Chemical profiles of and were investigated, resulting in the isolation of five new discorhabdin D derivatives and -. Their planar structures were solved by combination of NMR and HR-MS, while -based configurational analysis, computational techniques, and semisynthetic methods were used for the establishment of their absolute configurations. New natural products were tested for their growth inhibitory activity against the NCI-60 human tumor cell line panel, and two compounds and showed low micromolar potency.
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New Discorhabdin D Analogues from spp. Sponges.
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Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21701-1201, United States.
Chemical profiles of and were investigated, resulting in the isolation of five new discorhabdin D derivatives and -. Their planar structures were solved by combination of NMR and HR-MS, while -based configurational analysis, computational techniques, and semisynthetic methods were used for the establishment of their absolute configurations. New natural products were tested for their growth inhibitory activity against the NCI-60 human tumor cell line panel, and two compounds and showed low micromolar potency.
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Laboratory of Bioorganic Chemistry, Department of Physics, University of Trento, Via Sommarive 14, 38123 Trento, Italy.
In this study, Antarctic sponge-derived discorhabdin G was considered a hit for developing potential lead compounds acting as cholinesterase inhibitors. The hypothesis on the pharmacophore moiety suggested through molecular docking allowed us to simplify the structure of the metabolite. ADME prediction and drug-likeness consideration provided valuable support in selecting 5-methyl-2H-benzo[h]imidazo[1,5,4-de]quinoxalin-7(3H)-one as a candidate molecule.
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Department of Pharmacy, School of Life Sciences, Pharmacy and Chemistry, Kingston University, Penrhyn Road, Kingston upon Thames, London KT1 2EE, UK.
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Department of Biochemistry and Microbiology, Rhodes University, Makhanda 6140, South Africa.
Article Synopsis
- Pyrroloiminoquinones are cytotoxic alkaloids found mainly in marine sponges, characterized by a unique tricyclic structure and include compounds like makaluvamines and tsitsikammamines.
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New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge .
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GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, Kiel 24106, Germany.
sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the -hexane subextract of the Antarctic deep-sea sponge yielded the known compound (-)-(1R,2R,6R,8S,6'S)-discorhabdin B dimer () and two new derivatives, (-)-(1S,2R,6R,8S,6'S)-discorhabdin B dimer (2) and (-)-(1R,2R,6R,8S,6'S)-16',17'-dehydrodiscorhabdin B dimer (3). The chemical structures of compounds - were elucidated by means of HR-ESIMS, NMR, [], ECD spectroscopy, and a comparison with the previously reported discorhabdin analogs.
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