Ditercalinium chloride | CAS# 74517-42-3 | deplete mitochondrial DNA

MedKoo Cat#: 413181 | Name: Ditercalinium chloride

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ditercalinium chloride was originally synthesized for use as an anticancer drug and was then found to deplete mitochondrial DNA.

Chemical Structure

Ditercalinium chloride

CAS#74517-42-3 (chloride)

Theoretical Analysis

MedKoo Cat#: 413181

Name: Ditercalinium chloride

CAS#: 74517-42-3 (chloride)

Chemical Formula: C46H50Cl2N6O2

Exact Mass:

Molecular Weight: 789.85

Elemental Analysis: C, 69.95; H, 6.38; Cl, 8.98; N, 10.64; O, 4.05

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

82765-18-2 (cation) 74517-42-3 (chloride)

Synonym

Ditercalinium chloride; NSC335153; NSC-335153; NSC 335153

IUPAC/Chemical Name

2,2'-((4,4'-Bipiperidine)-1,1'-diyldiethylene)bis(10-methoxy-7H-pyrido(4,3-c)carbazolium) dichloride

InChi Key

FWBSWSRNGHRDFZ-UHFFFAOYSA-N

InChi Code

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

SMILES Code

COC1=CC2=C(NC3=C2C4=C[N+](CCN5CCC(C6CCN(CC[N+]7=CC=C8C=CC(NC9=C%10C=C(OC)C=C9)=C%10C8=C7)CC6)CC5)=CC=C4C=C3)C=C1.[Cl-].[Cl-]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 789.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Okamaoto M, Ohsato T, Nakada K, Isobe K, Spelbrink JN, Hayashi J, Hamasaki N, Kang D. Ditercalinium chloride, a pro-anticancer drug, intimately associates with mammalian mitochondrial DNA and inhibits its replication. Curr Genet. 2003 Aug;43(5):364-70. doi: 10.1007/s00294-003-0393-4. Epub 2003 Apr 5. PMID: 12679881. 2: Crow SD, Bailly C, Garbay-Jaureguiberry C, Roques B, Shaw BR, Waring MJ. DNA sequence recognition by the antitumor drug ditercalinium. Biochemistry. 2002 Jul 9;41(27):8672-82. doi: 10.1021/bi012207q. PMID: 12093285. 3: Lambert B, Jones BK, Roques BP, Le Pecq JB, Yeung AT. The noncovalent complex between DNA and the bifunctional intercalator ditercalinium is a substrate for the UvrABC endonuclease of Escherichia coli. Proc Natl Acad Sci U S A. 1989 Sep;86(17):6557-61. doi: 10.1073/pnas.86.17.6557. PMID: 2671994; PMCID: PMC297883. 4: Fellous R, Coulaud D, el Abed I, Roques BP, Le Pecq JB, Delain E, Gouyette A. Cytoplasmic accumulation of ditercalinium in rat hepatocytes and induction of mitochondrial damage. Cancer Res. 1988 Nov 15;48(22):6542-9. PMID: 3180068. 5: Esnault C, Brown SC, Segal-Bendirdjian E, Coulaud D, Mishal Z, Roques BP, Le Pecq JB. Selective alteration of mitochondrial function by Ditercalinium (NSC 335153), a DNA bisintercalating agent. Biochem Pharmacol. 1990 Jan 1;39(1):109-22. doi: 10.1016/0006-2952(90)90654-4. PMID: 2297352. 6: Hadrovic I, Rebmann P, Klärner FG, Bitan G, Schrader T. Molecular Lysine Tweezers Counteract Aberrant Protein Aggregation. Front Chem. 2019 Oct 1;7:657. doi: 10.3389/fchem.2019.00657. PMID: 31632951; PMCID: PMC6779714. 7: Dupont J, Schwaller MA, Dodin G. Ditercalinium, a nucleic acid binder, inhibits the respiratory chain of isolated mammalian mitochondria. Cancer Res. 1990 Dec 15;50(24):7966-72. PMID: 2174739. 8: Mendoza R, Markovits J, Jaffrezou JP, Muzard G, Le Pecq JB. DNase I susceptibility of bent DNA and its alteration by ditercalinium and distamycin. Biochemistry. 1990 May 29;29(21):5035-43. doi: 10.1021/bi00473a006. PMID: 2198937. 9: Lambert B, Segal-Bendirdjian E, Esnault C, Le Pecq JB, Roques BP, Jones B, Yeung AT. Recognition by the DNA repair system of DNA structural alterations induced by reversible drug-DNA interactions. Anticancer Drug Des. 1990 Feb;5(1):43-53. PMID: 2180423. 10: Segal-Bendirdjian E, Coulaud D, Roques BP, Le Pecq JB. Selective loss of mitochondrial DNA after treatment of cells with ditercalinium (NSC 335153), an antitumor bis-intercalating agent. Cancer Res. 1988 Sep 1;48(17):4982-92. PMID: 2842043.

View History

RK-59638

MedKoo CAT#: 464104

CAS#: unknown