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  1. Article ; Online: Synthesis of the Aminovinylcysteine-Containing C-Terminal Macrocycle of the Linaridins.

    Lutz, Joshua A / Taylor, Carol M

    Organic letters

    2020  Volume 22, Issue 5, Page(s) 1874–1877

    Abstract: ... ...

    Abstract N
    MeSH term(s) Bacteriocins/chemical synthesis ; Bacteriocins/chemistry ; Cyclization ; Cysteine/analogs & derivatives ; Cysteine/chemical synthesis ; Cysteine/chemistry ; Molecular Structure ; Peptides/chemistry ; Peptides/metabolism
    Chemical Substances Bacteriocins ; Peptides ; cypemycin (154277-21-1) ; S-allylcysteine (81R3X99M15) ; Cysteine (K848JZ4886)
    Language English
    Publishing date 2020-02-11
    Publishing country United States
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.0c00218
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Synthesis of the Aminovinylcysteine-Containing C-Terminal Macrocycle of the Linaridins

    Lutz, Joshua A / Taylor, Carol M

    Organic letters. 2020 Feb. 11, v. 22, no. 5

    2020  

    Abstract: N-Phthalimido-d-cysteine allyl ester was S-alkylated with 2-iodoethanol. The derived β-thioaldehyde was condensed with Nα-tetrachlorophthalimidovalinamide to afford a Z-thioenamide. Removal of the tetrachlorophthalimido protecting group and homologation ... ...

    Abstract N-Phthalimido-d-cysteine allyl ester was S-alkylated with 2-iodoethanol. The derived β-thioaldehyde was condensed with Nα-tetrachlorophthalimidovalinamide to afford a Z-thioenamide. Removal of the tetrachlorophthalimido protecting group and homologation with N-Boc-l-leucine afforded the linear tripeptide. Removal of the Boc and allyl protecting groups, followed by carbodiimide-mediated cyclization, led to the 13-membered ring with the aminovinylcysteine moiety embedded. This constitutes the C-terminal macrocycle of all known members of the linardin family of peptides, including the antileukemia agent, cypemycin.
    Keywords chemical reactions ; moieties ; organic compounds ; tripeptides
    Language English
    Dates of publication 2020-0211
    Size p. 1874-1877.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.0c00218
    Database NAL-Catalogue (AGRICOLA)

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  3. Article ; Online: Low-Efficacy Mu Opioid Agonists as Candidate Analgesics:

    Santos, Edna J / Akbarali, Hamid I / Bow, Eric W / Chambers, Dana R / Gutman, Eugene S / Jacobson, Arthur E / Kang, Minho / Lee, Young K / Lutz, Joshua A / Rice, Kenner C / Sulima, Agnieszka / Negus, S Stevens

    The Journal of pharmacology and experimental therapeutics

    2024  

    Abstract: Low efficacy mu opioid receptor (MOR) agonists may serve as novel candidate analgesics with improved safety relative to high-efficacy opioids. This study used a recently validated assay of pain-depressed behavior in mice to evaluate a novel series of MOR- ...

    Abstract Low efficacy mu opioid receptor (MOR) agonists may serve as novel candidate analgesics with improved safety relative to high-efficacy opioids. This study used a recently validated assay of pain-depressed behavior in mice to evaluate a novel series of MOR-selective C9-substituted phenylmorphan opioids with graded MOR efficacies. Intraperitoneal injection of dilute lactic acid (IP acid) served as a noxious stimulus to depress locomotor activity by mice in an activity chamber composed of two compartments connected by an obstructed door. Behavioral measures included (1) crosses between compartments (vertical activity over the obstruction) and (2) movement counts quantified as photobeam breaks summed across compartments (horizontal activity). Each drug was tested alone and as a pretreatment to IP acid. A charcoal-meal test and whole-body-plethysmography assessment of breathing in 5% CO
    Language English
    Publishing date 2024-04-18
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3106-9
    ISSN 1521-0103 ; 0022-3565
    ISSN (online) 1521-0103
    ISSN 0022-3565
    DOI 10.1124/jpet.124.002153
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Uf I Zs.40: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 2021: Bestellungen von Artikeln über das Online-Bestellformular
    ab Jg. 2022: Lesesaal (EG)

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  4. Article ; Online: Role of efficacy as a determinant of locomotor activation by mu-opioid receptor (MOR) ligands in female and male mice. II. Effects of novel MOR-selective phenylmorphans with high-to-low MOR efficacy.

    Santos, Edna J / Nassehi, Nima / Bow, Eric W / Chambers, Dana R / Gutman, Eugene S / Jacobson, Arthur E / Lutz, Joshua A / Marsh, Samuel A / Rice, Kenner C / Sulima, Agnieszka / Selley, Dana E / Negus, S Stevens

    Pharmacology research & perspectives

    2023  Volume 11, Issue 4, Page(s) e01111

    Abstract: Low-efficacy mu-opioid receptor (MOR) agonists represent promising therapeutics, but existing compounds (e.g., buprenorphine, nalbuphine) span a limited range of low MOR efficacies and have poor MOR selectivity. Accordingly, new and selective low- ... ...

    Abstract Low-efficacy mu-opioid receptor (MOR) agonists represent promising therapeutics, but existing compounds (e.g., buprenorphine, nalbuphine) span a limited range of low MOR efficacies and have poor MOR selectivity. Accordingly, new and selective low-efficacy MOR agonists are of interest. A novel set of chiral C9-substituted phenylmorphans has been reported to display improved MOR selectivity and a range of high-to-low MOR efficacies under other conditions; however, a full opioid receptor binding profile for these drugs has not been described. Additionally, studies in mice will be useful for preclinical characterization of these novel compounds, but the pharmacology of these drugs in mice has also not been examined. Accordingly, the present study characterized the binding selectivity and in vitro efficacy of these compounds using assays of opioid receptor binding and ligand-stimulated [
    MeSH term(s) Animals ; Female ; Male ; Mice ; Analgesics, Opioid/pharmacology ; Buprenorphine/pharmacology ; Guanosine 5'-O-(3-Thiotriphosphate) ; Ligands ; Receptors, Opioid, mu/agonists
    Chemical Substances Analgesics, Opioid ; Buprenorphine (40D3SCR4GZ) ; Guanosine 5'-O-(3-Thiotriphosphate) (37589-80-3) ; Ligands ; phenylmorphan (91190-14-6) ; tianeptine (0T493YFU8O) ; Receptors, Opioid, mu
    Language English
    Publishing date 2023-06-28
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, N.I.H., Intramural
    ZDB-ID 2740389-0
    ISSN 2052-1707 ; 2052-1707
    ISSN (online) 2052-1707
    ISSN 2052-1707
    DOI 10.1002/prp2.1111
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Discovery of a Potent Highly Biased MOR Partial Agonist among Diastereomeric C9-Hydroxyalkyl-5-phenylmorphans.

    Lutz, Joshua A / Sulima, Agnieszka / Gutman, Eugene S / Bow, Eric W / Luo, Dan / Kaska, Sophia / Prisinzano, Thomas E / Paronis, Carol A / Bergman, Jack / Imler, Gregory H / Kerr, Andrew T / Jacobson, Arthur E / Rice, Kenner C

    Molecules (Basel, Switzerland)

    2023  Volume 28, Issue 12

    Abstract: All possible diastereomeric C9-hydroxymethyl-, hydroxyethyl-, and hydroxypropyl-substituted 5-phenylmorphans were synthesized to explore the three-dimensional space around the C9 substituent in our search for potent MOR partial agonists. These compounds ... ...

    Abstract All possible diastereomeric C9-hydroxymethyl-, hydroxyethyl-, and hydroxypropyl-substituted 5-phenylmorphans were synthesized to explore the three-dimensional space around the C9 substituent in our search for potent MOR partial agonists. These compounds were designed to lessen the lipophilicity observed with their C9-alkenyl substituted relatives. Many of the 12 diastereomers that were obtained were found to have nanomolar or subnanomolar potency in the forskolin-induced cAMP accumulation assay. Almost all these potent compounds were fully efficacious, and three of those chosen for in vivo evaluation,
    MeSH term(s) Receptors, Opioid, mu ; Morphinans/chemistry ; Morphine ; Analgesics, Opioid/chemistry
    Chemical Substances phenylmorphan (91190-14-6) ; Receptors, Opioid, mu ; Morphinans ; Morphine (76I7G6D29C) ; Analgesics, Opioid
    Language English
    Publishing date 2023-06-15
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules28124795
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.MO 81: Show issues

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  6. Article ; Online: Influence of Sulfur on Acid-Mediated Enamide Formation.

    Lutz, Joshua A / Subasinghege Don, Visal / Kumar, Revati / Taylor, Carol M

    Organic letters

    2017  Volume 19, Issue 19, Page(s) 5146–5149

    Abstract: The acid-mediated condensation of acetamide with butanal dimethylacetal and ... ...

    Abstract The acid-mediated condensation of acetamide with butanal dimethylacetal and EtSCH
    Language English
    Publishing date 2017--06
    Publishing country United States
    Document type Journal Article ; Research Support, U.S. Gov't, Non-P.H.S. ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.7b02432
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: Influence of Sulfur on Acid-Mediated Enamide Formation

    Lutz, Joshua A / Subasinghege Don Visal / Kumar Revati / Taylor Carol M

    Organic letters. 2017 Oct. 06, v. 19, no. 19

    2017  

    Abstract: The acid-mediated condensation of acetamide with butanal dimethylacetal and EtSCH₂CH(OMe)₂, followed by dehydration, was investigated by electronic structure calculations that supported the prediction that the Z-geometry would be favored in the ... ...

    Abstract The acid-mediated condensation of acetamide with butanal dimethylacetal and EtSCH₂CH(OMe)₂, followed by dehydration, was investigated by electronic structure calculations that supported the prediction that the Z-geometry would be favored in the product. The reaction was investigated experimentally using suitably functionalized cysteine building blocks. Some side reactions and optimization of reaction conditions are reported, en route to identifying a mild, inexpensive Lewis acid that achieves a reasonable yield of (Z)-thioenamide 21 with high stereoselectivity.
    Keywords Lewis acids ; chemical reactions ; chemical structure ; cysteine ; prediction ; stereoselectivity ; sulfur
    Language English
    Dates of publication 2017-1006
    Size p. 5146-5149.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021%2Facs.orglett.7b02432
    Database NAL-Catalogue (AGRICOLA)

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