| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g | |||
| Other Sizes |
Purity: ≥98%
NSC5844 (also known as RE640), a 4-aminoquinoline derivative and a bisquinoline compound, is a novel and potent agonist of C-C chemokine receptor type 1 (CCR1).
| Targets |
Parasite; antimalarial
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|---|---|
| ln Vitro |
Compound 10, also known as NSC5844, is a derivative of 4-aminoquinoline that exhibits antitumor activity against MDA-MB-468 and MCF-7 cells, with GI50s of 7.35 ± 0.10 μM and 14.80 ± 0.35 μM, respectively[1]. With IC50s of 17 and 27 nM, respectively, NSC5844 (Compound 1) is cytotoxic to P. falciparum and inhibits the growth of chloroquine-sensitive (D-6) and -resistant (W-2) clones of P. falciparum[2].
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| ln Vivo |
On the basis of observations that several bisquinolines such as piperaquine possess notable activity against chloroquine-resistant malaria, 13 N,N-bis-(7-chloroquinolin-4-yl)alkanediamines were synthesized and screened against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Twelve of the thirteen bisquinolines had a significantly lower resistance index than did chloroquine; the resistance index was apparently unrelated to either in vitro or in vivo activity. Except for two compounds, there was a reasonable correlation between in vitro and in vivo activities. Seven of the thirteen bisquinolines had IC50's of less than 6 nM against both chloroquine-sensitive (D-6) and -resistant (W-2) clones of P. falciparum and were curative against P. berghei at doses of 640 mg/kg. In contrast to chloroquine, these bisquinolines did not show any toxic deaths at curative dose levels. Four bisquinolines, however, caused skin lesions at the site of injection. Maximum activity was seen in bisquinolines with a connecting bridge of two carbon atoms where decreased conformational mobility seemed to increase activity. Bisquinoline 3 (+/-)-trans-N1,N2-bis(7-chloroquinolin-4-yl)cyclohexane-1,2-diamin e was not only the most potent bisquinoline in vitro, but was clearly unique in its in vivo activity--80% and 100% cure rates were achieved at doses of 160 and 320 mg/kg, respectively. In summary, these preliminary results support the premise that bisquinolines may be useful agents against chloroquine-resistant malaria [2].
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| References |
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| Additional Infomation |
series of 4-aminoquinoline derivatives were synthesized by reacting 4-chloro-7-substituted quinolines with corresponding mono/dialkylamines. The structures of the synthesized compounds were characterized by nuclear magnetic resonance (NMR), fast atomic bombardment mass spectrometry (FAB-MS), and elemental analysis. Subsequently, the cytotoxicity of these compounds against two different human breast cancer cell lines, MCF7 and MDA-MB468, was investigated. Although all the compounds tested showed good activity against both cell lines, N'-(7-chloro-quinoline-4-yl)-N,N-dimethyl-ethane-1,2-diamine was the most active in the series. It showed particularly significant inhibitory effects on MDA-MB468 cells compared to chloroquine and amodiaquine. Butyl-(7-fluoro-quinoline-4-yl)amine showed stronger inhibitory effects on MCF-7 cells than chloroquine. Therefore, 4-aminoquinoline can serve as a prototype molecule for further development of novel anticancer drugs. [1]
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| Molecular Formula |
C20H16CL2N4
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|---|---|
| Molecular Weight |
383.27384185791
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| Exact Mass |
382.075
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| Elemental Analysis |
C, 62.68; H, 4.21; Cl, 18.50; N, 14.62
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| CAS # |
140926-75-6
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| PubChem CID |
221354
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| Appearance |
White to off-white Solid powder
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| LogP |
5.759
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
26
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| Complexity |
412
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1=CC=C2C(NCCNC3=CC=NC4=CC(Cl)=CC=C34)=CC=NC2=C1
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| InChi Key |
SSXYXSMMVMVYEV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H16Cl2N4/c21-13-1-3-15-17(5-7-23-19(15)11-13)25-9-10-26-18-6-8-24-20-12-14(22)2-4-16(18)20/h1-8,11-12H,9-10H2,(H,23,25)(H,24,26)
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| Chemical Name |
N,N'-bis(7-chloroquinolin-4-yl)ethane-1,2-diamine
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| Synonyms |
NSC5844; NSC-5844; 140926-75-6; N,N'-bis(7-chloroquinolin-4-yl)ethane-1,2-diamine; N1,N2-BIS(7-CHLOROQUINOLIN-4-YL)ETHANE-1,2-DIAMINE; 1,2-Ethanediamine, N1,N2-bis(7-chloro-4-quinolinyl)-; NCIStruc1_001200; NSC 5844; RE640; RE-640; R E640.
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~1 mg/mL (~2.61 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.6091 mL | 13.0456 mL | 26.0913 mL | |
| 5 mM | 0.5218 mL | 2.6091 mL | 5.2183 mL | |
| 10 mM | 0.2609 mL | 1.3046 mL | 2.6091 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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