- A Lipophilic Pt(IV) Oxaliplatin Derivative Enhances Antitumor Activity
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Side effects and acquired resistance by cancer cells limit the use of platinum anticancer drugs. Modification of oxaliplatin (OXA) into a lipophilic Pt(IV) complex [Pt(DACH)(OAc)(OPal)(ox)] (1), containing both lipophilic and hydrophilic axial ligands, was applied to improve performance and facilitate incorporation into polymeric nanoparticles. Complex 1 exhibited unique potency against a panel of cancer cells, including cisplatin-resistant tumor cells. [Pt(DACH)(OAc)(OPal)(ox)] incorporated nanoparticles (2) presented a mean diameter of 146 nm with encapsulation yields above 95% as determined by HPLC. Complexes 1 and 2 showed enhanced in vitro cellular Pt accumulation, DNA platination, and antiproliferative effect compared to OXA. Results of an orthotopic intraperitoneal model of metastatic ovarian cancer (SKOV-3) and a xenograft subcutaneous model of colon (HCT-116) tumor in SCID-bg mice showed that the activity of 1 and 2 significantly decreased tumor growth rates compared to control and OXA treatment groups. Consequently, these findings warrant further development toward clinical translation.
- Abu Ammar, Aiman,Raveendran, Raji,Gibson, Dan,Nassar, Taher,Benita, Simon
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Read Online
- Chemical synthesis of palmitoylated histone H4
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Palmitoylation is one of the post-translational modifications of proteins. Recently, palmitoyl modification was found in histone H4, one of the components of the nucleosome core. To analyze this unusual modification in the nuclear protein, we chemically synthesized Ser47-palmitoylated histone H4. The entire sequence of H4 was divided into three segments and each was prepared by Fmoc-solid-phase peptide synthesis (SPPS). The palmitoyl group was introduced as a preformed palmitoyl Ser during SPPS or introduced at the end of SPPS by selective deprotection of the hydroxy group of Ser47, followed by palmitoylation. After three segments were condensed in one-pot by the thioester method, the desired Ser47-palmitoylated H4 was obtained.
- Hojo, Hironobu,Suetake, Isao
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- Potential Vegetable-Based Diesel Fuels from Perkin Condensation of Furfuraldehyde and Fatty Acid Anhydrides
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Domestically produced biofuels may help to reduce dependence on imported oil for powering transportation and infrastructure in the future. In this report, we reacted medium-chain and long-chain fatty anhydrides (capric, caprylic, lauric, and palmitic) with furfuraldehyde by the Perkin condensation to produce 2-n-alkenylfurans. In the second step, the 2-n-alkenylfurans were hydrogenated to form 2-n-alkyltetrahydrofurans. Basic fuel property testing (melting point, density, kinematic viscosity, derived cetane number, and calorific value) of the 2-n-alkyltetrahydrofurans indicates they are potentially useful as fuels for diesel engines. The mixture composed of 2-octyl- and 2-decyltetrahydrofuran had the best combination of fuel properties including a low melting point (?39 °C), high cetane number (63.1), high flash point (98.2 °C), and low viscosity (2.26 mm2 s?1, 40 °C), which compares favorably with specifications for diesel #2 and biodiesel.
- Baldwin, Lawrence C.,Davis, Matthew C.,Hughes, Alicia M.,Lupton, David V.
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p. 571 - 583
(2019/04/08)
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- METHOD FOR SEPARATING HIGH-BOILING CARBOXYLIC ACID VINYL ESTER/CARBOXYLIC ACID MIXTURES
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The invention relates to a method for separating a mixture containing at least one carboxylic acid vinyl ester of general formula R′—C(O)O—CH═CH2 and at least one carboxylic acid of general formula R′—COOH, wherein R′ in either case can be an aliphatic group having 12 to 22 C atoms or a cycloaliphatic group having 12 to 22 C atoms, or an aromatic group having 12 to 22 C atoms, and R′ can be identical or different, characterized in that the carboxylic acid is converted to its anhydride R′—C(O)—O—C(O)—R′ and the carboxylic acid vinyl ester is subsequently separated.
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Paragraph 0044-0045
(2017/05/15)
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- A new synthesis route for the preparation of the avocadofuran (2-hexadecylfuran)
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A new synthetic route for the preparation of the insecticidal compound 2-hexadecylfuran is described in this study. The procedure starts from readily available furfuraldehyde and palmitic anhydride via two steps employing the Perkin reaction and resulting in a 25% overall yield. The method can be deemed as a practical and environmentally friendly route to prepare a potentially important class of insecticide.
- Davis, Matthew C.,Groshens, Thomas J.
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p. 242 - 248
(2016/10/22)
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- Use of glycerol carbonate in an efficient, one-pot and solvent free synthesis of 1,3-sn-diglycerides
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An efficient solvent-free synthesis of a variety of highly pure 1,3-sn-diglycerides (1,3-sn-diacylglycerols) in a two-step one pot process is described. Heating glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one) with fatty acid anhydrides 2a-d affords 1:1 mixtures of glycerol carbonate fatty esters 3a-3d and the corresponding fatty acids. Further heating the reaction mixtures in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 195-200 °C yields highly pure 1,3-sn-diglycerides 4a-4d.
- Kargar, Mojgan,Hekmatshoar, Rahim,Ghandi, Mehdi,Mostashari, Abdoljalil
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p. 259 - 264
(2013/07/27)
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- First total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol-a glycoglycerolipid of a marine alga with a high inhibitor activity against human Myt1-kinase
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The first total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol, a glycoglycerolipid isolated from a marine alga extract, is described. Starting from α-methylglucopyranoside the multistep strategy allows the stereoselective synthesis of the final compound using various protective group procedures as well as derivatization of partial molecule domains. The latter offers the development of lead structures for inhibitors of human Myt1-kinase.
- Goellner, Christiane,Philipp, Claudia,Dobner, Bodo,Sippl, Wolfgang,Schmidt, Matthias
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experimental part
p. 1628 - 1631
(2009/12/09)
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- Facile synthesis of carboxylic anhydrides using 4,5-dichloro-2-[(4-nitrophenyl)sulfonyl]pyridazin-3(2H)-one
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A novel and facile synthesis of carboxylic anhydrides from carboxylic acid using 4,5-dichloro-2-[(4-nitrophenyl)sulfonyl]pyridazin-3(2H)-one (2) is presented. Treatment of aliphatic or aromatic carboxylic acids with 2 in the presence of base in organic solvents gave the corresponding anhydrides in good or excellent yields.
- Kim, Jeum-Jong,Park, Yong-Dae,Song Lee, Woo,Cho, Su-Dong,Yoon, Yong-Jin
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p. 1517 - 1520
(2007/10/03)
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- A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetonitrile and triphenylphosphine
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Various carboxylic acids are converted into the corresponding carboxylic acid anhydrides treated with trichloroacetonitrile and triphenylphosphine in the presence of triethylamine at room temperature.
- Kim,Jang
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p. 395 - 399
(2007/10/03)
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- Synthesis and characterization of long chain alkyl acyl carnitine esters. Potentially biodegradable cationic lipids for use in gene delivery
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A series of alkyl acyl carnitine esters (alkyl 3-acyloxy-4- trimethylammonium butyrate chloride) were synthesized as potential biocompatible cationic lipids for use in gene transfer. The physicochemical properties of the lipids, liposomes prepared from them, and their complexes with DNA were characterized by differential scanning calorimetry (DSC), particle size, potential, and surface monolayer measurements. The transition temperatures and behavior at an air-water interface for this series are similar to phosphatidylcholines with the same hydrocarbon chain length. The physical properties of the L derivatives were not significantly different from the DL derivatives. At 70 °C, the acyl chains were readily hydrolyzed at pH 7. The influence of the aliphatic chain length (n = 12-18) on transfection efficiency in vitro was determined using cationic liposomes prepared from these lipids or their mixtures with the helper lipids, dioleoylphosphatidylethanolamine (DOPE), dioleoylphosphatidylcholine, monooleoylglycerol, and cholesterol (Chol). The mixture of myristyl 3- myristoyloxy-4-trimethylammonium butyrate chloride (MMCE, 4d) with DOPE at a 1:1 molar ratio mediated the highest transfection efficiency in cell culture. The mixture of oleyl 3-oleoyloxy-4-trimethylammonium butyrate chloride (OOCE, 4f) with Chol at a 1:1 molar ratio gave the highest transfection efficiency after intravenous administration in mice. In vivo gene expression using 4f was comparable to values obtained with the best cationic lipids reported to date.
- Wang, Jinkang,Guo, Xin,Xu, Yuhong,Barron, Lee,Szoka Jr., Francis C.
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p. 2207 - 2215
(2007/10/03)
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- Synthesis of anhydrides from acyl chlorides under ultrasound condition
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A convenient and general method for the synthesis of symmetrical anhydrides under ultrasound conditions is described.
- Hu, Yulai,Wang, Jin-Xian,Li, Shihua
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p. 243 - 248
(2007/10/03)
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- N-docosahexaenoyl, 3 hydroxytyramine: A dopaminergic compound that penetrates the blood-brain barrier and suppresses appetite
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Fatty acids with varying chain lengths (2-22 carbon atoms long) and degrees of unsaturation (0-6 double bonds) were used to synthesize dopaminergic compounds for a study of the carrier mediated transport of dopamine (DA) to the brain. The most active carrier was the all cis C22:6 fatty acid [docosahexaenoic acid,( DHA)]which increased DA uptake through the blood-brain barrier by greater than 7.5 fold. The DHA-DA compound, NMI 8739, depressed the general locomotor activity of mice in a dose dependent manner. It also suppressed the appetite of Balb c mice and Charles River rats by 50% and 95% respectively at a dose of 10 mg/kg. Daily administration of NMI-8739 for a three week period did not induce tolerance. These results demonstrate DHA's potential for the carrier mediated transport of small molecules to the brain.
- Shashoua, Victor E.,Hesse, Gary W.
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p. 1347 - 1357
(2007/10/03)
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- Synthesis of metal-chelating polymerizable phospholipids
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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.
- Singh,Tsao,Puranik
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p. 573 - 586
(2007/10/02)
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- Solid-liquid phase transfer and cobalt or palladium complex catalyzed synthesis of anhydrides from acyl chlorides
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Acyl chloride can efficiently be converted into anhydride under solid liquid phase transfer catalysis by using bis(triphenylphosphine)cobalt dichloride or bis (triphenylphospine)palladium dichloride as catalyst.
- Wang,Hu,Cui
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p. 3261 - 3268
(2007/10/02)
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- Synthesis of 1-palmitoyl-2-hexadecyl-sn-glycero-3-phospholine (PHPC)
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A general method for the chirospecific synthesis of 1-acyl-2-alkyl-sn-glycero-3-phosphocholines is described. 1-Palmityl-2-hexadecyl-sn-glycero-3-phosphocholine (PHPC) was synthesized in 18percent overall yield in ten steps via five new synthetic intermediates, and 1-acetyl-2-hexadecyl-sn-glycero-3-phosphocholine (AHPC) was also synthesized. 1-Acetyl-2-alkyl-sn-glycero-3-phosphocholines, which have not been found to exist in nature, are ether lipid analogs of 1,2-diacetyl-sn-glycero-3-phosphocholines, which are important components of cell membranes.Biophysical studies of hydrated bilayers of PHPC will be of interest in probing the critical importance of the central region of these amphiphilic molecules to the molecular assemblies that are found. Key words: 1-Acetyl-2-alkyl-sn-glycero-3-phosphocholine; 1-Palmitoyl-2-hexadecyl-sn-glycero-3-phosphocholine; PHPC; 1-acetyl-2-hexadecyl-sn-glycero-3-phosphocholine; AHPC; Palmitic anhydride
- Duclos, Richard I.
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p. 161 - 170
(2007/10/02)
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- DECOMPOSITION OF ALKYLARSONIC ACIDS BY ACYLATING AGENTS
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Benzylarsonic acid is decomposed by palmitoyl chloride, slowly in the absence and rapidly in the presence of pyridine, giving benzyl chloride.Benzylarsonic acid is decomposed by palmitic anhydride in the presence, but not in the absence, of pyridine giving palmitate and benzyl pyridinium cation.
- Tsivgoulis, Gerasimos M.,Sotiropoulos, Demetrios N.,Ioannou, Panayiotis V.
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p. 165 - 168
(2007/10/02)
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- A NEW SYNTHESIS OF CARBOXYLIC AND CARBONIC ACID ANHYDRIDES USING PHASE TRANSFER REACTIONS
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Acyl chlorides and alkylchloroformates smoothly reacted with one molar equivalent of sodium hydroxide, using liquid-liquid phase transfer conditions to afford high yields of the corresponding symmetrical carboxylic and carbonic hemiester anhydrides.Unstable anhydrides such as 4-nitrobenzoic, 2-furoic and methacrylic anhydrides, which are otherwise difficult to obtain, were easily prepared by this method.The reaction mechanism does not seem to involve intermediate hydrolysis of half the acid chloride into the corresponding sodium carboxylate.
- Plusquellec, Daniel,Roulleau, Fabienne,Lefeuvre, Martine,Brown, Eric
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p. 2471 - 2476
(2007/10/02)
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- A Convenient One-Pot Synthesis of Carboxylic Acid Anhydrides Using 1,1'-Oxalyldiimidazole
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Aliphatic, aromatic, and heteroaromatic carboxylic acids (5a-i) react with 1,1'-oxalyldiimidazole (6) in acetonitrile under reflux in the presence of methanesulfonic acid (12) to give the corresponding carboxylic acid anhydrides (9a-i) in 30-98percent yields.Keywords- dehydration; carboxylic acid anhydride; N-acylimidazole; 1,1'-carbonyldiimidazole; 1,1'-oxalyldiimidazole
- Kitagawa, Tokujiro,Kuroda, Hiroko,Sasaki, Hideaki
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p. 1262 - 1265
(2007/10/02)
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- Facile and Efficient Syntheses of Carboxylic Anhydrides and Amides Using (Trimethylsilyl)ethoxyacetylene
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(Trimethylsilyl)ethoxyacetylene, a stable and easy-handling reagent, serves as an excellent dehydrating agent for the synthesis of carboxylic anhydrides and amides from the corresponding carboxylic acids.By means of this reagent, various types of acid-sensitive carboxylic anhydrides and amides were obtained almost in quantative yields.Twenty-two examples of carboxylic anhydrides and 12 examples of amides were presented.
- Kita, Yasuyuki,Akai, Shuji,Ajimura, Naomi,Yoshigi, Mayumi,Tsugoshi, Teruhisa,et al.
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p. 4150 - 4158
(2007/10/02)
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- A MILD AND FACILE SYNTHESIS OF CARBOXYLIC ANHYDRIDES
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Reaction of carboxylic acids with trimethylsilylethoxyacetylene in an inert solvent under mild conditions affords the corresponding carboxylic anhydrides in almost quantitative yields.
- Kita, Y.,Akai, S.,Yoshigi, M.,Nakajima, Y.,Yasuda, H.,Tamura, Y.
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p. 6027 - 6030
(2007/10/02)
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- UNE METHODE SIMPLE ET RAPIDE DE PREPARATION DES ANHYDRIDES D'ACIDES CARBOXYLIQUES A PARTIR DE LEURS CHLORURES D'ACIDES, AVEC CATALYSE PAR TRANSFERT DE PHASE
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Symmetrical anhydrides of carboxylic acids were readily obtained, and in high yields under phase transfer conditions, i.e. by reacting the appropriate acid chloride in toluene solution (containing 0.1 eq. of n-Bu4N+ Cl-), with 20percent aqueous sodium hydroxide solution.
- Roulleau, Fabienne,Plusquellec, Daniel,Brown, Eric
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p. 4195 - 4196
(2007/10/02)
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- Synthesis and Tautomeric Structures of Acyl-Cyclopentane-1,2,4-triones
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A series of acyl-cyclopentane-1,2,4-triones containing alkyl substituents of different length have been prepared by acylating 3-substituted cyclopentane-1,2,4-triones, using gaseous BF3 as catalyst.The 1H and 13C n.m.r. spectra of these compounds have been analysed in order to gain information about the tautomeric forms favoured by the acyl-cyclopentanetriones.
- Franklin, Roger W.,Ward, Robert S.,Roberts, David W.
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p. 3246 - 3260
(2007/10/02)
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- Synthesis of fatty acid anhydrides by reaction with dicyclohexylcarbodiimide.
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A simple method is described for the preparation of caprylic, palmitic, stearic, and oleic anhydrides. Reaction of the free fatty acid and dicyclohexylcarbodiimide in carbon tetrachloride at room temperature gives the corresponding anhydrides in high yield (87-94%).
- Selinger,Lapidot
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p. 174 - 175
(2007/10/12)
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