Glaucine
(Synonyms: 海罌粟鹼,O,O-Dimethylisoboldine; S-(+)-Glaucine; NSC 34396) 目录号 : GC41486
An Analytical Reference Standard
Cas No.:475-81-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Glaucine is an alkaloid originally isolated from G. flavum that demonstrates antitussive properties. It is structurally related to papaverine , a non-selective phosphodiesterase (PDE) inhibitor. Glaucine selectively inhibits PDE4 (Kis = 3.4 µM in human bronchus and polymorphonuclear leukocytes). It has been shown to have bronchodilation and anti-inflammatory effects, inhibiting the spontaneous and histamine-induced tone in human isolated bronchus and augmenting cyclic AMP accumulation. Glaucine also binds to the benzothiazepine site on L-type Ca2+-channels in smooth muscle, blocking calcium ion signaling. This compound has been detected as a recreational drug capable of eliciting dissociative effects.
| Cas No. | 475-81-0 | SDF | |
| 别名 | 海罌粟鹼,O,O-Dimethylisoboldine; S-(+)-Glaucine; NSC 34396 | ||
| Canonical SMILES | COC1=C(OC)C2=C3[C@](N(C)CCC3=C1)([H])CC4=CC(OC)=C(OC)C=C42 | ||
| 分子式 | C21H25NO4 | 分子量 | 355.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml | 储存条件 | 4°C, protect from light |
| 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 | 2.8137 mL | 14.0687 mL | 28.1373 mL |
| 5 mM | 0.5627 mL | 2.8137 mL | 5.6275 mL |
| 10 mM | 0.2814 mL | 1.4069 mL | 2.8137 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。
Pharmacokinetics of Glaucine after intravenous and oral administrations and detection of systemic aporphine alkaloids after ingestion of tulip poplar shavings in horses
J Vet Pharmacol Ther 2022 May;45(3):273-282.PMID:35394081DOI:10.1111/jvp.13057.
Glaucine, an aporphine alkaloid with anti-tussive, anti-inflammatory, and anti-nociceptive properties, has been identified in post-race samples from racehorses. To investigate pharmacokinetics of Glaucine in horses, a three-way crossover study of intravenous and oral Glaucine (0.1 mg/kg) and orally administered tulip poplar shavings (50 g shavings = 0.001 mg/kg Glaucine) was performed in six horses. A two-compartment model best described IV administration with alpha ( t 1 / 2 α ) and beta ( t 1 / 2 β ) half-life lives of 0.3 (0.1-0.7) and 3.1 (2.4-7.8) h, respectively. The area under the curve ( AUC 0 ∞ iv ) was 45.4 (34.7-52.3) h*ng/ml, and the volume of distribution of the central (Vdc ) and peripheral (Vdp ) compartments was 2.7 (1.3-4.6) and 4.9 (4.3-8.2) L/kg, respectively. A one compartment model best described the oral administration of Glaucine with absorption ( t 1 / 2 ka ) and elimination ( t 1 / 2 kel ) half-lives of 0.09 (0.05-0.15) and 0.7 (0.6-0.8) h, respectively. The area under the curve ( AUC 0 ∞ PO ) was 15.1 (8.0-19.5) h·ng/ml. Bioavailability following oral administration was 17%-48%. Following ingestion of shavings, Glaucine and liriodenine were detectable in plasma for up to 16 and 48 h, respectively. Glaucine was quantifiable briefly in the urine from two horses. Liriodenine was quantifiable in urine for 12-20 h in four horses and for 48 h in two horses. The presence of liriodenine indicates ingestion of tulip poplar tree parts, however, does not rule out co-administration of purified Glaucine in horses.
Glaucine inhibits breast cancer cell migration and invasion by inhibiting MMP-9 gene expression through the suppression of NF-κB activation
Mol Cell Biochem 2015 May;403(1-2):85-94.PMID:25670016DOI:10.1007/s11010-015-2339-9.
Matrix metalloproteinase-9 (MMP-9) plays a central role in the invasion and metastasis of various types of cancer cells. Here, we demonstrate that Glaucine, an alkaloid isolated from the plant Corydalis turtschaninovii tuber (Papaveraceae), can inhibit the migration and invasion of human breast cancer cells. We further show that Glaucine significantly blocks phorbol 12-myristate 13-acetate (PMA)-induced MMP-9 expression and activity in a dose-dependent manner. Results from reporter gene and electrophoretic mobility shift assays revealed that Glaucine inhibits MMP-9 expression by suppressing activation of the nuclear transcription factor nuclear factor-κB (NF-κB). Moreover, Glaucine attenuates PMA-induced IκBα degradation and nuclear translocation of NF-κB. Finally, we also found that Glaucine inhibits invasion and MMP-9 expression in the highly metastatic MDA-MB-231 breast cancer cell line. Taken together, our findings indicate that the MMP-9 inhibitory activity of Glaucine and its abilities to attenuate IκBα and NF-κB activities may be therapeutically useful as a novel means of controlling breast cancer growth and invasiveness.
Effects of Glaucine and some Glaucine derivatives and of their combination with L-DOPA on the brain level of biogenic monoamines
Arch Int Pharmacodyn Ther 1982 Sep;259(1):83-92.PMID:7181577doi
Glaucine and two of its structural analogues exerted an inhibitory effect on phosphodiesterase activity in different tissue homogenates. In experiments on rats Glaucine applied intraperitoneally significantly increased the brain level of dopamine (DA) and did not change the content of noradrenaline and serotonin (5-HT). The combined application of L-DOPA and Glaucine or Glaucine derivatives produced a higher increase in brain DA than the increase which would be expected by simple summation of the effects of L-DOPA and Glaucine and of the Glaucine derivatives respectively. At the same time L-DOPA and Glaucine, applied together, caused a slighter decrease of brain 5-HT than the decrease produced by the same dose of L-DOPA when the latter was applied alone. It is suggested that the higher increase of brain DA produced by the combination of L-DOPA and the phosphodiesterase inhibitor Glaucine or its structural analogues is mainly due to the increased cAMP level.
Bronchodilator and anti-inflammatory activities of Glaucine: In vitro studies in human airway smooth muscle and polymorphonuclear leukocytes
Br J Pharmacol 1999 Aug;127(7):1641-51.PMID:10455321DOI:10.1038/sj.bjp.0702702.
1. Selective phosphodiesterase 4 (PDE4) inhibitors are of potential interest in the treatment of asthma. We examined the effects of the alkaloid S-(+)-glaucine, a PDE4 inhibitor, on human isolated bronchus and granulocyte function. 2. Glaucine selectively inhibited PDE4 from human bronchus and polymorphonuclear leukocytes (PMN) in a non-competitive manner (Ki=3.4 microM). Glaucine displaced [3H]-rolipram from its high-affinity binding sites in rat brain cortex membranes (IC50 approximately 100 microM). 3. Glaucine inhibited the spontaneous and histamine-induced tone in human isolated bronchus (pD2 approximately 4.5). Glaucine (10 microM) did not potentiate the isoprenaline-induced relaxation but augmented cyclic AMP accumulation by isoprenaline. The glaucine-induced relaxation was resistant to H-89, a protein kinase A inhibitor. Glaucine depressed the contractile responses to Ca2+ (pD'2 approximately 3.62) and reduced the sustained rise of [Ca2+]i produced by histamine in cultured human airway smooth muscle cells (-log IC50 approximately 4.3). 4. Glaucine augmented cyclic AMP levels in human polymorphonuclear leukocytes challenged with N-formyl-Met-Leu-Phe (FMLP) or isoprenaline, and inhibited FMLP-induced superoxide generation, elastase release, leukotriene B4 production, [Ca2+]i signal and platelet aggregation as well as opsonized zymosan-, phorbol myristate acetate-, and A23187-induced superoxide release. The inhibitory effect of Glaucine on superoxide generation by FMLP was reduced by H-89. 5. In conclusion, Ca2+ channel antagonism by Glaucine appears mainly responsible for the relaxant effect of Glaucine in human isolated bronchus while PDE4 inhibition contributes to the inhibitory effects of Glaucine in human granulocytes. The very low PDE4/binding site ratio found for Glaucine makes this compound attractive for further structure-activity studies.
Effect of the antitussive Glaucine on bronchomotor tone in man
Thorax 1983 Jul;38(7):537-42.PMID:6612639DOI:10.1136/thx.38.7.537.
In view of the observation that the antitussive agent Glaucine prevents histamine-induced bronchoconstriction in guinea pigs we investigated this agent for a possible peripheral action in man, using a new method for measuring changes in bronchomotor tone. The forced airflow oscillation method was used to determine respiratory resistance (Rrs) over a range of lung volumes (VL) in seven healthy supine subjects. Computer analysis of the hyperbolic relationship between Rrs and VL was used to determine the asymptotic resistance and yield estimates of lower airways conductance (Glaw). Specific lower airways conductance (sGlaw) was expressed as the slope of the linear plot of Glaw against VL and is a sensitive index of bronchomotor tone. After baseline measurements of sGlaw subjects received placebo or 60 mg Glaucine orally according to a double-blind crossover protocol. Histamine, 500 micrograms, was inhaled 45 minutes later. Measurements of sGlaw were repeated every 10 minutes for two hours. Although there was a trend towards bronchodilatation after Glaucine administration (sGlaw = 130% of baseline) there was no significant difference from the effect of placebo (sGlaw = 89% of baseline). After inhalation of histamine sGlaw fell to 26% of baseline after both Glaucine and placebo (p less than 0.01). In a further study three subjects received Glaucine and placebo according to an identical protocol except that the histamine was omitted. Again the increase in sGlaw failed to achieve significance. Glaucine does not affect the bronchoconstrictor response to histamine in man and there is no convincing evidence of an effect on resting bronchomotor tone.