C-1311 dihydrochloride - CAS 138154-55-9
Catalog number: 138154-55-9
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C20H26Cl2N4O3
Molecular Weight:
441.35
COA:
Inquire
Targets:
Ser/Thr Protease
Description:
C-1311 is a Fms-like tyrosine kinase 3 inhibitor under the development of Antisoma. It has shown activity in experimental tumour models both in vitro and in nude mice. C-1311 can delay progression of cells through the S phase which was followed by G2 arrest at the EC(99) dose as a mitosis inhibitor. Phase I clinical trials for treatment of solid tumours and a phase II clinical trials for the treatment of breast cancer were discontinued.
Purity:
98%
Appearance:
Powder
Synonyms:
Imidacrine; XLS-002; Symadex; Imidazoacridinone; CHEMBL3545337;5-(2-(diethylamino)ethylamino)--8-hydroxy-6H-imidazo(4,5,1-de)acridin-6-one
Solubility:
Soluble in DMSO
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
anticancer agents
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
InChIKey:
XJYNBZQTAZDMHZ-UHFFFAOYSA-N
InChI:
InChI=1S/C20H22N4O2.2ClH.H2O/c1-3-23(4-2)10-9-21-15-6-7-16-19-18(15)20(26)14-11-13(25)5-8-17(14)24(19)12-22-16;;;/h5-8,11-12,21,25H,3-4,9-10H2,1-2H3;2*1H;1H2
Canonical SMILES:
CCN(CC)CCNC1=C2C3=C(C=C1)N=CN3C4=C(C2=O)C=C(C=C4)O.O.Cl.Cl
Current Developer:
Antisoma
1.Bisimidazoacridones and related compounds: new antineoplastic agents with high selectivity against colon tumors.
Cholody WM;Hernandez L;Hassner L;Scudiero DA;Djurickovic DB;Michejda CJ J Med Chem. 1995 Aug 4;38(16):3043-52.
A new class of potent and highly selective antitumor agents has been synthesized. Bisimidazoacridones, where the tetracyclic ring systems are held together by either a N2-methyldiethylenetriamine or 3,3'-diamino-N-methyldipropylamine linker, and related asymmetrical compounds, where one of the imidazoacridone ring system was replaced by a triazoloacridone ring system, were found to be cytostatic and cytotoxic in vitro. Some of these compounds, such as 5,5'-[(methylimino)bis(3,1-propanediylimino)]bis[6H-imidazo[ 4,5,1-de]acridin-6-one] (4b) showed remarkably high activity and selectivity for colon cancer in the National Cancer Institute screen. This antitumor effect was also apparent in colony survival assays utilizing the colon cancer line, HCT-116, and in in vivo assays involving xenografts of tumor derived from HCT-116 in nude mice. The tested compounds exhibited relatively low acute toxicity and were well-tolerated by the treated animals. The bisimidazoacridones interact with nucleic acids in vitro but preliminary experimental and modeling data indicate that in spite of their structure, they may not be bis-intercalators. While the precise mode of action of these compounds is not yet understood, they appear to be excellent candidates for clinical development.
2.Bisimidazoacridones: effect of molecular environment on conformation and photophysical properties.
Tarasov SG;Casas-Finet JR;Cholody WM;Michejda CJ Photochem Photobiol. 1999 Oct;70(4):568-78.
Bisimidazoacridones (BIA) are highly selective antineoplastic and antiviral agents. Ultraviolet-visible spectroscopy and steady-state and time-resolved fluorescence spectroscopy studies were carried out to probe the behavior of BIA in aqueous and nonaqueous (organic solvents, colloid micelles) solutions. Three ranges of fluorescence lifetimes were revealed: approximately 0.2-0.5 ns (presumably reflecting the chromophore-chromophore interaction), approximately 1-5 ns (interpreted as linker-perturbed chromophore decay) and approximately 6-12 ns (nonperturbed chromophore decay). The pre-exponential and steady-state contributions of these components to the decay signal as well as the data on steady-state fluorescence intensities, wavelength maxima and bandwidths showed that the BIA conformations in solution were sensitive to the environment and influenced strongly by their propensity to minimize hydrophobic interactions. In water, the molecules tend to adopt condensed conformations that bring the two imidazoacridone moieties into close proximity (resulting in intramolecular fluorescence energy transfer), while in nonaqueous systems the conformations become more relaxed. The transfer from a polar to more lipophilic environment of macromolecules is suggested to be the main driving force for binding of BIA to biomacromolecules, such as nucleic acids.
3.Design of new drug molecules to be used in reversing multidrug resistance in cancer cells.
Mayur YC;Peters GJ;Prasad VV;Lemo C;Sathish NK Curr Cancer Drug Targets. 2009 May;9(3):298-306.
Over the past two decades, a number of chemical entities have been investigated in the continuing quest to reverse P-glycoprotein (P-gp) mediated multidrug resistance (MDR) in cancer cells and some have undergone clinical trials, but currently none are in clinical use. Unfortunately, most of these agents suffer clinically from their intrinsic toxicity or from undesired effects on the pharmacokinetics of the accompanying anti-cancer drugs. An acridonecarboxamide (GF120918), Imidazo acridone (C(1311)) and timethylene acridone derivative 1,3-bis(9-oxoacridin-10-yl)-propane (PBA) have already been shown to be among the group of compounds known to modify P-gp mediated MDR in cancer. In the recent past it has been identified that various N(10)-substituted acridones can reverse the multidrug resistance (MDR) in cancer by selectively inhibiting the multidrug resistance associated protein (MRP) and calmodulin dependent cyclic AMP phosphodiesterase. This article envisages the various drugs being developed for treating MDR in cancer cells and especially the acridone derivatives which are being developed by the author.
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