The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Aspirin-like Molecules that Covalently Inactivate Cyclooxygenase-2
Abstract
Many of aspirin's therapeutic effects arise from its acetylation of cyclooxygenase-2 (COX-2), whereas its antithrombotic and ulcerogenic effects result from its acetylation of COX-1. Here, aspirin-like molecules were designed that preferentially acetylate and irreversibly inactivate COX-2. The most potent of these compounds was o -(acetoxyphenyl)hept-2-ynyl sulfide (APHS). Relative to aspirin, APHS was 60 times as reactive against COX-2 and 100 times as selective for its inhibition; it also inhibited COX-2 in cultured macrophages and colon cancer cells and in the rat air pouch in vivo. Such compounds may lead to the development of aspirin-like drugs for the treatment or prevention of immunological and proliferative diseases without gastrointestinal or hematologic side effects.
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Citations
Cites
Selective inhibition of inducible cyclooxygenase 2 in vivo is antiinflammatory and nonulcerogenic.
Masferrer, J. L., Zweifel, B. S., Manning, P. T., Hauser, S. D., Leahy, K. M., Smith, W. G., Isakson, P. C., & Seibert, K. (1994) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.91.8.3228 · Cited by 1,310
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Cited by
The role of cyclooxygenases in inflammation, cancer, and development
Williams, C. S., Mann, M., & DuBois, R. N. (1999) · Oncogene · doi:10.1038/sj.onc.1203286 · Cited by 1,417
McAdam, B. F., Catella-Lawson, F., Mardini, I. A., Kapoor, S., Lawson, J. A., & FitzGerald, G. A. (1999) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.96.1.272 · Cited by 1,305
Stepan, A. F., Walker, D. P., Bauman, J., Price, D. A., Baillie, T. A., Kalgutkar, A. S., & Aleo, M. D. (2011) · Chemical Research in Toxicology · doi:10.1021/tx200168d · Cited by 698
Self-citationCyclooxygenase inhibitors – current status and future prospects
Dannhardt, G., & Kiefer, W. (2001) · European Journal of Medicinal Chemistry · doi:10.1016/s0223-5234(01)01197-7 · Cited by 657
Amir, M., & Shikha, K. (2004) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2004.02.008 · Cited by 373
Metadata
- Authors
- Kalgutkar, A. S., Crews, B. C., Rowlinson, S. W., Garner, C., Seibert, K., & Marnett, L. J.
- Venue
- Science
- Published
- 1998-05-22
- Volume
- 280
- Issue
- 5367
- Pages
- 1268-1270
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2009132110
- Cited by
- 258
- References
- 1
- FWCI
- 17.23
- Type
- journal article
- Language
- en
- Open access
- closed
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- Kalgutkar, A. S., Crews, B. C., Rowlinson, S. W., Garner, C., Seibert, K., & Marnett, L. J. (1998). Aspirin-like Molecules that Covalently Inactivate Cyclooxygenase-2. Science. https://doi.org/10.1126/science.280.5367.1268
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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