- A Cisplatin-Selective Fluorescent Probe for Real-Time Monitoring of Mitochondrial Platinum Accumulation in Living Cells
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Mitochondria have emerged as important targets for cisplatin in cancer therapy. Apart from cisplatin, anticancer Pt complexes based on similar scaffolds have also been developed to target mitochondria. Yet cellular processing of cisplatin or these mitocho
- Ong, Jun Xiang,Le, Hai Van,Lee, Violet Eng Yee,Ang, Wee Han
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Read Online
- Mitochondria-Targeting Magnetic Composite Nanoparticles for Enhanced Phototherapy of Cancer
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Photothermal therapy (PTT) and photodynamic therapy (PDT) are promising cancer treatment modalities in current days while the high laser power density demand and low tumor accumulation are key obstacles that have greatly restricted their development. Here
- Guo, Ranran,Peng, Haibao,Tian, Ye,Yang, Wuli,Shen, Shun
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Read Online
- Crystal structure of new carboxylate phosphabetaines and phosphonium salts conjugated with them
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Earlier unknown crystalline forms of three carboxylate phosphabetaines and conjugated with them phosphonium salts differing by β substituent with respect to the carboxylate group were studied. The structure of studied compounds in crystal is determined by
- Bakhtiyarova, Yu. V.,Aksunova,Galkina,Galkin,Lodochnikova,Kataeva
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Read Online
- Synthesis and pharmacological characterization of mitochondrial KATP channel openers with enhanced mitochondriotropic effects
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Mitochondria play a key role for deciding fate of cells and thus are considered an attractive target for pharmacological interventions focused on containment of myocardial ischemia/reperfusion (I/R) injury. Notably, the activation of mitochondrial potassi
- Testai, Lara,Sestito, Simona,Martelli, Alma,Gorica, Era,Flori, Lorenzo,Calderone, Vincenzo,Rapposelli, Simona
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- Azole-triphenylphosphonium conjugates combat antifungal resistance and alleviate the development of drug-resistance
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Azole antifungals are commonly used to treat fungal infections but have resulted in the occurrence of drug resistance. Therefore, developing azole derivatives (AZDs) that can both combat established drug-resistant fungal strains and evade drug resistance is of great importance. In this study, we synthesized a series of AZDs with a fluconazole (FLC) skeleton conjugated with a mitochondria-targeting triphenylphosphonium cation (TPP+). These AZDs displayed potent activity against both azole-sensitive and azole-resistant Candida strains without eliciting obvious resistance. Moreover, two representative AZDs, 20 and 25, exerted synergistic antifungal activity with Hsp90 inhibitors against C. albicans strains resistant to the combination treatment of FLC and Hsp90 inhibitors. AZD 25, which had minimal cytotoxicity, was effective in preventing C. albicans biofilm formation. Mechanistic investigation revealed that AZD 25 inhibited the biosynthesis of the fungal membrane component ergosterol and interfered with mitochondrial function. Our findings provide an alternative approach to address fungal resistance problems.
- Wang, Xin,Liu, Jun,Chen, Jinyao,Zhang, Ming,Tian, Chuan,Peng, Xiaoping,Li, Gang,Chang, Wenqiang,Lou, Hongxiang
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- Synthesis of Allylboranes via Cu(I)-Catalyzed B-H Insertion of Vinyldiazoacetates into Phosphine-Borane Adducts
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Cu(I) catalysts enable C-B bond formation via direct insertion of vinyldiazoacetates into B-H bonds of borane-phosphine Lewis adducts to form phosphine-protected allylboranes under mild conditions. The resulting allylborane-phosphine Lewis adducts can be used in the diastereoselective allylation of aldehydes directly without the need for removal of the phosphine. The allylation reaction proceeds with high diastereoselectivity and yields 5,6-disubstituted dihydropyranones after treatment with an appropriate acid.
- Drikermann, Denis,M??el, Robert S.,Al-Jammal, Walid K.,Vilotijevic, Ivan
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supporting information
p. 1091 - 1095
(2020/02/15)
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- Triazole compounds, preparation method and application of triazole compounds in antifungal drugs
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The invention discloses a series of novel triazole compounds obtained by coupling a triazole drug skeleton and diversified lipophilic cations through different chains, and also discloses a preparationmethod of the compounds and application of the compound
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Paragraph 0030; 0034-0035
(2020/09/20)
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- Asymmetric Construction of Cyclobutanes via Direct Vinylogous Michael Addition/Cyclization of β,γ-Unsaturated Amides
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The construction of cyclobutanes has attracted much attention because of its unique four-membered ring skeleton. Herein, we report the highly enantioselective direct vinylogous Michael reaction of β,γ-unsaturated pyrazole amides and nitroolefin using a squaramide catalyst. Cyclobutane derivatives were obtained by subsequent cyclization in good yields (up to 85%) with excellent enantioselectivities (up to 99% ee). Importantly, the large-scale reaction experiment confirmed the reliability of the vinylogous reaction. Furthermore, the synthetic utility of the vinylogous adducts and cyclobutane derivatives has been realized.
- Chen, Yuzhen,Huang, Huicai,Ma, Yan-Yan,Wang, Shuzhong,Wang, Yichen,Zhan, Ruoting,Zhao, Deng-Gao
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supporting information
p. 7135 - 7140
(2020/10/12)
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- Synthesis of [18 F]-γ-Fluoro-α,β-unsaturated Esters and Ketones via Vinylogous 18 F-Fluorination of α-Diazoacetates with [18 F]AgF
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This communication reports a method for the vinylogous radiofluorination of α-diazoacetates to generate [18 F]-γ-fluoro-α,β-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [18 F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated cholest-5-en-3-one derivative as well as a difluorinated product pertinent to drug discovery.
- Brooks, Allen F.,Ichiishi, Naoko,Jackson, Isaac M.,Lee, So Jeong,Sanford, Melanie S.,Scott, Peter J. H.,Thompson, Stephen
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supporting information
p. 4401 - 4407
(2019/11/21)
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- BETA-2 SELECTIVE ADRENERGIC RECEPTOR AGONISTS
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Aspects of the present disclosure include conformationally restricted analogs of catecholamine type compounds (e.g., isoprenaline, adrenaline, noradrenaline) which activate β2AR with high selectivity over β1AR. The subject beta-2 selective adrenergic rece
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Page/Page column 66
(2019/06/23)
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- Rational design of mitochondria-targeted pyruvate dehydrogenase kinase 1 inhibitors with improved selectivity and antiproliferative activity
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Herein, triphenylphosphonium cation moieties were incorporated into a dichloroacetophenone derivative, leading to the discovery of novel mitochondria-targeted and tumor-specific pyruvate dehydrogenase kinase 1 (PDK1) inhibitors. Biological studies suggest
- Xu, Biao,Yu, Zhimei,Xiang, Sichuan,Li, Yunshan,Zhang, Shao-Lin,He, Yun
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p. 275 - 284
(2018/06/20)
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- Tuning the Hydrophobicity of a Mitochondria-Targeted NO Photodonor
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A few compounds in which the nitric oxide (NO) photodonor N-[4-nitro-3-(trifluoromethyl)phenyl]propane-1,3-diamine is joined to the mitochondria-targeting alkyltriphenylphosphonium moiety via flexible spacers of variable length were synthesized. The lipop
- Sodano, Federica,Rolando, Barbara,Spyrakis, Francesca,Failla, Mariacristina,Lazzarato, Loretta,Gazzano, Elena,Riganti, Chiara,Fruttero, Roberta,Gasco, Alberto,Sortino, Salvatore
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p. 1238 - 1245
(2018/05/14)
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- Method for producing an aromatic heterocyclic compound, organic semiconductor material and organic semiconductor device
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PROBLEM TO BE SOLVED: To provide: an aromatic heterocyclic compound which has oxidation stability, high solubility, favorable film production properties and high charge transfer properties, and is suitable as an organic semiconductor material; and organic
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Paragraph 0094; 0096
(2017/06/20)
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- A mitochondrial-targeting and NO-based anticancer nanosystem with enhanced photo-controllability and low dark-toxicity
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Compared to the generation of singlet oxygen in photodynamic therapy, photo-generation of nitric oxide (NO) would not be limited by the concentration of molecular oxygen. However, therapeutic applications of exogenous nitric oxide are usually limited by i
- Xu, Jiangsheng,Zeng, Fang,Wu, Hao,Wu, Shuizhu
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p. 4904 - 4912
(2015/06/25)
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- AROMATIC HETEROCYCLIC COMPOUND, MANUFACTURING METHOD THEREOF, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC SEMICONDUCTOR DEVICE
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Provided are an organic semiconductor material having a high charge mobility, oxidation stability, and solvent solubility, an organic semiconductor device using the same, and a novel aromatic heterocyclic compound to be used for the same and a production
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Paragraph 0183; 0184; 0185; 0187
(2016/11/28)
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- Functionalized phosphonium-based ionic liquids as efficient catalysts for the synthesis of cyclic carbonate from expoxides and carbon dioxide
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A series of novel functionalized phosphonium-based ionic liquids (FPBILs) were synthesized by a simple method, and first evaluated as catalysts for the synthesis of cyclic carbonates through the cycloaddition of CO2 to epoxides in the absence of co-catalyst and solvent. The FPBILs perform well in the cycloaddition reaction, especially the carboxyl-functionalized one. Over [Ph3PC2H4COOH]Br, the yield of propylene carbonate is 97.3% (TOF = 64.9 h-1) at 130 C and 2.5 MPa in 3 h. The synergistic effects of polarization induced by hydrogen bonding and nucleophilic attack of Br-anion account for the excellent performance. Furthermore, the FPBILs with moderate methylene chain length show superior catalytic activity. It is because they have both strong acidity and weak electrostatic interaction between phosphonium cation and halide anion. The strong acidity facilitates the ring-opening of epoxyl, and the weak electrostatic interaction enhances the nucleophilic attack capability of Br -. It is envisaged that the metal- and solvent-free process has high potential for the catalytic conversion of CO2 into value-added chemicals.
- Dai, Wei-Li,Jin, Bi,Luo, Sheng-Lian,Luo, Xu-Biao,Tu, Xin-Man,Au, Chak-Tong
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p. 183 - 188
(2014/01/06)
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- Triphenylphosphonium salts of 1,2,4-benzothiadiazine 1,1-dioxides related to diazoxide targeting mitochondrial ATP-sensitive potassium channels
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The present work aims at identifying new ion channel modulators able to target mitochondrial ATP-sensitive potassium channels (mitoKATP channels). An innovative approach should consist in fixing a cationic and hydrophobic triphenylphosphonium f
- Constant-Urban, Céline,Charif, Mounia,Goffin, Eric,Van Heugen, Jean-Claude,Elmoualij, Bena?ssa,Chiap, Patrice,Mouithys-Mickalad, Ange,Serteyn, Didier,Lebrun, Philippe,Pirotte, Bernard,De Tullio, Pascal
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p. 5878 - 5881
(2013/10/22)
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- Dual targeting of adenosine A2A receptors and monoamine oxidase B by 4H-3,1-benzothiazin-4-ones
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Blockade of A2A adenosine receptors (A2AARs) and inhibition of monoamine oxidase B (MAO-B) in the brain are considered attractive strategies for the treatment of neurodegenerative diseases such as Parkinson's disease (PD). In the present study, benzothiazinones, e.g., 2-(3-chlorophenoxy)- N-(4-oxo-4H-3,1-benzothiazin-2-yl)acetamide (13), were identified as a novel class of potent MAO-B inhibitors (IC50 human MAO-B: 1.63 nM). Benzothiazinones with large substituents in the 2-position, e.g., methoxycinnamoylamino, phenylbutyrylamino, or chlorobenzylpiperazinylbenzamido residues (14, 17, 27, and 28), showed high affinity and selectivity for A 2AARs (Ki human A2AAR: 39.5-69.5 nM). By optimizing benzothiazinones for both targets, the first potent, dual-acting A2AAR/MAO-B inhibitors with a nonxanthine structure were developed. The best derivative was N-(4-oxo-4H-3,1-benzothiazin-2-yl)-4-phenylbutanamide (17, Ki human A2A, 39.5 nM; IC50 human MAO-B, 34.9 nM; selective versus other AR subtypes and MAO-A), which inhibited A 2AAR-induced cAMP accumulation and showed competitive, reversible MAO-B inhibition. The new compounds may be useful tools for validating the A2AAR/MAO-B dual target approach in PD.
- St??el, Anne,Schlenk, Miriam,Hinz, Sonja,Küppers, Petra,Heer, Jag,Gütschow, Michael,Müller, Christa E.
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p. 4580 - 4596
(2013/07/19)
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- Special features of the interaction of pyridine and quinoline derivatives, and related compounds with triphenylphosphine
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Using pyridine, quinoline, and related compounds as examples, it has been shown that their interaction with triphenylphosphine occurs via different pathways. Reaction of triphenylphosphine with N-vinylisonicotinic acid chloride leads to the mixture of 1,2
- Khachikyan,Simonyan,Manukyan,Indzhikyan
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p. 1359 - 1364
(2013/09/23)
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- Phosphorus-based functional groups as hydrogen bonding templates for rotaxane formation
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We report on the use of the hydrogen bond acceptor properties of some phosphorus-containing functional groups for the assembly of a series of [2]rotaxanes. Phosphinamides, and the homologous thio- and selenophosphinamides, act as hydrogen bond acceptors t
- Ahmed, Rehan,Altieri, Andrea,DSouza, Daniel M.,Leigh, David A.,Mullen, Kathleen M.,Papmeyer, Marcus,Slawin, Alexandra M. Z.,Wong, Jenny K. Y.,Woollins, J. Derek
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supporting information; experimental part
p. 12304 - 12310
(2011/10/01)
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- Reaction of 2,3-dihalopropionic acids and their derivatives with P- and N-nucleophiles
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3-(Triphenylphosphoniochlorido)acrylic and 2,3-dichloropropionic acids react with triphenylphosphine to form 1,2-bis(triphenylphosphoniochlorido) ethane. Under analogous conditions, 2,3-dibromopropionic acid undergoes debromination followed by triphenylphosphine addition to give, after water treatment, 3-(triphenylphosphoniobromido)propionic acid. 2,3- Dihalopropionitriles react similarly, providing 3-(triphenylphosphoniohalido) propionitriles. The reaction of 2,3-dibromopropionamide with triphenylphosphine was performed to show that E-(triphenylphosphoniobromido)acrylic acid is capable, by contrast to what was reported previously, of reacting with triphenylphosphine. Pyridine forms with 2,3-dihalopropionic acids vinylpyridinium halides, while the reactions with aliphatic amines gives rise to dehydrohalogenation products.
- Khachikyan,Tovmasyan,Indzhikyan
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p. 1889 - 1894
(2008/02/03)
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- BICYCLIC SUBSTITUTED INDOLE-DERIVATIVE STEROID HORMONE NUCLEAR RECEPTOR MODULATORS
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The present invention provides a compound of the formula: Formula (I); or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising an effective amount of a compound of Formula I in combination with a suitable carrier, diluent, or excipient, and methods for treating physiological disorders, particularly congestive heart disease, hypertension, and atherosclerosis, comprising administering to a patient in thereof an effective amount of a compound of Formula I. X-16125
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(2010/02/14)
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- Total synthesis of optically active m-phenylene PGl2 derivative: Beraprost
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The optical isomers of m-phenylene PGl2 derivative, Beraprost, were synthesized in practical scales from optically active carboxy- cyclopenta[b]benzofurans (12 and 13) by Wittig and Wadsworth reactions as key reactions via the intermediate diols (16a and 16b).
- Wakita, Hisanori,Yoshiwara, Hideo,Nishiyama, Hisao,Nagase, Hiroshi
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p. 1085 - 1110
(2007/10/03)
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- Effective synthesis of ferrulactone II based on the use of 2-carboxyethyltriphenylphosphonium bromide
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A simple synthesis of S,3Z-dodecen-11-olide, a component of the aggregation pheromone of the rusty grain beetle Cryptolestes ferrugineus (Stephen), was developed.The key stage was Wittig olefination of C9-aldehyde, prepared from S-propylene oxide, with C3
- Cheskis, B. A.,Shpiro, N. A.,Moiseenkov, A. M.
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p. 760 - 763
(2007/10/02)
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- Prostaglandin analogues
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New trans-Δ2 -prostaglandins of the formula STR1 (wherein R1 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 10 carbon atoms, R2 represents a 1,1-dimethyl-pentyl group or a 2-ethylheptyl group, the wavy line indicates attachment of the depicted group in α-configuration or racemic form consisting of equimolecular mixtures of α-configuration and β-configuration and the C2 -C3 and C13 -C14 double bonds are trans), which are useful for the treatment of hypertension, contraception menstrual regulation.
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- Trans-Δ2 -prostaglandins
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New process for the preparation of trans-Δ2 -prostaglandins of the formula SPC1 (wherein A represents a grouping of the PGE, PGF or PGA type, X represents --CH2 CH2 -- or trans --CH=CH--, R1 represents an alkyl radical of 1 to 10 carbon atoms or an alkyl radical of 1 to 6 carbon atoms carrying a phenyl substituent or a cycloalkyl substituent of 5 to 7 carbon atoms, R2 represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms) and alkyl esters thereof having 1 to 10 carbon atoms in the chain, which comprises reacting a cyclopentane derivative of the formula: SPC2 (where R3 represents a 2-tetrahydropyranyl group unsubstituted or substituted by at least one alkyl radical, or a 1-ethoxyethyl group) with an alkyl phosphonate of the general formula: EQU1 (wherein R4 represents a methyl or ethyl radical, and R5 represents an alkyl radical of 1 to 10 carbon atoms), optionally hydrolyzing the resulting trans-Δ2 -prostaglandin ester of the general formula: SPC3 To the corresponding acid, optionally converting the 9α-hydroxy radical in the ester or acid product to an oxo group, and hydrolyzing the tetrahydropyranyloxy or ethoxyethoxy groups in the resulting trans-Δ2 -prostaglandin compound of the formula: SPC4 (wherein R6 represents a hydrogen atom or an alkyl radical of 1 to 10 carbon atoms, Z represents EQU2 or C=O) to hydroxy radicals to obtain a trans-Δ2 -PGF or trans-Δ2 -PGE compound of the formula: SPC5 And, if desired, converting the PGE alicyclic ring (Z represents C=O) into that of a PGA compound. The trans-Δ2 -prostaglandin products, which are new compounds except for trans-Δ2 -PGE1, possess typical pharmacological properties of the `natural` prostaglandins.
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- Phenyl-substituted prostaglandin-F type analogs
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This invention is a group of phenyl-substituted PGE-type, PGF-type, PGA-type and PGB-type compounds, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.
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