a nucleoside-polyamine adduct inhibitor of spermidine synthase.
AID203902Inhibitory activity against spermine synthase; NI=No inhibition1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
AID203896Inhibition of spermine synthase activity in rat ventral prostate was evaluated1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Synthesis and biological evaluation of S-adenosyl-1,12-diamino-3-thio-9-azadodecane, a multisubstrate adduct inhibitor of spermine synthase.
AID203875Inhibition of spermidine synthase activity was evaluated1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Synthesis and biological evaluation of S-adenosyl-1,12-diamino-3-thio-9-azadodecane, a multisubstrate adduct inhibitor of spermine synthase.
AID203876Inhibitory activity against spermidine synthase1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
AID203877Inhibition of spermidine synthase at 10 uM concentration of the compound1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
AID203905Inhibition of spermine synthase at 25 uM concentration of the compound1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
AID203879Inhibition of spermidine synthase at 25 uM concentration of the compound1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
AID162818Inhibition of prokaryotic Escherichia coli Putrescine aminopropyltransferase was determined1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Synthesis and biochemical evaluation of adenosylspermidine, a nucleoside-polyamine adduct inhibitor of spermidine synthase.
AID226564Inhibitory activity against spermine synthase2001Journal of medicinal chemistry, Jan-04, Volume: 44, Issue:1
Terminally alkylated polyamine analogues as chemotherapeutic agents.
AID162820Inhibition of Putrescine aminopropyl transferase (PAPT) in rat liver1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Synthesis and biochemical evaluation of adenosylspermidine, a nucleoside-polyamine adduct inhibitor of spermidine synthase.
AID203904Inhibition of spermine synthase at 100 uM concentration of the compound1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
AID203878Inhibition of spermidine synthase at 100 uM concentration of the compound1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
AID203882Inhibition of spermidine synthase at 50 uM concentration of the compound1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
Synthesis and evaluation of some stable multisubstrate adducts as specific inhibitors of spermidine synthase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (62.50)18.7374
1990's2 (12.50)18.2507
2000's4 (25.00)29.6817
2010's0 (0.00)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: 11.56

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.56 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		1.9610sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
putrescine
[no description available]		2.6630alkane-alpha,omega-diamineantioxidant;
fundamental metabolite
spermidine
[no description available]		4.1750polyazaalkane;
triamine		autophagy inducer;
fundamental metabolite;
geroprotector
spermine
[no description available]		2.8940polyazaalkane;
tetramine		antioxidant;
fundamental metabolite;
immunosuppressive agent
eflornithine
Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.		3.7930alpha-amino acid;
fluoroamino acid		trypanocidal drug
n(1),n(11)-diethylnorspermine
N(1),N(11)-diethylnorspermine: structure given in first source		3.110
n(1), n(12)-diethylspermine
N(1), N(12)-diethylspermine: structure in first source. N(1),N(12)-diethylspermine : A substituted spermine that is spermine in which a hydrogen attached to each of the primary amino groups has been replaced by an ethyl group.		3.110polyazaalkane;
secondary amino compound;
substituted spermine;
tetramine		antineoplastic agent
dicyclohexylamine
dicyclohexylamine: potent inhibitor of spermidine synthase; RN given refers to parent cpd		1.9610primary aliphatic amine
melarsen oxide
melarsen oxide: inhibits glutathione reductase		3.110
n(1),n(14)-bis(ethyl)homospermine
N(1),N(14)-bis(ethyl)homospermine: structure given in first source; depletes polyamines and inhibits the growth of tumor cells in tissue culture		3.110
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		4.94120adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
mdl 27695
MDL 27695: structure given in first source		3.110
trypanothione
trypanothione disulfide : An organic disulfide resulting from the formal oxidative coupling of the thiol groups of N(1),N(8)-bis(glutathionyl)-spermidine from the insect-parasitic trypanosomatid Crithidia fasciculata.		3.1310organic disulfide
n(1),n(8)-diethylspermidine
N(1),N(8)-diethylspermidine: regulator of ornithine decarboxylase		3.110
5'-methylthioadenosine
5'-methylthioadenosine: structure. 5'-S-methyl-5'-thioadenosine : Adenosine with the hydroxy group at C-5' substituted with a methylthio (methylsulfanyl) group.		1.9610thioadenosinealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
s-adenosyl-1,12-diamino-3-thio-9-azadodecane
S-adenosyl-1,12-diamino-3-thio-9-azadodecane: structure given in first source		3.4920
mitoguazone
Mitoguazone: Antineoplastic agent effective against myelogenous leukemia in experimental animals. Also acts as an inhibitor of animal S-adenosylmethionine decarboxylase.. mitoguazone : A hydrazone obtained by formal condensation of the two carbonyl groups of methylglyoxal with the primary amino groups of two molecules of aminoguanidine.		3.110guanidines;
hydrazone		antineoplastic agent;
apoptosis inducer;
EC 4.1.1.50 (adenosylmethionine decarboxylase) inhibitor
bis((3-(aminoiminomethyl)phenyl)methylene)carbonimidic dihydrazide trihydrochloride
bis((3-(aminoiminomethyl)phenyl)methylene)carbonimidic dihydrazide trihydrochloride: structure given in first source		3.1310
robenidine
Robenidine: An anticoccidial agent mainly for poultry.		3.1310
s-adenosylmethionine
(R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.		1.9610organic cation;
sulfonium compound		coenzyme;
cofactor;
human metabolite;
micronutrient;
Mycoplasma genitalium metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Opportunistic Infections
An infection caused by an organism which becomes pathogenic under certain conditions, e.g., during immunosuppression.		02.9210
Leishmania Infection
[description not available]		02.9510
African Sleeping Sickness
[description not available]		02.9510
American Trypanosomiasis
[description not available]		02.9510
Leishmaniasis
A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).		02.9510
Trypanosomiasis, African
A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.		02.9510
Chagas Disease
Infection with the protozoan parasite TRYPANOSOMA CRUZI, a form of TRYPANOSOMIASIS endemic in Central and South America. It is named after the Brazilian physician Carlos Chagas, who discovered the parasite. Infection by the parasite (positive serologic result only) is distinguished from the clinical manifestations that develop years later, such as destruction of PARASYMPATHETIC GANGLIA; CHAGAS CARDIOMYOPATHY; and dysfunction of the ESOPHAGUS or COLON.		02.9510
Experimental Hepatoma
[description not available]		01.9610
Cell Transformation, Viral
An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.		01.9610
Acute Confusional Senile Dementia
[description not available]		0210
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		0210
Di Guglielmo Disease
[description not available]		01.9610
Leukemia, Erythroblastic, Acute
A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.		01.9610
Cancer of Colon
[description not available]		01.9710
Colonic Neoplasms
Tumors or cancer of the COLON.		01.9710
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		01.9710