The DOI matches its Crossref record; 38 of the 38 references it cites were found in a registry or an index.
A Near-IR Uncaging Strategy Based on Cyanine Photochemistry
Open accessAbstract
The development of photocaging groups activated by near-IR light would enable new approaches for basic research and allow for spatial and temporal control of drug delivery. Here we report a near-IR light-initiated uncaging reaction sequence based on readily synthesized C4'-dialkylamine-substituted heptamethine cyanines. Phenol-containing small molecules are uncaged through sequential release of the C4'-amine and intramolecular cyclization. The release sequence is initiated by a previously unexploited photochemical reaction of the cyanine fluorophore scaffold. The uncaging process is compatible with biological milieu and is initiated with low intensity 690 nm light. We show that cell viability can be inhibited through light-dependent release of the estrogen receptor antagonist, 4-hydroxycyclofen. In addition, through uncaging of the same compound, gene expression is controlled with near-IR light in a ligand-dependent CreER(T)/LoxP-reporter cell line derived from transgenic mice. These studies provide a chemical foundation that we expect will enable specific delivery of small molecules using cytocompatible, tissue penetrant near-IR light.
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Cites
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Cited by
Liu, Y., Li, Y., Koo, S., Sun, Y., Liu, Y., Liu, X., Pan, Y., Zhang, Z., Du, M., Lu, S., et al. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00553 · Cited by 537
Mechanisms of drug release in nanotherapeutic delivery systems
Wong, P. T., & Choi, S. K. (2015) · Chemical Reviews · doi:10.1021/cr5004634 · Cited by 507
Optochemical Control of Biological Processes in Cells and Animals
Ankenbruck, N., Courtney, T., Naro, Y., & Deiters, A. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201700171 · Cited by 419
Light: A Magical Tool for Controlled Drug Delivery
Tao, Y., Chan, H. F., Shi, B., Li, M., & Leong, K. W. (2020) · Advanced Functional Materials · doi:10.1002/adfm.202005029 · Cited by 309
Light-induced control of protein destruction by opto-PROTAC
Liu, J., Chen, H., Ma, L., He, Z., Wang, D., Liu, Y., Lin, Q., Zhang, T., Gray, N., Kaniskan, H. Ü., et al. (2020) · Science Advances · doi:10.1126/sciadv.aay5154 · Cited by 292
Metadata
- Authors
- Gorka, A. P., Nani, R. R., Zhu, J., Mackem, S., & Schnermann, M. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2014-09-24
- Volume
- 136
- Issue
- 40
- Pages
- 14153-14159
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1995838905
- Cited by
- 267
- References
- 38
- FWCI
- 8.19
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Gorka, A. P., Nani, R. R., Zhu, J., Mackem, S., & Schnermann, M. J. (2014). A Near-IR Uncaging Strategy Based on Cyanine Photochemistry. Journal of the American Chemical Society. https://doi.org/10.1021/ja5065203
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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