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Details

Stereochemistry ACHIRAL
Molecular Formula C46H50N6O2
Molecular Weight 718.9282
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of DITERCALINIUM

SMILES

COC1=CC2=C(NC3=C2C4=C(C=C3)C=C[N+](CCN5CCC(CC5)C6CCN(CC[N+]7=CC=C8C=CC9=C(C%10=CC(OC)=CC=C%10N9)C8=C7)CC6)=C4)C=C1

InChI

InChIKey=NHUWXMNVGMRODJ-UHFFFAOYSA-P
InChI=1S/C46H48N6O2/c1-53-35-5-9-41-37(27-35)45-39-29-51(21-15-33(39)3-7-43(45)47-41)25-23-49-17-11-31(12-18-49)32-13-19-50(20-14-32)24-26-52-22-16-34-4-8-44-46(40(34)30-52)38-28-36(54-2)6-10-42(38)48-44/h3-10,15-16,21-22,27-32H,11-14,17-20,23-26H2,1-2H3/p+2

HIDE SMILES / InChI
Ditercalinium is the antineoplastic agent. Ditercalinium itself is not a natural product, however, it is derived from the natural product 5,11-dimethyl-6H-pyrido-[4,3- b]carbazole (ellipticine) that was isolated in 1959. It is a rare example of a noncovalent DNA-binding ligand that forms bisintercalation complexes via the major groove of the double helix. Ditercalinium selectively recognizes certain GC-rich sequences in DNA. It preferentialy binds with antiparallel quadruplex sequence d(AG(3)[T(2)AG(3)](3)). Ditercalinium chloride can deplete mitochondrial DNA in both mouse and human cells. Ditercalinium chloride inhibits human DNA polymerase gamma activity as efficiently as does ethidium bromide. Ethidium bromide distributes diffusely in the mitochondria of HeLa cells, while ditercalinium chloride distributes granularly and hence may be strongly associated with mitochondrial DNA.

Approval Year

PubMed

PubMed

TitleDatePubMed
Natural product DNA major groove binders.
2012-02
Ditercalinium chloride, a pro-anticancer drug, intimately associates with mammalian mitochondrial DNA and inhibits its replication.
2003-08
Tight binding of the antitumor drug ditercalinium to quadruplex DNA.
2002-12-02
DNA sequence recognition by the antitumor drug ditercalinium.
2002-07-09
Inhibitors of human immunodeficiency virus integrase.
1993-03-15
Name Type Language
2,2'-((4,4'-BIPIPERIDINE)-1,1'-DIYLDIETHYLENE)BIS(10-METHOXY-7H-PYRIDO(4,3-C)CARBAZOLIUM)
Preferred Name English
DITERCALINIUM
Common Name English
DITERCALINIUM ION
Common Name English
DITERCALINIUM CATION
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C582
Created by admin on Mon Mar 31 18:17:46 GMT 2025 , Edited by admin on Mon Mar 31 18:17:46 GMT 2025
Code System Code Type Description
PUBCHEM
3119
Created by admin on Mon Mar 31 18:17:46 GMT 2025 , Edited by admin on Mon Mar 31 18:17:46 GMT 2025
PRIMARY
CAS
82765-18-2
Created by admin on Mon Mar 31 18:17:46 GMT 2025 , Edited by admin on Mon Mar 31 18:17:46 GMT 2025
PRIMARY
MESH
C042804
Created by admin on Mon Mar 31 18:17:46 GMT 2025 , Edited by admin on Mon Mar 31 18:17:46 GMT 2025
PRIMARY
NCI_THESAURUS
C83682
Created by admin on Mon Mar 31 18:17:46 GMT 2025 , Edited by admin on Mon Mar 31 18:17:46 GMT 2025
PRIMARY
FDA UNII
VFS4ZUK33P
Created by admin on Mon Mar 31 18:17:46 GMT 2025 , Edited by admin on Mon Mar 31 18:17:46 GMT 2025
PRIMARY