Vasicinone
(Synonyms: 鸭嘴花碱酮,(-)-Vasicinone) 目录号 : GC41255
A bronchodilator alkaloid
Cas No.:486-64-6
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Vasicinone is a quinazoline alkaloid that can be isolated from A. vasica leaves and demonstrates bronchodilatory activity. It also is reported to possess antioxidant activity in nitric oxide and ABTS radical scavenging assays.
| Cas No. | 486-64-6 | SDF | |
| 别名 | 鸭嘴花碱酮,(-)-Vasicinone | ||
| Canonical SMILES | O[C@H]1CCN2C1=NC(C=CC=C3)=C3C2=O | ||
| 分子式 | C11H10N2O2 | 分子量 | 202.2 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 20 mg/ml,DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml | 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.9456 mL | 24.728 mL | 49.456 mL |
| 5 mM | 0.9891 mL | 4.9456 mL | 9.8912 mL |
| 10 mM | 0.4946 mL | 2.4728 mL | 4.9456 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。
Induction of Autophagy by Vasicinone Protects Neural Cells from Mitochondrial Dysfunction and Attenuates Paraquat-Mediated Parkinson's Disease Associated α-Synuclein Levels
Nutrients 2020 Jun 7;12(6):1707.PMID:32517337DOI:10.3390/nu12061707.
Mitochondrial dysfunction and disturbed mitochondrial dynamics were found to be common phenomena in the pathogenesis of Parkinson's disease (PD). Vasicinone is a quinazoline alkaloid from Adhatoda vasica. Here, we investigated the autophagy/mitophagy-enhancing effect of Vasicinone and explored its neuroprotective mechanism in paraquat-mimic PD modal in SH-SY5Y cells. Vasicinone rescued the paraquat-induced loss of cell viability and mitochondrial membrane potential. Subsequently, the accumulation of mitochondrial reactive oxygen species (ROS) was balanced by an increase in the expression of antioxidant enzymes. Furthermore, Vasicinone restored paraquat-impaired autophagy and mitophagy regulators DJ-1, PINK-1 and Parkin in SH-SY5Y cells. The Vasicinone mediated autophagy pathways were abrogated by treatment with the autophagy inhibitor 3-MA, which lead to increases α-synuclein accumulation and decreased the expression of p-ULK and ATG proteins and the autophagy marker LC3-II compared to that observed without 3-MA treatment. These results demonstrated that Vasicinone exerted neuroprotective effects by upregulating autophagy and PINK-1/Parkin mediated mitophagy in SH-SY5Y cells.
Effect of Vasicinone against Paraquat-Induced MAPK/p53-Mediated Apoptosis via the IGF-1R/PI3K/AKT Pathway in a Parkinson's Disease-Associated SH-SY5Y Cell Model
Nutrients 2019 Jul 19;11(7):1655.PMID:31331066DOI:10.3390/nu11071655.
Vasicinone is a quinazoline alkaloid isolated from the Adhatoda vasica plant. In this study, we explored the neuroprotective effect and underlying molecular mechanism of Vasicinone against paraquat-induced cellular apoptosis in SH-SY5Y cells. Vasicinone reduced the paraquat-induced loss of cell viability, rescued terminal deoxynucleotide transferase-mediated dUTP nick end-labeling (TUNEL)-positive apoptotic nuclei, and suppressed generation of reactive oxygen species (ROS) in a dose-dependent manner. Western blotting analysis revealed that Vasicinone increased the phosphorylation of IGF1R/PI3K/AKT cell survival signaling molecules and downregulated the paraquat-induced, mitogen-activated protein kinase (MAPK)/c-Jun N-terminal kinase (JNK)-mediated apoptotic pathways compared to that observed in cells not treated with Vasicinone. This protection depended critically on the activation of IGF1R, and the silencing of IGF1R by siRNA completely abrogated the protective effect of Vasicinone in SH-SY5Y cells. Our findings indicated that Vasicinone is a potential candidate for the treatment of Parkinson's disease and possibly other oxidative stress-related neurodegenerative disorders.
Anti-Proliferative Activities of Vasicinone on Lung Carcinoma Cells Mediated via Activation of Both Mitochondria-Dependent and Independent Pathways
Biomol Ther (Seoul) 2018 Jul 1;26(4):409-416.PMID:29310422DOI:10.4062/biomolther.2017.097.
Vasicinone, a quinazoline alkaloid from Adhatoda vasica Nees. is well known for its bronchodilator activity. However its anti-proliferative activities is yet to be elucidated. Here-in we investigated the anti-proliferative effect of Vasicinone and its underlying mechanism against A549 lung carcinoma cells. The A549 cells upon treatment with various doses of Vasicinone (10, 30, 50, 70 μM) for 72 h showed significant decrease in cell viability. Vasicinone treatment also showed DNA fragmentation, LDH leakage, and disruption of mitochondrial potential, and lower wound healing ability in A549 cells. The Annexin V/PI staining showed disrupted plasma membrane integrity and permeability of PI in treated cells. Moreover Vasicinone treatment also lead to down regulation of Bcl-2, Fas death receptor and up regulation of PARP, BAD and cytochrome c, suggesting the anti-proliferative nature of Vasicinone which mediated apoptosis through both Fas death receptors as well as Bcl-2 regulated signaling. Furthermore, our preliminary studies with Vasicinone treatment also showed to lower the ROS levels in A549 cells and have potential free radical scavenging (DPPH, Hydroxyl) activity and ferric reducing power in cell free systems. Thus combining all, Vasicinone may be used to develop a new therapeutic agent against oxidative stress induced lung cancer.
Simultaneous determination of vasicine and Vasicinone by High-performance liquid chromatography in roots of eight Sida species
Ayu 2016 Apr-Jun;37(2):135-139.PMID:29200752DOI:10.4103/ayu.AYU_49_16.
Introduction: Sida L. is a medicinally important genus widely used in conventional systems of medicine in India. Aim: The present study aims toward simultaneous determination of two bioactive compounds vasicine and Vasicinone in root extracts of eight Sida spp. from Western Ghats, India. Materials and methods: Determination of vasicine and Vasicinone was undertaken in methanolic root extracts (10% w/v) of Sida acuta, Sida cordata, Sida cordifolia, Sida rhombifolia, Sida spinosa, Sida indica, Sida retusa and Sida mysorensis by high performance liquid chromatography (HPLC) method. The standards were prepared with the concentration of mg/mL. Data were expressed as mean values of three reading and relative standard deviations. The separation was achieved on a Waters, Nova-Pack, C18 (250 mm × 4.6 mm, 5 μ) column, with acetonitrile - 0.1 M phosphate buffer-glacial acetic acid (15: 85: 1, v/v/v) as solvent system at a flow-rate of 1.0 mL/min. The effluent was monitored using ultraviolet detection at a wavelength of 300 nm. Results: Both calibration curves of standard showed good linear regression (R2 > 0.994). The limit of detection and the limit of quantification for vasicine was 0.110 and 0.333 μg/mL and for Vasicinone was 0.059 and 0.179 μg/mL respectively. The vasicine content was highest in S. cordifolia (9.891 ± 0.495 μg/100 mg) and Vasicinone content was rich in S. cordata (33.013 ± 1.651 μg/100 mg.) The content of Vasicinone was higher than vasicine. Conclusion: HPLC method provides simple, accurate, and reproducible quantitative analysis for simultaneous determination of vasicine and Vasicinone. Among the selected Sida species, S. cordifolia and S. cordata were found to be rich in the vasicine and Vasicinone contents, respectively.
Synthesis of Optically Active Vasicinone Based on Intramolecular Aza-Wittig Reaction and Asymmetric Oxidation(1)
J Org Chem 1996 Oct 18;61(21):7316-7319.PMID:11667656DOI:10.1021/jo9609283.
Both optical isomers of a quinazoline alkaloid, Vasicinone, were synthesized by two different methods. The first method used (3S)-3-hydroxy-gamma-lactam as a chiral synthon, which was, after O-TBDMS protection, o-azidobenzoylated followed by treatment with tri-n-butylphosphine to afford (S)-(-)-vasicinone via the tandem Staudinger/intramolecualr aza-Wittig reaction. The second method utilized asymmetric oxygenation of deoxyvasicinone with (1S)-(+)- or (1R)-(-)-(10-camphorsulfonyl)oxaziridine (the Davis reagent), respectively. The aza-enolate anion of deoxyvasicinone was treated with (S)-(+)-reagent to afford (R)-(+)-vasicinone in 71% ee, while the reaction with (R)-(-)-reagent gave (S)-(-)-vasicinone in 62% ee. The optical purity was analyzed by HPLC on specially modified cellulose as a stationary phase. These results provided a facile method to prepare both optical isomers of Vasicinone and confirmed the recently reversed stereochemistry of natural (-)-vasicinone.