Evidence map›Paper›PMID 37734424›Full record

ArticleBioorganic & medicinal chemistry letters2024

Design and synthesis of a library of C2-substituted sulfamidoadenosines to probe bacterial permeability.

Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geißen, Melissa L Boby, Bradley S Sherborne, Derek S Tan

Abstract read
In one paragraph

Article in Bioorganic & medicinal chemistry letters, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
–field-weighted citation impact
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

2 citing papers in PubMed.

  1. Article
  2. 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

8 authors.

Shibin ZhaoChemical Biology Program, Sloan Kettering Institute, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Julian MacerenChemical Biology Program, Sloan Kettering Institute, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Mia ChungChemical Biology Program, Sloan Kettering Institute, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Samantha StoneChemical Biology Program, Sloan Kettering Institute, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Raphael GeißenChemical Biology Program, Sloan Kettering Institute, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA; Doctoral Program, Faculty of Biology, Albert-Ludwigs-Universität Freiburg,79104 Freiburg im Breisgau, Germany.
Melissa L BobyChemical Biology Program, Sloan Kettering Institute, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA; Pharmacology Graduate Program, Weill Cornell Graduate School of Medical Sciences, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Bradley S SherborneMerck & Co., Inc. Rahway, NJ 07065, USA.
Derek S TanChemical Biology Program, Sloan Kettering Institute, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA; Pharmacology Graduate Program, Weill Cornell Graduate School of Medical Sciences, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA; Tri-Institutional Research Program, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA. Electronic address: tand@mskcc.org.

Funding

X-RAY CRYSTALLOGRAPHYP30CA008748 · NCI · SLOAN-KETTERING INSTITUTE FOR CANCER RES · PI Hongbiao Carl Lekaye · 1985 to 2026
$347.4M
Predictive Models for Small-Molecule Accumulation in Gram-Negative BacteriaR01AI136795 · NIAID · SLOAN-KETTERING INST CAN RESEARCH · PI TAN, DEREK S, ZGURSKAYA, HELEN I · 2018 to 2022
$6.5M
Predoctoral Training in Pharmacological SciencesT32GM073546 · NIGMS · WEILL MEDICAL COLL OF CORNELL UNIV · PI GROSS, STEVEN S · 2006 to 2020
$3.1M
NCI NIH HHS P30 CA008748NIAID NIH HHS R01 AI136795NIGMS NIH HHS T32 GM073546
6 · The paper itself

Abstract

Antibiotic resistance is a major threat to public health, and Gram-negative bacteria pose a particular challenge due to their combination of a low permeability cell envelope and efflux pumps. Our limited understanding of the chemical rules for overcoming these barriers represents a major obstacle in antibacterial drug discovery. Several recent efforts to address this problem have involved screening compound libraries for accumulation in bacteria in order to understand the structural properties required for Gram-negative permeability. Toward this end, we used cheminformatic analysis to design a library of sulfamidoadenosines (AMSN) having diverse substituents at the adenine C2 position. An efficient synthetic route was developed with installation of a uniform cross-coupling reagent set using Sonogashira and Suzuki reactions of a C2-iodide. The potential utility of these compounds was demonstrated by pilot analysis of selected analogues for accumulation in Escherichia coli.

Indexed as

Anti-Bacterial AgentsGram-Negative BacteriaAdenosineDrug DiscoveryEscherichia coliPermeabilityAdenosineAnti-Bacterial AgentsAntibiotic resistanceDiversity-oriented synthesisDrug discoveryGram-negative bacteriaNucleoside analogue

Identifiers

PMID37734424
PMCPMC10842738

What OpenQuestion holds

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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.