New teixobactin analogues with a total lactam ring

Article

Scioli, G., Marinaccio, L., Bauer, M., Kamysz, W., Parmar, A., Newire, E., Singh, I., Stefanucci, A. and Mollica, A. 2023. New teixobactin analogues with a total lactam ring. ACS Medicinal Chemistry Letters. 14 (12), pp. 1603-1892. https://doi.org/10.1021/acsmedchemlett.3c00435
TypeArticle
TitleNew teixobactin analogues with a total lactam ring
AuthorsScioli, G., Marinaccio, L., Bauer, M., Kamysz, W., Parmar, A., Newire, E., Singh, I., Stefanucci, A. and Mollica, A.
Abstract

Teixobactin is a new antibiotic peptide with strong efficacy against several Gram-positive resistant bacteria, the structure of which is extremely difficult to obtain in the laboratory via multistep conventional synthesis. To face the increasing antibiotic resistant bacteria, it is fundamental to introduce new types of antibiotics with innovative mechanisms of action without resistance; thus, many scientists are studying and developing new methods to synthesize teixobactin analogues. In this work, seven Arg10-teixobactin analogues with a total lactam ring have been prepared via solid phase peptide synthesis. In order to obtain the total lactam ring, d-Thr8 was replaced by (2R,3S)-diamino-propionic acid. To verify their antimicrobial activity and efficacy, each analogue was tested with MIC against different resistant pathogens, showing an interesting activity for Nle11 containing compounds.

KeywordsTeixobactin; Cyclic peptide; Solid phase peptide synthesis; SPPS; Resin; Resistance; Bacteria
Sustainable Development Goals3 Good health and well-being
Middlesex University ThemeHealth & Wellbeing
PublisherAmerican Chemical Society
JournalACS Medicinal Chemistry Letters
ISSN1948-5875
Publication dates
Online14 Nov 2023
Print14 Dec 2023
Publication process dates
Submitted25 Sep 2023
Accepted09 Nov 2023
Deposited16 Oct 2024
Output statusPublished
Publisher's version
License
File Access Level
Open
Copyright Statement

Copyright © 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0 .

Digital Object Identifier (DOI)https://doi.org/10.1021/acsmedchemlett.3c00435
Permalink -

https://repository.mdx.ac.uk/item/1v4xq7

Log in to edit

Download files

Publisher's version
scioli-et-al-2023-new-teixobactin-analogues-with-a-total-lactam-ring.pdf
License: CC BY 4.0
File access level: Open

  • 13
    total views
  • 3
    total downloads
  • 4
    views this month
  • 2
    downloads this month

Export as

Related outputs

Development of teixobactin analogues containing hydrophobic, non-proteogenic amino acids that are highly potent against multidrug-resistant bacteria and biofilms
Parmar, A., Lakshminarayanan, R., Iyer, A., Goh, E.T.L., To, T.Y., Yam, J.K.H., Yang, L., Newire, E., Robertson, M.C., Prior, S.H., Breukink, E., Madder, M. and Singh, I. 2023. Development of teixobactin analogues containing hydrophobic, non-proteogenic amino acids that are highly potent against multidrug-resistant bacteria and biofilms. European Journal of Medicinal Chemistry. 261. https://doi.org/10.1016/j.ejmech.2023.115853
Identification of a Type IV-A CRISPR-Cas system located exclusively on IncHI1B/IncFIB plasmids in Enterobacteriaceae
Newire, E., Aydin, A., Juma, S., Enne, V. and Roberts, A. 2020. Identification of a Type IV-A CRISPR-Cas system located exclusively on IncHI1B/IncFIB plasmids in Enterobacteriaceae. Frontiers in Microbiology. 11. https://doi.org/10.3389/fmicb.2020.01937
Isolation of an antimicrobial-resistant, biofilm-forming, Klebsiella grimontii isolate from a reusable water bottle
Hubbard, A.T.M., Newire, E., Botelho, J., Reiné, J., Wright, E., Murphy, E.A., Hutton, W. and Roberts, A.P. 2020. Isolation of an antimicrobial-resistant, biofilm-forming, Klebsiella grimontii isolate from a reusable water bottle. MicrobiologyOpen. 9 (6), pp. 1128-1134. https://doi.org/10.1002/mbo3.1023
Mobile colistin resistance gene mcr-1 detected on an IncI1 plasmid in Escherichia coli from meat
Brouwer, M.S.M., Goodman, R.N., Kant, A., Newire, E., Roberts, A.P. and Veldman, K.T. 2020. Mobile colistin resistance gene mcr-1 detected on an IncI1 plasmid in Escherichia coli from meat. Journal of Global Antimicrobial Resistance. 23, pp. 145-148. https://doi.org/10.1016/j.jgar.2020.08.018
Presence of Type I-F CRISPR/Cas systems is associated with antimicrobial susceptibility in Escherichia coli
Aydin, S., Personne, Y., Newire, E., Laverrick, R., Russell, O., Roberts, A. and Enne, V. 2017. Presence of Type I-F CRISPR/Cas systems is associated with antimicrobial susceptibility in Escherichia coli . Journal of Antimicrobial Chemotherapy. 72 (8), p. 2213–2218. https://doi.org/10.1093/jac/dkx137
Detection of new SHV-12, SHV-5 and SHV-2a variants of extended spectrum Beta-lactamase in Klebsiella pneumoniae in Egypt
Newire, E., Ahmed, S., House, B., Valiente, E. and Pimentel, G. 2013. Detection of new SHV-12, SHV-5 and SHV-2a variants of extended spectrum Beta-lactamase in Klebsiella pneumoniae in Egypt. Annals of Clinical Microbiology and Antimicrobials. 12. https://doi.org/10.1186/1476-0711-12-16
Laboratory-based surveillance for acute febrile illness in Egypt: a focus on leptospirosis
Parker, T.M., Ismail, T., Fadeel, M.A., Maksoud, M.A., Morcos, M., Newire, E., Wasfy, M.O., Murray, C.K., Pimentel, G., El-Sayed, N. and Hajjeh, R. 2006. Laboratory-based surveillance for acute febrile illness in Egypt: a focus on leptospirosis. American Society of Tropical Medicine and Hygiene 55th Annual Meeting. Atlanta, Georgia, USA 12 - 16 Nov 2006 American Society of Tropical Medicine and Hygiene. https://doi.org/10.4269/ajtmh.2006.75.1