Lipopeptide Explained

Symbol:N/A
Cyclic lipopeptide antibiotics
Tcdb:1.D.15
Opm Family:163
Opm Protein:1t5n

A lipopeptide is a molecule consisting of a lipid connected to a peptide.[1] They are able to self-assemble into different structures.[2] [3] Many bacteria produce these molecules as a part of their metabolism, especially those of the genus Bacillus, Pseudomonas and Streptomyces.[4] Certain lipopeptides are used as antibiotics.[5] [6] Due to the structural and molecular properties such as the fatty acid chain, it poses the effect of weakening the cell function or destroying the cell.[7] [8] Other lipopeptides are toll-like receptor agonists. Certain lipopeptides can have strong antifungal and hemolytic activities.[9] It has been demonstrated that their activity is generally linked to interactions with the plasma membrane,[10] and sterol components of the plasma membrane could play a major role in this interaction.[11] [12] It is a general trend that adding a lipid group of a certain length (typically C10–C12) to a lipopeptide will increase its bactericidal activity.[13] Lipopeptides with a higher amount of carbon atoms, for example 14 or 16, in its lipid tail will typically have antibacterial activity as well as anti-fungal activity. Therefore, an increase in the alkyl chain can make lipopeptides soluble in water.[7] As well, it opens the cell membrane of the bacteria, so antimicrobial activity can take place.[14]

Lipopeptide detergents (LPDs) are composed of amphiphiles and two alkyl chains which are located on the last part of the peptide backbone. They were designed to mimic the architecture of the native membranes in which two alkyl chains in a lipid molecule facially interact with the hydrophobic segment of MPs.[15]

See also

Further reading

Notes and References

  1. Hamley IW . Lipopeptides: from self-assembly to bioactivity . Chemical Communications . 51 . 41 . 8574–83 . May 2015 . 25797909 . 10.1039/c5cc01535a . free .
  2. Kirkham S, Castelletto V, Hamley IW, Inoue K, Rambo R, Reza M, Ruokolainen J . Self-Assembly of the Cyclic Lipopeptide Daptomycin: Spherical Micelle Formation Does Not Depend on the Presence of Calcium Chloride . ChemPhysChem . 17 . 14 . 2118–22 . July 2016 . 27043447 . 10.1002/cphc.201600308 . 44681934 .
  3. Hamley IW, Kirkham S, Dehsorkhi A, Castelletto V, Reza M, Ruokolainen J . Toll-like receptor agonist lipopeptides self-assemble into distinct nanostructures . Chemical Communications . 50 . 100 . 15948–51 . December 2014 . 25382300 . 10.1039/c4cc07511k . free .
  4. Coutte F, Lecouturier D, Dimitrov K, Guez JS, Delvigne F, Dhulster P, Jacques P . Microbial lipopeptide production and purification bioprocesses, current progress and future challenges . Biotechnology Journal . 12 . 7 . 1600566 . July 2017 . 28636078 . 10.1002/biot.201600566 .
  5. US . 6911525 . granted . 28 February 2002 . Lipopeptides as antibacterial agents . Hill J, et al. . Cubist Pharmaceuticals Inc .
  6. Steenbergen JN, Alder J, Thorne GM, Tally FP . Daptomycin: a lipopeptide antibiotic for the treatment of serious Gram-positive infections . The Journal of Antimicrobial Chemotherapy . 55 . 3 . 283–8 . March 2005 . 15705644 . 10.1093/jac/dkh546 . free .
  7. Czechowicz . Paulina . Nowicka . Joanna . 2018-01-01 . Antimicrobial Activity of Lipopeptides . Advancements of Microbiology . en . 57 . 3 . 213–227 . 10.21307/PM-2018.57.3.213. free .
  8. Raaijmakers . Jos M. . De Bruijn . Irene . Nybroe . Ole . Ongena . Marc . November 2010 . Natural functions of lipopeptides from Bacillus and Pseudomonas: more than surfactants and antibiotics . FEMS Microbiology Reviews . 34 . 6 . 1037–1062 . 10.1111/j.1574-6976.2010.00221.x . 1574-6976 . 20412310. free .
  9. Maget-Dana R, Peypoux F . Iturins, a special class of pore-forming lipopeptides: biological and physicochemical properties . Toxicology . 87 . 1–3 . 151–74 . February 1994 . 8160184 . 10.1016/0300-483X(94)90159-7.
  10. Nasir MN, Besson F, Deleu M . Interactions des antibiotiques ituriniques avec la membrane plasmique. Apport des systèmes biomimétiques des membranes (synthèse bibliographique). . Biotechnologie, Agronomie, Société et Environnement. . September 2013 . 17 . 3 . 505–16 .
  11. Nasir MN, Besson F . Interactions of the antifungal mycosubtilin with ergosterol-containing interfacial monolayers . Biochimica et Biophysica Acta (BBA) - Biomembranes . 1818 . 5 . 1302–8 . May 2012 . 22306791 . 10.1016/j.bbamem.2012.01.020 . free .
  12. Nasir MN, Besson F . Specific interactions of mycosubtilin with cholesterol-containing artificial membranes . Langmuir: The ACS Journal of Surfaces and Colloids . 27 . 17 . 10785–92 . September 2011 . 21766869 . 10.1021/la200767e .
  13. Lipopeptides as the Antifungal and Antibacterial Agents: Applications in Food Safety and Therapeutics. Kanwar. Shamsher S.. Meena. Khem Raj. 2015. BioMed Research International. 2015. 473050. 10.1155/2015/473050. 25632392. 4303012. en. free.
  14. Nasompag . Sawinee . Dechsiri . Punpimon . Hongsing . Nuttaya . Phonimdaeng . Prasart . Daduang . Sakda . Klaynongsruang . Sompong . Camesano . Terri A. . Patramanon . Rina . October 2015 . Effect of acyl chain length on therapeutic activity and mode of action of the CX-KYR-NH2 antimicrobial lipopeptide . Biochimica et Biophysica Acta (BBA) - Biomembranes . en . 1848 . 10 . 2351–2364 . 10.1016/j.bbamem.2015.07.004. 26170198 . free .
  15. Book: Shuguang . Zhang . Karolina . Corin . Sotirios . Koutsopoulos . Peptide surfactants in membrane protein purification and stabilization . Peptide Applications in Biomedicine, Biotechnology and Bioengineering . 2018 . Elsevier Science . 978-0-08-100736-5 .

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