143-28-2Relevant articles and documents
Purification and characterization of a novel extracellular lipase catalyzing hydrolysis of oleyl benzoate from Acinetobacter nov. sp. strain KM109.
Mitsuhashi,Yamashita,Hwan,Ihara,Nihira,Yamada
, p. 1959 - 1964 (1999)
A new lipase (OBase) which efficiently hydrolyzes oleyl benzoate (OB) was found in the culture supernatant of Acinetobacter nov. sp. strain KM109, a new isolate growing in a minimum medium containing OB as the sole carbon source. OBase was purified to homogeneity with 213-fold purification and 0.8% yield. The molecular weight was estimated to be 62,000 +/- 1,000 by SDS-PAGE under denatured-reduced conditions and to be 50,000 +/- 1,000 by gel-filtration HPLC under native conditions; these findings indicate that OBase is a monomeric enzyme. The optimum temperature and pH of OBase were about 45 degrees C and pH 8. Temperature and pH stabilities were at or lower than 35 degrees C and in a range of pH 6-8, respectively. Purified OBase preferentially hydrolyzed p-nitrophenyl benzoate (pNPB) over p-nitrophenyl acetate (pNPA) or p-nitrophenyl caproate (pNPC) [pNPB/pNPA = 20 and pNPB/pNPC = 5.4], indicating that OBase has a high affinity for benzoyl esters. Partial amino-acid sequences of OBase fragments obtained after lysyl endopeptidase treatment showed no similarity with known proteins.
Tuning the Thermo-Sensitivity of Micellar Systems through a Blending Approach
El Asmar, Arlette,Gimello, Olinda,Morandi, Ga?lle,Le Cerf, Didier,Lapinte, Vincent,Burel, Fabrice
, p. 4307 - 4315 (2016)
This paper reports an original and easy route toward thermosensitive micelles based on a lipidic core and with adjustable cloud point temperatures (TCP) through a simple blending approach between two copolymers of different TCP. The cationic ring-opening polymerization (CROP) of various 2-alkyl-2-oxazoline monomers was first investigated from both mesylated and tosylated lipoinitiators and different lipid-b-poly(2-methyl-2-oxazoline), lipid-b-poly(2-ethyl-2-oxazoline), lipid-b-poly(2-isopropyl-2-oxazoline) and lipid-b-poly((2-ethyl-2-oxazoline)-co-(2-isopropyl-2-oxazoline)) copolymers were synthesized. Blending of lipid-b-p(EtOx) and lipid-b-p(iPrOx) copolymers in various proportions were then prepared and their TCP investigated through UV-visible spectroscopy. Very interesting results were obtained as the blends exhibit a single TCP ranging from 35 to 45 °C. Furthermore, the blends TCP correspond to those of the statistical lipid-b-p((EtOx)-co-(iPrOx)) for the same p(EtOx)/p(iPrOx) content up to 52 wt % of p(EtOx). The blending approach is then an attractive strategy to control the TCP of micellar systems through a simple and easy formulation approach rather than fastidious syntheses.
Synthesis of pH-sensitive micelles from linseed oil using atom transfer radical polymerisation (ATRP)
Hespel, Louise,Kaifas, Elise,Lecamp, Laurence,Picton, Luc,Morandi, Ga?lle,Burel, Fabrice
, p. 4344 - 4352 (2012)
This paper reports the synthesis of an amphiphilic copolymer from linseed oils and its successive auto-association in water into pH-sensitive micelles. An original ATRP lipoinitiator is first designed from linseed oil in two steps. tert-butyl acrylate (tBA) polymerization is consequently initiated from this original initiator and amphiphilic copolymers are obtained after subsequent acidolysis of the PtBA block into poly(acrylic acid) (PAA). The ability of a lipid-b-PAA copolymer to auto-associate in water is finally investigated through different techniques (Fluorescence, Surface Tension, QELS). This copolymer forms well-defined micelles in acidic media with a low critical micellar concentration (cmc) of 7.6 mg L-1 and dissociates when the pH is raised above 7.
SYNTHESIS OF MUSCALURE - THE PHEROMONE OF Musca domestica
Verba, G. G.,Abdukakharov, V. S.,Abduvakhabov, A. A.
, p. 655 - 657 (1985)
A method for obtaining cis-tricos-9-ene (muscalure) - the pheromone of the housefly - from the readily available ethyl oleate has been developed.
Balancing the efficacy vs. the toxicity of promiscuous natural products: Paclitaxel-based acid-labile lipophilic prodrugs as promising chemotherapeutics
Chittiboyina, Amar G.,Claudio, Pier Paolo,Haider, Saqlain,McChesney, James D.,Penfornis, Patrice
, (2021/10/19)
TumorSelect is an anticancer technology that combines cytotoxics, nanotechnology, and knowledge of human physiology to develop innovative therapeutic interventions with minimal undesirable side effects commonly observed in conventional chemotherapy. Tumors have a voracious appetite for cholesterol which facilitates tumor growth and fuels their proliferation. We have transformed this need into a stealth delivery system to disguise and deliver anticancer drugs with the assistance of both the human body and the tumor cell. Several designer prodrugs are incorporated within pseudo-LDL nanoparticles, which carry them to tumor tissues, are taken up, internalized, transformed into active drugs, and inhibit cancer cell proliferation. Highly lipophilic prodrug conjugates of paclitaxel suitable for incorporation into the pseudo-LDL nanoparticles of the TumorSelect delivery vehicle formulation were designed, synthesized, and evaluated in the panel of 24-h NCI-60 human tumor cell line screening to demonstrate the power of such an innovative approach. Taxane prodrugs, viz., ART-207 was synthesized by tethering paclitaxel to lipid moiety with the aid of a racemic solketal as a linker in cost-effective, simple, and straightforward synthetic transformations. In addition to the typical 24-h NCI screening protocol, these compounds were assessed for growth inhibition or killing of ovarian cell lines for 48 and 72h-time intervals and identified the long-lasting effectiveness of these lipophilic prodrugs. All possible, enantiomerically pure isomers of ART-207 were also synthesized, and cytotoxicities were biosimilar to racemic ART-207, suggesting that enantiopurity of linker has a negligible effect on cell proliferation. To substantiate further, ART-207 was evaluated for its in vivo tumor reduction efficacy by studying the xenograft model of ovarian cancer grown in SCID mice. Reduced weight loss (a measure of toxicity) in the ART-207 group was observed, even though it was dosed at 2.5x the paclitaxel equivalent of Abraxane. As a result, our delineated approach is anticipated to improve patient quality of life, patient retention in treatment regimes, post-treatment rapid recovery, and overall patient compliance without compromising the efficacy of the cytotoxic promiscuous natural products.
A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids
Hamberg, Mats
, p. 489 - 494 (2021/04/19)
Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese-based Wurtz type coupling of alkyl bromides. 22-Bromo-3(Z),6(Z),9(Z),12(Z),15(Z),18(Z)-docosahexaene, easily prepared from 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)-docosahexaenoic acid, was coupled to homologous ω-bromoesters by stirring for 4 hours at 40°C in the presence of manganese powder, a nickel catalyst and terpyridine. This afforded in yields of 70–75% a series of ω3-hexaenoates of chain lengths of 32–40 carbons. The corresponding fatty acids of >98% purity were obtained following saponification and final purification. By using methyl [2,2,3,3,4,4-2H6]10-bromodecanoate as coupling partner it was possible to prepare a very long chain fatty acid in isotopically labeled form, i.e., [2,2,3,3,4,4-2H6]14(Z),17(Z),20(Z),23(Z),26(Z),29(Z)-dotriacontahexaenoic acid. Also prepared were the monounsaturated long chain fatty acids 15(Z)-octadecenoic acid and 15(Z)-tetracosenoic acid. Very long chain fatty acids have been isolated from retina and other tissues and are of biological relevance. The methodology described will assist in further analytical and biological studies in this field.
SYNTHESIS OF PHEROMONE DERIVATIVES VIA Z-SELECTIVE OLEFIN METATHESIS
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Paragraph 0218, (2021/12/28)
Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.
OLEIC ACID DERIVATIVES AS TREATMENTS FOR FRIEDREICH ATAXIA AND INHIBITORS OF FERROPTOSIS
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Paragraph 00167, (2021/05/21)
The invention relates to compounds of Formula I or Formula II: to compositions comprising such compounds, and to methods of use thereof for treating neurdegenerative disorders, such as Friedreich ataxia.
Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities
Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto
supporting information, p. 2544 - 2550 (2019/11/13)
Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.
Hydrosilylation of Esters Catalyzed by Bisphosphine Manganese(I) Complex: Selective Transformation of Esters to Alcohols
Bagh, Bidraha,Behera, Rakesh R.,Ghosh, Rahul,Khamari, Subrat,Panda, Surajit
supporting information, p. 3642 - 3648 (2020/04/20)
Selective and efficient hydrosilylations of esters to alcohols by a well-defined manganese(I) complex with a commercially available bisphosphine ligand are described. These reactions are easy alternatives for stoichiometric hydride reduction or hydrogenation, and employing cheap, abundant, and nonprecious metal is attractive. The hydrosilylations were performed at 100 °C under solvent-free conditions with low catalyst loading. A large variety of aromatic, aliphatic, and cyclic esters bearing different functional groups were selectively converted into the corresponding alcohols in good yields.
