Lipopeptides

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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

  1. ^ 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 .
  2. 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 .
  3. 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).
  4. 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 .
  5. 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 .
  6. 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 .
  7. 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 .
  8. 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 .
  9. 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 .
  10. 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).
  11. 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 .
  12. ^ 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 .