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  1. Article: Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore

    Brumley, David A / Gunasekera, Sarath P / Chen, Qi-Yin / Paul, Valerie J / Luesch, Hendrik

    Organic letters. 2020 May 16, v. 22, no. 11

    2020  

    Abstract: New modified depsipeptides and geometric isomers, termed anaenamides A (1a) and B (1b), along with the presumptive biosynthetic intermediate, anaenoic acid (2), were discovered from a marine cyanobacterium from Guam. Structures were confirmed by total ... ...

    Abstract New modified depsipeptides and geometric isomers, termed anaenamides A (1a) and B (1b), along with the presumptive biosynthetic intermediate, anaenoic acid (2), were discovered from a marine cyanobacterium from Guam. Structures were confirmed by total synthesis. The alkylsalicylic acid fragment and the C-terminal α-chlorinated α,β-unsaturated ester are novelties in cyanobacterial natural products. Cancer cell viability assays indicated that the C-terminal unit serves as the pharmacophore and that the double-bond geometry impacts the cytotoxicity.
    Keywords biosynthesis ; cell viability ; cytotoxicity ; depsipeptides ; geometry ; neoplasm cells ; pharmacology ; Guam
    Language English
    Dates of publication 2020-0516
    Size p. 4235-4239.
    Publishing place American Chemical Society
    Document type Article
    Note NAL-AP-2-clean
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.0c01281
    Database NAL-Catalogue (AGRICOLA)

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  2. Article ; Online: Discovery, Synthesis, and Biological Evaluation of Anaenamides C and D from a New Marine Cyanobacterium,

    Brumley, David A / Gunasekera, Sarath P / Sauvage, Thomas / Dos Santos, Larissa A H / Chen, Qi-Yin / Paul, Valerie J / Luesch, Hendrik

    Journal of natural products

    2022  Volume 85, Issue 3, Page(s) 581–589

    Abstract: Our ongoing efforts to explore the chemical space associated with marine cyanobacteria from coral reefs of Guam have yielded two new members of the anaenamide family of natural products, anaenamides C ( ...

    Abstract Our ongoing efforts to explore the chemical space associated with marine cyanobacteria from coral reefs of Guam have yielded two new members of the anaenamide family of natural products, anaenamides C (
    MeSH term(s) Amides/pharmacology ; Cyanobacteria/chemistry ; HEK293 Cells ; Humans ; NF-E2-Related Factor 2 ; Phylogeny
    Chemical Substances Amides ; NF-E2-Related Factor 2
    Language English
    Publishing date 2022-02-15
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.1c01073
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 1144: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

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  3. Article: Discovery, Synthesis, and Biological Evaluation of Anaenamides C and D from a New Marine Cyanobacterium, Hormoscilla sp

    Brumley, David A. / Gunasekera, Sarath P. / Sauvage, Thomas / dos Santos, Larissa A. H. / Chen, Qi-Yin / Paul, Valerie J. / Luesch, Hendrik

    Journal of natural products. 2022 Feb. 15, v. 85, no. 3

    2022  

    Abstract: Our ongoing efforts to explore the chemical space associated with marine cyanobacteria from coral reefs of Guam have yielded two new members of the anaenamide family of natural products, anaenamides C (3) and D (4). These compounds were isolated from a ... ...

    Abstract Our ongoing efforts to explore the chemical space associated with marine cyanobacteria from coral reefs of Guam have yielded two new members of the anaenamide family of natural products, anaenamides C (3) and D (4). These compounds were isolated from a novel Hormoscilla sp. (VPG16-58). Our phylogenetic profiling (16S rDNA) of this cyanobacterium indicated that VPG16-58 is taxonomically distinct from the previously reported producer of the anaephenes, VPG16-59 (Hormoscilla sp.), and other previously documented species of the genus Hormoscilla. The planar structures of 3 and 4 were determined via spectroscopic methods, and absolute configurations of the α-hydroxy acids were assigned by enantioselective HPLC analysis. To address the requirement for sufficient material for testing, we first adapted our published linear synthetic approach for 1 and 2 to generate anaenoic acid (7), which served as a point for diversification, providing the primary amides 3 and 4 from synthetic intermediates 5 and 6, respectively. The compounds were then tested for effects on HCT116 colon cancer cell viability and in an ARE-luciferase reporter gene assay for Nrf2 modulation using HEK293 human embryonic kidney cells. Our findings indicate that, in contrast to cytotoxic methyl esters 1 and 2, the primary amides 3 and 4 activate the Nrf2 pathway at noncytotoxic concentrations. Overall, our data suggest that the anaenamide scaffold is tunable to produce differential biological outcomes.
    Keywords amides ; biological assessment ; cell viability ; colorectal neoplasms ; corals ; cytotoxicity ; enantioselectivity ; humans ; kidneys ; neoplasm cells ; phylogeny ; reporter genes ; spectroscopy ; Guam
    Language English
    Dates of publication 2022-0215
    Size p. 581-589.
    Publishing place American Chemical Society and American Society of Pharmacognosy
    Document type Article
    ZDB-ID 304325-3
    ISSN 1520-6025 ; 0163-3864
    ISSN (online) 1520-6025
    ISSN 0163-3864
    DOI 10.1021/acs.jnatprod.1c01073
    Database NAL-Catalogue (AGRICOLA)

    More links

    Kategorien

    In stock of ZB MED Cologne/Königswinter

    Zs.A 1144: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (1.OG)
    ab Jg. 2022: Lesesaal (EG)

    Order via subito

    This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.

  4. Article ; Online: Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore.

    Brumley, David A / Gunasekera, Sarath P / Chen, Qi-Yin / Paul, Valerie J / Luesch, Hendrik

    Organic letters

    2020  Volume 22, Issue 11, Page(s) 4235–4239

    Abstract: New modified depsipeptides and geometric isomers, termed anaenamides A ( ...

    Abstract New modified depsipeptides and geometric isomers, termed anaenamides A (
    MeSH term(s) Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Cell Proliferation/drug effects ; Cell Survival/drug effects ; Cyanobacteria/chemistry ; Dose-Response Relationship, Drug ; Drug Discovery ; Drug Screening Assays, Antitumor ; HCT116 Cells ; Halogenation ; Humans ; Molecular Structure ; Structure-Activity Relationship
    Chemical Substances Antineoplastic Agents
    Language English
    Publishing date 2020-05-16
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.0c01281
    Database MEDical Literature Analysis and Retrieval System OnLINE

    More links

    Kategorien

    Order via subito

    This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.

    Inter-library loan at ZB MED

    Your chosen title can be delivered directly to ZB MED Cologne location if you are registered as a user at ZB MED Cologne.

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