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.
-
Plattner,J.J. et al.
, p. 4933 - 4934 (1969)
-
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
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
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.
