Improving Oral Bioavailability of Peptides by Multiple N‐Methylation: Somatostatin Analogues
Abstract
Full methyl jacket? A complete library of the N-methylated somatostatin cyclopeptidic analogue Veber–Hirschmann peptide cyclo(-PFwKTF-) has been prepared with the aim of improving its bioavailability. Several analogues from the library were found to bind to the somatostatin receptor in the nanomolar range and one of them shows a significant oral bioavailability of 10 %. Conformational analysis shows that N-methylation is allowed at specific positions without affecting the bioactive conformation.
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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 · see citing works
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Muppidi, A., Doi, K., Edwardraja, S., Drake, E. J., Gulick, A. M., Wang, H.-G., & Lin, Q. (2012) · Journal of the American Chemical Society · doi:10.1021/ja306864v · Cited by 156 · see citing works
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- Authors
- Biron, E., Chatterjee, J., Ovadia, O., Langenegger, D., Brueggen, J., Hoyer, D., Schmid, H. A., Jelinek, R., Gilon, C., Hoffman, A., & Kessler, H.
- Affiliations
- Technical University of Munich (DE)
- Hebrew University of Jerusalem (IL)
- Novartis Institutes for BioMedical Research (CH)
- Ben-Gurion University of the Negev (IL)
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2008-03-18
- Volume
- 47
- Issue
- 14
- Pages
- 2595-2599
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2065889205
- Cited by
- 374
- References
- 1
- Citations by year
- 2026: 16 · 2025: 24 · 2024: 18 · 2023: 21 · 2022: 23 · 2021: 21 · 2020: 14 · 2019: 27 · 2018: 37 · 2017: 21 · 2016: 14 · 2015: 27 · 2014: 28 · 2013: 11 · 2012: 17
- FWCI
- 7.22
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
- Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuropeptides and Animal Physiology
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biochemical and Structural Characterization
- Keywords
- somatostatin analogues, N-methylation, oral bioavailability, cyclopeptides, somatostatin receptor binding, conformational analysis, peptide libraries, bioactive conformation
- MeSH terms
- Administration, Oral, Animals, Biological Availability, Humans, Methylation, Models, Molecular, Somatostatin, Molecular Structure, Caco-2 Cells, Rats
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