Evidence map›Paper›PMID 23929690›Full record

ArticleChemMedChem2013

Evaluating prodrug strategies for esterase-triggered release of alcohols.

Christian Perez, Kevin B Daniel, Seth M Cohen

Abstract read
In one paragraph

Article in ChemMedChem, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.

0numbers the graph read from it
0cells of the map it votes in
16citing papers in PubMed
1.0field-weighted citation impact, top 24% of its field
1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

16 citing papers in PubMed, 37 citations in OpenAlex.

  1. Review
  2. Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Review
  8. Structure-Activity Relationship of Heterocyclic P2YJournal of medicinal chemistry · 2021
    Article
  9. Article
  10. Review
  11. Review
  12. Article
  13. Exploring hydrogen peroxide responsive thiazolidinone-based prodrugs.Chemical communications (Cambridge, England) · 2015
    Article
  14. Modern prodrug design for targeted oral drug delivery.Molecules (Basel, Switzerland) · 2014
    Article
  15. Article
  16. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

3 authors at 1 institution in 1 country.

Christian PerezDepartment of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA).
Kevin B Daniel
Seth M Cohen
University of California, San Diego · US

Funding

Insight and Optimization of Metalloprotein InhibitorsR01GM098435 · NIGMS · UNIVERSITY OF CALIFORNIA, SAN DIEGO · PI THEODORAKIS, EMMANUEL A · 2011 to 2018
$2.2M
NIGMS NIH HHS R01 GM098435
6 · The paper itself

Abstract

Prodrugs are effective tools in overcoming drawbacks typically associated with drug formulation and delivery. Those employing esterase-triggered functional groups are frequently utilized to mask polar carboxylic acids and phenols, increasing drug-like properties such as lipophilicity. Herein we detail a comprehensive assessment for strategies that effectively release hydroxy and phenolic moieties in the presence of an esterase. Matrix metalloproteinases (MMPs) serve as our proof-of-concept target. Three distinct ester-responsive protecting groups are incorporated into MMP proinhibitors containing hydroxy moieties. Analytical evaluation of the proinhibitors demonstrates that the use of a benzyl ether group appended to the esterase trigger leads to considerably faster kinetics of conversion and enhanced aqueous stability when compared with more conventional approaches where the trigger is directly attached to the inhibitor. Biological assays confirm that all protecting groups effectively cleave in the presence of esterase to generate the active inhibitor. The superior reaction-based prodrug strategies presented here should serve as a platform for esterase-responsive prodrug design in the future.

Indexed as

AlcoholsAnimalsCatecholsEnzyme InhibitorsEsterasesLiverMatrix MetalloproteinasesProdrugsProtein BindingSwineAlcoholscatecholCatecholsEnzyme InhibitorsEsterasesMatrix MetalloproteinasesProdrugsenzyme‐triggered releaseesterasesmatrix metalloproteinasesmetalloenzymesprodrugs

Identifiers

PMID23929690
PMCPMC3918245
OpenAlexW2131693985

What OpenQuestion holds

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Read underepoch 390

Registered trials

None linked

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.