The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Rational design and synthesis of an orally bioavailable peptide guided by NMR amide temperature coefficients
Open accessAbstract
Significance: Peptides are valuable leads for drug development, offering advantages over other molecular classes. Specifically, they can bind potently and selectively to drug targets, including protein–protein interactions that are too challenging for small-molecule therapeutics. However, peptides are poor drugs because of their low in vivo stability and poor oral bioavailability. We propose a strategy for improving the oral bioavailability of peptides by identifying appropriate amides for chemical modification using temperature coefficients measured by NMR. The modified peptides have improved solvation properties, making them more membrane permeable. This approach for identifying sites for modification is a rapid method for guiding peptide drug design.
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Cites
Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001) · Advanced Drug Delivery Reviews · doi:10.1016/s0169-409x(00)00129-0 · Cited by 18,139
Molecular properties that influence the oral bioavailability of drug candidates
Veber, D. F., Johnson, S. R., Cheng, H.-Y., Smith, B. R., Ward, K. W., & Kopple, K. D. (2002) · Journal of Medicinal Chemistry · doi:10.1021/jm020017n · Cited by 8,420
Improving Oral Bioavailability of Peptides by Multiple N‐Methylation: Somatostatin Analogues
Biron, E., Chatterjee, J., Ovadia, O., Langenegger, D., Brueggen, J., Hoyer, D., Schmid, H. A., Jelinek, R., Gilon, C., Hoffman, A., et al. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705797 · Cited by 374
Cited by
The Current State of Peptide Drug Discovery: Back to the Future?
Henninot, A., Collins, J. C., & Nuss, J. M. (2018) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.7b00318 · Cited by 1,113
Macrocyclic Peptides as Drug Candidates: Recent Progress and Remaining Challenges
Vinogradov, A. A., Yin, Y., & Suga, H. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.8b13178 · Cited by 848
Orally Absorbed Cyclic Peptides
Nielsen, D. S., Shepherd, N. E., Xu, W., Lucke, A. J., Stoermer, M. J., & Fairlie, D. P. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00838 · Cited by 445
Self-citationThe Vast Structural Diversity of Antimicrobial Peptides
Koehbach, J., & Craik, D. J. (2019) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2019.04.012 · Cited by 294
Self-citationSystemic delivery of peptides by the oral route: Formulation and medicinal chemistry approaches
Brayden, D. J., Hill, T. A., Fairlie, D. P., Maher, S., & Mrsny, R. J. (2020) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2020.05.007 · Cited by 253
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Metadata
- Authors
- Wang, C. K., Northfield, S. E., Colless, B., Chaousis, S., Hamernig, I., Lohman, R.-J., Nielsen, D. S., Schroeder, C. I., Liras, S., Price, D. A., Fairlie, D. P., & Craik, D. J.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 2014-11-21
- Volume
- 111
- Issue
- 49
- Pages
- 17504-17509
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W2129178272
- Cited by
- 171
- References
- 3
- FWCI
- 5.84
- Type
- journal article
- Language
- en
- Open access
- green
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- Wang, C. K., Northfield, S. E., Colless, B., Chaousis, S., Hamernig, I., Lohman, R.-J., Nielsen, D. S., Schroeder, C. I., Liras, S., Price, D. A., Fairlie, D. P., & Craik, D. J. (2014). Rational design and synthesis of an orally bioavailable peptide guided by NMR amide temperature coefficients. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.1417611111
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