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Details

Stereochemistry ACHIRAL
Molecular Formula C46H50N6O2.2Cl
Molecular Weight 789.834
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DITERCALINIUM CHLORIDE

SMILES

[Cl-].[Cl-].COC1=CC=C2NC3=CC=C4C=C[N+](CCN5CCC(CC5)C6CCN(CC[N+]7=CC8=C9C(NC%10=CC=C(OC)C=C9%10)=CC=C8C=C7)CC6)=CC4=C3C2=C1

InChI

InChIKey=FWBSWSRNGHRDFZ-UHFFFAOYSA-N
InChI=1S/C46H48N6O2.2ClH/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;2*1H

HIDE SMILES / InChI

Molecular Formula C46H48N6O2
Molecular Weight 716.9123
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Ditercalinium chloride, a pro-anticancer drug, intimately associates with mammalian mitochondrial DNA and inhibits its replication.
2003 Aug
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:03:50 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:50 GMT 2023
Record UNII
40Z22S8DO8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DITERCALINIUM CHLORIDE
INN  
INN  
Official Name English
NSC-335153
Code English
2,2'-((4,4'-BIPIPERIDINE)-1,1'-DIYLDIETHYLENE)BIS(10-METHOXY-7H-PYRIDO(4,3-C)CARBAZOLIUM) DICHLORIDE
Common Name English
ditercalinium chloride [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C582
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C77561
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
NSC
335153
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
EVMPD
SUB06330MIG
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL1182165
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
MESH
C042804
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
FDA UNII
40Z22S8DO8
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
CAS
74517-42-3
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID80996033
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
INN
5294
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
SMS_ID
100000081857
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
PUBCHEM
71541
Created by admin on Fri Dec 15 16:03:50 GMT 2023 , Edited by admin on Fri Dec 15 16:03:50 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY