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Acetals as pH-Sensitive Linkages for Drug Delivery
Abstract
pH-Sensitive linkages designed to undergo hydrolysis at mildly acidic pH can trigger the release of therapeutics selectively at targets such as tumor and inflammatory tissues and in the endosomes and lysosomes of cells. Acetals have the potential to be used as linkages for a range of alcohol functionalities, and, by altering their chemical structure, it is possible to tune their hydrolysis rate. The syntheses of four conjugates of model drug molecules with PEO using acetals of varying chemical structure are described herein. Primary and secondary alcohols, as well as syn-1,2-diols, were incorporated in the conjugates. The hydrolysis kinetics were investigated by HPLC, and the conjugates had half-lives ranging from less than 1 min to several days at pH 5.0, with slower hydrolysis at pH 7.4 in all cases. These acetal linkages are therefore promising for use in a variety of drug delivery applications ranging from polymer-drug conjugates to pH-sensitive micelles and nanoparticulate systems.
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Citations
Cited by
Kocak, G., Tuncer, C., & Bütün, V. (2017) · Polymer Chemistry · doi:10.1039/c6py01872f · Cited by 1,189
Mechanisms and biomaterials in pH-responsive tumour targeted drug delivery: A review
Kanamala, M., Wilson, W. R., Yang, M., Palmer, B. D., & Wu, Z. (2016) · Biomaterials · doi:10.1016/j.biomaterials.2016.01.061 · Cited by 1,004
Functionalized micellar systems for cancer targeted drug delivery
Sutton, D., Nasongkla, N., Blanco, E., & Gao, J. (2007) · Pharmaceutical Research · doi:10.1007/s11095-006-9223-y · Cited by 557
pH-responsive polymer nanoparticles for drug delivery
Deirram, N., Zhang, C., Kermaniyan, S. S., Johnston, A. P. R., & Such, G. K. (2019) · Macromolecular Rapid Communications · doi:10.1002/marc.201800917 · Cited by 531
Yang, Q., Wang, S., Fan, P., Wang, L., Di, Y., Lin, K., & Xiao, F.-S. (2005) · Chemistry of Materials · doi:10.1021/cm051198v · Cited by 490
Metadata
- Authors
- Gillies, E. R., Goodwin, A. P., & Fréchet, J. M. J.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-10-09
- Volume
- 15
- Issue
- 6
- Pages
- 1254-1263
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W2040273584
- Cited by
- 330
- References
- 0
- FWCI
- 2.71
- Type
- journal article
- Language
- en
- Open access
- closed
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- Gillies, E. R., Goodwin, A. P., & Fréchet, J. M. J. (2004). Acetals as pH-Sensitive Linkages for Drug Delivery. Bioconjugate Chemistry. https://doi.org/10.1021/bc049853x
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