17814-85-6Relevant articles and documents
Synthesis of Methyl (5Z,9Z,17R)-17-Methylnonadeca-5,9-dienoate, the (R)-Enantiomer of the Structure Proposed for a Metabolite of the Philippine Sponge Plakinastrella sp.
Takagi, Miho,Takikawa, Hirosato,Mori, Kenji
, p. 2065 - 2069 (2001)
The (R)-enantiomer (1) of methyl (5Z,9Z)-17-methylnonadeca-5,9-dienoate, the structure proposed for a metabolite of the Philippine sponge, Plakinastrella sp., was synthesized. The 1H- and 13C-NMR spectra of the synthetic material were different from those reported for the natural product. The proposed structure 1 is therefore incorrect.
Mitochondria-Targeted Lupane Triterpenoid Derivatives and Their Selective Apoptosis-Inducing Anticancer Mechanisms
Ye, Yaqing,Zhang, Tao,Yuan, Huiqing,Li, Defeng,Lou, Hongxiang,Fan, Peihong
, p. 6353 - 6363 (2017)
Betulin and betulinic acid have been widely studied for their anticancer activities. However, their further development is limited due to low bioavailability, poor aqueous solubility, and limited intracellular accumulation. In the present study, a triphenylphosphonium cation moiety was linked to betulin and betulinic acid to specifically target them to cancer cell mitochondria. Biological characterization established that uptake of mitochondria-targeted compound 1a in the mitochondria of cancer cells was increased compared to betulin. The mitochondria-targeted derivatives of betulin and betulinic acid showed stronger cytotoxicity than their parent drugs and exhibited more cytotoxic effects in cancer cells than normal cells. The mechanisms may involve the mitochondrial apoptotic pathway, probably caused by the induction of reactive oxygen species production and reducing mitochondrial membrane potential. More importantly, 1a significantly inhibited cancer cell proliferation and migration in an in vivo zebrafish xenograft model. Collectively, these results encourage further study of 1a analogs as anticancer agents.
Synthesis and Kinetic Studies of a Simple Prostacyclin Model
Bergman, Nils-Ake,Jansson, Marie,Chiang, Yvonne,Kresge, A. Jerry,Yin, Ya
, p. 4449 - 4453 (1987)
A simple prostacyclin model, (Z)-6,9-epoxynon-5-enoic acid, has been synthesized, and the rate of hydrolysis of the vinyl ether functional group of it and its methyl ester has been measured by monitoring UV spectral changes over the pH range 1-8 at 25.0 +/- 0.1 deg C and total ionic strength 0.1 M.The measurements show that (Z)-6,9-epoxynon-5-enoic acid is 82 times more reactive than its methyl ester at high pH when the carboxylic acid group is in an ionized form.The present results indicate that the simple model closely mimics the behavior of prostacyclin.
Rational design of mitochondria-targeted pyruvate dehydrogenase kinase 1 inhibitors with improved selectivity and antiproliferative activity
Xu, Biao,Yu, Zhimei,Xiang, Sichuan,Li, Yunshan,Zhang, Shao-Lin,He, Yun
, p. 275 - 284 (2018)
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
Convenient approach for the synthesis of ONO-LB-457, a potent leukotriene B4 receptor antagonist
Hamri, Salha,Jouha, Jabrane,Oumessaoud, Asmaa,Pujol,Khouili, Mostafa,Guillaumet, Gérald
, (2020/12/07)
This study reports a new approach for the synthesis of 5-[2-(2-carboxyethyl)-3-[6-(4-methoxyphenyl)-(5E)-hexen-1-yloxy]phenoxy]pentanoic acid V (ONO-LB-457), previously described by Konno and col. and which is considered a highly potent and orally active
Binding and action of triphenylphosphonium analog of chloramphenicol upon the bacterial ribosome
Chen, Chih-Wei,Pavlova, Julia A.,Lukianov, Dmitrii A.,Tereshchenkov, Andrey G.,Makarov, Gennady I.,Khairullina, Zimfira Z.,Tashlitsky, Vadim N.,Paleskava, Alena,Konevega, Andrey L.,Bogdanov, Alexey A.,Osterman, Ilya A.,Sumbatyan, Natalia V.,Polikanov, Yury S.
, (2021/04/23)
Chloramphenicol (CHL) is a ribosome-targeting antibiotic that binds to the peptidyl transferase center (PTC) of the bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving the properties of this inhib
A mitochondrial targeting of the nano drug delivery system and its preparation method and application
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Paragraph 0046; 0062-0063, (2019/04/18)
The invention discloses a mitochondrion-targeting nano-drug delivery system, comprising polyethylene glycol connected with TPP and thioketal linker connected with a chemotherapeutic drug, the polyethylene glycol and the thioketal linker are connected with
Impact of Mitochondrion-Targeting Group on the Reactivity and Cytostatic Pathway of Platinum(IV) Complexes
Jin, Suxing,Hao, Yigang,Zhu, Zhenzhu,Muhammad, Nafees,Zhang, Zhenqin,Wang, Kun,Guo, Yan,Guo, Zijian,Wang, Xiaoyong
, p. 11135 - 11145 (2018/09/14)
Platinum(IV) complexes are prodrugs of cisplatin with multiple potential advantages over platinum(II) drugs. Mitochondria play pivotal roles in producing energy and inducing death of cancer cells. Two platinum(IV) complexes, namely, c,c,t-[Pt(NH3)2Cl2(OH)(OCOCH2CH2CH2CH2PPh3)]Br and c,c,t-[Pt(NH3)2Cl2(OCOCH2CH2CH2CH2PPh3)2]Br2, were designed to explore the effect of mitochondrion-targeting group(s) on the bioactivity and cytotoxicity of platinum(IV) complexes. The complexes were characterized by electrospray ionization mass spectrometry, reverse-phase high-performance liquid chromatography, and multinuclear (1H, 13C, 31P, and 195Pt) NMR spectroscopy. The introduction of triphenylphosphonium targeting group(s) markedly influences the reactivity and cytotoxicity of the Pt(IV) complexes. The targeted complex displays more potent disruptive effect on mitochondria but less inhibitory effect on cancer cells than cisplatin. The lipophilicity of the Pt(IV) complexes is enhanced by the targeting group(s), while their reactivity to DNA is decreased. As a result, the mitochondrial morphology and adenosine triphosphate producing ability are impaired, which constitutes an alternative pathway to inhibit cancer cells. This study shows that both the reactivity of platinum(IV) center and the property of axial targeting ligand exert influences on the cytotoxicity of targeted Pt(IV) complexes. For targeting groups with pharmacological activities, their intrinsic function could enrich the anticancer mechanism of Pt(IV) complexes.
Quaternary phosphonium salt modified dendritic polymer preparation and application of
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Paragraph 0143; 0144; 0145, (2018/01/19)
The invention belongs to the technical field of biological materials, and particularly relates to preparation and application of a quaternary phosphonium salt modified dendriform molecule. The invention provides a quaternary phosphonium salt and a prepara
Combination of Lewis Basic Selenium Catalysis and Redox Selenium Chemistry: Synthesis of Trifluoromethylthiolated Tertiary Alcohols with Alkenes
Zhu, Zechen,Luo, Jie,Zhao, Xiaodan
supporting information, p. 4940 - 4943 (2017/09/23)
A new and efficient method for diaryl selenide catalyzed vicinal CF3S hydroxylation of 1,1-multisubstitued alkenes has been developed. Various trifluoromethylthiolated tertiary alcohols could be readily synthesized under mild conditions. This method is also effective for the intramolecular cyclization of alkenes tethered by carboxylic acid, hydroxy, sulfamide, or ester groups and is associated with the introduction of a CF3S group. Mechanistic studies have revealed that the pathway involves a redox cycle between Se(II) and Se(IV) and Lewis basic selenium catalysis.
