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Phosphatidylcholines,soya Sale

(Synonyms: 磷脂酰胆碱(大豆),Soybean phosphatidylcholine) 目录号 : GC38833

磷脂酰胆碱,大豆是一种来自大豆的磷脂酰胆碱,用于制备脂质体。

Phosphatidylcholines,soya Chemical Structure

Cas No.:97281-47-5

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实验参考方法

Cell experiment [1]:

Cell lines

Human fibroblasts

Preparation Method

Human fibroblasts were incubated for 72 h with low (50 µM) and high (200 µM) concentrations of large, unilamellar (LUV) soya-phosphatidylcholines liposomes in the presence and absence of vitamin E (soya-phosphatidylcholines:vitamin E; 10:0.5).

Reaction Conditions

50 µM and 200 µM, 72h

Applications

No significant changes in cell viability were observed between untreated fibroblasts and those incubated with 50 µM soya-phosphatidylcholines liposomes. In contrast, a marked loss of cells was apparent at a concentration of 200 µM soya-phosphatidylcholines liposomes which was reversible by the addition of vitamin E.

Animal experiment [2]:

Animal models

Male Wistar albino rats (200-250 g)

Preparation Method

Treatment of soya phosphatidylcholines (5 mg/kg/d and 10 mg/kg/d, i.p.) and dexamethasone (2.5 mg/kg/d, i.p.) were started from the 28th day of study till the end of the study in respective groups. At the end of the experiment, lung function parameters, total and differential leukocytes count in blood and BALf; inflammatory cytokines (IL-4, IL-5, and IL-13) and metabolic parameters (glucose, cholesterol, and triglyceride) in serum were measured in all the rats. Histopathological examination of lungs was performed in all rats.

Dosage form

5 mg/kg/d and 10 mg/kg/d, i.p.

Applications

The results displayed lung function parameters, total and differential leukocytes count in blood and BALf; inflammatory cytokines (IL-4, IL-5, and IL-13) and triglyceride shown significantly decreased, but serum glucose and cholesterol level has no change.

References:

[1]. Berrocal MC, et al. Vitamin E improves the uptake of unsaturated soya lecithin liposomes by human fibroblasts in vitro. J Microencapsul. 1998 May-Jun;15(3):347-59.

[2]. Thakur VR, et al. An anti-asthmatic activity of natural Toll-like receptor-4 antagonist in OVA-LPS-induced asthmatic rats. Clin Exp Pharmacol Physiol. 2018 Nov;45(11):1187-1197.

产品描述

Phosphatidylcholines,soya is an essential phospholipid from soybean for cell formation, growth, and death.[1] It is always used in the preparation of liposomes.[2] Soya lecithin origin phosphatidylcholine (Soya PC) was identified as a natural TLR4 antagonist by the computational study.[3]

In vitro, fibroblasts display sensitivity toward the soybean phosphatidylcholine liposomes with an IC50 of 150 μM. Because of the lesser efficency with these liposomes bind to cells, in vitro experiment it shown that phosphatidylcholine liposomes produced no detectable growth inhibitory effects (IC50 > 400 lM) . soya-phosphatidylcholines liposomes present in abundance linoleic acid, which as an essential fatty acid normally obtained from external sources, resulting in the proliferation of the broblasts seen at concentrations below 50 μM and the reduction in cell proliferation occurring at soya-phosphatidylcholines phospholipid concentrations above 50 μM.[2] In vitro, treatment with 10 and 50 μM soya-phosphatidylcholines liposomes, there exsits an increase in the number of fibroblasts per well comparedto the control group, while at phospholipid concentrations exceeding 100μM, a clear inhibitory effect was observed.[4]

In vivo experiment it demonstrated that treatment with 5 mg/kg and 10 mg/kg Soya phosphatidylcholines significantly decreased the respiration rate whereas, tidal volume and airflow rate were found to be significantly increased compared to asthmatic rats. In the meanwhile, the total leukocytes and differential leukocytes count, eosinophils, lymphocytes in the blood of asthmatic rats also showed significantly decreased after treatment with 5 mg/kg and 10 mg/kg Soya PC. In vivo test it indicated that serum triglyceride level was obviously decreased in soya phosphatidylcholines (5 mg/kg and 10 mg/kg) treated asthmatic rats, however, treatment with 5 mg/kg and 10 mg/kg Soya phosphatidylcholines did not show the modulation in serum glucose and cholesterol level in asthmatic rats.

References:
[1]. Chiang YP, et al. Sphingomyelin synthases 1 and 2 exhibit phosphatidylcholine phospholipase C activity. J Biol Chem. 2021 Dec;297(6):101398.
[2]. Berrocal MC, et al. Comparison of the effects of dimyristoyl and soya phosphatidylcholine liposomes on human fibroblasts. Drug Deliv. 2000 Jan-Mar;7(1):37-44.
[3]. Thakur VR, et al. An anti-asthmatic activity of natural Toll-like receptor-4 antagonist in OVA-LPS-induced asthmatic rats. Clin Exp Pharmacol Physiol. 2018 Nov;45(11):1187-1197.
[4]. Berrocal MC, et al. Aging of soya-PC liposomes containing vitamin E reverses the stimulating effects of freshly prepared liposomes on growth of fibroblasts in culture. Drug Deliv. 1998;5(4):243-50.

Phosphatidylcholines,soya 是大豆中细胞形成、生长和死亡所必需的磷脂。[1]常用于脂质体的制备。[2] 大豆卵磷脂来源的磷脂酰胆碱 (Soya PC) 经计算研究确定为天然 TLR4 拮抗剂。[3]

在体外,成纤维细胞对大豆磷脂酰胆碱脂质体表现出敏感性,IC50 为 150 μM。由于这些脂质体与细胞结合的效率较低,体外实验表明磷脂酰胆碱脂质体没有产生可检测的生长抑制作用 (IC50 > 400 μM)。大豆磷脂酰胆碱脂质体富含亚油酸,亚油酸作为一种必需脂肪酸,通常从外部来源获得,导致成纤维细胞在浓度低于 50 μM 时增殖,而大豆磷脂酰胆碱磷脂浓度高于 50 时细胞增殖减少μM.[2] 在体外,用10和50μM大豆磷脂酰胆碱脂质体处理,与对照组相比,每孔成纤维细胞数量增加,而当磷脂浓度超过100μM时,观察到明显的抑制作用。[4]

体内实验表明,与哮喘大鼠相比,用 5 mg/kg 和 10 mg/kg 大豆磷脂酰胆碱处理可显着降低呼吸率,而潮气量和气流率显着增加。同时,用5mg/kg和10mg/kg Soya PC处理后,哮喘大鼠血液中的总白细胞和白细胞分类计数、嗜酸性粒细胞、淋巴细胞也有显着下降。体内试验表明,大豆磷脂酰胆碱(5mg/kg和10mg/kg)治疗哮喘大鼠血清甘油三酯水平明显降低,而5mg/kg和10mg/kg大豆磷脂酰胆碱治疗没有表现出调节作用对哮喘大鼠血糖和胆固醇水平的影响。

Chemical Properties

Cas No. 97281-47-5 SDF
别名 磷脂酰胆碱(大豆),Soybean phosphatidylcholine
Canonical SMILES [Phosphatidylcholines,soya]
分子式 C42H80NO8P 分子量 758.06
溶解度 Ethanol: 50 mg/mL 储存条件 Store at -20°C
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1 mM 1.3192 mL 6.5958 mL 13.1916 mL
5 mM 0.2638 mL 1.3192 mL 2.6383 mL
10 mM 0.1319 mL 0.6596 mL 1.3192 mL
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Research Update

Effect of soya phosphatidylcholine and possible underlying mechanism on ischemia/reperfusion injury in isolated perfused rat heart: an experimental and computational study

Can J Physiol Pharmacol 2022 Mar;100(3):252-258.PMID:34990309DOI:10.1139/cjpp-2021-0056.

This study was designed to assess the effect of soya phosphatidylcholine (SPC) against ischemia/reperfusion (I/R) injury and the possible underlying mechanism using experimental and computational studies. I/R injury was induced by global ischemia for 30 min followed by reperfusion for 120 min. The perfusion of the SPC was performed for 10 min before inducing global ischemia. In the mechanistic study, the involvement of specific cellular pathways was identified using various inhibitors such as ATP-dependent potassium channel (KATP) inhibitor (glibenclamide), protein kinase C (PKC) inhibitor (chelerythrine), non-selective nitric oxide synthase inhibitor (L-NAME), and endothelium remover (Triton X-100). The computational study of various ligands was performed on toll-like receptor 4 (TLR4) protein using AutoDock version 4.0. SPC (100 μM) significantly decreased the levels of cardiac damage markers and %infarction compared with the vehicle control (VC). Furthermore, cardiodynamics (indices of left ventricular contraction (dp/dtmax), indices of left ventricular relaxation (dp/dtmin), coronary flow, and antioxidant enzyme levels were significantly improved as compared with VC. This protective effect was attenuated by glibenclamide, chelerythrine, and Triton X-100, but it was not attenuated by L-NAME. The computational study showed a significant bonding affinity of SPC to the TLR4-MD2 complex. Thus, SPC reduced myocardial I/R injury in isolated perfused rat hearts, which might be governed by the KATP channel, PKC, endothelium response, and TLR4-MyD88 signaling pathway.

Vitamin E improves the uptake of unsaturated soya lecithin liposomes by human fibroblasts in vitro

J Microencapsul 1998 May-Jun;15(3):347-59.PMID:9608397DOI:10.3109/02652049809006862.

Liposomes may exert certain toxic effects on human cells depending on their composition and concentration when used as drug carriers. In this study, the behaviour of human fibroblasts in the presence of soya phosphatidylcholine (soya-PC) liposomes and the effect of the incorporation of vitamin E into the membrane of such liposomes, was investigated. Human fibroblasts were incubated for 72 h with low (50 microM) and high (200 microM) concentrations of large, unilamellar (LUV) soya-PC liposomes in the presence and absence of vitamin E (soya-PC:vitamin E; 10:0.5). The resulting cultures were studied by scanning and transmission electron microscopy, fluorescence microscopy and labelling with rhodamine B. The large unilamellar soya-PC liposomes obtained were of mean diameter 86.4 nm (soya-PC) and 78.3 nm (soya-PC: vitamin E). No significant changes in cell viability were observed between untreated fibroblasts and those incubated with 50 microM soya-PC liposomes. In contrast, a marked loss of cells was apparent at a concentration of 200 microM soya-PC liposomes which was reversible by the addition of vitamin E. Morphological changes including the production of microvilli or 'bubbling' of the cell membrane, were incurred by some of the fibroblasts on addition of soya-PC liposomes. The addition of vitamin E did not affect the changes produced at the lower liposome concentrations but was able to reduce the cytotoxic effects occurring at higher concentrations, possibly by inhibiting the formation of liposome aggregates. The use of PC-soya liposomes containing vitamin E at high concentrations is proposed as a means of delivering high doses of drugs.

Enhancement of absorption and hepatoprotective potential through soya-phosphatidylcholine-andrographolide vesicular system

J Liposome Res 2013 Jun;23(2):110-8.PMID:23506220DOI:10.3109/08982104.2012.753456.

Andrographis paniculata is a medicinal herb used extensively for various ailments and contains therapeutically active phytoconstituent, andrographolide (AN). Although hepatoprotective activity of AN is established, but their bioavailability is restricted due to its rapid clearance. The aim of this study, therefore, was to formulate AN herbosomes (ANH) through complexation with naturally occurring soya-phosphatidylcholine (SPC), in order to enhance absorption. Prepared andrographolide-soy phosphatidylcholine (AN-SPC) complex prepared was subjected for characterisation of complex and formation of vesicular system known as ANH using rotary evaporation techniques. This complex was subjected to in vitro study using everted small intestine sac technique which showed significantly increased absorption of AN from the ANH as compared to the plain AN. The hepatoprotective potential of ANH and plain AN was evaluated using carbon tetrachloride inducing hepatotoxicity rat model and compared, in which ANH equivalent to 50 mg/kg of plain AN significantly restore serum glutamate oxalacetate transaminase (112.4 ± 9.67 for AN whereas 90.2 ± 4.23 for ANH) and serum glutamate pyruvate transaminase (109.3 ± 7.89 for AN whereas 90.6 ± 4.34 for ANH) level as compared to control group. The ANH showed significantly better absorption than plain AN and this effect of ANH was also comparable to the standard drug (Silymarin). The findings of present study reveal that ANH has better bioavailability as shown by in vitro absorption study and hence improved hepatoprotection as compared to plain AN at equivalent dose.

Doxorubicin biocompatible O/W microemulsion stabilized by mixed surfactant containing soya phosphatidylcholine

Colloids Surf B Biointerfaces 2006 Aug 1;51(1):54-61.PMID:16814997DOI:10.1016/j.colsurfb.2006.05.005.

Microemulsions (ME) containing soya phosphatidylcholine (SPC)/polyoxyethylenglycerol trihydroxystearate 40 (EU)/sodium oleate (SO) as surfactant cholesterol (CHO) as oil phase and aqueous buffer were studied. Pseudo-ternary phase diagrams of the investigated systems were obtained at constant SPC/EU/SO weight ratio 3.5:3.5:3.0 by titration, in order to characterize the proportions between the components to form clear systems. The dynamic light scattering results showed that the size of the oil droplets decreases significantly with the ratio of surfactant/oil phase added to system. Depending on the composition ME system could exhibit a thixotropic behavior. The apparent viscosity increased 25- and 13-folds with cholesterol concentration for drug-free and drug-load ME, respectively. It was also verified that the octanol/aqueous buffer partition coefficient (KO/B) of doxorubicin (DOX) was pH dependent increasing abruptly above pH 6.0. It was possible to incorporate 2.24 mg/ml of DOX into ME. The incorporation of DOX in the ME systems increased the droplets size for all surfactant concentrations used in the system. The results suggest that DOX interacts with the microstructure of the ME at the studied pH increasing significantly the drug solubility. It was possible to conclude that the investigated ME can be a very promising vehicle as drug-carrier for administration of doxorubicin.