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1,2-Dipalmitoyl-sn-glycero-3-PE-N-(cap biotin) (sodium salt)

(Synonyms: biotin-cap-DPPE) 目录号 : GC41823

A biotinylated phospholipid

1,2-Dipalmitoyl-sn-glycero-3-PE-N-(cap biotin) (sodium salt) Chemical Structure

Cas No.:384835-52-3

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5mg
¥599.00
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10mg
¥1,079.00
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25mg
¥2,399.00
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产品描述

1,2-Dipalmitoyl-sn-glycero-3-PE-N-(cap biotin) is a biotinylated phospholipid. It has been used in PEGylated polyamidoamine-dendrimer-conjugated supported lipid bilayers (SLB) to isolate circulating tumor cells and tumor cell microembolis from patient-derived blood by antibody-coated microfluidics. [1]  It has also been used as a component of SLBs to detect protein-ligand binding with ortho-conjugated Texas Red DHPE. [2] In addition, 1,2-dipalmitoyl-sn-glycero-3-PE-N-(cap biotin) has been used in SLBs partitioned into nanowells to create DNA curtains, which can be used as a high-throughput tool for detection of protein-DNA interactions at the single molecule level.[3]

Reference:
[1]. Yeh, P.-Y., Chen, Y.-R., Wang, C.-F., et al. Promoting multivalent antibody-antigen interactions by tethering antibody molecules on a PEGylated dendrimer-supported lipid bilayer. Biomolecules 19(2), 426-437 (2018).
[2]. Jung, H., Robison, A.D., and Cremer, P.S. Detecting protein-ligand binding on supported bilayers by local pH modulation. J. Am. Chem. Soc. 131(3), 1006-1014 (2009).
[3]. Visnapuu, M.-L., Fazio, T., Wind, S., et al. Parallel arrays of geometric nanowells for assembling curtains of DNA with controlled lateral dispersion. Langmuir 24(19), 11293-11299 (2008).

Chemical Properties

Cas No. 384835-52-3 SDF
别名 biotin-cap-DPPE
化学名 hexadecanoic acid, 1,1'-[(1R)-1-[19-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-3-hydroxy-3-oxido-8,15-dioxo-2,4-dioxa-7,14-diaza-3-phosphanonadec-1-yl]-1,2-ethanediyl] ester, monosodium salt
Canonical SMILES O=C(CCCCCCCCCCCCCCC)OC[C@@H](OC(CCCCCCCCCCCCCCC)=O)COP(OCCNC(CCCCCNC(CCCC[C@H]1[C@](NC(N2)=O)([H])[C@]2([H])CS1)=O)=O)([O-])=O.[Na+]
分子式 C53H98N4O11PS•Na 分子量 1053.4
溶解度 Slightly soluble in DMSO 储存条件 Store at -20°C
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1 mM 0.9493 mL 4.7465 mL 9.4931 mL
5 mM 0.1899 mL 0.9493 mL 1.8986 mL
10 mM 0.0949 mL 0.4747 mL 0.9493 mL
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Research Update

Fluorescence modulation sensing of positively and negatively charged proteins on lipid bilayers

Biointerphases 2013 Dec;8(1):1.PMID:24706114DOI:10.1186/1559-4106-8-1.

Background: Detecting ligand-receptor binding on cell membrane surfaces is required to understand their function and behavior. Detection platforms can also provide an avenue for the development of medical devices and sensor biotechnology. The use of fluorescence techniques for such purposes is highly desirable as they provide high sensitivity. Herein, we describe a technique that utilizes the sensitivity of fluorescence without directly tagging the analyte of interest to monitor ligand-receptor interactions on supported lipid bilayers. The fluorescence signal is modulated according to the charge state of the target analyte. The binding event elicits protonation or deprotonation of pH-responsive reporter dyes embedded in the lipid bilayer. Methods: Supported lipid membranes containing ortho-conjugated rhodamine B-POPE (1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine), which fluoresces in its protonated but not in its deprotonated form, were utilized as sensor platforms for biotin-avidin and biotin-streptavidin binding events. The membranes contained 5 mol% biotin-PE (1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine-N-(cap biotinyl) (sodium salt) as a capture ligand. Supported lipid bilayers were formed in the channels of microfluidic devices and the fluorescence intensity of the dye was monitored as protein was introduced. Results: The binding of avidin, which is positively charged at pH 7.2, made the bilayer surface charge more positive, which in turn deprotonated the ortho-rhodamine B dye, reducing its fluorescence. The binding of streptavidin, which is negatively charged at pH 7.2, had the opposite effect. Reducing the ionic strength of the analyte solution by removing 150 mM NaCl from the 10 mM phosphate buffered saline (PBS) solution raised the apparent pKa of the ortho-rhodamine B titration point by about 1 pH unit. This could be exploited in conjunction with bulk solution pH changes to turn the rhodamine B-POPE dye into a sensor for streptavidin involving a decrease, rather than an increase, in the fluorescence response, at pH values below streptavidin's pI value. Conclusions: This study demonstrates the ability to monitor ligand-receptor interactions on supported lipid bilayers through the protonation or deprotonation of reporter dyes for both negatively and positively charged analytes over a range of pH and ionic strength conditions. Specifically, the sensitivity and pH-operating range of this technique can be optimized by modulating the sensing conditions which are employed.

Surface labeling of enveloped viruses assisted by host cells

ACS Chem Biol 2012 Apr 20;7(4):683-8.PMID:22248430DOI:10.1021/cb2001878.

Labeling of virus opens new pathways for the understanding of viruses themselves and facilitates the utilization of viruses in modern biology, medicine, and materials. Based on the characteristic that viruses hijack their host cellular machineries to survive and reproduce themselves, a host-cell-assisted strategy is proposed to label enveloped viruses. By simply feeding Vero cells with commercial 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine-N-(cap biotinyl) (sodium salt) (Biotin-Cap-PE), we obtained biotinylated Vero cells whose membrane systems were modified with biotin. Subsequently, pseudorabies viruses (PrV) were cultivated in the biotinylated Vero cells, and the PrV progenies were spontaneously labeled with Biotin-Cap-PE during viral natural assembly process. Since the viral natural assembly process was employed for the labeling, potential threats of genetic engineering and difficulties in keeping viral natural bioactivity were avoided. Importantly, this labeling strategy for enveloped virus greatly reduces the technical complexity and allows researchers from different backgrounds to apply it for their specified demands.