The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Synthesis and characterization of new psoralen derivatives with superior photoreactivity with DNA and RNA
Abstract
The synthesis of five new psoralen derivatives is described. Three of these, 4'-hydroxymethyl-4,5',8-trimethylpsoralen, 4'-methoxymethyl-4,5',8-trimethylpsoralen, and 4'-aminomethyl-4,5',8-trimethylpsoralen hydrochloride, and characterized with respect to their photoreactivity with DNA and RNA. They are found to be greatly superior to 4,5',8-trimethylpsoralen and 8-methoxypsoralen, the two commonly used psoralens, in their abilities to saturate the photoreactive sites on DNA and RNA without repeated addition of reagent. A simplified mechanism for the photoreaction of psoralens with nucleic acids is presented and provides a basis for understanding the superior properties of these compounds. The compounds have superior reactivity not only with isolated DNA and RNA but also in viruses and in cells. Psoralens are shown for the first time to cross-link RNA double helices.
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Citations
Cites
Photochemotherapy of Psoriasis with Oral Methoxsalen and Longwave Ultraviolet Light
Parrish, J. A., Fitzpatrick, T. B., Tanenbaum, L., & Pathak, M. A. (1974) · New England Journal of Medicine · doi:10.1056/nejm197412052912301 · Cited by 1,376
Cited by
Psoralen Photochemistry and Nucleic Acid Structure
Hearst, J. E. (1981) · Journal of Investigative Dermatology · doi:10.1111/1523-1747.ep12479229 · Cited by 66
Self-citationSmith, S. I., & Brodbelt, J. S. (2010) · The Analyst · doi:10.1039/b924023c · Cited by 25
Metadata
- Authors
- Isaacs, S. T., Shen, C.-K. J., Hearst, J. E., & Rapoport, H.
- Venue
- Biochemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1977-03-22
- Volume
- 16
- Issue
- 6
- Pages
- 1058-1064
- ISSN
- 0006-2960 (ISSN-L)
- 1520-4995
- OpenAlex
- W2068567113
- Cited by
- 309
- References
- 1
- FWCI
- 9.17
- Type
- journal article
- Language
- en
- Open access
- closed
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- The paper
- Isaacs, S. T., Shen, C.-K. J., Hearst, J. E., & Rapoport, H. (1977). Synthesis and characterization of new psoralen derivatives with superior photoreactivity with DNA and RNA. Biochemistry. https://doi.org/10.1021/bi00625a005
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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).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
