Lipopeptide

{{Short description|Compound consisting of a short peptide chain conjugated with an acyl chain}}

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{{Infobox protein family

| Symbol = N/A

| Name = Cyclic lipopeptide antibiotics

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| caption =

| Pfam =

| Pfam_clan =

| InterPro =

| SMART =

| PROSITE =

| MEROPS =

| SCOP =

| TCDB = 1.D.15

| OPM family = 163

| OPM protein = 1t5n

| CAZy =

| CDD =

}}

A lipopeptide is a molecule consisting of a lipid connected to a peptide.{{cite journal | vauthors = Hamley IW | title = Lipopeptides: from self-assembly to bioactivity | journal = Chemical Communications | volume = 51 | issue = 41 | pages = 8574–83 | date = May 2015 | pmid = 25797909 | doi = 10.1039/c5cc01535a | url = http://centaur.reading.ac.uk/40450/1/c5cc01535a.pdf | doi-access = free }} They are able to self-assemble into different structures.{{cite journal | vauthors = Kirkham S, Castelletto V, Hamley IW, Inoue K, Rambo R, Reza M, Ruokolainen J | title = Self-Assembly of the Cyclic Lipopeptide Daptomycin: Spherical Micelle Formation Does Not Depend on the Presence of Calcium Chloride | journal = ChemPhysChem | volume = 17 | issue = 14 | pages = 2118–22 | date = July 2016 | pmid = 27043447 | doi = 10.1002/cphc.201600308 | s2cid = 44681934 | url = http://centaur.reading.ac.uk/66618/3/02.09.2016%20IWH%20DaptomycinAngewChem.pdf }}{{cite journal | vauthors = Hamley IW, Kirkham S, Dehsorkhi A, Castelletto V, Reza M, Ruokolainen J | title = Toll-like receptor agonist lipopeptides self-assemble into distinct nanostructures | journal = Chemical Communications | volume = 50 | issue = 100 | pages = 15948–51 | date = December 2014 | pmid = 25382300 | doi = 10.1039/c4cc07511k | doi-access = free }} Many bacteria produce these molecules as a part of their metabolism, especially those of the genus Bacillus, Pseudomonas and Streptomyces.{{cite journal | vauthors = Coutte F, Lecouturier D, Dimitrov K, Guez JS, Delvigne F, Dhulster P, Jacques P | title = Microbial lipopeptide production and purification bioprocesses, current progress and future challenges | journal = Biotechnology Journal | volume = 12 | issue = 7 | pages = 1600566 | date = July 2017 | pmid = 28636078 | doi = 10.1002/biot.201600566 }} Certain lipopeptides are used as antibiotics.{{cite patent |country= US |number= 6911525 |status= granted |pubdate= 28 February 2002 | title = Lipopeptides as antibacterial agents |inventor= Hill J, et al. | assign1 = Cubist Pharmaceuticals Inc }}{{cite journal | vauthors = Steenbergen JN, Alder J, Thorne GM, Tally FP | title = Daptomycin: a lipopeptide antibiotic for the treatment of serious Gram-positive infections | journal = The Journal of Antimicrobial Chemotherapy | volume = 55 | issue = 3 | pages = 283–8 | date = March 2005 | pmid = 15705644 | doi = 10.1093/jac/dkh546 | doi-access = free }} 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.{{cite journal |last1=Czechowicz |first1=Paulina |last2=Nowicka |first2=Joanna |date=2018-01-01 |title=Antimicrobial Activity of Lipopeptides |journal=Advancements of Microbiology |language=en |volume=57 |issue=3 |pages=213–227 |doi=10.21307/PM-2018.57.3.213|doi-access=free }}{{cite journal |last1=Raaijmakers |first1=Jos M. |last2=De Bruijn |first2=Irene |last3=Nybroe |first3=Ole |last4=Ongena |first4=Marc |date=November 2010 |title=Natural functions of lipopeptides from Bacillus and Pseudomonas: more than surfactants and antibiotics |journal=FEMS Microbiology Reviews |volume=34 |issue=6 |pages=1037–1062 |doi=10.1111/j.1574-6976.2010.00221.x |issn=1574-6976 |pmid=20412310|doi-access=free }} Other lipopeptides are toll-like receptor agonists. Certain lipopeptides can have strong antifungal and hemolytic activities.{{cite journal | vauthors = Maget-Dana R, Peypoux F | title = Iturins, a special class of pore-forming lipopeptides: biological and physicochemical properties | journal = Toxicology | volume = 87 | issue = 1–3 | pages = 151–74 | date = February 1994 | pmid = 8160184 | doi = 10.1016/0300-483X(94)90159-7}} It has been demonstrated that their activity is generally linked to interactions with the plasma membrane,{{cite journal | vauthors = Nasir MN, Besson F, Deleu M | title = Interactions des antibiotiques ituriniques avec la membrane plasmique. Apport des systèmes biomimétiques des membranes (synthèse bibliographique). | journal = Biotechnologie, Agronomie, Société et Environnement. | date = September 2013 | volume = 17 | issue = 3 | pages = 505–16 }} and sterol components of the plasma membrane could play a major role in this interaction.{{cite journal | vauthors = Nasir MN, Besson F | title = Interactions of the antifungal mycosubtilin with ergosterol-containing interfacial monolayers | journal = Biochimica et Biophysica Acta (BBA) - Biomembranes | volume = 1818 | issue = 5 | pages = 1302–8 | date = May 2012 | pmid = 22306791 | doi = 10.1016/j.bbamem.2012.01.020 | doi-access = free }}{{cite journal | vauthors = Nasir MN, Besson F | title = Specific interactions of mycosubtilin with cholesterol-containing artificial membranes | journal = Langmuir: The ACS Journal of Surfaces and Colloids | volume = 27 | issue = 17 | pages = 10785–92 | date = September 2011 | pmid = 21766869 | doi = 10.1021/la200767e }} 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.{{cite journal|title=Lipopeptides as the Antifungal and Antibacterial Agents: Applications in Food Safety and Therapeutics|last1=Kanwar|first1=Shamsher S.|last2=Meena|first2=Khem Raj|date=2015|journal=BioMed Research International|volume=2015|pages=473050|doi=10.1155/2015/473050|pmid=25632392|pmc=4303012|language=en|doi-access=free}} 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. As well, it opens the cell membrane of the bacteria, so antimicrobial activity can take place.{{cite journal |last1=Nasompag |first1=Sawinee |last2=Dechsiri |first2=Punpimon |last3=Hongsing |first3=Nuttaya |last4=Phonimdaeng |first4=Prasart |last5=Daduang |first5=Sakda |last6=Klaynongsruang |first6=Sompong |last7=Camesano |first7=Terri A. |last8=Patramanon |first8=Rina |date=October 2015 |title=Effect of acyl chain length on therapeutic activity and mode of action of the CX-KYR-NH2 antimicrobial lipopeptide |journal=Biochimica et Biophysica Acta (BBA) - Biomembranes |language=en |volume=1848 |issue=10 |pages=2351–2364 |doi=10.1016/j.bbamem.2015.07.004|pmid=26170198 |doi-access=free }}

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.{{cite book | first1 = Shuguang | last1 = Zhang | first2 = Karolina | last2 = Corin | editor-first = Sotirios | editor-last = Koutsopoulos | chapter = Peptide surfactants in membrane protein purification and stabilization | title = Peptide Applications in Biomedicine, Biotechnology and Bioengineering | date = 2018 | publisher = Elsevier Science | isbn = 978-0-08-100736-5 }}