Amsacrine - CAS 51264-14-3
Catalog number: 51264-14-3
Category: Inhibitor
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Molecular Formula:
C21H19N3O3S
Molecular Weight:
393.46
COA:
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Targets:
Topoisomerase
Description:
Amsacrine is an antineoplastic agent which can intercalate into the DNA of tumor cells. It also expresses topoisomerase inhibitor activity, specifically inhibiting topoisomerase II.
Purity:
>98%
Synonyms:
AMSA; m-AMSA; CI-880; SN-11841; acridinyl anisidide
MSDS:
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InChIKey:
XCPGHVQEEXUHNC-UHFFFAOYSA-N
InChI:
InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)
Canonical SMILES:
COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42
1.Amsacrine analog-loaded solid lipid nanoparticle to resolve insolubility for injection delivery: characterization and pharmacokinetics.
Fang YP1, Chuang CH2, Wu PC1, Huang YB1, Tzeng CC3, Chen YL3, Liu YT1, Tsai YH1, Tsai MJ4. Drug Des Devel Ther. 2016 Mar 4;10:1019-28. doi: 10.2147/DDDT.S97161. eCollection 2016.
Amsacrine analog is a novel chemotherapeutic agent that provides potentially broad antitumor activity when compared to traditional amsacrine. However, the major limitation of amsacrine analog is that it is highly lipophilic, making it nonconductive to intravenous administration. The aim of this study was to utilize solid lipid nanoparticles (SLN) to resolve the delivery problem and to investigate the biodistribution of amsacrine analog-loaded SLN. Physicochemical characterizations of SLN, including particle size, zeta potential, entrapment efficiency, and stability, were evaluated. In vitro release behavior was also measured by the dialysis method. In vivo pharmacokinetics and biodistribution behavior of amsacrine analog were investigated and incorporated with a non invasion in vivo imaging system to confirm the localization of SLN. The results showed that amsacrine analog-loaded SLN was 36.7 nm in particle size, 0.37 in polydispersity index, and 34.
2.Antiproliferative Effect of Novel Aminoacridine-based Compounds.
Munder A, Moskovitz Y, Redko B, Levy AR, Ruthstein S, Gellerman G, Gruzman A1. Med Chem. 2015;11(4):373-82.
We tested the antiproliferative activity and mechanism of the action of several novel aminoacridine derivatives. Six different cancer cell lines were used to evaluate the potential cytotoxic effect of eleven aminoacridine-based molecules. A standard MTT assay was used for cell bioavailability analysis. Additionally, the potential cytotoxic effect of the tested compounds on non-cancer cells was investigated in rat skeletal muscle myotubes (L6) and in bovine aortic smooth muscle cells. In order to investigate whether the DNA binding activity of tested compounds correlated with their cytotoxic effect, circular dichroism (CD) measurement and DNA T4 ligase assay were performed. Finally, the potential mutagenic activity of the lead compound 5 was investigated. The cytotoxic effect of compound 5 in cancer cells was obtained in lower concentrations than the well-known: 9- aminoacridine based drug, amsacrine. The lead compound binds to DNA, but in a different mode than the parent molecules.
3.Risk factors for outcome in refractory acute myeloid leukemia patients treated with a combination of fludarabine, cytarabine, and amsacrine followed by a reduced-intensity conditioning and allogeneic stem cell transplantation.
Pfrepper C1, Klink A2, Behre G3, Schenk T2, Franke GN3, Jentzsch M3, Schwind S3, Al-Ali HK3, Hochhaus A2, Niederwieser D3, Sayer HG2,4. J Cancer Res Clin Oncol. 2016 Jan;142(1):317-24. doi: 10.1007/s00432-015-2050-y. Epub 2015 Sep 30.
INTRODUCTION: Hematopoietic stem cell transplantation (HCT) is considered a standard treatment for high-risk acute myeloid leukemia (AML) in first or second complete remission (CR). Unfortunately, not all patients achieve complete remission prior to HCT. We sought to establish predictive factors for survival after HCT for refractory AML after FLAMSA-RIC.
4.CK0403, a 9‑aminoacridine, is a potent anti‑cancer agent in human breast cancer cells.
Sun YW1, Chen KY2, Kwon CH3, Chen KM1. Mol Med Rep. 2016 Jan;13(1):933-8. doi: 10.3892/mmr.2015.4604. Epub 2015 Nov 23.
3‑({4‑[4‑(Acridin‑9‑ylamino)phenylthio]phenyl}(3‑hydroxypropyl)amino)propan‑1‑ol (CK0403) is a sulfur‑containing 9‑anilinoacridine analogue of amsacrine and was found to be more potent than its analogue 2-({4-[4-(acridin-9-ylamino)phenylthio]phenyl}(2‑hydroxyethyl)amino)ethan‑1‑ol (CK0402) and amsacrine in the inhibition of the topoisomerase II‑catalyzed decatenation reaction. A previous study by our group reported that CK0402 was effective against numerous breast cancer cell lines, and the combination of CK0402 with herceptin enhanced its activity in HER2(+) SKBR‑3 cells. In order to identify novel chemotherapeutic agents with enhanced potency, the present study explored the potential of CK0403 in the treatment of breast cancer. First, the growth inhibitory activity of CK0403 in the breast cancer cell lines MCF‑7, MDA‑MB‑231, BT474 and SKBR‑3, as well as in the non‑cancerous MCF‑10A cell line, was examined using a sulforhodamine B assay.
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