82002-20-8Relevant academic research and scientific papers
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
supporting information, 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.
Sterol-modified phospholipids: Cholesterol and phospholipid chimeras with improved biomembrane properties
Huang, Zhaohua,Szoka Jr., Francis C.
experimental part, p. 15702 - 15712 (2009/03/12)
We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37°C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.
IMPROVED PROCESS FOR THE PREPARATION OF OXIDIZED PHOSPHOLIPIDS
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Page/Page column 42, (2008/06/13)
Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.
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
Structure-Activity Relationship in PAF-acether. 3. Hydrophobic Contribution to Agonistic Activity
Godfroid, Jean-Jacques,Broquet, Colette,Jouquey, Simone,Lebbar, Mariya,Heymans, Francoise,et al.
, p. 792 - 797 (2007/10/02)
The synthesis of some selected PAF-acether homologues with an alkoxy-chain length from C1 to C20 in position 1 is described.All agonist activities are closely correlated among themselves and with the calculated fatty-chain hydrophobicity.After a discussio
NEW METHOD FOR THE SYNTHESIS OF GLYCOSYL GLYCERIDES. - THE STEREOSELECTIVE REDUCTION OF GLYCOSIDES OF 1-ALKYLOXY-3-HYDROXYACETONE -
Mukaiyama, Teruaki,Tanaka, Shin,Asami, Masatoshi
, p. 433 - 436 (2007/10/02)
Glycosides of 1-hexadecyloxy-3-hydroxyacetone are prepared from 1-halidosugars and 1-O-hexadecyl-2-O-benzylglycerol.The glycosides are converted to the corresponding alcohols, precursors to the synthesis of glycosyl glycerides, by the stereoselective redu
