ArticleJournal of medicinal chemistry2010
Design, synthesis, and evaluation of duocarmycin O-amino phenol prodrugs subject to tunable reductive activation.
Article in Journal of medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
17 citing papers in PubMed.
- Insights into Free Drug Release from EfficaciousACS chemical biology · 2025Article
- BorylationOrganic & biomolecular chemistry · 2024Article
- A tautomerized ligand enabled meta selective C-H borylation of phenol.Nature communications · 2023Article
- Rapid Construction of a Chloromethyl-Substituted Duocarmycin-like Prodrug.Molecules (Basel, Switzerland) · 2023Article
- 40 Years of Duocarmycins: A Graphical Structure/Function Review of Their Chemical Evolution, from SAR to Prodrugs and ADCs.JACS Au · 2022Review
- Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.The Journal of organic chemistry · 2019Review
- Hypoxia-activated prodrugs and redox-responsive nanocarriers.International journal of nanomedicine · 2018Review
- The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.The Journal of organic chemistry · 2017Article
- A five-membered lactone prodrug of CBI-based analogs of the duocarmycins.Tetrahedron letters · 2015Article
- Asymmetric synthesis of a CBI-based cyclic N-acyl O-amino phenol duocarmycin prodrug.The Journal of organic chemistry · 2014Article
- A fundamental relationship between hydrophobic properties and biological activity for the duocarmycin class of DNA-alkylating antitumor drugs: hydrophobic-binding-driven bonding.Journal of medicinal chemistry · 2013Article
- Synthesis and Evaluation of anLetters in organic chemistry · 2013Article
- Evaluation of a reductively activated duocarmycin prodrug against murine and human solid cancers.Cancer biology & therapy · 2013Article
- Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs.Journal of medicinal chemistry · 2013Article
- A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct.Journal of medicinal chemistry · 2012Article
- Fluorinated amino-derivatives of the sesquiterpene lactone, parthenolide, as (19)f NMR probes in deuterium-free environments.Journal of medicinal chemistry · 2011Article
- Asymmetric synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI).The Journal of organic chemistry · 2011Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
7 authors.
Funding
Abstract
A series of N-acyl O-amino derivatives of seco-CBI-indole(2) are reported and examined as prototypical members of a unique class of reductively activated (cleaved) prodrugs of the duocarmycin and CC-1065 family of antitumor agents. These prodrugs were designed to be potentially preferentially activated in hypoxic tumor environments which carry an intrinsically higher concentration of "reducing" nucleophiles (e.g., thiols) capable of activating such derivatives by nucleophilic cleavage of a weak N-O bond. A remarkable range of stabilities and a resulting direct correlation with in vitro/in vivo biological potencies was observed for these prodrugs, even enlisting subtle variations in the electronic and steric environment around the weak N-O bond. An in vivo evaluation of several of the prodrugs demonstrates that some approach the potency and exceed the efficacy of the free drug itself (CBI-indole(2)), suggesting the prodrugs may offer an additional advantage related to a controlled or targeted release.
Indexed as
Identifiers
What OpenQuestion holds
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.