ArticleJournal of the American Chemical Society2019
Computationally Assisted Discovery and Assignment of a Highly Strained and PANC-1 Selective Alkaloid from Alaska's Deep Ocean.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 67 citations in OpenAlex.
- Molecular rearrangements as powerful tools in diversity-oriented natural products synthesis: a review.RSC advances · 2026Review
- Evolution of Strategies Toward the Total Synthesis of Aleutianamine.The Journal of organic chemistry · 2026Article
- Optimized Biomimetic Syntheses of Discorhabdin B and Aleutianamine Drives a Deeper Exploration of Their Anticancer Potential.Journal of the American Chemical Society · 2026Article
- On the Discorhabdins Leading to the Aleutianamine Ring System: A One-Step in Situ Transformation Characterized Through Computational and Experimental Studies and Its Implications on Biosynthesis, Synthesis, and Pharmacology.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Thiophene Derivatives as Versatile Precursors for (Hetero)Arene and Natural Product Synthesis.Angewandte Chemie (International ed. in English) · 2026Review
- Aleutianamine B, A Novel Chiral Sulfoxide Isolated fromJournal of natural products · 2026Article
- The Biosynthetic Pathway to the Pyrroloiminoquinone Marine Natural Product Ammosamide C.Journal of the American Chemical Society · 2025Article
- Convergent Total Synthesis of Aleutianamine.Journal of the American Chemical Society · 2025Article
- A Divergent Synthesis of Numerous Pyrroloiminoquinone Alkaloids Identifies Promising Antiprotozoal Agents.Journal of the American Chemical Society · 2024Article
- Computationally-Assisted Discovery and Assignment of a New Class of 6/6/5/5 Fused-Ring Diterpene Acting as Pregnane X Receptor Ligands fromJournal of natural products · 2024Article
- Divergent total syntheses of pyrroloiminoquinone alkaloids enabled by the development of a Larock/Buchwald-Hartwig annulation/cyclization.Chemical science · 2024Article
- Manzamine A reduces androgen receptor transcription and synthesis by blocking E2F8-DNA interactions and effectively inhibits prostate tumor growth in mice.Molecular oncology · 2024Article
- Unified Synthesis and Biological Evaluation of Makaluvamine J and Its Analogs.Molecules (Basel, Switzerland) · 2024Article
- Platanosides from Platanus × acerifolia: New molecules, SAR, and target validation of a strong lead for drug-resistant bacterial infections and the associated sepsis.Bioorganic chemistry · 2024Article
- Total Synthesis of Aleutianamine.Journal of the American Chemical Society · 2023Article
- Chemistry of Isoeugenol and Its Oxidation Products: Mechanism and Kinetics of Isoeugenol as a Skin Sensitizer.Chemical research in toxicology · 2023Article
- Prenylated flavonoids with significant anti-hepatoma activity from Daphne giraldii and effects on Fibroblast Growth Factor Receptor 1 (FGFR1).European journal of medicinal chemistry · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Current Perspectives on Pyrroloiminoquinones: Distribution, Biosynthesis and Drug Discovery Potential.Molecules (Basel, Switzerland) · 2022Review
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Authors and funding
14 authors at 6 institutions in 2 countries.
Funding
Abstract
We report here the orchestration of molecular ion networking and a set of computationally assisted structural elucidation approaches in the discovery of a new class of pyrroloiminoquinone alkaloids that possess selective bioactivity against pancreatic cancer cell lines. Aleutianamine represents the first in a new class of pyrroloiminoquinone alkaloids possessing a highly strained multibridged ring system, discovered from Latrunculia ( Latrunculia) austini Samaai, Kelly & Gibbons, 2006 (class Demospongiae, order Poecilosclerida, family Latrunculiidae) recovered during a NOAA deep-water exploration of the Aleutian Islands. The molecule was identified with the guidance of mass spectrometry, nuclear magnetic resonance, and molecular ion networking (MoIN) analysis. The structure of aleutianamine was determined using extensive spectroscopic analysis in conjunction with computationally assisted quantifiable structure elucidation tools. Aleutianamine exhibited potent and selective cytotoxicity toward solid tumor cell lines including pancreatic cancer (PANC-1) with an IC
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