4167-02-6

Usage

Chemical Properties

Clear Colourless Liquid

Uses

A phosphorylating agent.

InChI:InChI=1/C2H4BrCl2O2P/c3-1-2-7-8(4,5)6/h1-2H2

Upstream product

• 540-51-2 2-bromoethanol 

Downstream Products

• 113977-57-4 phosphoric acid-(2-bromo-ethyl ester)-phenethyl ester 
• 79907-73-6 L-2.3-Dipalmitoyl-glycerin-phosphorsaeure-1-mono-(β-brom-aethylester) 
• 18498-22-1 DL-1.2-Distearoyl-glycerin-phosphorsaeure-⁽³⁾-mono-2-brom-aethylester 
• 816-94-4 {2-[(2,3-bis-stearoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium betaine 
• 19229-69-7 Dioleo-β-lecithin 
• 13699-47-3 didecanoylphosphatidylcholine 
• 18656-40-1 1,2-dilauroylphosphatidylcholine 
• 18194-24-6 dimyristoylphosphatidylcholine 
• 5655-10-7 1,3-distearoylglycero-2-phosphocholine 
• 69483-37-0 1,2-di-O-hexadecyl-3-O-<<2-(trimethylamino)ethyl>phosphoryl>-rac-glycerol 
• 24675-16-9 Diundecano-DL-α-lecithin 
• 18678-97-2 rac.-1-Palmitoyl-glycerin-benzylether-⁽²⁾-phosphorsaeure-⁽³⁾-monocholinester 
• 18678-98-3 Rac_. 1-O-Hexadecyl-2-O-benzylglycero-3-phosphocholin 
• 90581-95-6 1-palmitoyl-2-hexadecyl-phosphatidylcholine 

Relevant academic research and scientific papers

Novel cationic polyene glycol phospholipids as DNA transfer reagents - Lack of a structure-activity relationship due to uncontrolled self-assembling processes

Cationic glycol phospholipids were synthesized introducing chromophoric, rigid polyenoic C20:5 and C30:9 chains next to saturated flexible alkyl chains of variable lengths C6-20:0. Surface properties and liposome formation

Novel alkylphospholipid-DTC hybrids as promising agents against endocrine related cancers acting via modulation of Akt-pathway

A new series of 2-(alkoxy(hydroxy)phosphoryloxy)ethyl dialkylcarbodithioate derivatives was synthesized and evaluated against endocrine related cancers, acting via modulation of Akt-pathway. Eighteen compounds were active at 7.24-100 μM against MDA-MB-231 or MCF-7 cell lines of breast cancer. Three compounds (14, 18 and 22) were active against MCF-7 cells at IC50 significantly better than miltefosine and most of the compounds were less toxic towards non-cancer cell lines, HEK-293. On the other hand, twelve compounds exhibited cell growth inhibiting activity against prostate cancer cell lines, either PC-3 or DU-145 at 14.69-95.20 μM. While nine of these were active against both cell lines. The most promising compounds 14 and 18 were about two and five fold more active than miltefosine against DU-145 and MCF-7 cell lines respectively and significantly down regulated phospho-Akt. Possibly anti-cancer and pro-apoptotic activity was mostly due to blockade of Akt-pathway.

Synthesis and properties of a plasmalogen quinone

A novel phospholipid quinone bearing hexadecyl ether chains has been synthesized and employed in the preparation of redox-active, quinone-functionalized liposomes.

Synthesis of metal-chelating polymerizable phospholipids

Two routes for the synthesis of metal chelating phospholipids are reported. An iminodiacetic acid functionality served as metal chelating site in the polar headgroup region of a phospholipid while a tricosa-10,12-diynoyl group linked to the glycerol backbone, made up the polymerizable hydrocarbon region.

The 2-acetylthioethyl ester group: A versatile protective group for P-OH-groups

Phosphodiesters are bridging elements in nucleic acids. In nature and synthesis, their negative charge protects them from hydrolysis and controls their solubility profile. RNA is a promising material for gene technology but cellular uptake is low due to negative charges. Synthetic oligonucleotides were delivered into cells by a prodrug approach relying on the enzymatic release of the polyphosphodiester oligonucleotides. In synthetic chemistry, a protective group for the P–OH functionality is often necessary, e.g. due to solubility or chemical incompatibility. Several methods for P–OH protection were proposed, but often with low selectivity or harsh conditions. Here, we present the 2-acetylthioethyl group as a versatile protective group for low molecular weight or polymeric phosphodiesters, which can be cleaved under acidic conditions in water or by hydrazine in THF to release the P–OH-functionality, but olefins remain intact. This straightforward use allows designing various synthetic polyphosphodiesters, e.g. for flame-retardant or dispersants.

NOVEL CATIONIC CAROTENOID-BASED LIPIDS FOR CELLULAR NUCLEIC ACID UPTAKE

The synthesis and self-assembling properties of a model compound in a new class of cationic phospholipids with a highly unsaturated conjugated carotenoid fatty acid are described. In addition, the potential of this new lipid as a nucleic acid carrier was evaluated through lipoplex formulations employing 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) as helper lipid with and without the polycationic peptide, protamine, together with a plasmid DNA (pDNA). Lipoplexes composed of this novel unsaturated lipid exhibited pDNA binding and protection from DNase I degradation when formulated with protamine. Cellular uptake of the liposomes could be monitored by the visible color of the carotenoid moieties. The new cationic lipid gene delivery vector revealed comparable transfection efficiency to the commercial lipid, 1,2-dimyristoyl-sn-glycero-3-ethylphophocholine (EPC), in Chinese hamster ovary-K1 (CHO-K1) cells and performed equally to Lipofectamine 2000 when the formulation included protamine.

Compounds for determining the activity of phospholipase A2

Compounds for determining the activity of phospholipase A2, are described herein, and include embodiments having formula (1) wherein L1 is derived from an ether (R1—OR2)m, wherein R1 and R2 are independently selected and are derived from a hydrocarbon having 1 to 12 carbon atoms, with m being an integer from 1 to 4, or from a hydrocarbon R having 1 to 20 carbon atoms; F is unsubstituted or substituted pyrene as a flouraphore; Q is a quencher, and L2 is C(O)-L1 or C(O)-L1-NH, wherein L1 is as defined above. These compounds may be used to determine the activity of phospholipase A2, in particular PAF-AH.

Synthesis of archaeal bipolar lipid analogues: A way to versatile drug/gene delivery systems

(Chemical Equation Presented) A synthetic route for the preparation of symmetrical and unsymmetrical archaeal tetraether-like analogues has been described. The syntheses are based upon the elaboration of hemimacrocyclic tetraether lipid cores from versati

Methods employing and compositions containing defined oxidized phospholipids for prevention and treatment of atherosclerosis

Novel synthetic forms of etherified oxidized phospholipids and methods of utilizing same for preventing and treating atherosclerosis and other related disorders, as well as inflammatory disorders, immune mediated diseases, autoimmune diseases and proliferative disorders, are provided. In addition, methods of synthesizing etherified and esterified oxidized phospholipids and of using same for preventing and treating atherosclerosis and other related disorders are also provided.

Lipid analogs for treating viral infections

A method of treating viral infections, and in particular HIV-1, hepatitis B virus and herpes viruses, is disclosed. The method comprising administering to a subject in need of such treatment an infection-combating amount of a phospholipid or phospholipid derivative.