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MedKoo Cat#: 522995 | Name: DB-766

Description:

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

DB-766 is a potential chemotherapeutic candidate for Chagas' disease treatment. DB-766 exhibits strong trypanocidal activity and excellent selectivity for bloodstream trypomastigotes and intracellular amastigotes (Y strain), giving IC(50)s of 60 and 25 nM, respectively. The trypanocidal efficacy of DB766, suggesting that this AIA may represent a new lead compound candidate to Chagas.

Chemical Structure

DB-766
DB-766
CAS#423165-22-4

Theoretical Analysis

MedKoo Cat#: 522995

Name: DB-766

CAS#: 423165-22-4

Chemical Formula: C34H34N6O3

Exact Mass: 574.2692

Molecular Weight: 574.69

Elemental Analysis: C, 71.06; H, 5.96; N, 14.62; O, 8.35

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 #
No Data
Synonym
DB-766; DB 766; DB766.
IUPAC/Chemical Name
N,N''-(furan-2,5-diylbis(3-isopropoxy-4,1-phenylene))dipicolinimidamide
InChi Key
QCFKWNGTLZQXRE-UHFFFAOYSA-N
InChi Code
InChI=1S/C34H34N6O3/c1-21(2)41-31-19-23(39-33(35)27-9-5-7-17-37-27)11-13-25(31)29-15-16-30(43-29)26-14-12-24(20-32(26)42-22(3)4)40-34(36)28-10-6-8-18-38-28/h5-22H,1-4H3,(H2,35,39)(H2,36,40)
SMILES Code
CC(OC1=CC(NC(C2=NC=CC=C2)=N)=CC=C1C3=CC=C(C4=CC=C(NC(C5=NC=CC=C5)=N)C=C4OC(C)C)O3)C
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
>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
DB766 also exerts striking effects upon different parasite stocks, including those naturally resistant to benznidazole, and displays higher activity in vitro than the reference drugs. By fluorescent and transmission electron microscopy analyses, we found that this AIA localizes in DNA-enriched compartments and induces considerable damage to the mitochondria. DB766 effectively reduces the parasite load in the blood and cardiac tissue and presents efficacy similar to that of benznidazole in mouse models of T. cruzi infection employing the Y and Colombian strains, using oral and intraperitoneal doses of up to 100 mg/kg/day that were given after the establishment of parasite infection. This AIA ameliorates electrocardiographic alterations, reduces hepatic and heart lesions induced by the infection, and provides 90 to 100% protection against mortality, which is similar to that provided by benznidazole.

Preparing Stock Solutions

The following data is based on the product molecular weight 574.69 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.

Recalculate based on batch purity %
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: Pandharkar T, Zhu X, Mathur R, Jiang J, Schmittgen TD, Shaha C, Werbovetz KA. Studies on the antileishmanial mechanism of action of the arylimidamide DB766: azole interactions and role of CYP5122A1. Antimicrob Agents Chemother. 2014 Aug;58(8):4682-9. doi: 10.1128/AAC.02405-14. Epub 2014 Jun 2. PubMed PMID: 24890590; PubMed Central PMCID: PMC4135980. 2: Srivastava A, Sweat JM, Azizan A, Vesely B, Kyle DE. Real-time PCR to quantify Leishmania donovani in hamsters. J Parasitol. 2013 Feb;99(1):145-50. doi: 10.1645/GE-3221.1. Epub 2012 Aug 27. PubMed PMID: 22924923. 3: Reid CS, Farahat AA, Zhu X, Pandharkar T, Boykin DW, Werbovetz KA. Antileishmanial bis-arylimidamides: DB766 analogs modified in the linker region and bis-arylimidamide structure-activity relationships. Bioorg Med Chem Lett. 2012 Nov 15;22(22):6806-10. doi: 10.1016/j.bmcl.2012.06.037. Epub 2012 Jun 16. PubMed PMID: 22765899. 4: Zhu X, Liu Q, Yang S, Parman T, Green CE, Mirsalis JC, de Nazaré Correia Soeiro M, Mello de Souza E, da Silva CF, da Gama Jaen Batista D, Stephens CE, Banerjee M, Farahat AA, Munde M, Wilson WD, Boykin DW, Wang MZ, Werbovetz KA. Evaluation of arylimidamides DB1955 and DB1960 as candidates against visceral leishmaniasis and Chagas' disease: in vivo efficacy, acute toxicity, pharmacokinetics, and toxicology studies. Antimicrob Agents Chemother. 2012 Jul;56(7):3690-9. doi: 10.1128/AAC.06404-11. Epub 2012 Apr 16. PubMed PMID: 22508306; PubMed Central PMCID: PMC3393454. 5: Batista Dda G, Batista MM, de Oliveira GM, Britto CC, Rodrigues AC, Stephens CE, Boykin DW, Soeiro Mde N. Combined treatment of heterocyclic analogues and benznidazole upon Trypanosoma cruzi in vivo. PLoS One. 2011;6(7):e22155. doi: 10.1371/journal.pone.0022155. Epub 2011 Jul 26. PubMed PMID: 21814568; PubMed Central PMCID: PMC3144210. 6: Cortes HC, Muller N, Boykin D, Stephens CE, Hemphill A. In vitro effects of arylimidamides against Besnoitia besnoiti infection in Vero cells. Parasitology. 2011 Apr;138(5):583-92. doi: 10.1017/S0031182011000114. Epub 2011 Feb 24. PubMed PMID: 21349220. 7: Batista Dda G, Batista MM, de Oliveira GM, do Amaral PB, Lannes-Vieira J, Britto CC, Junqueira A, Lima MM, Romanha AJ, Sales Junior PA, Stephens CE, Boykin DW, Soeiro Mde N. Arylimidamide DB766, a potential chemotherapeutic candidate for Chagas' disease treatment. Antimicrob Agents Chemother. 2010 Jul;54(7):2940-52. doi: 10.1128/AAC.01617-09. Epub 2010 May 10. PubMed PMID: 20457822; PubMed Central PMCID: PMC2897275. 8: Wang MZ, Zhu X, Srivastava A, Liu Q, Sweat JM, Pandharkar T, Stephens CE, Riccio E, Parman T, Munde M, Mandal S, Madhubala R, Tidwell RR, Wilson WD, Boykin DW, Hall JE, Kyle DE, Werbovetz KA. Novel arylimidamides for treatment of visceral leishmaniasis. Antimicrob Agents Chemother. 2010 Jun;54(6):2507-16. doi: 10.1128/AAC.00250-10. Epub 2010 Apr 5. PubMed PMID: 20368397; PubMed Central PMCID: PMC2876428.