- Interaction of 10-(octyloxy) decyl-2-(trimethylammonium) ethyl phosphate with mimetic membranes and cytotoxic effect on leukemic cells
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10-(Octyloxy) decyl-2-(trimethylammonium) ethyl phosphate (ODPC) is an alkylphospholipid that can interact with cell membranes because of its amphiphilic character. We describe here the interaction of ODPC with liposomes and its toxicity to leukemic cells
- dos Santos,Thome,Ferreira,Yoneda,Nobre,Daghastanli,Scheucher,Gimenes-Teixeira,Constantino,de Oliveira,Faca,Falcao,Greene,Rego,Ciancaglini
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- LIPID PRODRUGS OF NEUROSTEROIDS
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00384-00385
(2021/08/13)
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- Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
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Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
- Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 3583 - 3588
(2020/08/05)
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- LIPID PRODRUGS OF PREGNANE NEUROSTEROIDS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00334; 00335
(2020/02/23)
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- LIPID PRODRUGS OF JAK INHIBITORS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00453-00454
(2020/09/12)
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- LIPID PRODRUGS OF BTK INHIBITORS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00405; 00462; 00463
(2020/09/12)
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- LIPID PRODRUGS OF GLUCOCORTICOIDS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00446; 00447
(2020/09/12)
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- Systematic synthesis of novel phosphoglycolipid analogues as potential agonists of GPR55
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Rhodopsin-like G protein-coupled receptor (GPCR) GPR55 is attracting attention as a pharmaceutical target, because of its relationship with various physiological and pathological events. Although GPR55 was initially deorphanized as a cannabinoid receptor,
- Abe, Junpei,Ding, Feiqing,Greimel, Peter,Guy, Adam T.,Hirabayashi, Yoshio,Ito, Yukishige,Kamiguchi, Hiroyuki
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supporting information
p. 8467 - 8473
(2020/11/05)
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- SYNTHETIC INNATE IMMUNE RECEPTOR LIGANDS AND USES THEREOF
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An adjuvant formulation includes a monophosphoryl Lipid A (MPLA) analogue, a Pam3CSK4 analogue, or a muramyldipeptide (MDP) analogue, or combinations thereof. The adjuvant may be formulated in soluble form or in a nanoparticle, such as polylactic glycolic acid nanoparticles. A vaccine formulation comprises the adjuvant formulation and an immunogen. Methods of vaccinating an animal include delivering the vaccine formulation to the animal.
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Paragraph 0050
(2020/06/10)
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- LYMPHATIC SYSTEM-DIRECTING LIPID PRODRUGS
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a provided lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00463; 00464
(2019/03/17)
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- Additional nucleophile-free FeCl3-catalyzed green deprotection of 2,4-dimethoxyphenylmethyl-protected alcohols and carboxylic acids
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The deprotection of the methoxyphenylmethyl (MPM) ether and ester derivatives can be generally achieved by the combinatorial use of a catalytic Lewis acid and stoichiometric nucleophile. The deprotections of 2,4-dimethoxyphenylmethyl (DMPM)-protected alcohols and carboxylic acids were found to be effectively catalyzed by iron(III) chloride without any additional nucleophile to form the deprotected mother alcohols and carboxylic acids in excellent yields. Since the present deprotection proceeds via the self-assembling mechanism of the 2,4-DMPM protective group itself to give the hardly-soluble resorcinarene derivative as a precipitate, the rigorous purification process by silica-gel column chromatography was unnecessary and the sufficiently-pure alcohols and carboxylic acids were easily obtained in satisfactory yields after simple filtration.
- Sawama, Yoshinari,Masuda, Masahiro,Honda, Akie,Yokoyama, Hiroki,Park, Kwihwan,Yasukawa, Naoki,Monguchi, Yasunari,Sajiki, Hironao
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p. 778 - 784
(2016/07/16)
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- TOCOPHEROL AND TOCOPHERYL QUINONE DERIVATIVES AS CORRECTORS OF LYSOSOMAL STORAGE DISORDERS
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The subject invention relates to improved tocopheryl quinone derivatives and tocopherol derivatives having improved pharmacokinetics in vivo that can, in some embodiments, be useful in the treatment of Lysosomal Storage Disorders, restoration of normal mi
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Paragraph 0081-0082
(2016/08/17)
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- Design, Synthesis, and Immunological Evaluation of Benzyloxyalkyl-Substituted 1,2,3-Triazolyl α-GalCer Analogues
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Replacement of the amide moiety in the structure of α-GalCer with a 1,2,3-triazole linker is known to elicit a response skewed toward Th2 immunity, and glycolipids containing an aromatic ring in the terminus of their acyl or phytosphingosine structural component exhibit an enhanced Th1 immune response. In the current study, synthesis and immunological screening of a focused library of benzyloxyalkyl-substituted 1,2,3-triazolyl α-GalCer analogues are reported. The novel α-GalCer analogues activate invariant natural killer T (iNKT) cells via CD1d mediated presentation, which was confirmed by in vitro tests performed on iNKT hybridomas incubated with CD1d proteins. When tested on isolated murine splenocytes, the T1204B and T1206B compounds stimulated higher levels of both IFN-γ and IL-4 cytokine expression in vitro compared to that of α-GalCer.
- Verma, Yogesh Kumar,Reddy, Bonam Srinivasa,Pawar, Mithun S.,Bhunia, Debabrata,Sampath Kumar, Halmuthur M.
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supporting information
p. 172 - 176
(2016/03/01)
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- Influence of the side-chain structure and molecular weight on the re-entrant behaviors of mesogen-jacketed liquid crystalline polymers
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Three series of mesogen-jacketed liquid crystalline polymers (MJLCPs) containing different terminal groups (phenmethyl, diphenylmethyl and triphenylmethyl) in the side chains, abbreviated as Pv-m-Bn, Pv-m-DPM, Pv-m-Tr (m = 2, 4, 6, 8, 10, and 12, which are the number of methylene units between the terephthalate core and terminal groups in the side chains), were designed and successfully synthesized via free-radical polymerization. Molecular characterization of the polymers was performed by 1H NMR, GPC and TG analysis. The phase structures and transitions of the polymers were investigated by a combination of techniques including DSC, POM and 1D/2D WAXD. The experimental results revealed that all the polymers exhibited excellent thermal stabilities and the re-entrant behaviors of the MJLCPs were found to be strongly dependent on the structure of the side-chain, i.e., the spacer length increased with the volume of the terminal groups when the polymers exhibited the re-entrant isotropic phase. On the other hand, a series of MJLCPs, poly{2,5-bis[(diphenylmethoxy-ethyl)oxycarbonyl]-styrenes} (Pv-2-DPMs), with different molecular weights (Mn) and narrow Mn distributions have been successfully synthesized via ATRP. The results indicated that when the Mn was below 1.73 × 104 g mol-1, only the isotropic phase was observed. When Mn was between 3.40 × 104 g mol-1 and 8.48 × 104 g mol-1, a re-entrant isotropic phase was formed at low temperatures and a columnar nematic phase at high temperatures. By further increasing the Mn to exceed 9.71 × 104 g mol-1, a stable columnar nematic phase was developed. This work provides two effective ways to design and synthesize MJLCPs with re-entrant behaviors; moreover, it is meaningful to deeply understand the structure-property relationships of MJLCPs.
- Xiang, Zheng,Chen, Sheng,Luo, Yongbing,Li, Ping,Zhang, Hailiang
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p. 78516 - 78527
(2016/09/09)
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- FeCl3-catalyzed self-cleaving deprotection of methoxyphenylmethyl-protected alcohols
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4-Methoxyphenylmethyl ethers are widely utilized as alcohol protecting groups. FeCl3 effectively catalyzes the deprotection of methoxyphenylmethyl-type ethers in a self-cleaving manner to produce oligomeric derivatives and alcohols. Remarkably, the highly pure mother alcohols can be obtained without silica gel column chromatography by using the 2,4-dimethoxyphenylmethyl group as a protective group.
- Sawama, Yoshinari,Masuda, Masahiro,Asai, Shota,Goto, Ryota,Nagata, Saori,Nishimura, Shumma,Monguchi, Yasunari,Sajiki, Hironao
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supporting information
p. 434 - 437
(2015/03/03)
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- Specific maltose derivatives modulate the swarming motility of nonswarming mutant and inhibit bacterial adhesion and biofilm formation by pseudomonas aeruginosa
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We have demonstrated that specific synthetic maltose derivatives activate the swarming motility of a Pseudomonas aeruginosa nonswarming mutant (rhlA) at low concentration, but inhibit it at high concentration. Although these molecules are not microbicidal, active maltose derivatives with bulky hydrocarbon groups inhibited bacterial adhesion, and exhibited biofilm inhibition and dispersion (IC50 ~20 μM and DC50 ~30 μM, respectively). Because the swarming motility of the rhlA mutant is abolished by the lack natural rhamnolipids, the swarming activation suggests that maltose derivatives are analogues of rhamnolipids. Together, these results suggest a new approach of controlling multiple bacterial activities (bacterial adhesion, biofilm formation, and swarming motility) by a set of disaccharide-based molecules.
- Shetye, Gauri S.,Singh, Nischal,Jia, Changqing,Nguyen, Chan D.K.,Wang, Guirong,Luk, Yan-Yeung
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p. 1514 - 1523
(2014/07/21)
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- Mitochondria-Targeted Inhibitors of Cytochrome C Peroxidase for Protection from Apoptosis
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The present application is directed to novel imidazole-substituted fatty acids that have been functionalized with an alkyl triphenylphosphonium group, compositions comprising these compounds and their use as inhibitors of cytochrome c peroxidase, in particular for the treatment and prevention of apoptosis.
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Paragraph 0314-0316
(2013/08/15)
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- Total synthesis of nominal gobienine A
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The lichen-derived glycoconjugate gobienine A is structurally more complex than most glycolipids isolated from higher plants by virtue of the all-cis substituted γ-lactone substructure embedded into its macrocyclic frame. A concise entry into this very epimerization-prone and hence challenging structural motif is presented, which relies on an enantioselective cyanohydrin formation, an intramolecular Blaise reaction, a palladium-catalyzed alkoxycarbonylation, and a diastereoselective hydrogenation of the tetrasubstituted alkene in the resulting butenolide. This strategy, in combination with ring-closing olefin metathesis for the formation of the macrocyclic perimeter, allowed the proposed structure of gobienine A (1) to be formed in high overall yield. The recorded spectral data show that the structure originally attributed to gobienine A is incorrect and that it is not the epimerization-prone ester site on the butanolide ring that is the locus of misassignment; rather, the discrepancy must be more profound. Copyright
- Kondoh, Azusa,Arlt, Alexander,Gabor, Barbara,Fürstner, Alois
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supporting information
p. 7731 - 7738
(2013/07/19)
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- Synthesis and properties of monofluorinated dimyristoylphosphatidylcholine derivatives: Potential fluorinated probes for the study of membrane topology
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The synthesis of three monofluorinated dimyristoylphosphatidylcholine derivatives (F-DMPC), with the fluorine atom located on the acyl chain in position 2 of the glycerol (sn-2) is described. The synthetic strategy relies on the coupling of 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (lyso-PC) and three different fluorinated fatty acids. The latter were obtained from two different and complementary synthetic routes. Preliminary FTIR studies suggest that the presence of the fluorine atom does not significantly perturb the lipid conformational order and phase transition temperature and that these monofluorinated PC derivatives could be used as probes for the study of membrane topology, i.e. the location of drugs, peptides or proteins in membranes. The Royal Society of Chemistry 2012.
- Guimond-Tremblay, Jonathan,Gagnon, Marie-Claude,Pineault-Maltais, Jozy-Ann,Turcotte, Vanessa,Auger, Michele,Paquin, Jean-Franois
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supporting information; experimental part
p. 1145 - 1148
(2012/03/07)
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- Regio- and chemoselective one-step 3-O-alkylenation of unprotected ascorbic acid using ω-iodoalkanols
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A regio- and chemoselective alkylenation employing unprotected ascorbic acid and a series of unprotected iodoalkanols in the presence of sodium hydrogen carbonate in dimethyl sulfoxide is described. This atom economic high yielding procedure delivers the
- Muller, Thierry,Heuschling, Paul,Luu, Bang
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scheme or table
p. 217 - 220
(2009/06/05)
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- Triethyl- (or trimethyl-)silyl triflate-catalyzed reductive cleavage of triphenylmethyl (trityl) ethers with triethylsilane
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(Matrix presented) A triphenylmethyl (trityl) ether was reductively and instantaneously cleaved by triethylsilane in the presence of a catalytic amount of TES- (or TMS)-triflate. The reaction conditions are mild enough to achieve reduction in the presence
- Imagawa, Hiroshi,Tsuchihashi, Tomoko,Singh, Rajesh K.,Yamamoto, Hirofumi,Sugihara, Takumichi,Nishizawa, Mugio
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p. 153 - 155
(2007/10/03)
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- Synthesis and antiproliferative activity of alkylphosphocholines
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Alkylphosphocholines (APC) with one or more methylene groups in the alkyl chain replaced by oxygen atoms or carbonyl groups, or both have been assembled modularly using ω-diols as central building blocks. Out of 25 new compounds of this kind, 11 were evaluated for their antiproliferative activity on four cell lines and compared with miltefosine to evaluate their hemolytic activity (HA) and cytotoxicity on non-tumoral cells (MT2), used as markers of adverse effects. Compound 13 was more active on cancer cell lines than on non-tumoral cells and the data were similar for MTT and thymidine incorporation assays. It had less HA than miltefosine. Compound 13 could therefore be a candidate for the preparation of compounds with higher cytotoxicity on cancer cells and lower general toxicity.
- Agresta, Mandy,D'Arrigo, Paola,Fasoli, Ezio,Losi, Daniele,Pedrocchi-Fantoni, Giuseppe,Riva, Simona,Servi, Stefano,Tessaro, Davide
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p. 201 - 210
(2007/10/03)
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- An efficient synthesis of sulfobacin A (flavocristamide B), sulfobacin B, and flavocristamide A
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Sulfobacin A (flavocristamide B, 1), sulfobacin B (2), and flavocristamide A (3), biologically active sulfonolipids, have been efficiently synthesized utilizing the asymmetric aldol reaction of the Schiff base 8 derived from glycine ester and (+)-2-hydroxy-3-pinanone (HyPN). (C) 2000 Elsevier Science Ltd.
- Shioiri, Takayuki,Irako, Naoko
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p. 9129 - 9142
(2007/10/03)
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- Total synthesis of sulfobacin A (flavocristamide B)
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Sulfobacin A (1), a novel von Willebrand factor receptor antagonist isolated from the culture broth of Chryseobacterium sp. NR 2993, was efficiently synthesized for the first time.
- Irako, Naoko,Shioiri, Takayuki
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p. 5793 - 5796
(2007/10/03)
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- Synthesis of topostins B567 and D654 (WB-3559D, flavolipin), DNA topoisomerase I inhibitors of bacterial origin
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Topostins B567 (2b) and D654 (3b) (WB-3559D, flavolipin) have been efficiently synthesized from 1,10-decanediol (5)in 11 and 13 steps, respectively, involving an asymmetric hydrogenation of the β-keto ester 14 using (R)-BINAp ruthenium bromide and a peptide coupling using diethyl phosphorocyanidate (DEPC, (EtO)2P(O)CN) as key steps.
- Shioiri, Takayuki,Terao, Yoshihiro,Irako, Naoko,Aoyama, Toyohiko
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p. 15701 - 15710
(2007/10/03)
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- Synthesis of the Cyclostellettamines A-F and Related Bis(3-alkylpyridinium) Macrocycles
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A general method was developed for the synthesis of a variety of symmetric and asymmetric macrocyclic bispyridines. 3-Hydroxyalkylpyridines 18-20 were prepared, converted to the corresponding iodides and protected on the pyridine nitrogen with a p-methoxy
- Wanner, Martin J.,Koomen, Gerrit-Jan
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p. 889 - 895
(2007/10/03)
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- Highly selective Silver(I) oxide mediated monoprotection of symmetrical diols
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Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.
- Bouzide, Abderrahim,Sauve, Gilles
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p. 5945 - 5948
(2007/10/03)
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- Monobenzylation of 1,n-diols via dibutylstannylene intermediates
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Symmetrical primary 1,n-diols, HO(CH2)(n)OH, of any chain length from n = 2-10, can be selectively monobenzylated via sequential treatment with dibutyltin oxide and benzyl bromide.
- Mash, Eugene A.,Kantor, Liza T. A.,Waller, Stephen C.
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p. 507 - 514
(2007/10/03)
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- Deprotection of mono and dimethoxy phenyl methyl ethers using catalytic amounts of DDQ
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4-Methoxy and 3,4 dimethoxy benzyl ethers have been deprotected with catalytic amounts of DDQ by oxidative recycling of the byproduct DDHQ with FeCl3 for the first time.
- Chandrasekhar,Sumithra,Yadav
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p. 1645 - 1646
(2007/10/03)
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- The First Total Synthesis of (+)-Bullatacin, a Potent Antitumor Annonaceous Acetogenin, and (+)-(15,24)-bisepi-Bullatacin
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This paper reports the first total synthesis of the natural product (+)-bullatacin (1), a representative of potent antitumor Annonaceous acetogenins, as well as a stereoisomer (+)-(15,24)-bisepi-bullatacin (2).In this synthesis, a new, efficient method has been developed to introduce the γ-lactone into the bistetrahydrofuran skeleton through in situ alkylation of epoxide 4 by the α-sulfonyl carbanion of phenylsulfone 5.The methylated γ-lactone was successfully synthesized by a sequence of reactions comprising an aldol reaction, an acidic lactonization, and elimination under mild, basic condition.
- Naito, Hiroyuki,Kawahara, Eiji,Maruta, Katsunori,Maeda, Minoru,Sasaki, Shigeki
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p. 4419 - 4427
(2007/10/02)
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- Four New Polyacetylenic Glucosides, Methyl β-D-Glucopyranosyl Helianthenate C-F, from Jerusalem Artichoke (Helianthus tuberosus L.)
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Four new polyacetylenic glucosides isolated from the leaf of Jerusalem artichoke (Helianthus tuberosus L.) were characterized as methyl β-D-glucopyranosyl helianthenate C (5), D (6), E (7), and F (8).The absolute stereochemistry of the glucosyloxymethine
- Matsuura, Hideyuki,Yoshihara, Teruhiko,Ichihara, Akitami
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p. 1492 - 1498
(2007/10/02)
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