Lawsone methyl ether
(Synonyms: 2-甲氧基-1,4-萘并醌,2-?Methoxy-?1,?4-?naphthoquinone) 目录号 : GC63825
2-Methoxy-1,4-naphthoquinone, isolated from the leaves of Impatiens glandulifera, specifically suppressed the expression of PKC βI, δ, and ζ in a concentration-dependent manner in Raji cells.
Cas No.:2348-82-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Methoxy-1,4-naphthoquinone, isolated from the leaves of Impatiens glandulifera, specifically suppressed the expression of PKC βI, δ, and ζ in a concentration-dependent manner in Raji cells.
2-Methoxy-1,4-naphthoquinone (MNQ) exhibits antifungal, antimicrobial activities and showed strong killing effect on K562, HL-60, Raji, MCF-7, H-23, IMR-32, LA-174-T, HSC-2, and SK-MEL-28. MNQ is able to trigger the intrinsic apoptotic pathway in K562 cells, as well as causing p53-dependent cell cycle arrest in the p53-wild type cell line. MNQ inhibits the TCF/β-catenin (TOP) transcriptional activity at IC50 2.9 μM, while it decreases the transcriptional activity of FOP (mutated TCF-binding site)-transfected cell. MNQ exerts an anti-metastatic effect against MDA-MB-231 cells. MNQ has remarkable selectivity towards PKCβI and ζ suppression. MNQ suppresses PKCδ moderately, where MNQ suppresses half of the PKCδ expression at the concentration of 10 μM. MNQ does not suppress PKC βII[1]. MNQ is able to inhibit the invasion and migration characteristics of a highly metastatic MDA-MB-231 cancer cell line[2].
[1] Wong Teck Yew, et al. Journal of Applied Pharmaceutical Science. 2015, 5(08), pp001-005. [2] Liew K, et al. Toxicol In Vitro. 2014, 28(3):335-9.
| Cas No. | 2348-82-5 | SDF | Download SDF |
| 别名 | 2-甲氧基-1,4-萘并醌,2-?Methoxy-?1,?4-?naphthoquinone | ||
| 分子式 | C11H8O3 | 分子量 | 188.18 |
| 溶解度 | DMSO : 50 mg/mL (265.70 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.3141 mL | 26.5703 mL | 53.1406 mL |
| 5 mM | 1.0628 mL | 5.3141 mL | 10.6281 mL |
| 10 mM | 0.5314 mL | 2.657 mL | 5.3141 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Synergistic interactions between artocarpin-rich extract, Lawsone methyl ether and ampicillin on anti-MRSA and their antibiofilm formation
Lett Appl Microbiol 2022 May;74(5):777-786.PMID:35100449DOI:10.1111/lam.13662.
Artocarpin-rich extract (ARE) was prepared using a green technology and standardized to contain 49·6% w/w artocarpin, while Lawsone methyl ether was prepared using a green semi-synthesis. ARE, LME and ampicillin exhibited weak anti-MRSA activity with the MICs of 31·2-62·5 µg/ml. Based on the checkerboard assay, the synergistic interaction between ARE (0·03 µg/ml) and LME (0·49 µg/ml) against four MRSA isolates were observed with the fractional inhibitory concentration index (FICI) value of 0·008, while those of ARE (1·95-7·81 µg/ml) and ampicillin (0·49 µg/ml) as well as LME (0·49-1·95 µg/ml) and ampicillin (0·49 µg/ml) were 0·016-0·257. The time kill confirmed the synergistic interactions against MRSA with different degrees. The combination of ARE and LME as well as its combinations with ampicillin altered the membrane permeability of MRSA, which led to release of the intracellular materials. In addition, each compound inhibited the biofilm formation of standard MRSA (DMST 20654) and the clinical isolate (MRSA 1096). These findings suggested that cocktails containing ARE and LME might be used to overcome problems associated with MRSA. Additionally, the results implied that combination of either ARE or LME with available conventional antibiotic agents might be effective in countering these perilous pathogens.
Antifungal activity of Lawsone methyl ether in comparison with chlorhexidine
J Oral Pathol Med 2011 Jan;40(1):90-6.PMID:20738748DOI:10.1111/j.1600-0714.2010.00921.x.
Objective: The aim of this study was to determine the antifungal activity of Lawsone methyl ether mouthwash (LME) in comparison with chlorhexidine mouthwash (CHX) in vitro and in vivo. Materials and methods: For in vitro study, each mouthwash preparation was added into the inoculum of Candida. The turbidity was recorded after incubation at 37°C for 48 h. Candidal culture was performed and the number of colony of Candida albicans was recorded. For in vivo study, a crossover clinical trial was conducted in 22 HIV-infected subjects and 32 denture wearers. Clinical examination was performed and oral rinse technique was carried out immediately before and 0, 1, 2 h after using each mouthwash. Allergy and subjective assessment of the mouthwashes were recorded. Statistical analysis was performed using one-way ANOVA and linear mixed effect modeling. Results: In vitro, antifungal activity of 0.25% LME was significantly greater than that of 0.12% CHX (P < 0.05) and comparable with that of 0.2% CHX. In vivo, antifungal activity up to 2 hours of 0.025% LME mouthwash was evidenced in both groups of subjects, although significantly lower than that of 0.12% CHX. No allergic reaction was reported. LME mouthwash was graded to have less bitter taste than that of CHX. Subjects' satisfaction on taste and smell of LME mouthwash was significantly greater than that of CHX (P < 0.05). Conclusions: Lawsone methyl ether mouthwash possesses potent antifungal activity both in vitro and in vivo. However, concentration of the mouthwash needs to be adjusted in addition to further clinical trials on long-term use.
Effects of Lawsone methyl ether mouthwash on oral Candida in HIV-infected subjects and subjects with denture stomatitis
J Oral Pathol Med 2013 Oct;42(9):698-704.PMID:23586936DOI:10.1111/jop.12060.
Objectives: To determine (i) effects of Lawsone methyl ether (LME) mouthwash on antifungal drug resistance of oral Candida, (ii) effects of LME mouthwash on changes in genotype of oral Candida, and (iii) allergy and subjects' satisfaction on LME mouthwash in comparison with chlorhexidine (CHX). Materials and methods: A randomized clinical trial was conducted in HIV-infected subjects and denture wearers receiving either LME or CHX mouthwash. Candidal culture by oral rinse technique was performed as baseline and after using the mouthwash for 2 weeks. Antifungal drug resistance and changes in genotype of oral Candida were assessed by microdilution assay, inverted repeat polymerase chain reaction and restriction fragment length polymorphism assays, respectively. Allergy and subjects' satisfaction on the mouthwashes were recorded. Statistical analysis was performed using Chi-squared and Fisher's exact tests. Results: Twenty-nine HIV-infected subjects (age range, 26-54 years; mean age, 41 years) and 38 denture wearers (age range, 27-76 years; mean age, 55 years) were enrolled. C. albicans was the most common specie found in both groups followed by C. tropicalis, C. parapsilosis, and C. glabrata. Neither antifungal drug resistance nor significant changes in genotyping of Candida were noted among those receiving LME mouthwash. Subjects' satisfaction on taste and smell of LME mouthwash was comparable to that of CHX. Conclusions: Use of LME mouthwash for 2 weeks neither led to antifungal drug resistance nor significant changes in genotype of oral Candida. Thus, LME may be an alternative mouthwash in prophylaxis of oral candidiasis among those at risk of developing the disease.
Synergistic effect on anti-methicillin-resistant Staphylococcus aureus among combinations of α-mangostin-rich extract, Lawsone methyl ether and ampicillin
Lett Appl Microbiol 2020 Nov;71(5):510-519.PMID:32770753DOI:10.1111/lam.13369.
α-Mangostin-rich extract (AME) exhibited satisfactory inhibitory activities against all tested MRSA strains, with minimum inhibitory concentrations (MICs) of 7·8-31·25 µg ml-1 , whereas Lawsone methyl ether (LME) and ampicillin revealed weak antibacterial activity with MICs of 62·5-125 µg ml-1 . However, the combination of AME and LME showed synergistic effects against all tested MRSA strains with fractional inhibitory concentration index (FICI) values of 0·008-0·009, while the combination of AME and ampicillin, as well as LME and ampicillin produced synergistic effects with FICIs of 0·016-0·257. A time-kill assay against MRSA (DMST 20654 strain) revealed a 6-log reduction in CFU per ml, which completely inhibited bacterial growth for the combinations of AME and LME, AME and ampicillin, and LME and ampicillin at a 8-h incubation, while those against MRSA (2468 strain) were at 10-h incubation. The combination of α-mangostin and LME as well as the combinations of each compound with ampicillin synergized the alteration of membrane permeability. In addition, α-mangostin, LME and ampicillin inhibited the biofilm formation of MRSA. These findings indicated that the combinations of AME and LME or each of them in combination with ampicillin had enhanced antibacterial activity against MRSA. Therefore, these compounds might be used as the antibacterial cocktails for treatment of MRSA.
Increased production of naphthoquinones in Impatiens balsamina root cultures by elicitation with methyl jasmonate
Bioresour Technol 2010 Nov;101(22):8777-83.PMID:20620051DOI:10.1016/j.biortech.2010.06.067.
Impatiens balsamina root cultures were treated with yeast extract (YE), Candida albicans homogenate (CAH), Trichophyton rubrum homogenate (TRH), chitosan (CHI) and methyl jasmonate (MJ). Different elicitors, depending on concentrations used exerted differential effects on the production of the three main naphthoquinones, lawsone (2-hydroxy-1,4-naphthoquinone), Lawsone methyl ether and methylene-3,3'-bilawsone. Treatment with MJ (400microM) was capable of increasing production of lawsone, and Lawsone methyl ether up to 8.6- and 11.3-fold higher, respectively, compared to the level in untreated cultures. Treatment of 21-day-old root cultures with 300microM MJ for 36h resulted in the production of 10.0, 0.78 and 0.23mg/g DW of lawsone, its methyl ether and methylene-3,3'-bilawsone, respectively. Such levels are sufficient for commercial production.