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Details

Stereochemistry ACHIRAL
Molecular Formula C26H28N6.4ClHO4
Molecular Weight 826.375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N,N,N',N'-TETRAKIS(2-PYRIDINYLMETHYL)-1,2-ETHANEDIAMINE TETRAPERCHLORATE

SMILES

OCl(=O)(=O)=O.OCl(=O)(=O)=O.OCl(=O)(=O)=O.OCl(=O)(=O)=O.C(CN(CC1=NC=CC=C1)CC2=NC=CC=C2)N(CC3=CC=CC=N3)CC4=CC=CC=N4

InChI

InChIKey=JKBQPGLRYWUSND-UHFFFAOYSA-N
InChI=1S/C26H28N6.4ClHO4/c1-5-13-27-23(9-1)19-31(20-24-10-2-6-14-28-24)17-18-32(21-25-11-3-7-15-29-25)22-26-12-4-8-16-30-26;4*2-1(3,4)5/h1-16H,17-22H2;4*(H,2,3,4,5)

HIDE SMILES / InChI

Molecular Formula C26H28N6
Molecular Weight 424.5407
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClHO4
Molecular Weight 100.459
Charge 0
Count
MOL RATIO 4 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

N,N,N',N'-TETRAKIS(2-PYRIDYLMETHYL)ETHYLENEDIAMINE (TPEN) is a heavy metal chelator with strong affinities for Zn2+, Fe2+, and Mn2+. TPEN inhibits lamin assembly, destabilizes nuclear architecture and may independently protect nuclei from apoptosis in vitro. TPEN prevents HIF-1alpha from interacting with CBP, so reducing expression of HIF-1alpha target genes. TPEN was able to pass through the blood-brain barrier and the neuronal membrane, leading to successful intracellular zinc chelation - zinc chelation could be a potentially effective way for ischemic stroke treatment. TPEN exhibits robust anti-tumor activity in vivo in colon cancer mouse xenografts. In vivo experiments show that TPEN-loaded, aptamer-targeted liposomes reduce tumor growth in a human prostate cancer xenograft model.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat: 5 or 15 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Human DU145 prostate cancer cells were exposed to TPEN (5 uM, 6 h) in both normoxic and hypoxic (1% O2) conditions and the levels of HIF-1a protein were measured by Western blotting. TPEN dramatically increased the amount of HIF-1a in both normoxic cells and hypoxic cells.
Substance Class Chemical
Record UNII
447DAN30LD
Record Status Validated (UNII)
Record Version