- Synthesis of halogenated 1-O-alkylglycerols from ricinoleic acid derivatives
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Resistance to the existing drugs and increasing numbers of diseases result in identifying new drug candidates with new forms of activity. As marine organisms are well known to provide a wide range of original compounds, Herein, we report the synthesis of new non-natural brominated, iodinated and chlorinated-substituted 1-O-alkylglycerols 5–7, analogs of a prominent 1-O-alkylglycerol (AKG) of the natural shark liver oil (SLO) mixture, namely the AKGs 18:1, n-9.
- Pemha, René,Pegnyemb, Dieudonné Emmanuel,Mosset, Paul
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- Synthesis and biological evaluation of four new ricinoleic acid-derived 1-o-alkylglycerols
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Aseries of novel substituted 1-O-alkylglycerols (AKGs) containing methoxy (8), gem-difluoro (9), azide (10) and hydroxy (11) group at 12 position in the alkyl chain were synthesized from commercially available ricinoleic acid (12). The structures of these new synthesized AKGs were established by NMR experiments as well as from the HRMS and elementary analysis data. The antimicrobial activities of the studied AKGs 8-11 were evaluated, respectively, and all compounds exhibited antimicrobial activity to different extents alone and also when combined with some commonly used antibiotics (gentamicin, tetracycline, ciprofloxacin and ampicillin). AKG 11 was viewed as a lead compound for this series as it exhibited significantly higher antimicrobial activity than compounds 8-10.
- Pemha, René,Kuete, Victor,Pagès, Jean-Marie,Pegnyemb, Dieudonné Emmanuel,Mosset, Paul
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- Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins
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Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields. This journal is
- Giomi, Donatella,Salvini, Antonella,Ceccarelli, Jacopo,Brandi, Alberto
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- Preparation of functionalized castor oil derivatives with tunable physical properties using heterogeneous acid and base catalysts
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Functionalized castor oil derivatives namely ring-opened glyceryl ricinoleates, epoxy alkyl ricinoleates, and ring-opened alkyl ricinoleates were successfully prepared through two reaction chemistry viz., ring opening and transesterification using epoxidized castor oil (ECO) as a raw material. Amberlyst 15, the most active catalyst among several acid catalysts screened, showed a maximum conversion of 82% for ring opening of ECO with methanol. In another chemistry, 91% yield of epoxy methyl ricinoleate was achieved through transesterification of ECO with methanol using CaAl-layered double hydroxide (LDH) derived oxides as base catalyst. The scope is extendable to many nucleophiles and alcohols for both reactions respectively. Ring-opened alkyl ricinoleates were prepared both in two-pot and one-pot reactions using both acid and base catalysts together. The catalysts were recyclable and were successfully scaled at 25 g. The physical properties of these castor-based derivatives bestow the opportunity to design tailor-made materials suiting industrial needs.
- Sankaranarayanan, Sivashunmugam,Srinivasan, Kannan
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- Synthesis and antibacterial activity of ricinoleic acid glycosides
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The antibacterial properties of twenty-eight novel ricinoleic acid glycosides synthesized by Koenigs-Knorr glycosylation are reported. Seven of them were found to show promising wide spectrum antibacterial activity against Gram positive bacteria of which two compounds, the mannopyranosyl- and the arabinofuranosyl derivatives, were proven effective against various non-clinical/clinical/NorA-overexpressed/resistant strains of Staphylococcus aureus as well as other Gram +ve bacteria such as Bacillus subtilis ATCC 6051 and Micrococcus luteus MTCC 2470. It was found that both the presence of the sugar and its structure are necessary and important for the compounds to be bioactive. The methyl ester protection of the carboxylic acid moiety of the ricinoleic acid unit was also found to be important for imparting good bioactivity to the molecule. Based on the membrane permeability and cell disintegration studies, these compounds are found to increase the bacterial cell membrane permeability, subsequently causing cell death.
- Kuppala, Ramakrishna,Govindarajan, Mugunthan,Tambat, Rushikesh,Patel, Neeraj,Nandanwar, Hemraj,Bhutani, Kamlesh K.,Kartha, K. P. Ravindranathan
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- Design and synthesis of a castor oil based plasticizer containing THEIC and diethyl phosphate groups for the preparation of flame-retardant PVC materials
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A fine chemical product based on a castor oil containing THEIC and diethyl phosphate groups (THEIC-MR-phosphate) was designed and synthesized, and it was used as a substitute flame retardant plasticizer to prepare PVC materials instead of the commercial plasticizer dioctyl phthalate (DOP). The performance of the PVC materials plasticized with THEIC-MR-phosphate was investigated with TGA, DSC, cone calorimeter analysis, and tensile tests. The results indicated that the addition of THEIC-MR-phosphate improved the flame retardant properties of the PVC materials. The time to ignition (TI) increased from 10 s to 25 s, the pHRR value decreased from 167.5 kW m-2 to 52.1 kW m-2, the av-HRR value decreased from 44.7 kW m-2 to 21.1 kW m-2, and the t-pHRR value increased from 45.0 s (D-1) to 73.0 s (N-3). These data indicated that the THEIC-MR-phosphate was effective in increasing the PVC material resistance to fire, and it not only decreased the HRR, but also delayed the fire process.
- Jia, Puyou,Hu, Lihong,Feng, Guodong,Bo, Caiying,Zhou, Jing,Zhang, Meng,Zhou, Yonghong
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- LIPID CONJUGATE PREPARED FROM SCAFFOLD MOIETY
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The application relates to a lipid conjugate of formula M-X1-L wherein M is a molecule of interest such as a drug moiety; X1 is a linker group such as ester, ether or carbamate; and L is a lipid scaffold represented by formula (lId): -L1-[L2(H)(X2R)]n-L3-[L4(H)(X2R)]p-L5-L6 and wherein L comprises 5 to 40 carbon atoms and 0 to 2 carbon-carbon double bonds. The lipid conjugate can be formulated in a drug delivery vehicle such as a lipid nanoparticle (LNP).
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Page/Page column 54-55
(2020/10/18)
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- Fatty acid based biocarbonates: Al-mediated stereoselective preparation of mono-, di- and tricarbonates under mild and solvent-less conditions
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A catalytic method for the preparation of a series of fatty acid derived biocarbonates has been developed using a binary Al-complex/PPNCl catalyst. This catalyst system allows conversion of fatty acid derived epoxides under comparatively mild reaction conditions (70-85 °C, 10 bar) while maintaining high levels of diastereospecificity with cis/trans ratios of up to 97:3 in the products. The comparative catalysis data obtained for the reactions catalysed only by the nucleophilic halide based components show that the presence of the Al-complex is crucial for the retention of the original stereochemistry.
- Pe?a Carrodeguas,Cristòfol,Fraile,Mayoral,Dorado,Herrerías,Kleij
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supporting information
p. 3535 - 3541
(2017/08/15)
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- Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters
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In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1H NMR, 13C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8’R)-8’ hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2’R)(2’-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8’R)-8’-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation between the observed and predicted antimicrobial activities.
- Ahmad, Anis,Ahmad, Aiman,Sudhakar, Raja,Varshney, Himani,Subbarao, Naidu,Ansari, Saba,Rauf, Abdul,Khan, Asad U.
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p. 3412 - 3431
(2017/11/16)
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- [1 + 1]-Condensation of 12-Oxo-Derivatives of Ricinoleic Acid Esters with Hydrazine Hydrate on the Route to Macrocycles
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The reactivities of the keto analogs of methyl ricinolate and its triglyceride with hydrazine hydrate were studied. The ester was found to be inert, which made it possible to synthesize a macrocyclic azine with a side chain hydrazone moiety from a 12-oxo-derivative.
- Ishmuratov, G. Yu.,Yakovleva,Vydrina,Rubleva,Ishmuratova,Tolstikov
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p. 231 - 233
(2017/07/05)
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- Synthesis of Fatty Acetoacetates Under Microwave Irradiation Catalysed by Sulfamic Acid in a Solvent-Free System
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The 1,3-dicarbonyl compounds are important building blocks to obtain products with various biological activities and technological applications. In this work, we used a simple transesterification method to develop fatty acetoacetates in a solvent-free medium using a green catalyst, sulfamic acid (NH2SO3H), under microwave irradiation. The experimental results demonstrate good yields in a short reaction time (13?min), which makes this method an efficient approach to synthesize fatty acetoacetates from a wide range of saturated, unsaturated, and polyunsaturated long chain fatty alcohols, and ricinoleic derivatives. Experiments of recycling of the catalyst were performed and no decrease in catalytic activity of sulfamic acid was observed.
- Weber, Andressa C. H.,Batista, Thaís C.,Gon?alves, Bruno,Hack, Carolina R. L.,Porciuncula, Larissa M.,Treptow, Tamara G. M.,D’Oca, Caroline Da R. Montes,Russowsky, Dennis,D’Oca, Marcelo G. Montes
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p. 1399 - 1406
(2016/09/28)
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- Newly synthesized bolaamphiphiles from castor oil and their aggregated morphologies for potential use in drug delivery
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The present study focused on synthesizing bolaamphiphiles from the readily available and inexpensive castor oil, a vegetable oil, which contains about 90% of ricinoleic acid. Two classes of symmetric and asymmetric bolaamphiphiles with acetylcholine head groups were synthesized and characterized by spectroscopic analysis. These novel bolaamphiphilic compounds self-assemble in aqueous media to form stable cationic spherical nano-sized vesicles that are potential drug delivery systems.
- Ewonkem, Monique B.,Grinberg, Sarina,Lemcoff, Gabriel,Shaubi, Eleonora,Linder, Charles,Heldman, Eliahu
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p. 8557 - 8571
(2018/04/05)
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- Antiproliferative activity of synthetic fatty acid amides from renewable resources
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In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line - the most aggressive CNS cancer.
- Dos Santos, Daiane S.,Piovesan, Luciana A.,D'Oca, Caroline R. Montes,Hack, Carolina R. Lopes,Treptow, Tamara G.M.,Rodrigues, Marieli O.,Vendramini-Costa, Débora B.,Ruiz, Ana Lucia T.G.,De Carvalho, Jo?o Ernesto,D'Oca, Marcelo G. Montes
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p. 340 - 347
(2015/02/02)
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- Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid
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(R)-Ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products.
- Kula, Józef,Bonikowski, Radoslaw,Szewczyk, Malgorzata,Ciolak, Kornelia
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p. 137 - 141
(2014/07/08)
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- Transesterification of triacetin and castor oil with methanol catalyzed by supported polyaniline-sulfate. A role of polymer morphology
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Polyaniline-sulfate deposited on three different carriers was studied for transesterification of triacetin and castor oil with methanol at mild reaction conditions (temperature of 55 °C). Multi-wall carbon nanotubes (CNT), carbon and silica were coated with polyaniline sulfate (ca. 20 wt%) during polymerization of aniline. Because of different textural and hydrophobic properties of the carriers, the polymer coatings of various morphologies were obtained as evidenced by the electron microscopy technique. A uniform coating of CNT with polymer resulted in the most extended polymer structure. Nanorods of polymer forming branched dendritic structures appeared in the other two carbon and silica carriers. The acid capacity and the strength of acid sites were similar in all studied catalysts. All the samples were found to be active solid acid catalysts in methanolysis of both studied triglycerides and CNT-coated polyaniline sulfate exhibited the highest activity. The course of reaction during methanolysis of triacetin on CNT-containing catalyst was similar to that in the presence of soluble sulfuric acid. On the other hand, a partial blockage of active sites was observed in carbon and silica coated with polyaniline sulfate. A blockage effect was ascribed to strong interaction of acid sites with more polar reagents among them diacetin and glycerol. These interactions were facilitated by aggregated fibriral morphology of the polymer coating resulting in locally high density of acid sites.
- Drelinkiewicz,Kalemba-Jaje,Lalik,Zi?ba,Mucha,Konyushenko,Stejskal
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- Designing and synthesis of novel antimicrobial heterocyclic analogs of fatty acids
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Novel series of long chain isoxazole derivatives were designed as inhibitors of Cytochrome P450-14DM14a-demethylase from Candida albicans and ribosomal subunit of S12 protein from Escherichia coli. The novel compounds (6-10) were synthesized through 1,3-dipolar cycloaddition of nitrile oxide to long chain alkynoic acid and alkenyl/hydroxyalkenyl esters and tested for their antimicrobial activity by disk diffusion assay and MIC by broth micro dilution method. After predicting the hidden potential and drug-likeness of compounds, ADMET-related descriptors were also calculated to predict pharmacokinetic properties. Molecular docking studies have been performed to evaluate possible mode of action of molecules in active site of receptor. Compounds (9 and 10) showed excellent antimicrobial activity nearly equivalent to the control compounds.
- Ahmad, Aiman,Ahmad, Anis,Varshney, Himani,Rauf, Abdul,Rehan, Mohd,Subbarao, Naidu,Khan, Asad U.
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p. 887 - 900
(2013/12/04)
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- METHOD FOR THE SYNTHESIS OF AN OMEGA-AMINO ACID OR ESTER STARTING FROM A MONOUNSATURATED FATTY ACID OR ESTER
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The invention relates to a method for the synthesis of ω-amino alkanoic acids or esters thereof starting from unsaturated natural fatty acids passing through an ω-unsaturated nitrile intermediate compound.
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(2011/10/04)
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- Synthesis and antituberculosis activity of new fatty acid amides
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This work reports the synthesis of new fatty acid amides from C16:0, 18:0, 18:1, 18:1 (OH), and 18:2 fatty acids families with cyclic and acyclic amines and demonstrate for the first time the activity of these compounds as antituberculosis agents against Mycobacterium tuberculosis H37Rv, M. tuberculosis rifampicin resistance (ATCC 35338), and M. tuberculosis isoniazid resistance (ATCC 35822). The fatty acid amides derivate from ricinoleic acid were the most potent one among a series of tested compounds, with a MIC 6.25 μg/mL for resistance strains.
- D'Oca, Caroline Da Ros Montes,Coelho, Tatiane,Marinho, Tamara Germani,Hack, Carolina Rosa Lopes,Da Costa Duarte, Rodrigo,Da Silva, Pedro Almeida,D'Oca, Marcelo Gonalves Montes
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scheme or table
p. 5255 - 5257
(2010/10/03)
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- Activity and stability of polyaniline-sulfate-based solid acid catalysts for the transesterification of triglycerides and esterification of fatty acids with methanol
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A polymeric catalyst, polyaniline-sulfate, was studied in the transesterification of triglycerides (triacetin, castor oil) and esterification of fatty acid, ricinoleic acid with methanol at mild conditions (temperature of 50-60 °C). Polymer powder (PANI-S) and three samples of various contents of polymer deposited on carbon support were examined. The samples of catalysts, before and after catalytic tests were characterized by BET, FT-IR, XRD and SEM techniques. The acid capacity was also determined. All the samples were found to be active solid acid catalysts in both tested reactions. Catalytic performance of polyaniline-sulfate-based catalysts for methanolysis of triacetin (glycerol triacetate) the shortest triglyceride molecule differed from that for vegetable oil, castor oil, consisting of long chain triglycerides of ricinoleic acid. In transesterification of triacetin PANI-S powder was more active than carbon-supported catalysts. In methanolysis of vegetable oil the outermost surface of catalysts was mainly involved and much higher activity was exhibited by carbon-supported catalysts with deposited polymer, especially with low content of polymer (13.1 wt.%). The activity of polyaniline-sulfate-based catalysts was almost stable during recycling use in tested reactions. After five successive catalytic runs, their activities were found to be ca. 80-95% relative to the activities of fresh catalysts.
- Zi?ba,Drelinkiewicz,Konyushenko,Stejskal
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experimental part
p. 169 - 181
(2010/11/04)
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- Method of producing dicarboxylic acids
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A method of producing dicarboxylic acids (e.g., α,ω dicarboxylic acids) by reacting a compound having a terminal COOH (e.g., unsaturated fatty acid such as oleic acid) and containing at least one carbon-carbon double bond with a second generation Grubbs catalyst in the absence of solvent to produce dicarboxylic acids. The method is conducted in an inert atmosphere (e.g., argon, nitrogen). The process also works well with mixed unsaturated fatty acids obtained from soybean, rapeseed, tall, and linseed oils.
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(2009/05/29)
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- Impact of free hydroxylated and methyl-branched fatty acids on the organization of lipid membranes
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Differential scanning calorimetry (DSC) has been applied to study the effect of free hydroxylated and methyl-branched fatty acids on the physico-chemical properties of lipid membranes. First, the impact of free hydroxy fatty acids (HFAs) on dimyristoylphosphatidylcholine (DMPC) model membranes was monitored only as a function of chain length and position of the attached hydroxyl group. Second, racemic vs. enantiopure anteiso fatty acids (AFAs) and HFAs were investigated to address the question of which role does a fatty acid's chirality play on its membrane pertubing effect. The DSC thermograms revealed that the main gel to liquid-crystalline phase transition of the DMPC bilayers which results in a disordering effect of the lipid hydrocarbon chains was affected in different ways depending on the nature of the incorporated fatty acid. Long-chain 2- and 3-HFAs stabilized the gel phase by reducing the phase transition temperature (Tm), whereas short-chain HFAs and long-chain HFAs with the hydroxy group remote from the head group stabilized the more disordered liquid-crystalline state. Additionally, we observed that enantiopure (S)-14-methylhexadecanoic acid ((S)-a17:0) and (R)-2-hydroxy octadecanoic acid and the corresponding racemates had contrary effects upon incorporation into DMPC bilayers. In both cases, the pure enantiomers alleviated the liquid-crystalline state of the biological model membrane.
- Jenske, Ramona,Lindstroem, Fredrick,Groebner, Gerhard,Vetter, Walter
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experimental part
p. 26 - 32
(2010/01/16)
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- KHSO4-SiO2-MeOH An efficient selective solid-supported system for deprotection of alcohols from esters
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KHSO4-SiO2 can efficiently deprotect alcohols from esters through transesterification in methanol under mild condition. Esters of aromatic alcohols are easily transesterified at room temperature compared to the corresponding aliphatic or alicyclic alcohol. NAcetyl compounds and ethers are resistant to the reagent under the above condition. The method is very useful for preparation of biodiesel methyl ricinoleate from castor oil.
- Goswami, Amrit,Das, Ram N.,Borthakur, Naleen
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p. 1893 - 1895
(2008/09/19)
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- PROCESS FOR PREPARING CONJUGATED LINOLEIC ACID AND DERIVATIVES THEREOF FROM RICINOLEIC ACID
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A process for preparing conjugated linoleic acid (CLA) or derivatives thereof from ricinoleic acid, lower alkyl esters of ricinoleic acid, or salts thereof. The CLA is formed by reacting a carboxylic acid, or anhydride, anhydride equivalent, or ester thereof with the ricinoleic acid or derivative to form an intermediate having a carboxylic ester at the 12-hydroxy position of the ricinoleic acid or derivative, and reacting the intermediate with a base to form a cis-9, trans-11 conjugated linoleic acid.
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(2008/06/13)
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- Synthesis of enantiomerically pure 2,3,4,6-tetrasubstituted tetrahydropyrans by Prins-type cyclization of methyl ricinoleate and aldehydes
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The AlCl3-catalyzed Prins-type cyclization of methyl ricinoleate (1), an enantiomerically pure renewable compound, with aldehydes such as heptanal (2a), isobutyraldehyde (2b), pivaldehyde (2c) and benzaldehyde (2d) is a simple reaction for the diastereoselective synthesis of enantiomerically pure 2,3,6-trialkyl-substituted 4-chlorotetrahydropyrans. The respective 4-hydroxytetrahydropyrans are obtained e.g. with aldehydes 2a and 2d using montmorillonite KSF/O as the catalyst. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Biermann, Ursula,Luetzen, Arne,Metzger, Juergen O.
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p. 2631 - 2637
(2007/10/03)
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- Lactic acid and ricinoleic acid based copolyesters
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Copolyesters based on purified ricinoleic (RA) and lactic (LA) acids with different RA:LA ratios were synthesized by thermal polycondensation and by transesterification of high molecular weight poly(lactic acid) (PLA) with ricinoleic acid and repolyesterification. Thermal polycondensation resulted in random P(LA-RA) copolyesters of molecular weights between 2000 and 8000 with the polymers containing 20% or more RA were liquid at room temperature. Transesterification of high molecular weight PLA with pure ricinoleic acid and repolymerization of those oligomers by condensation resulted in multiblock P(PLA-RA) copolyesters of molecular weights between 6000 and 14000. Polymers containing 50% RA were liq uid at room temperature. 1H NMR spectroscopy analysis coupled with information from DSC allowed de ;ermination of the polymer structure. Polymers prepared by thermal polycondensation are random cope lymers (h > 1), while the copolymers prepared by transesterification have a multiblock character (h LA) decreased from 12 to 4 for the LA-RA 9:1 and 5:5 copolymers prepared by thermal polycondensation and from 50 to 17 for the corresponding LA-RA copolymers prepared by transesterification. Thermal analysis by DSC revealed crystalline structure for polyester synthesized by transesterification. For polyesters synthesized by random condensation on y P(LA-RA) 90:10 w/w contained crystalline domains.
- Slivniak, Raia,Domb, Abraham J.
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p. 5545 - 5553
(2008/02/01)
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- Polymeric formulations for drug delivery
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Poly(ester-anhydrides) or polyesters formed from ricinoleic acid and natural fatty diacids and their method of preparation and its use for delivering bioactive agents including small drug molecules, peptides and proteins, DNA and DNA complexes with cationic lipids or polymers or nano and microparticles loaded with bioactive agents are disclosed herein. The drug delivery compositions are administered to a patient in a liquid form, increase in viscosity in vivo to form a drug depot or implant, and are able to release the incorporated bioactive agent for weeks. In the preferred embodiment, the drug delivery formulations are administered by injection. In one embodiment, the compositions are suitable for local or regional delivery of drugs to diseased sites, such as treating solid tumors and bone infections. In a preferred embodiment, the drug delivery compositions are suitable for site-specific chemotherapy for the treatment of solid tumors including: squamous cell carcinoma (SCC) of the head and neck, prostate cancer, and sarcomas for intratumoral injection or insertion.
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- Syntheses and QSAR studies of sorbic, cinnamic and ricinoleic acid derivatives as potential antibacterial agents
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Amides and esters of sorbic, cinnamic and ricinoleic acid have been synthesized and evaluated for their antibacterial activity against gram (+) ve S. aureus, B. subtilis and gram (-) ve E. coli. Most of the compounds have shown moderate to good activity against microorganisms under test. Linear regression analysis of descriptors related to lipophilicity, steric and electronic parameters against antibacterial activity have been performed. QSAR studies indicated the predominance of electronic and steric parameters over the lipophilicity parameters in contributing antibacterial activity.
- Narasimhan,Kothawade,Pharande,Mourya,Dhake
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p. 2828 - 2834
(2007/10/03)
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- Production of conjugated linoleic acids through KOH-catalyzed dehydration of ricinoleic acid
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Production of conjugated linoleic acids (CLA) using castor oil as starting material involves conversion of ricinoleic acid to methyl 12-mesyloxy-octadec-9-enoate (MMOE) followed by dehydration. This process usually uses 1,8-diazabicyclo-(5.4.0)-undec-7-ene (DBU) as an expensive dehydrating reagent. The present study reports that potassium hydroxide (KOH) can serve as a dehydrating reagent in replacement of DBU. The results showed that conversion of MMOE to CLA catalyzed by KOH was an efficient reaction, with a 77% conversion efficiency at 80°C. The CLA isomeric profile produced in KOH-catalyzed dehydration reaction was similar to that catalyzed by DBU. The CLA mixture produced in KOH-catalyzed dehydration of MMOE at 80°C contained 72% 9c,11t-18:2 and 26% 9c,11c-18:2 while in that catalyzed by DBU, 9c,11t-18:2 and 9c,11c-18:2 accounted for 78 and 16%, respectively. It was found that the temperature of dehydration was an important factor in the determination of CLA isomer composition and yield of conversion. Elevating the temperature from 78 to 180°C decreased not only the conversion efficiency but also production of total c,t-18:2 and c,c-18:2 isomers regardless of dehydration catalyzed by either DBU or KOH. It is concluded that KOH may replace DBU as a dehydrating reagent in conversion of MMOE to CLA when the reaction conditions are optimized.
- Yang, Lin,Huang, Yu,Wang, Han Qing,Chen, Zhen-Yu
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- Synthesis of optically active methyl 12-oxo-9,10-epoxyoctadecanoate
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The procedure for synthesizing optically active methyl 12-oxo-9,10-epoxyoctadecanoate (enantiomeric purity ～90%) was developed, starting from ricinolic acid methyl ester.
- Davletbakova,Baibulatova,Dokichev,Muslukhov,Yunusova,Yunusov
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p. 1220 - 1222
(2007/10/03)
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- Synthesis of phosphatidylcholines containing ricinoleic acid
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1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields. The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only β-methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphocholine), respectively.
- Borsotti, Gianpietro,Guglielmetti, Gianfranco,Spera, Silvia,Battistel, Ezio
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p. 10219 - 10227
(2007/10/03)
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- Synthesis and stereochemistry of some bicyclic γ-lactones from parasitic wasps (Hymenoptera: Braconidae). Utility of hydrolytic kinetic resolution of epoxides and palladium(II)-catalyzed hydroxycyclization-carbonylation-lactonization of ene-diols
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A palladium(II)-catalyzed hydroxycyclization-carbonylation-lactonization sequence with appropriate pent-4-ene-1,3-diols provides efficient access to the bicyclic γ-lactones, 5-n-butyl- and 5-n-hexyltetrahydrofuro-[3,2-b]furan-2(3H)-ones (3) and (4), respectively, in both racemic and enantiomeric forms. Some of the substrate pent-4-ene-1,3-diols of high enantiomeric excess (ee) have been derived from racemic terminal epoxides by hydrolytic kinetic resolution (HKR) using cobalt (III) - salen complexes. (9Z,12R)-(+)-Ricinoleic acid also serves as a "chiral pool" source of other pent-4-ene-1,3-diols. These syntheses and enantioselective gas chromatography confirm the structures and absolute stereochemistry of the lactones in some species of parasitic wasps (Hymenoptera: Braconidae). The highly abundant 5-n-hexyltetrahydrofuro-[3,2-b]furan-2(3H)-one (4) in Diachasmimorpha kraussii and D. longicaudata is of high ee (>99%) with (3aR,5R,6aR) stereochemistry.
- Paddon-Jones,McErlean,Hayes,Moore,Konig,Kitching
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p. 7487 - 7495
(2007/10/03)
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- Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom
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Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 A2/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel- to liquid-crystalline phase transition temperature (T(m))passed through a minimum of -15.1°C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine.
- Negelmann, Lars,Pisch, Sandra,Bornscheuer, Uwe,Schmid, Rolf D.
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p. 117 - 134
(2007/10/03)
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