Page last updated: 2024-11-04

n,n,n',n'-tetrakis(2-pyridylmethyl)ethylenediamine

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

Description

N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine: a zinc ion chelating agent; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine : An N-substituted diamine that is ethylenediamine in which the four amino hydrogens are replaced by 2-pyridylmethyl groups. [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 CID5519
CHEMBL ID1472575
CHEBI ID88217
SCHEMBL ID231092
MeSH IDM0129718

Synonyms (65)

Synonym
BRD-K10385824-001-02-8
n,n,n',n'-tetrakis (2-pyridylmethyl)-ethylenediamine
n,n,n',n'-tetrakis(2-pyridylmethyl)ethane-1,2-diamine
tpen
BIO1_001430
BIO2_000433
BIO1_000452
BIO1_000941
BIO2_000913
BSPBIO_001186
IDI1_002188
n,n,n',n'-tetrakis(2-pyridylmethyl)ethylenediamine
NCGC00163483-01
1,2-ethanediamine, n,n,n',n'-tetrakis(2-pyridinylmethyl)-
n,n,n',n'-tetrakis(2-pyridyl-methyl)ethylenediamine
1,2-ethanediamine, n,n,n',n'-tetrakis(2-pyridinylmethyl)-, (oc-6-11)-
KBIOGR_000526
KBIO3_000952
KBIO2_005662
KBIO2_000526
KBIO2_003094
KBIO3_000951
KBIOSS_000526
NCGC00163483-02
16858-02-9
HMS1990L07
HMS1792L07
HMS1362L07
T1487
n,n,n',n'-tetrakis(pyridin-2-ylmethyl)ethane-1,2-diamine
FT-0675081
r9ptu1u29i ,
unii-r9ptu1u29i
tpeda
AKOS015903640
tpen [mi]
S6962
chebi:88217 ,
CHEMBL1472575
SCHEMBL231092
ethyl2,4-difluorobenzoylacetate
n(1),n(1),n(2),n(2)-tetrakis[(pyridin-2-yl)methyl]ethane-1,2-diamine
AC-27933
HMS3403L07
n1,n1,n2,n2-tetrakis(pyridin-2-ylmethyl)ethane-1,2-diamine
mfcd00036918
DTXSID50168583
EX-A1234
(2-{bis[(pyridin-2-yl)methyl]amino}ethyl)bis[(pyridin-2-yl)methyl]amine
AS-70319
CS-6042
HY-100202
J-010468
BCP21291
Q27160135
tpen - cas 16858-02-9
bdbm367675
us10227327, tpen
n,n,n',n'-tetrakis(2-pyridinylmethyl)-1,2-ethanediamine
n,n,n',n'-tetrakis(2-pyridylmethyl)-1,2-diaminoethane
A907766
n,n,n',n'-tetrakis(2-pyridylmethyl)-1,2-ethylenediamine
n,n,n inverted exclamation mark ,n inverted exclamation mark -tetrakis(2-pyridylmethyl)ethylenediamine
SY052905
1,2-ethanediamine, n^1,n^1,n^2,n^2-tetrakis(2-pyridinylmethyl)-

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Ammonium tetrathiomolybdate was itself toxic after injection into the hippocampus, but this toxicity was reduced by formation of a metal ion/tetrathiomolybdate complex with Cu+2."( Comparative effects of metal chelating agents on the neuronal cytotoxicity induced by copper (Cu+2), iron (Fe+3) and zinc in the hippocampus.
Armstrong, C; Lees, GJ; Leong, W, 2001
)
0.31
" These findings suggest that the toxic effect of thiol oxidants present during chronic gastritis is partially due to dysregulation of [Zn(2+)](i) early in the process and that zinc chelation can protect, but not rescue, gastric glands exposed to toxic doses of NH(2)Cl."( Monochloramine-induced toxicity and dysregulation of intracellular Zn2+ in parietal cells of rabbit gastric glands.
Blass, AL; Dubach, JM; Kohler, JE; Naik, HB; Soybel, DI; Tai, K, 2010
)
0.36
" Acute exposure to high levels of biphenyl has been observed to cause skin irritation and toxic effects on the liver and kidneys."( Biphenyl-induced cytotoxicity is mediated by an increase in intracellular Zn
Abe, S; Ae, M; Imura, N; Inubushi, T; Kamemura, N; Sugimoto, M; Yusuke, B, 2019
)
0.51

Compound-Compound Interactions

ExcerptReferenceRelevance
" fumigatus In vitro both chelators had an indifferent effect when employed in combination with caspofungin."( Administration of Zinc Chelators Improves Survival of Mice Infected with Aspergillus fumigatus both in Monotherapy and in Combination with Caspofungin.
Atrouni, A; Calera, JA; Cavaillon, JM; d'Enfert, C; Ibrahim-Granet, O; Laskaris, P; Latgé, JP; Munier-Lehmann, H, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
"The bioavailability of endothelial nitric oxide (NO) is regulated by transition metals but their mechanisms of action on NO synthesis and degradation are not clearly understood."( [Transition metals and nitric oxide production in human endothelial cells].
Brunet, A; David-Dufilho, M; Devynck, J; Devynck, MA; Privat, C; Richard, MJ, 2001
)
0.31
" Therefore, total Zn and labile Zn were quantitatively determined in living nematodes as individual biomarkers of Zn uptake and bioavailability with inductively coupled plasma tandem mass spectrometry (ICP-MS/MS) or a multi-well method using the fluorescent probe ZinPyr-1."( Zn homeostasis in genetic models of Parkinson's disease in Caenorhabditis elegans.
Aschner, M; Baesler, J; Bornhorst, J; Haase, H; Kopp, JF; Pohl, G; Schwerdtle, T, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" When the cells were cultured in divalent cation-depleted medium, each dose-response curve was shifted to about a four-fold lower concentration range."( Implication of extracellular zinc exclusion by recombinant human calprotectin (MRP8 and MRP14) from target cells in its apoptosis-inducing activity.
Chazin, WJ; Hunter, MJ; Nakatani, Y; Yamazaki, M; Yui, S, 2002
)
0.31
" Male and female rats dosed at 536."( Rat pancreatitis produced by 13-week administration of zinc oxide nanoparticles: biopersistence of nanoparticles and possible solutions.
Che, JH; Cho, WS; Cho, Y; Jang, A; Jeong, J; Kang, BC; Kim, H; Kim, T; Ko, S; Lee, JK; Na, Y; Park, JS; Seok, SH; You, JR, 2013
)
0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
chelatorA ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
copper chelatorA chelator that is any compound containing a ligand (typically organic) which is able to form a bond to a central copper atom at two or more points.
[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 (3)

ClassDescription
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
tertiary amino compoundA compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
N-substituted diamine
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency0.63100.004023.8416100.0000AID485290
TDP1 proteinHomo sapiens (human)Potency7.78290.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency11.22020.180013.557439.8107AID1460
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency31.62280.016525.307841.3999AID602332
survival motor neuron protein isoform dHomo sapiens (human)Potency14.12540.125912.234435.4813AID1458
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency4.46681.000010.475628.1838AID1457
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID764622Induction of apoptosis in rat PC12 cells after 24 hrs by trypan blue exclusion assay2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1.
AID1898396Antibacterial activity against methicillin-resistant Staphylococcus aureus BAA-1707 assessed as bacterial growth inhibition incubated for 16 hrs by broth microdilution susceptibility test2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1361057Antibiofilm activity against methicillin-resistant Staphylococcus epidermidis ATCC 35984 after 24 hrs by CBD assay2018European journal of medicinal chemistry, Jul-15, Volume: 155Halogenated quinolines bearing polar functionality at the 2-position: Identification of new antibacterial agents with enhanced activity against Staphylococcus epidermidis.
AID1898412Bactericidal activity against methicillin-resistant Staphylococcus epidermidis ATCC 35984 planktonic cells assessed as planktonic eradication incubated for 24 hrs followed by incubation for overnight in fresh medium by Calgary biofilm device assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1395973Antibacterial activity against methicillin-resistant Staphylococcus aureus BAA-1707 after 16 to 18 hrs by broth microdilution method2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
An Efficient Buchwald-Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration.
AID764613Induction of apoptosis in rat PC12 cells assessed as ROS induction by DHE oxidation-based fluorometric assay2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1.
AID1361056Bactericidal activity against methicillin-resistant Staphylococcus epidermidis ATCC 35984 planktonic cells after 24 hrs by CBD assay2018European journal of medicinal chemistry, Jul-15, Volume: 155Halogenated quinolines bearing polar functionality at the 2-position: Identification of new antibacterial agents with enhanced activity against Staphylococcus epidermidis.
AID1898409Antibiofilm activity against methicillin-resistant Staphylococcus aureus BAA-1707 biofilms assessed as biofilm eradication incubated for 24 hrs followed by incubation for 24 hrs in fresh medium by Calgary biofilm device assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID764616Induction of apoptosis in rat PC12 cells assessed as ROS induction at 25 uM measured after 1 to 4 hrs by DHR oxidation-based fluorometric assay2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1.
AID1898415Antibiofilm activity against methicillin-resistant vancomycin-resistant Enterococcus faecium ATCC 700221 biofilms assessed as biofilm eradication incubated for 24 hrs followed by incubation for 24 hrs in fresh medium by Calgary biofilm device assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1847346Antibacterial activity against Citrobacter freundii expressing NDM-1 assessed as decrease in meropenem MIC at 8 mg/L incubated for 18 to 20 hrs by broth microdilution method2021European journal of medicinal chemistry, Nov-05, Volume: 223Recent research and development of NDM-1 inhibitors.
AID1361062Hemolytic activity against human RBC at 200 uM after 1 hr relative to control2018European journal of medicinal chemistry, Jul-15, Volume: 155Halogenated quinolines bearing polar functionality at the 2-position: Identification of new antibacterial agents with enhanced activity against Staphylococcus epidermidis.
AID1361059Antibiofilm activity against methicillin-resistant Staphylococcus aureus BAA-1707 after 24 hrs by CBD assay2018European journal of medicinal chemistry, Jul-15, Volume: 155Halogenated quinolines bearing polar functionality at the 2-position: Identification of new antibacterial agents with enhanced activity against Staphylococcus epidermidis.
AID1898413Antibiofilm activity against methicillin-resistant Staphylococcus epidermidis ATCC 35984 biofilms assessed as biofilm eradication incubated for 24 hrs followed by incubation for 24 hrs in fresh medium by Calgary biofilm device assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID764612Induction of apoptosis in rat PC12 cells at 25 uM after 24 hrs by trypan blue exclusion assay in presence of caspase-3 inhibitor C3-I2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1.
AID1898408Bactericidal activity against methicillin-resistant Staphylococcus aureus BAA-1707 planktonic cells assessed as planktonic eradication incubated for 24 hrs followed by incubation for overnight in fresh medium by Calgary biofilm device assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1395979Bactericidal activity against methicillin-resistant Staphylococcus aureus BAA-1707 planktonic cells after 24 hrs by calgary biofilm device method2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
An Efficient Buchwald-Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration.
AID1898418Hemolytic activity against human RBC at 200 uM measured after 1 hr2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1182518Radioprotective activity against gamma-irradiated human MOLT4 cells preincubated for 1 hr at <50 uM before gamma-irradiation measured after 18 hrs by erythrosine B dye-exclusion test2014Bioorganic & medicinal chemistry, Aug-01, Volume: 22, Issue:15
Design and synthesis of 8-hydroxyquinoline-based radioprotective agents.
AID1361058Bactericidal activity against methicillin-resistant Staphylococcus aureus BAA-1707 planktonic cells after 24 hrs by CBD assay2018European journal of medicinal chemistry, Jul-15, Volume: 155Halogenated quinolines bearing polar functionality at the 2-position: Identification of new antibacterial agents with enhanced activity against Staphylococcus epidermidis.
AID764626Metal chelating activity of the compound assessed as zinc affinity by UV spectroscopy2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1.
AID764611Induction of apoptosis in rat PC12 cells at 25 uM after 24 hrs by trypan blue exclusion assay in presence of ZnSO42013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1.
AID1395988Induction of biofilm eradication of vancomycin-resistant Enterococcus faecium ATCC 700221 after 24 hrs by calgary biofilm device method2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
An Efficient Buchwald-Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration.
AID1582935Cytotoxicity against human Fibroblast assessed as reduction in cell viability incubated for 48 hrs by cell titer-glo assay
AID764621Induction of apoptosis in rat PC12 cells assessed as procaspase-3 activation at 25 uM after 24 hrs by fluorometric assay2013Bioorganic & medicinal chemistry, Sep-01, Volume: 21, Issue:17
Synthesis and initial in vitro biological evaluation of two new zinc-chelating compounds: comparison with TPEN and PAC-1.
AID1898417Antibiofilm activity against Enterococcus faecalis OG1RF ATCC 47077 biofilms assessed as biofilm eradication incubated for 24 hrs followed by incubation for 24 hrs in fresh medium by Calgary biofilm device assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1361050Antibacterial activity against methicillin-resistant Staphylococcus aureus BAA-1707 after 16 to 18 hrs by broth microdilution method2018European journal of medicinal chemistry, Jul-15, Volume: 155Halogenated quinolines bearing polar functionality at the 2-position: Identification of new antibacterial agents with enhanced activity against Staphylococcus epidermidis.
AID1898416Bactericidal activity against methicillin-resistant Enterococcus faecalis OG1RF ATCC 47077 planktonic cells assessed as planktonic eradication incubated for 24 hrs followed by incubation for overnight in fresh medium by Calgary biofilm device assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1898414Bactericidal activity against methicillin-resistant vancomycin-resistant Enterococcus faecium ATCC 700221 planktonic cells assessed as planktonic eradication incubated for 24 hrs followed by incubation for overnight in fresh medium by Calgary biofilm devi2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1898397Antibacterial activity against methicillin-resistant Staphylococcus aureus BAA-44 assessed as bacterial growth inhibition incubated for 16 hrs by broth microdilution susceptibility test2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1395989Hemolytic activity in human RBC at 200 uM after 1 hr relative to control2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
An Efficient Buchwald-Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration.
AID1847345Antibacterial activity against Citrobacter freundii expressing NDM-1 assessed as decrease in meropenem MIC at 4 mg/L incubated for 18 to 20 hrs by broth microdilution method2021European journal of medicinal chemistry, Nov-05, Volume: 223Recent research and development of NDM-1 inhibitors.
AID1361049Antibacterial activity against methicillin-resistant Staphylococcus epidermidis ATCC 35984 after 16 to 18 hrs by broth microdilution method2018European journal of medicinal chemistry, Jul-15, Volume: 155Halogenated quinolines bearing polar functionality at the 2-position: Identification of new antibacterial agents with enhanced activity against Staphylococcus epidermidis.
AID1395987Bactericidal activity against vancomycin-resistant Enterococcus faecium ATCC 700221 planktonic cells after 24 hrs by calgary biofilm device method2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
An Efficient Buchwald-Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration.
AID1898400Antibacterial activity against Enterococcus faecalis OG1RF ATCC 47077 assessed as bacterial growth inhibition incubated for 16 hrs by broth microdilution susceptibility test2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
A Modular Synthetic Route Involving
AID1395980Induction of biofilm eradication of methicillin-resistant Staphylococcus aureus BAA-1707 after 24 hrs by calgary biofilm device method2018Journal of medicinal chemistry, 05-10, Volume: 61, Issue:9
An Efficient Buchwald-Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration.
AID1632922Metal chelating activity assessed as compound-Zn2+ complex formation2016Bioorganic & medicinal chemistry letters, 10-01, Volume: 26, Issue:19
Dual action Smac mimetics-zinc chelators as pro-apoptotic antitumoral agents.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (395)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (1.52)18.7374
1990's53 (13.42)18.2507
2000's152 (38.48)29.6817
2010's150 (37.97)24.3611
2020's34 (8.61)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.63

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 Index9.63 (24.57)
Research Supply Index6.00 (2.92)
Research Growth Index5.63 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (1.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other396 (98.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]