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1 Biometals and Biological Chemistry, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France.
2 Membrane Biophysics and NMR, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France.
3 Membrane Biophysics and NMR, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France; Institut Universitaire de France, France.
4 Biometals and Biological Chemistry, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France. Electronic address: vlebrun@unistra.fr.
5 Biometals and Biological Chemistry, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France. Electronic address: pfaller@unistra.fr.
Merwan Bouraguba et al. J Inorg Biochem. 2020 Dec.
Affiliations
1 Biometals and Biological Chemistry, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France.
2 Membrane Biophysics and NMR, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France.
3 Membrane Biophysics and NMR, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France; Institut Universitaire de France, France.
4 Biometals and Biological Chemistry, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France. Electronic address: vlebrun@unistra.fr.
5 Biometals and Biological Chemistry, Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67 000 Strasbourg, France. Electronic address: pfaller@unistra.fr.
Depending on the coordination, copper ions can have a very high activity in catalyzing the production of reactive oxygen species. Thus interest arose in increasing the activity of antimicrobial peptides (AMPs) by equipping them with a Cu-binding unit. Several examples, native and engineered, have been investigated with the motif Xxx-Zzz-His, called Amino Terminal Cu(II)- and Ni(II)-binding (ATCUN) motif. Here we investigate a short AMP that was equipped either with Xxx-Zzz-His or Xxx-His. Xxx-His is a shorter motif and yields a more redox active copper complex. The control AMP, Xxx-His-AMP and Xxx-Zzz-His-AMP were investigated toward Cu-binding, Reactive Oxygen Species (ROS) production and antimicrobial activity in E. coli. The data indicate that these Cu-binding motifs have very limited impact on antimicrobial activity and low ROS production capability.
Keywords: Antimicrobial peptide; Copper; Metallopeptide; N-terminal Cu(II) binding site; Reactive oxygen species; Redox.
Copyright © 2020 Elsevier Inc. All rights reserved.
Gonzalez P, Bossak K, Stefaniak E, Hureau C, Raibaut L, Bal W, Faller P. Gonzalez P, et al. Chemistry. 2018 Jun 7;24(32):8029-8041. doi: 10.1002/chem.201705398. Epub 2018 Mar 24. Chemistry. 2018. PMID: 29336493 Free PMC article. Review.
Santoro A , Walke G , Vileno B , Kulkarni PP , Raibaut L , Faller P . Santoro A , et al. Chem Commun (Camb). 2018 Oct 18;54(84):11945-11948. doi: 10.1039/c8cc06040a. Chem Commun (Camb). 2018. PMID: 30288543
Gonzalez P, Vileno B, Bossak K, El Khoury Y, Hellwig P, Bal W, Hureau C, Faller P. Gonzalez P, et al. Inorg Chem. 2017 Dec 18;56(24):14870-14879. doi: 10.1021/acs.inorgchem.7b01996. Epub 2017 Nov 30. Inorg Chem. 2017. PMID: 29190078
Esmieu C, Ferrand G, Borghesani V, Hureau C. Esmieu C, et al. Chemistry. 2021 Jan 21;27(5):1777-1786. doi: 10.1002/chem.202003949. Epub 2020 Dec 14. Chemistry. 2021. PMID: 33058356
Miyamoto T, Kamino S, Odani A, Hiromura M, Enomoto S. Miyamoto T, et al. Yakugaku Zasshi. 2014;134(7):797-800. doi: 10.1248/yakushi.14-00017-4. Yakugaku Zasshi. 2014. PMID: 24989468 Review. Japanese.
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Subject: 1 selected item: 29336493 - PubMed
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Affiliations
1 Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67000, Strasbourg, France.
2 University of Strasbourg Institute for Advanced Study (USIAS), Strasbourg, France.
3 Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5a, 02-106, Warsaw, Poland.
4 LCC-CNRS, Université de Toulouse, CNRS, Toulouse, France.
Paulina Gonzalez et al. Chemistry. 2018.
Affiliations
1 Institut de Chimie, UMR 7177, CNRS-Université de Strasbourg, 4 rue Blaise Pascal, 67000, Strasbourg, France.
2 University of Strasbourg Institute for Advanced Study (USIAS), Strasbourg, France.
3 Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5a, 02-106, Warsaw, Poland.
4 LCC-CNRS, Université de Toulouse, CNRS, Toulouse, France.
Peptides and proteins with N-terminal amino acid sequences NH2 -Xxx-His (XH) and NH2 -Xxx-Zzz-His (XZH) form well-established high-affinity CuII -complexes. Key examples are Asp-Ala-His (in serum albumin) and Gly-His-Lys, the wound healing factor. This opens a straightforward way to add a high-affinity CuII -binding site to almost any peptide or protein, by chemical or recombinant approaches. Thus, these motifs, NH2 -Xxx-Zzz-His in particular, have been used to equip peptides and proteins with a multitude of functions based on the redox activity of Cu, including nuclease, protease, glycosidase, or oxygen activation properties, useful in anticancer or antimicrobial drugs. More recent research suggests novel biological functions, mainly based on the redox inertness of CuII in XZH, like PET imaging (with 64 Cu), chelation therapies (for instance in Alzheimer's disease and other types of neurodegeneration), antioxidant units, Cu transporters and activation of biological functions by strong CuII binding. This Review gives an overview of the chemical properties of Cu-XH and -XZH motifs and discusses the pros and cons of the vastly different biological applications, and how they could be improved depending on the application.
Keywords: amino acids; copper complexes; metallopeptides; motifs.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Scheme of the equatorial Cu II -coordination of the two motifs, Xxx-His (left)…
Scheme of the equatorial CuII-coordination of the two motifs, Xxx-His (left) and Xxx-Zzz-His (right). L depicts an external ligand, could be solvent or other ligand.
A: Asp stabilizing the protonated form of the N-terminal amine by forming a…
A: Asp stabilizing the protonated form of the N-terminal amine by forming a H-bond resulting in creation of a 6-memeberd ring. B: Asn stabilizing the deprotonated form of the N-terminal amine via a H-bond with a formation of a 6-membered ring. C: Arg could decrease the pKa of the amide via an electrostatic interaction with the oxygen of the amide bond. This should facilitate the deprotonation and hence the CuII binding. D: Asp could stabilize the protonated form of the amide by forming a H-bond. This should decrease the affinity of CuII, because CuII binding requires the deprotonation of this amide.
Scheme of the electrochemical (blue…
Scheme of the electrochemical (blue arrow) and chemical (orange arrow) redox properties of…
Scheme of the electrochemical (blue arrow) and chemical (orange arrow) redox properties of Cu-XZH and Cu-XH.3. Occurrence and Possible Roles in Biology
Maiti BK, Govil N, Kundu T, Moura JJG. Maiti BK, et al. iScience. 2020 Nov 10;23(12):101792. doi: 10.1016/j.isci.2020.101792. eCollection 2020 Dec 18. iScience. 2020. PMID: 33294799 Free PMC article. Review.
Gonzalez P, Vileno B, Bossak K, El Khoury Y, Hellwig P, Bal W, Hureau C, Faller P. Gonzalez P, et al. Inorg Chem. 2017 Dec 18;56(24):14870-14879. doi: 10.1021/acs.inorgchem.7b01996. Epub 2017 Nov 30. Inorg Chem. 2017. PMID: 29190078
Bouraguba M, Glattard E, Naudé M, Pelletier R, Aisenbrey C, Bechinger B, Raibaut L, Lebrun V, Faller P. Bouraguba M, et al. J Inorg Biochem. 2020 Dec;213:111255. doi: 10.1016/j.jinorgbio.2020.111255. Epub 2020 Sep 11. J Inorg Biochem. 2020. PMID: 32980641
Bossak-Ahmad K, Mital M, Płonka D, Drew SC, Bal W. Bossak-Ahmad K, et al. Inorg Chem. 2019 Jan 7;58(1):932-943. doi: 10.1021/acs.inorgchem.8b03051. Epub 2018 Dec 24. Inorg Chem. 2019. PMID: 30582328
DiSpirito AA, Semrau JD, Murrell JC, Gallagher WH, Dennison C, Vuilleumier S. DiSpirito AA, et al. Microbiol Mol Biol Rev. 2016 Mar 16;80(2):387-409. doi: 10.1128/MMBR.00058-15. Print 2016 Jun. Microbiol Mol Biol Rev. 2016. PMID: 26984926 Free PMC article. Review.
Skomorokhova EA, Sankova TP, Orlov IA, Savelev AN, Magazenkova DN, Pliss MG, Skvortsov AN, Sosnin IM, Kirilenko DA, Grishchuk IV, Sakhenberg EI, Polishchuk EV, Brunkov PN, Romanov AE, Puchkova LV, Ilyechova EY. Skomorokhova EA, et al. Nanotechnol Sci Appl. 2020 Dec 31;13:137-157. doi: 10.2147/NSA.S287658. eCollection 2020. Nanotechnol Sci Appl. 2020. PMID: 33408467 Free PMC article.
Maiti BK, Govil N, Kundu T, Moura JJG. Maiti BK, et al. iScience. 2020 Nov 10;23(12):101792. doi: 10.1016/j.isci.2020.101792. eCollection 2020 Dec 18. iScience. 2020. PMID: 33294799 Free PMC article. Review.
Mital M, Szutkowski K, Bossak-Ahmad K, Skrobecki P, Drew SC, Poznański J, Zhukov I, Frączyk T, Bal W. Mital M, et al. Int J Mol Sci. 2020 Dec 2;21(23):9200. doi: 10.3390/ijms21239200. Int J Mol Sci. 2020. PMID: 33276669 Free PMC article.
Malikidogo KP, Martin H, Bonnet CS. Malikidogo KP, et al. Pharmaceuticals (Basel). 2020 Nov 30;13(12):436. doi: 10.3390/ph13120436. Pharmaceuticals (Basel). 2020. PMID: 33266014 Free PMC article. Review.
Wezynfeld NE, Tobolska A, Mital M, Wawrzyniak UE, Wiloch MZ, Płonka D, Bossak-Ahmad K, Wróblewski W, Bal W. Wezynfeld NE, et al. Inorg Chem. 2020 Oct 5;59(19):14000-14011. doi: 10.1021/acs.inorgchem.0c01773. Epub 2020 Sep 14. Inorg Chem. 2020. PMID: 32924459 Free PMC article.

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Copper-binding motifs Xxx-His or Xxx-Zzz-His (ATCUN ...
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