ArticleChemical science2013
Precursor-Directed Generation of Amidine Containing Ammosamide Analogs: Ammosamides E-P.
Article in Chemical science, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Actinomycetes: A Source of Anticancer Metabolites.Current medicinal chemistry · 2025Review
- Exploring the Nonenzymatic Origin of Duclauxin-like Natural Products.Journal of natural products · 2024Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Mechanism of Action of Ribosomally Synthesized and Post-Translationally Modified Peptides.Chemical reviews · 2022Review
- Biomimetic Total Synthesis and Investigation of the Non-Enzymatic Chemistry of Oxazinin A.Angewandte Chemie (International ed. in English) · 2022Article
- Promising bioactive compounds from the marine environment and their potential effects on various diseases.Journal, genetic engineering & biotechnology · 2022Review
- Discovery of ammosesters by mining the Streptomyces uncialis DCA2648 genome revealing new insight into ammosamide biosynthesis.Journal of industrial microbiology & biotechnology · 2021Article
- A look around the West Indies: The spices of life are secondary metabolites.Bioorganic & medicinal chemistry · 2020Review
- Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D.Organic letters · 2020Article
- Elucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B.Organic letters · 2019Article
- An efficient nickel/silver co-catalyzed remote C-H amination of 8-aminoquinolines with azodicarboxylates at room temperature.RSC advances · 2018Article
- Precursor-Directed Generation of Indolocarbazoles with Topoisomerase IIα Inhibitory Activity.Marine drugs · 2018Article
- Carpatizine, a novel bridged oxazine derivative generated by non-enzymatic reactions.Organic & biomolecular chemistry · 2017Article
- Precursor-directed in situ synthesis of Saccharothriolides G and H by the Actinomycete Saccharothrix sp. A1506.The Journal of antibiotics · 2017Article
- Biosynthetic Pathway Connects Cryptic Ribosomally Synthesized Posttranslationally Modified Peptide Genes with Pyrroloquinoline Alkaloids.Cell chemical biology · 2016Article
- Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids.Nature communications · 2016Article
- Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non-enzymatic Biosynthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Detailed Mechanistic Study of the Non-enzymatic Formation of the Discoipyrrole Family of Natural Products.Journal of the American Chemical Society · 2016Article
- Discoipyrroles A-D: isolation, structure determination, and synthesis of potent migration inhibitors from Bacillus hunanensis.Journal of the American Chemical Society · 2013Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Ammosamides E-F (1-2), are amidine analogs of the ammosamide family of alkaloids isolated from a marine-derived Streptomyces variabilis. Further studies with S. variabilis revealed a variety of aryl and alkyl amines added into the fermentation media could be efficiently incorporated into the ammosamide framework to generate a library of precursor-directed amidine analogs, ammosamides G-P (9 - 18). We demonstrate that the amines are introduced via non-enzymatic addition to the iminium ion of ammosamide C. Biological evaluation of the amidine analogs against quinone reductase 2 (QR2) showed low nM potency for a number of analogs. When tested for in vivo activity against a panel of non-small cell lung cancer (NSCLC) cell-lines there was a clear increase in potency by incorporation of lipophilic alkylamines, with the most potent compounds having sub μM IC(50) values (0.4 to 0.8 μM).
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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.