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Cited by 94Parasites and Host InteractionsHelminth infection and controlChemical Synthesis and Analysis

Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the Acanthocheilonema viteae Product ES-62 Prevents Development of Collagen-Induced Arthritis

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Al-Riyami, Lamyaa, Pineda, Miguel A., Rzepecka, Justyna, Huggan, Judith K., Khalaf, Abedawn I., Suckling, Colin J., Scott, Fraser J., Rodgers, David T. +2 more·2013·Journal of Medicinal Chemistry
DOI 10.1021/jm401251pPMC PMC4125414
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Abstract

In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects on relevant macrophage cytokine responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in an in vivo model of inflammation, collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development.

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  • Due to their small size, stability, and lack of immunogenicity and efficacy, 11a and 12b are now being developed as therapeutic agents.

    “Two small molecule analogs (SMAs) of PC, termed 11a and 12b, can replicate many of the suppressive effects of ES-62, and due to their small size, stability, and lack of immunogenicity and efficacy are now being developed as therapeutic agents (Al-Riyami et al., 2013).”

    From Modulation of Host Immunity by Helminths: The Expanding Repertoire of Parasite Effector Molecules (2018) · cites this paper as Al-Riyami et al., 2013

    The Results (Selection of Compound for in Vivo Evaluation; page unavailable) report that both 11a and 12b mimic an ES-62 suppressive effect, while the Discussion and Conclusions say 11a is too small to be immunogenic and is a therapeutic candidate. The copy reports efficacy against arthritis development for 11a, but does not establish stability or lack of immunogenicity for 12b, or say that both compounds are now being developed as therapeutic agents. (LLM, conf=0.87)

    Experimental — accuracy not yet measured

  • Two small molecule analogs of phosphorylcholine, termed 11a and 12b, can replicate many of the suppressive effects of ES-62.

    “Two small molecule analogs (SMAs) of PC, termed 11a and 12b, can replicate many of the suppressive effects of ES-62, and due to their small size, stability, and lack of immunogenicity and efficacy are now being developed as therapeutic agents (Al-Riyami et al., 2013).”

    From Modulation of Host Immunity by Helminths: The Expanding Repertoire of Parasite Effector Molecules (2018) · cites this paper as Al-Riyami et al., 2013

    In Results (‘Selection of Compound for in Vivo Evaluation’; page unavailable), the paper says both 11a and 12b mimicked ES-62 by suppressing IL-12p40 responses, but 12b was less effective than 11a against some IL-6 responses. The Discussion reports ES-62-like protection against arthritis for 11a; it does not establish that protection for 12b. The paper presents these compounds as potential drug candidates, rather than establishing that both are being developed as therapeutic agents. (LLM, conf=0.86)

    Experimental — accuracy not yet measured

  • Synthetic small molecule variants of phosphorylcholine can reproduce many anti-inflammatory effects of ES-62.

    “synthetic small molecule variants of PC can reproduce many anti-inflammatory effects of the parent molecule”

    From Modulation of Host Immunity by Helminths: The Expanding Repertoire of Parasite Effector Molecules (2018) · cites this paper as Al-Riyami et al., 2013

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Authors
Al-Riyami, L., Pineda, M. A., Rzepecka, J., Huggan, J. K., Khalaf, A. I., Suckling, C. J., Scott, F. J., Rodgers, D. T., Harnett, M. M., & Harnett, W.
Affiliations
  • Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, U.K.
  • University of Glasgow (GB)
  • University of Strathclyde (GB)
Corresponding author
Harnett, William
ORCID
Venue
Journal of Medicinal Chemistry
Publisher
American Chemical Society (ACS)
Published
2013-11-25
Volume
56
Issue
24
Pages
9982-10002
ISSN
  • 0022-2623 (ISSN-L)
  • 1520-4804
DOI
10.1021/jm401251p
PMC
PMC4125414
OpenAlex
W1977245225
Cited by
94
References
0
Citations by year
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FWCI
8.49
Type
journal article
Language
en
Open access
Licence
Locations
  • Journal of Medicinal Chemistry (publishedVersion, other-oa)
  • Europe PMC (PubMed Central) (publishedVersion)
  • PubMed Central (publishedVersion)
  • PubMed (publishedVersion)
  • ENLIGHTEN (Jurnal Bimbingan dan Konseling Islam) (submittedVersion)
  • University of Huddersfield Repository (University of Huddersfield) (submittedVersion)
Funders
  • Wellcome Trust (WT086852)
  • Biotechnology and Biological Sciences Research Council (BB/E013929/1)
  • Arthritis Research UK (18413)
Topics
  • Life Sciences › Immunology and Microbiology › Parasitology › Parasites and Host Interactions
  • Health Sciences › Veterinary › Small Animals › Helminth infection and control
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
Keywords
ES-62, Acanthocheilonema viteae, anti-inflammatory drug design, collagen-induced arthritis, MyD88, DBA/1 mice
MeSH terms
Animals, Anti-Inflammatory Agents, Non-Steroidal, Arthritis, Cells, Cultured, Collagen, Male, Mice, Inbred BALB C, Mice, Inbred DBA, Drug Design, Molecular Structure, Helminth Proteins, Mice, Small Molecule Libraries

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

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