Lipopeptides
Lipopeptides are peptides that are modified with lipids .
properties
Typical hydrophobic modifications to peptides are e.g. B. palmitoylation , myristylation , farnesylation , GPI anchor and geranylgeranylation . Through these modifications ( lipid anchors ), lipopeptides bind to cell membranes . In addition, they are amphiphilic and accumulate in aqueous solutions above their respective critical micelle concentration .
Some lipopeptides activate the innate immune response via toll-like receptors 1, 2 and 6. The CSK 4 motif with one to three palmitoylations binds to TLR.
The analysis of lipopeptides is done by some form of immunostaining or by LC-MS .
Applications
Some linear or cyclic lipopeptides are used as antibiotics or have antibiotic effects, e.g. B. daptomycin , bacillomycin , echinocandins such as caspofungin , Jagaricin , Malacidine , mycosubtilin , iturin A , fengycin and surfactin . The antibiotic effect of lipopeptides is based on a different mechanism than other types of antibiotics, which makes it difficult to develop resistance .
Furthermore, lipopeptides are being investigated for use as feed additive , chemotherapeutic , thrombolytic and as vesicle formers . As vesicle formers z. B. the cell penetrating peptide TAT 48-60 with one to four alkyl groups or palmitoylated Ala - Gly - Phe - Leu - Arg are used. The lipopeptide Palmitoyl- Lys - Thr -Thr-Lys- Ser (short: C16-KTTKS) is used to smooth expression lines (trade name Matrikine ). Certain lipopeptides ( pepducins ) are being studied to modulate G proteins .
Individual evidence
- ^ A b c Ian W. Hamley: Lipopeptides: from self-assembly to bioactivity. In: Chemical Communications . 51, 2015, p. 8574, doi: 10.1039 / c5cc01535a , PMID 25797909 .
- ↑ T. Schneider, A. Müller, H. Miess, H. Gross: Cyclic lipopeptides as antibacterial agents - potent antibiotic activity mediated by intriguing mode of actions. In: International Journal of Medical Microbiology . Volume 304, number 1, January 2014, pp. 37-43, doi: 10.1016 / j.ijmm.2013.08.009 , PMID 24119568 .
- ↑ JA Hutchinson, S. Burholt, IW Hamley: Peptide hormones and lipopeptides: from self-assembly to therapeutic applications. In: Journal of Peptide Science . Volume 23, number 2, February 2017, pp. 82-94, doi: 10.1002 / psc.2954 , PMID 28127868 , PMC 5324658 (free full text).
- ↑ J. Zemenová, D. Sýkora, L. Maletínská, J. Kuneš: Lipopeptides as therapeutics: applications and in vivo quantitative analysis. In: Bioanalysis . Volume 9, number 2, January 2017, pp. 215-230, doi: 10.4155 / bio-2016-0206 , PMID 27960546 .
- ↑ S. Patel, S. Ahmed, JS Eswari: Therapeutic cyclic lipopeptides mining from microbes: latest strides and hurdles. In: World Journal of Microbiology & Biotechnology. Volume 31, Number 8, August 2015, pp. 1177-1193, doi: 10.1007 / s11274-015-1880-8 , PMID 26041368 .
- ↑ T. Schneider, A. Müller, H. Miess, H. Gross: Cyclic lipopeptides as antibacterial agents - potent antibiotic activity mediated by intriguing mode of actions. In: International Journal of Medical Microbiology. Volume 304, number 1, January 2014, pp. 37-43, doi: 10.1016 / j.ijmm.2013.08.009 , PMID 24119568 .
- ↑ a b c I. Mnif, D. Ghribi: Review lipopeptides biosurfactants: Mean classes and new insights for industrial, biomedical, and environmental applications. In: Biopolymers. Volume 104, number 3, May 2015, pp. 129-147, doi: 10.1002 / bip.22630 , PMID 25808118 .
- ↑ JJ Koh, S. Lin, RW Beuerman, S. Liu: Recent advances in synthetic lipopeptides as anti-microbial agents: designs and synthetic approaches. In: Amino Acids. Volume 49, Number 10, October 2017, pp. 1653–1677, doi: 10.1007 / s00726-017-2476-4 , PMID 28823054 .
- ↑ H. Zhao, D. Shao, C. Jiang, J. Shi, Q. Li, Q. Huang, MS Rajoka, H. Yang, M. Jin: Biological activity of lipopeptides from Bacillus. In: Applied Microbiology and Biotechnology . Volume 101, Number 15, August 2017, pp. 5951-5960, doi: 10.1007 / s00253-017-8396-0 , PMID 28685194 .
- ↑ P. Zhang, AG Cheetham, YA Lin, H. Cui: Self-assembled Tat nanofibers as effective drug carrier and transporter. In: ACS Nano . Volume 7, number 7, July 2013, pp. 5965-5977, doi: 10.1021 / nn401667z , PMID 23758167 , PMC 3799919 (free full text).
- ↑ M. Mazza, R. Notman, J. Anwar, A. Rodger, M. Hicks, G. Parkinson, D. McCarthy, T. Daviter, J. Moger, N. Garrett, T. Mead, M. Briggs, AG Schätzlein, IF Uchegbu: Nanofiber-based delivery of therapeutic peptides to the brain. In: ACS Nano. Volume 7, Number 2, February 2013, pp. 1016-1026, doi: 10.1021 / nn305193d , PMID 23289352 .
- ^ V. Castelletto, IW Hamley, J. Perez, L. Abezgauz, D. Danino: Fibrillar superstructure from extended nanotapes formed by a collagen-stimulating peptide. In: Chemical Communications. Volume 46, Number 48, December 2010, pp. 9185-9187, doi: 10.1039 / c0cc03793a , PMID 21031196 .