Musk ketone
(Synonyms: 酮麝香) 目录号 : GC65442Musk ketone (MK) 是一种应用广泛的人工香料。Musk ketone 对 Hep G2 细胞具有致突变性和致伤性作用,通过激活 PI3K/Akt 信号通路诱导神经干细胞在脑缺血时增殖分化。 Musk ketone 通过抑制细胞凋亡 (apoptosis) 对脑卒中损伤起到神经保护作用。
Cas No.:81-14-1
Sample solution is provided at 25 µL, 10mM.
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Musk ketone (MK) is a widely used artificial fragrance. Musk ketone shows mutagenic and comutagenic effects in Hep G2 cells and induces neural stem cell proliferation and differentiation in cerebral ischemia via activation of the PI3K/Akt signaling pathway. In the brain, musk ketone is neuroprotective against stroke injury through inhibition of cell apoptosis[1][2][3].
[1]. Yamagishi T, et al. Identification of musk xylene and musk ketone in freshwater fish collected from the Tama River, Tokyo. Bull Environ Contam Toxicol. 1981 May;26(5):656-62. [2]. Mersch-Sundermann V, et al. Musk ketone enhances benzo(a)pyrene induced mutagenicity in human derived Hep G2 cells. Mutat Res. 2001 Aug 22;495(1-2):89-96. [3]. Zhou Z, et al. Musk Ketone Induces Neural Stem Cell Proliferation and Differentiation in Cerebral Ischemia via Activation of the PI3K/Akt Signaling Pathway. Neuroscience. 2020 May 21;435:1-9.
Cas No. | 81-14-1 | SDF | Download SDF |
别名 | 酮麝香 | ||
分子式 | C14H18N2O5 | 分子量 | 294.3 |
溶解度 | DMSO : 250 mg/mL (849.47 mM; Need ultrasonic) | 储存条件 | Store at -20°C, sealed storage, away from moisture and light |
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10 mM | 0.3398 mL | 1.6989 mL | 3.3979 mL |
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Musk ketone induces apoptosis of gastric cancer cells via downregulation of sorbin and SH3 domain containing 2
Mol Med Rep 2021 Jun;23(6):450.PMID:33880576DOI:10.3892/mmr.2021.12089.
Musk ketone exerts antiproliferative effects on several types of cancer, such as lung and breast cancer. However, the effects and underlying mechanisms of action of Musk ketone in gastric cancer (GC) are poorly understood. The present study aimed to investigate the effects of Musk ketone in GC cells. The present study indicated that Musk ketone exerted significant anticancer effects on GC cells. The IC50 values of Musk ketone were 4.2 and 10.06 µM in AGS and HGC‑27 cells, respectively. Low dosage of Musk ketone significantly suppressed the proliferation and colony formation of AGS and HGC‑27 cells. Cell cycle arrest and apoptosis were induced by Musk ketone. Furthermore, microarray data indicated that Musk ketone treatment led to downregulation of various genes, including sorbin and SH3 domain containing 2 (SORBS2). Reverse transcription‑quantitative PCR and immunoblotting results indicated that Musk ketone repressed mRNA and protein expression levels of SORBS2. It was also shown that knockdown of SORBS2 inhibited the proliferation and colony formation of HGC‑27 cells. The antiproliferative effects of Musk ketone were decreased in HGC‑27 cells with SORBS2 silencing. In summary, the present study indicated that Musk ketone suppressed the proliferation and growth of GC partly by downregulating SORBS2 expression.
Musk xylene and Musk ketone amino metabolites in the aquatic environment
Toxicol Lett 1999 Dec 20;111(1-2):5-15.PMID:10630699DOI:10.1016/s0378-4274(99)00190-3.
The monoamino metabolites of the nitro musk fragrances musk xylene (MX) and Musk ketone (MK) were analysed simultaneously with their parent compounds by GC/ECD, GC/PND and GC/EI/MS in the various compartments of the aquatic environment. In this review the data of the metabolites 4-NH2-MX, 2-NH2-MX, and 2-NH2-MK in five river water and seven sewage samples, six sediment samples and in a total of 33 biota samples are summarized and discussed. In the effluents of two municipal sewage plants low nitro musk concentrations and comparatively high levels of the amino metabolites (maximum concentrations: 34 ng 4-NH2-MX/L, 250 ng 2-NH2-MK/L) were analysed indicating that besides adsorption to the sludge the metabolization pathway plays an important role in the sewage plant. In water samples from the river Elbe the transformation products were the dominant compounds as well. In general, in water samples the concentrations of 2-NH2-MK exceeded those of the main MX metabolite 4-NH2-MX significantly. In biota samples 4-NH2-MX seems to be the main metabolite, very often its contents were higher than those of the parent compound. Maximum concentrations of 4-NH2-MX were found in tenches from a sewage pond (3600 microg/kg lipid), a species dependent bioaccumulation was discussed. The bioconcentration of 2-NH2-MK in biota samples is relatively low. There are only few toxicological studies on the mixed amino nitroaromatics, whose data indicate the relevance of the monoamino metabolites in environmental analysis and toxicology and the urgent need of further investigations.
Musk ketone Induces Neural Stem Cell Proliferation and Differentiation in Cerebral Ischemia via Activation of the PI3K/Akt Signaling Pathway
Neuroscience 2020 May 21;435:1-9.PMID:32112919DOI:10.1016/j.neuroscience.2020.02.031.
Traditional Chinese medicine has been reported to influence the proliferation and differentiation of neural stem cells (NSCs) that may be protective against nervous system diseases. Recent evidence indicates the importance of Musk ketone in nerve recovery and preventing secondary damage after cerebral ischemic injury. A middle cerebral artery occlusion (MCAO) rat model was established by a transient filament model, and rats were treated with Musk ketone (0.9 or 1.8 μM). Next, an in vitro oxygen-glucose deprivation (OGD) cell model was established to study the effect of Musk ketone on the proliferation and differentiation of NSCs. To determine the potential mechanisms of Musk ketone involved in activities of NSCs, the effect of Musk ketone on the PI3K/Akt signaling pathway activation was assessed. Furthermore, NSCs were treated with Musk ketone in the presence of PI3K/Akt inhibitor Akti-1/2 to examine their roles on NSC proliferation and differentiation. Musk ketone reduced cerebral ischemic injury in a dose-dependent manner in rats. In addition, NSCs treated with Musk ketone showed enhanced proliferation and differentiation along with increased PI3K/Akt signaling pathway activation. The effects of muck ketone were reversed by Akti-1/2. Altogether, Musk ketone promoted NSC proliferation and differentiation and protected against cerebral ischemia by activating the PI3K/Akt signaling pathway, highlighting the potential of Musk ketone as a physiologically validated approach for the treatment of cerebral ischemia.
Native musk and synthetic Musk ketone strongly induced the growth repression and the apoptosis of cancer cells
BMC Complement Altern Med 2016 Dec 8;16(1):511.PMID:27931220DOI:10.1186/s12906-016-1493-2.
Background: Musk is widely used in clinical practice for its anti-cancer properties. Here, we treated various types of cancer using musk to determine which cancers are sensitive to musk treatment. We also compared effects of native musk and synthetic Musk ketone in cancer cells. Furthermore, we investigated mechanisms underlying effects of musk. Methods: Twenty two cancer cell lines were treated with musk. Cell proliferation and apoptosis analyses were carried out. Native musk and synthetic Musk ketone were analyzed by gas chromatograph-mass spectrometer (GC-MS) assay. Differentially expressed genes were determined by microarray and quantitative real-time polymerase chain reaction. Results: Native musk strongly induced the growth repression and the apoptosis in the majority of cancer cell lines in a dose-dependent manner, but distinct types of cancer showed significantly different reactions. Cancer cells which originated from epithelial cells showed higher sensitivity for musk treatment. By contrast, leukaemia and lymphoma cells were not sensitive. GC-MS analysis demonstrated that native musk contains more than 30 contents in which Musk ketone is a major component; synthetic Musk ketone was consistent with natural Musk ketone, and the used sample of synthetic Musk ketone contained only sole component. Similar to native musk, synthetic Musk ketone induced the growth repression and the apoptosis of cancer cells. Additionally, numerous genes were differentially expressed in lung cancer cells after native musk treatment. These differentially expressed genes were involved in many signalling pathways. Among these pathways, apoptosis-related pathways included interleukin family, tumor necrosis factor family, and MAPK signalling pathway. Native musk and synthetic Musk ketone can up-regulate IL-24 (interleukin family) and DDIT3 (MAPK signalling pathway) in lung cancer cells. Conclusions: This research provided strong evidence that native musk and synthetic Musk ketone can induce the growth repression and the apoptosis of cancer cells. However, the selection of sensitive cancer patient for individualized treatment is a key step in clinical application. Synthetic Musk ketone can substitute for native musk to treat cancer patients. Musk might induce the growth repression and the apoptosis of lung cancer cells through up-regulating IL-24 and DDIT3 expressions.
Evaluation of health risks caused by Musk ketone
Int J Hyg Environ Health 2001 May;203(4):293-9.PMID:11434209DOI:10.1078/1438-4639-00047.
Among the nitro musks, Musk ketone (MK) as a synthetic compound with a typical musk odor is widely used in cosmetics. In the European Community the total amount used in fragrances has been reported to be 110 tons/a. Additionally, relevant amounts of MK are used in Indian joss sticks. As a result of its inherently low biodegradability MK has been detected in the aquatic environment (surface water, sediments, edible fish). Moreover, it has been shown that MK concentrates in human fatty tissue and breast milk, indicating that humans are constantly exposed. Several studies provided convincing evidence of lack of a genotoxic potential for MK. However, MK was identified as a strong inducer of phase I enzymes in rodents and a cogenotoxicant in vitro in human derived cells in rather low doses, suggesting that exposure to MK might increase the susceptibility to health hazards caused by carcinogens in humans.