ArticleACS chemical biology2020
Tutuilamides A-C: Vinyl-Chloride-Containing Cyclodepsipeptides from Marine Cyanobacteria with Potent Elastase Inhibitory Properties.
Article in ACS chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
What it found
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Who cites it
29 citing papers in PubMed, 53 citations in OpenAlex.
- Marine-derived Peptides As Anti-biofilm and Anti-virulence Agents: Mechanistic Insights and Applications Against Microbial Pathogens.Probiotics and antimicrobial proteins · 2026Review
- Recent advances in piperidones as privileged scaffolds for drug discovery and development.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2026Review
- Structure Determination and Biosynthesis of Dapalides A-C, Glycosylated Kahalalide F Analogues from the Marine CyanobacteriumJournal of natural products · 2025Article
- Total Syntheses of Stereoisomeric Congeners of Rufomycin Natural Products Having Anti-Mycobacterial Activity.Organic letters · 2025Article
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Review
- Review of Marine Cyanobacteria and the Aspects Related to Their Roles: Chemical, Biological Properties, Nitrogen Fixation and Climate Change.Marine drugs · 2023Review
- Marine Organisms as a Prolific Source of Bioactive Depsipeptides.Marine drugs · 2023Review
- Computational Approaches to Enzyme Inhibition by Marine Natural Products in the Search for New Drugs.Marine drugs · 2023Review
- Depsipeptides Targeting Tumor Cells: Milestones from In Vitro to Clinical Trials.Molecules (Basel, Switzerland) · 2023Review
- Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018-2022).Molecules (Basel, Switzerland) · 2023Review
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Preparation, identification, and molecular docking of novel elastase inhibitory peptide from walnut (Food chemistry. Molecular sciences · 2022Article
- Cosmetic Application of Cyanobacteria Extracts with a Sustainable Vision to Skincare: Role in the Antioxidant and Antiaging Process.Marine drugs · 2022Article
- Native metabolomics identifies the rivulariapeptolide family of protease inhibitors.Nature communications · 2022Article
- Cyanobacterial secondary metabolites towards improved commercial significance through multiomics approaches.World journal of microbiology & biotechnology · 2022Review
- Peptide Human Neutrophil Elastase Inhibitors from Natural Sources: An Overview.International journal of molecular sciences · 2022Review
- Article
- StandardisedFrontiers in pharmacology · 2022Article
- Cyanobacteria and microalgae bioactive compounds in skin-ageing: potential to restore extracellular matrix filling and overcome hyperpigmentation.Journal of enzyme inhibition and medicinal chemistry · 2021Review
Corrections and comments
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Authors and funding
14 authors at 6 institutions in 5 countries.
Funding
Abstract
Marine cyanobacteria (blue-green algae) have been shown to possess an enormous capacity to produce structurally diverse natural products that exhibit a broad spectrum of potent biological activities, including cytotoxic, antifungal, antiparasitic, antiviral, and antibacterial activities. Using mass-spectrometry-guided fractionation together with molecular networking, cyanobacterial field collections from American Samoa and Palmyra Atoll yielded three new cyclic peptides, tutuilamides A-C. Their structures were established by spectroscopic techniques including 1D and 2D NMR, HR-MS, and chemical derivatization. Structure elucidation was facilitated by employing advanced NMR techniques including nonuniform sampling in combination with the 1,1-ADEQUATE experiment. These cyclic peptides are characterized by the presence of several unusual residues including 3-amino-6-hydroxy-2-piperidone and 2-amino-2-butenoic acid, together with a novel vinyl chloride-containing residue. Tutuilamides A-C show potent elastase inhibitory activity together with moderate potency in H-460 lung cancer cell cytotoxicity assays. The binding mode to elastase was analyzed by X-ray crystallography revealing a reversible binding mode similar to the natural product lyngbyastatin 7. The presence of an additional hydrogen bond with the amino acid backbone of the flexible side chain of tutuilamide A, compared to lyngbyastatin 7, facilitates its stabilization in the elastase binding pocket and possibly explains its enhanced inhibitory potency.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.