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Keywords = PIP HSQMBC IPAP

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11 pages, 1990 KiB  
Article
Suberitamides A–C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity
by Chang-Kwon Kim, Dongdong Wang, Brice A. P. Wilson, Josep Saurí, Donna Voeller, Stanley Lipkowitz, Barry R. O’Keefe and Kirk R. Gustafson
Mar. Drugs 2020, 18(11), 536; https://doi.org/10.3390/md18110536 - 28 Oct 2020
Cited by 5 | Viewed by 3174
Abstract
Three new aryl alkaloids named suberitamides A–C (13), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass [...] Read more.
Three new aryl alkaloids named suberitamides A–C (13), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (1), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond 1H-13C spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (1) and B (2) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC50 values of approximately 11 μM. Full article
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