17364-21-5Relevant academic research and scientific papers
Isolation and characterization of seven lyso platelet-activating factors and two lyso phosphatidylcholines from the crude drug 'Suitetsu' (the leech, Hirudo nipponica)
Noda,Tanaka,Nishi,Inoue,Miyahara
, p. 1366 - 1368 (1993)
Nine lyso glycerophospholipids were isolated in the pure state from the crude drug 'Suitetsu', which is the dried body of the leech, Hirudo nipponica (Hirudidae). They were identified as 1-O-hexadecyl-(1), 1-O-octadecyl-(2), 1- O-tetradecyl-(3), 1-O-9-cis-hexadecenyl-(4), 1-O-hexadecanoyl-(5), 1-O- pentadecyl-(6), 1-O-15-methylhexadecyl-(7), 1-O-octadecanoyl-(8) and 1-O- heptadecyl-sn-glycero-3-phosphocholine (9). Two of them (5 and 8) are lysophosphatidylcholines and the other seven are lyso platelet-activating factors. One of them has an alkenyl carbon chain.
An effective reagent to functionalize alcohols with phosphocholine
Xu, Lianyan L.,Berg, Lawrence J.,Jamin Keith,Townsend, Steven D.
supporting information, p. 767 - 770 (2020/02/11)
Phosphocholine is a small haptenic molecule that is both a precursor and degradation product of choline. Phosphocholine decorates a number of biologics such as lipids and oligosaccharides. In this study, an air and bench stable phosphocholine donor has been developed and evaluated with a number of alcohol acceptors. Using a one-pot, three-step sequence, (phosphitylation, oxidation, and phosphate deprotection) phosphocholine derivatives are synthesized in high yields. Of particular interest is the synthesis of miltefosine, the lone oral drug approved to treat leishmaniasis. Due to its prohibitive expense ($1500 per g), miltefosine is not accesable for the majority of the world's patients. Based on the described reaction sequence, this drug can be produced for $25 per g.
Design, synthesis and cytotoxicity of chimeric erlotinib-alkylphospholipid hybrids
Alam, Md. Maqusood,Hassan, Ahmed H.E.,Lee, Kun Won,Cho, Min Chang,Yang, Ji Seul,Song, Jiho,Min, Kyung Hoon,Hong, Jongki,Kim, Dong-Hyun,Lee, Yong Sup
, p. 51 - 62 (2018/11/27)
Two series of erlotinib-alkylphospholipid hybrids were prepared and evaluated for their antiproliferative activities against a panel of four cell lines representing lung, breast, liver and skin cancers using erlotinib and miltefosine as reference standards. Amide analogs elicited more enhanced cytotoxic activity than analogous esters. Amide derivatives 8d and 8e exhibited promising broad-spectrum antiproliferative activity and higher efficacy than reference erlotinib and miltefosine. Their cellular GI50 values was in the ranges of 24.7–46.9 μM and 26.8–43.1 μM for 8e and 8d respectively. Assay results of the inhibitory activity of the prepared compounds on EGFR kinase reaction and Akt phosphorylation in conjugation with statistical correlation analysis indicated that other mechanisms might contribute to their elicited cytotoxicities. In addition, statistical correlation analysis revealed that mechanisms of elicited cytotoxicities for amide series might be different from ester series. In addition, correlation analysis indicated variations in the mechanisms according to the types of cell line.
Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs
Pedersen, Palle J.,Christensen, Mikkel S.,Ruysschaert, Tristan,Linderoth, Lars,Andresen, Thomas L.,Melander, Fredrik,Mouritsen, Ole G.,Madsen, Robert,Clausen, Mads H.
supporting information; experimental part, p. 3408 - 3415 (2010/03/31)
The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol he
Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue
Andresen, Thomas L.,Jensen, Simon S.,Madsen, Robert,J?rgensen, Kent
, p. 7305 - 7314 (2007/10/03)
The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinicall
Synthesis and chemical transformations of 4-hexadecyloxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane
Malekin,Khromova,Kisin,Kruglyak,Kurochkin
, p. 677 - 682 (2007/10/03)
Cyclophosphorylation of 1-hexadecylglycerol with phosphorus oxychloride afforded 4-hexadecyl-oxymethyl-2-oxo-2-chloro-1,3,2-dioxaphospholane (I) with high yield. By means of 1H, 13C, and 31P NMR, it was shown to be a 1 : 9 mixture of two stable epimers with equatorial and axial configuration of the chlorine atom, respectively. Phospholane (I) entered into nucleophilic reactions with KHCO3 and HN(Pri)2 to give 80-85% yields of the chlorine substitution products with the phospholane cycle remaining intact. Interaction of the phospholane (I) with water or choline tosylate also initially produced substituted phospholanes, as shown by NMR. Subsequent hydrolysis led to the cleavage of the phospholane ring and to formation of isomeric 1-hexadecylglycero-2- and 3-phosphates and 1-hexadecylglycero-2- and 3-phosphocholines, respectively. A method for the separation of isomeric phosphates was developed, which made it possible to isolate 1-hexadecylglycero-2-phosphate and 1-hexadecylglycero-3-phosphate.
New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis
Massing, Ulrich,Eibl, Hansjoerg
, p. 211 - 224 (2007/10/02)
A convenient synthesis of new and enantiometrically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described.Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol.These intermediates are converted to 2-O-benzyl- or 2-O-alkyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol.The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition.Also, triglycerides with three different alkyl chains, ester of ether, can be prepared.As an example of the varsatility of the new intermediates, we describe the synthesis of 1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosphocho;ine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol. Keywords: Synthetic phospholipids; PAF; Phospholipid analogues; Synthesis; Chiral pool; Glyceraldehyde; C-3 building blocks; Optical purity
Influence of α-branched fatty acid chains on the thermotropic behaviour of racemic 1-O-hexadecyl-2-acyl-glycero-3-phosphocholines
Rattay, Bernd,Brezesinski, Gerald,Dobner, Bodo,Foerster, Guenter,Nuhn, Peter
, p. 81 - 92 (2007/10/02)
Phosphatidylcholines containing an α-branched palmitic acid ester linked to position C2 of the glycerol backbone were synthesized and characterized using differential scanning calorimetry and X-ray diffraction. As the length of the sidegroup substituted on the palmitic acid chain is changed, the calorimetric parameters pass through a minimum. The polymorphic behaviour is different when the sidegroup is larger, or smaller, than propyl. The comparison of the physicochemical parameters of isomers differing in the bonding of the branched chain fatty acid to the glycerol backbone (to position C1 or C2, respectively) shows that the chains are nonequivalent. Keywords: Phosphatidylcholine; Branched chain fatty acids; Microcalorimetry; X-ray diffraction; Polymorphism
