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1,2-Dimyristoyl-sn-glycero-3-phosphate (sodium salt)

(Synonyms: 1,2-二豆蔻酰-SN-甘油-3-磷酸单钠盐,DMPA) 目录号 : GC41806

A phospholipid

1,2-Dimyristoyl-sn-glycero-3-phosphate (sodium salt) Chemical Structure

Cas No.:80724-31-8

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100mg
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产品描述

Phosphatidic acids (PAs) can be formed by the acylation of lysophosphatidic acids, the phosphorylation of diacylglycerols, or the removal of the choline group from phosphatidylcholine.[1] They have important roles in intracellular and extracellular signaling. [2][3] 1,2-Dimyristoyl-sn-glycero-3-phosphate is a phospholipid containing the long-chain (14:0) myristic acid inserted at the sn-1 and sn-2 positions. It may be useful in evaluating the role of PAs in micelles, liposomes, and artificial membranes.

Reference:
[1]. Athenstaedt, K., and Daum, G. Phosphatidic acid, a key intermediate in lipid metabolism. European Journal of Biochemistry 266, 1-16 (1999).
[2]. English, D. Phosphatidic acid: A lipid messenger involved in intracellular and extracellular signalling. Cellular Signalling 8, 341-347 (1996).
[3]. Gomez-Cambronero, J. New concepts in phospholipase D signaling in inflammation and cancer. ScientificWorldJournal 10, 1356-1369 (2010).

Chemical Properties

Cas No. 80724-31-8 SDF
别名 1,2-二豆蔻酰-SN-甘油-3-磷酸单钠盐,DMPA
化学名 1,2-dimyristoyl-sn-glycero-3-phosphate, monosodium salt
Canonical SMILES O=C(CCCCCCCCCCCCC)OC[C@@H](OC(CCCCCCCCCCCCC)=O)COP([O-])(O)=O.[Na+]
分子式 C31H60O8P•Na 分子量 614.8
溶解度 1.6mg/mL in chloroform 储存条件 Store at -20°C
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1 mM 1.6265 mL 8.1327 mL 16.2655 mL
5 mM 0.3253 mL 1.6265 mL 3.2531 mL
10 mM 0.1627 mL 0.8133 mL 1.6265 mL
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Research Update

Enhanced bactericidal potency of nanoliposomes by modification of the fusion activity between liposomes and bacterium

Int J Nanomedicine 2013;8:2351-60.PMID:23847417DOI:10.2147/IJN.S42617.

Background: Pseudomonas aeruginosa represents a good model of antibiotic resistance. These organisms have an outer membrane with a low level of permeability to drugs that is often combined with multidrug efflux pumps, enzymatic inactivation of the drug, or alteration of its molecular target. The acute and growing problem of antibiotic resistance of Pseudomonas to conventional antibiotics made it imperative to develop new liposome formulations to overcome these mechanisms, and investigate the fusion between liposome and bacterium. Methods: The rigidity, stability and charge properties of phospholipid vesicles were modified by varying the cholesterol, 1,2-dioleoyl-sn-glycero-3-phosphatidylethanolamine (DOPE), and negatively charged lipids 1,2-dimyristoyl-sn-glycero-3-phosphoglycerol sodium salt (DMPG), 1,2-dimyristoyl-sn-glycero-3-phopho-L-serine sodium salt (DMPS), 1,2-Dimyristoyl-sn-glycero-3-phosphate monosodium salt (DMPA), nature phosphatidylserine sodium salt from brain and nature phosphatidylinositol sodium salt from soybean concentrations in liposomes. Liposomal fusion with intact bacteria was monitored using a lipid-mixing assay. Results: It was discovered that the fluid liposomes-bacterium fusion is not dependent on liposomal size and lamellarity. A similar degree of fusion was observed for liposomes with a particle size from 100 to 800 nm. The fluidity of liposomes is an essential pre-request for liposomes fusion with bacteria. Fusion was almost completely inhibited by incorporation of cholesterol into fluid liposomes. The increase in the amount of negative charges in fluid liposomes reduces fluid liposomes-bacteria fusion when tested without calcium cations due to electric repulsion, but addition of calcium cations brings the fusion level of fluid liposomes to similar or higher levels. Among the negative phospholipids examined, DMPA gave the highest degree of fusion, DMPS and DMPG had intermediate fusion levels, and PI resulted in the lowest degree of fusion. Furthermore, the fluid liposomal encapsulated tobramycin was prepared, and the bactericidal effect occurred more quickly when bacteria were cultured with liposomal encapsulated tobramycin. Conclusion: The bactericidal potency of fluid liposomes is dramatically enhanced with respect to fusion ability when the fusogenic lipid, DOPE, is included. Regardless of changes in liposome composition, fluid liposomes-bacterium fusion is universally enhanced by calcium ions. The information obtained in this study will increase our understanding of fluid liposomal action mechanisms, and help in optimizing the new generation of fluid liposomal formulations for the treatment of pulmonary bacterial infections.

Effect of the phospholipid chain length and head group on beta-phase formation of poly(9,9-dioctylfluorene) enclosed in liposomes

Photochem Photobiol 2013 Nov-Dec;89(6):1471-8.PMID:23865822DOI:10.1111/php.12143.

We have studied the effect of head group and alkyl chain length on β-phase formation in poly(9,9-dioctylfluorene) (PFO) solubilized in phospholipid liposomes. Systems studied have three different alkyl chain lengths (1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine [DMPC], 1,2-didodecanoyl-sn-glycero-3-phosphatidylcholine [DLPC], 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine [DPPC]) and head groups (1,2-Dimyristoyl-sn-glycero-3-phosphate monosodium salt [DMPA], 1,2-dimyristoyl-sn-glycero-3-phosphoethanolamine [DMPE] and 1,2-dimyristoyl-sn-glycero-3-phospho-l-serine sodium salt [DMPS]). Changes in liposome size upon addition of PFO are followed by dynamic light scattering. All the phospholipids induce the formation of PFO β-phase, which is followed by the emission intensity and deconvolution of the absorption spectra. Both the head group and alkyl chain length affect the yield of β-phase. The photophysics of PFO incorporated in liposomes is characterized by stationary and time-resolved fluorescence, whereas the polymer-phospholipid interactions have been studied by the effect of the PFO concentration on the phospholipid phase transitions (differential scanning calorimetry [DSC]).

Folding of cytosine-based nucleolipid monolayer by guanine recognition at the air-water interface

J Colloid Interface Sci 2019 Mar 1;537:694-703.PMID:30481730DOI:10.1016/j.jcis.2018.11.036.

Monolayers of a cytosine-based nucleolipid (1,2-dipalmitoyl-sn-glycero-3-(cytidine diphosphate) (ammonium salt), CDP-DG) at basic subphase have been prepared at the air-water interface both in absence and presence of guanine. The formation of the complementary base pairing is demonstrated by combining surface experimental techniques, i.e., surface pressure (π)-area (A), Brewster angle microscopy (BAM), infrared spectroscopy (PM-IRRAS) and computer simulations. A folding of the cytosine-based nucleolipid molecules forming monolayer at the air-water interface occurs during the guanine recognition as absorbate host and is kept during several compression-expansion processes under set experimental conditions. The specificity between nitrogenous bases has been also registered. Finally, mixed monolayers of CDP-DG and a phospholipid (1,2-Dimyristoyl-sn-glycero-3-phosphate (sodium salt), DMPA) has been studied and a molecular segregation of the DMPA molecules has been inferred by the additivity rule.