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
SMILES
[Cl-].[Cl-].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=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
| 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 |
| 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 |
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
| Title | Date | PubMed |
|---|---|---|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:17:54 GMT 2025
by
admin
on
Mon Mar 31 18:17:54 GMT 2025
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| Record UNII |
40Z22S8DO8
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C582
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C77561
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335153
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SUB06330MIG
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CHEMBL1182165
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C042804
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40Z22S8DO8
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5294
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100000081857
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71541
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |