ArticleJournal of natural products2013
Synthesis of a 2-aryl-3-aroyl indole salt (OXi8007) resembling combretastatin A-4 with application as a vascular disrupting agent.
Article in Journal of natural products, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed.
- Targeting Tumor-Associated Hypoxia with Bioreductively Activatable Prodrug Conjugates Derived from Dihydronaphthalene, Benzosuberene, and Indole-based Inhibitors of Tubulin Polymerization.RSC medicinal chemistry · 2025Article
- Benzosuberene and Tetracyclic Analogues as Colchicine Site Inhibitors of Tubulin Polymerization.ACS medicinal chemistry letters · 2025Article
- Evaluating Therapeutic Efficacy of the Vascular Disrupting Agent OXi8007 Against Kidney Cancer in Mice.Cancers · 2025Article
- Drug-Linker Constructs Bearing Unique Dual-Mechanism Tubulin Binding Payloads Tethered through Cleavable and Non-Cleavable Linkers.Tetrahedron · 2025Article
- Design, Synthesis and Biological Evaluation of 2-Phenyl Indole Analogues of OXi8006 as Colchicine Site Inhibitors of Tubulin Polymerization and Vascular Disrupting Agents.Bioorganic & medicinal chemistry · 2025Article
- Application of Chlorosulfonyl Isocyanate (CSI) in the Synthesis of Fused Tetracyclic Ketone Ring Systems.The Journal of organic chemistry · 2024Article
- Synthesis and biological evaluation of structurally diverse 6-aryl-3-aroyl-indole analogues as inhibitors of tubulin polymerization.European journal of medicinal chemistry · 2024Article
- Synthesis of the Hypoxia-Inducible Factor-2Tetrahedron letters · 2023Article
- Structure Guided Design, Synthesis, and Biological Evaluation of Oxetane-Containing Indole Analogues.Bioorganic & medicinal chemistry · 2023Article
- Oxygen-Sensing Chemiluminescent Iridium(III) 1,2-Dioxetanes: Unusual Coordination and Activity.Analysis & sensing · 2023Article
- Boron Trifluoride Etherate Promoted Regioselective 3-Acylation of Indoles with Anhydrides.Molecules (Basel, Switzerland) · 2022Article
- Article
- Design, Synthesis and Biological Evaluation of Prodrugs of 666-15 as Inhibitors of CREB-Mediated Gene Transcription.ACS medicinal chemistry letters · 2022Article
- Non-Invasive Evaluation of Acute Effects of Tubulin Binding Agents: A Review of Imaging Vascular Disruption in Tumors.Molecules (Basel, Switzerland) · 2021Review
- Synthesis and Biological Evaluation of 1-(Diarylmethyl)-1Pharmaceuticals (Basel, Switzerland) · 2021Article
- Pyrrolo[2',3':3,4]cyclohepta[1,2-Journal of medicinal chemistry · 2020Article
- Structure Guided Design, Synthesis, and Biological Evaluation of Novel Benzosuberene Analogues as Inhibitors of Tubulin Polymerization.Journal of medicinal chemistry · 2019Article
- 3-Vinylazetidin-2-Ones: Synthesis, Antiproliferative and Tubulin Destabilizing Activity in MCF-7 and MDA-MB-231 Breast Cancer Cells.Pharmaceuticals (Basel, Switzerland) · 2019Article
- Synthesis of dihydronaphthalene analogues inspired by combretastatin A-4 and their biological evaluation as anticancer agents.MedChemComm · 2018Article
- Synthesis and Biological Evaluation of Benzocyclooctene-based and Indene-based Anticancer Agents that Function as Inhibitors of Tubulin Polymerization.MedChemComm · 2016Article
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Authors and funding
18 authors.
Funding
Abstract
The natural products colchicine and combretastatin A-4 are potent inhibitors of tubulin assembly, and they have inspired the design and synthesis of a large number of small-molecule, potential anticancer agents. The indole-based molecular scaffold is prominent among these SAR modifications, leading to a rapidly increasing number of agents. The water-soluble phosphate prodrug 33 (OXi8007) of 2-aryl-3-aroylindole-based phenol 8 (OXi8006) was prepared by chemical synthesis and found to be strongly cytotoxic against selected human cancer cell lines (GI₅₀ = 36 nM against DU-145 cells, for example). The free phenol, 8 (OXi8006), was a strong inhibitor (IC₅₀ = 1.1 μM) of tubulin assembly. The corresponding phosphate prodrug 33 (OXi8007) also demonstrated pronounced interference with tumor vasculature in a preliminary in vivo study utilizing a SCID mouse model bearing an orthotopic PC-3 (prostate) tumor as imaged by color Doppler ultrasound. The combination of these results provides evidence that the indole-based phosphate prodrug 33 (OXi8007) functions as a vascular disrupting agent that may prove useful for the treatment of cancer.
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