Daniquidone

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

MedKoo CAT#: 205960

CAS#: 67199-66-0

Description: Daniquidone, also known as Batracylin, is a water-insoluble heterocyclic amide with potential antineoplastic activity. Daniquidone inhibits topoisomerases I and II, thereby inhibiting DNA replication and repair, and RNA and protein synthesis. The acetylated form of daniquidone is highly toxic and is capable of inducing unscheduled DNA synthesis; rapid acetylators are more likely to experience toxicity with this agent.


Price and Availability

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Daniquidone is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205960
Name: Daniquidone
CAS#: 67199-66-0
Chemical Formula: C15H11N3O
Exact Mass: 249.09021
Molecular Weight: 249.27
Elemental Analysis: C, 72.28; H, 4.45; N, 16.86; O, 6.42


Synonym: Batracylin; Daniquidone

IUPAC/Chemical Name: 8-aminoisoindolo[1,2-b]quinazolin-12(10H)-one

InChi Key: SRIOCKJKFXAKHK-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H11N3O/c16-10-5-6-13-9(7-10)8-18-14(17-13)11-3-1-2-4-12(11)15(18)19/h1-7H,8,16H2

SMILES Code: O=C1C2=C(C3=NC4=C(C=C(N)C=C4)CN31)C=CC=C2


Technical Data

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, not in water

Shelf Life:
>5 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Dzierzbicka K, Januchta W, Skladanowski A. Novel approaches in the synthesis of batracylin and its analogs: rebirth of an old player? Curr Med Chem. 2012;19(26):4475-87. PubMed PMID: 22830346.

2: Rao VA, Agama K, Holbeck S, Pommier Y. Batracylin (NSC 320846), a dual inhibitor of DNA topoisomerases I and II induces histone gamma-H2AX as a biomarker of DNA damage. Cancer Res. 2007 Oct 15;67(20):9971-9. PubMed PMID: 17942930.

3: Guillaumel J, Léonce S, Pierré A, Renard P, Pfeiffer B, Arimondo PB, Monneret C. Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds. Eur J Med Chem. 2006 Mar;41(3):379-86. Epub 2006 Jan 25. PubMed PMID: 16442188.

4: Trzonkowski P, Dzierzbicka K, Bociewicz J, Szmit E, Myśliwski A. Biological activity of conjugates of muramyl dipeptides with batracylin derivatives. Int Immunopharmacol. 2005 Feb;5(2):241-51. PubMed PMID: 15652755.

5: Dzierzbicka K, Trzonkowski P, Sewerynek P, Myśliwski A. Synthesis and cytotoxic activity of conjugates of muramyl and normuramyl dipeptides with batracylin derivatives. J Med Chem. 2003 Mar 13;46(6):978-86. PubMed PMID: 12620074.

6: Dzierzbicka K, Kawula J, Kołodziejczyk AM. [Batracylin (BAT)--potential antineoplastic agent]. Postepy Biochem. 2002;48(1):48-53. Review. Polish. PubMed PMID: 12101524.

7: Stevens GJ, Burkey JL, McQueen CA. Toxicity of the heterocyclic amine batracylin: investigation of rodent N-acetyltransferase activity and potential contribution of cytochrome P450 3A. Cell Biol Toxicol. 2000;16(1):31-9. PubMed PMID: 10890504.

8: Stevens GJ, Payton M, Sim E, McQueen CA. N-acetylation of the heterocyclic amine batracylin by human liver. Drug Metab Dispos. 1999 Sep;27(9):966-71. PubMed PMID: 10460792.

9: Stevens GJ, LaVoie EJ, McQueen CA. The role of acetylation in the mutagenicity of the antitumor agent, batracylin. Carcinogenesis. 1996 Jan;17(1):115-9. PubMed PMID: 8565119.

10: Meegalla SK, Stevens GJ, McQueen CA, Chen AY, Yu C, Liu LF, Barrows LR, LaVoie EJ. Synthesis and pharmacological evaluation of isoindolo[1,2-b]quinazolinone and isoindolo[2,1-a]benzimidazole derivatives related to the antitumor agent batracylin. J Med Chem. 1994 Sep 30;37(20):3434-9. PubMed PMID: 7932571.