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      Palladium-Catalyzed Synthesis and Anticancer Activity of Paclitaxel–Dehydroepiandrosterone Hybrids

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          Abstract

          According to the activity–structure relationship of the C-13 side chain in paclitaxel or docetaxel, eighteen novel paclitaxel–dehydroepiandrosterone (DHEA) hybrids were designed and synthesized by Pd(II)-catalyzed Suzuki–Miyaura cross-coupling of 17-trifluoromethanesulfonic enolate-DHEA with different aryl boronic acids. The in vitro anticancer activity of the hybrids against a human liver cancer cell line (HepG-2) was evaluated by MTT assay, showing that most of these hybrids possessed moderate antiproliferative activity against the HepG-2 cancer cell line. Among these hybrids, three ones ( 7b, 7g, and 7i) with ortho-substituents in the phenyl group of the D-ring of DHEA analogues exhibited moderate anticancer activity. The optimal compound 7i showed superior anticancer activity against the HepG-2 cell line with an IC 50 value of 26.39 μM.

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          Insights into the mechanism of microtubule stabilization by Taxol.

          Susan Band Horwitz, Pascal Verdier-Pinard, Ruth H. Angeletti … (2006)
          The antitumor drug Taxol stabilizes microtubules and reduces their dynamicity, promoting mitotic arrest and cell death. Upon assembly of the alpha/beta-tubulin heterodimer, GTP bound to beta-tubulin is hydrolyzed to GDP reaching a steady-state equilibrium between free tubulin dimers and microtubules. The binding of Taxol to beta-tubulin in the polymer results in cold-stable microtubules at the expense of tubulin dimers, even in the absence of exogenous GTP. However, there is little biochemical insight into the mechanism(s) by which Taxol stabilizes microtubules. Here, we analyze the structural changes occurring in both beta- and alpha-tubulin upon microtubule stabilization by Taxol. Hydrogen/deuterium exchange (HDX) coupled to liquid chromatography-electrospray ionization MS demonstrated a marked reduction in deuterium incorporation in both beta-and alpha-tubulin when Taxol was present. Decreased local HDX in peptic peptides was mapped on the tubulin structure and revealed both expected and new dimer-dimer interactions. The increased rigidity in Taxol microtubules was distinct from and complementary to that due to GTP-induced polymerization. The Taxol-induced changes in tubulin conformation act against microtubule depolymerization in a precise directional way. These results demonstrate that HDX coupled to liquid chromatography-electrospray ionization MS can be effectively used to study conformational effects induced by small ligands on microtubules. The present study also opens avenues for locating drug and protein binding sites and for deciphering the mechanisms by which their interactions alter the conformation of microtubules and tubulin dimers.
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            Novel Steroidal Inhibitors of Human Cytochrome P45017.alpha.-Hydroxylase-C17,20-lyase): Potential Agents for the Treatment of Prostatic Cancer

            Martin Rowlands, Michael Jarman, S. Barrie … (1995)
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              Synthesis of Functionalized Alkenes by a Transition-Metal-Free Zweifel Coupling.

              Roly J. Armstrong, Worawat Niwetmarin, Varinder K Aggarwal (2017)
              The Zweifel reaction is a powerful method for the synthesis of alkenes, serving as a transition-metal-free alternative to the Suzuki-Miyaura reaction. To date, the scope of the Zweifel coupling has been rather narrow and has focused mainly on the coupling of vinyllithium reagents to synthesize simple aryl- and alkyl-substituted olefins. Herein, the development of a general transition-metal-free coupling process enabling the coupling of Grignard reagents or organolithiums is described. This method enables the enantiospecific synthesis of a wide variety of functionalized acyclic and cyclic olefin products.
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Omega
                Journal ID (iso-abbrev): ACS Omega
                Journal ID (publisher-id): ao
                Journal ID (coden): acsodf
                Title: ACS Omega
                Publisher: American Chemical Society
                ISSN (Electronic): 2470-1343
                Publication date (Electronic): 09 March 2020
                Publication date Collection: 17 March 2020
                Volume: 5
                Issue: 10
                Pages: 5589-5600
                Affiliations
                [† ]School of Life Science and Engineering, Southwest Jiaotong University , No. 111, Erhuan Road, Chengdu 610031, PR China
                [‡ ]Chengdu Institute of Biology, Chinese Academy of Sciences , No. 9, Section 4, South Renmin Road, Chengdu 610041, PR China
                Author notes
                [* ]E-mail: fangdm@ 123456cib.ac.cn (D.-M.F.).
                [* ]E-mail: gaof@ 123456swjtu.edu.cn (F.G.).
                Article
                DOI: 10.1021/acsomega.0c00558
                PMC ID: 7081646
                SO-VID: d555fa82-25a3-4117-b0a0-f63d3c4864c0
                Copyright © Copyright © 2020 American Chemical Society
                License:

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

                History
                Date received : 07 February 2020
                Date accepted : 26 February 2020
                Categories
                Subject: Article
                Custom metadata
                document-id-old-9 ao0c00558
                document-id-new-14 ao0c00558
                ccc-price

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