Exploring Structure–Activity Relationships in Synthetic Antimicrobial Peptides (synAMPs) by a Ferrocene Scan

Slootweg, J. Chris; Prochnow, Pascal; Bobersky, Sandra; Bandow, Julia E.; Metzler‐Nolte, Nils

doi:10.1002/ejic.201600799

Cited by 15 publications

(9 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Metzler-Nolte group specializes in the design and synthesis of peptide–metal complex conjugates [ 67 , 68 , 69 ]. Motivated by their long-standing experience in bioconjugation chemistry [ 70 , 71 , 72 , 73 ], they recently explored how to introduce cobalt complexes to peptide delivery systems, as those have yet not been extensively studied for their anticancer potential [ 37 ]. To achieve the coupling, the authors designed a Schiff base ligand by condensation of salicylaldehyde with 3,4-diamino benzoic acid ( Scheme 3 ).…”

Section: Amide Bond Formation and Related Chemistrymentioning

confidence: 99%

Recent Advances and Trends in Chemical CPP–Drug Conjugation Techniques

2021

View full text Add to dashboard Cite

This review summarizes recent developments in conjugation techniques for the synthesis of cell-penetrating peptide (CPP)–drug conjugates targeting cancer cells. We will focus on small organic molecules as well as metal complexes that were used as cytostatic payloads. Moreover, two principle ways of coupling chemistry will be discussed direct conjugation as well as the use of bifunctional linkers. While direct conjugation of the drug to the CPP is still popular, the use of bifunctional linkers seems to gain increasing attention as it offers more advantages related to the linker chemistry. Thus, three main categories of linkers will be highlighted, forming either disulfide acid-sensitive or stimuli-sensitive bonds. All techniques will be thoroughly discussed by their pros and cons with the aim to help the reader in the choice of the optimal conjugation technique that might be used for the synthesis of a given CPP–drug conjugate

show abstract

Section: Amide Bond Formation and Related Chemistrymentioning

confidence: 99%

Recent Advances and Trends in Chemical CPP–Drug Conjugation Techniques

2021

View full text Add to dashboard Cite

show abstract

“…Some synthetic antimicrobial peptides alternate residues with aromatic and with cationic chains. In a recent work, the structure-activity relationships of the synthetic AMPs 29 ( Figure 3 , center) was explored using a ferrocene scan [ 131 ].…”

Section: Discovery Of New Ampsmentioning

confidence: 99%

The Road from Host-Defense Peptides to a New Generation of Antimicrobial Drugs

2018

View full text Add to dashboard Cite

Host-defense peptides, also called antimicrobial peptides (AMPs), whose protective action has been used by animals for millions of years, fulfill many requirements of the pharmaceutical industry, such as: (1) broad spectrum of activity; (2) unlike classic antibiotics, they induce very little resistance; (3) they act synergically with conventional antibiotics; (4) they neutralize endotoxins and are active in animal models. However, it is considered that many natural peptides are not suitable for drug development due to stability and biodisponibility problems, or high production costs. This review describes the efforts to overcome these problems and develop new antimicrobial drugs from these peptides or inspired by them. The discovery process of natural AMPs is discussed, as well as the development of synthetic analogs with improved pharmacological properties. The production of these compounds at acceptable costs, using different chemical and biotechnological methods, is also commented. Once these challenges are overcome, a new generation of versatile, potent and long-lasting antimicrobial drugs is expected.

show abstract

“…It is posited that the presence of different antimicrobial agents in these hybrids leads to multiple mechanisms of antimicrobial activity that could mitigate the evolution of resistance since it is more challenging for microorganisms to deal with multiple mechanisms of action . Many reports feature this approach in combating resistance as evidenced by numerous examples of dual action, bioconjugates or hybrid antimicrobial macromolecules and materials . For this approach to succeed, the hybrid is expected to exert superior activity over its constituent agents .…”

Section: Introductionmentioning

confidence: 99%

Quaternized and Thiazole‐Functionalized Free Radical‐Generating Organometallic Dendrimers as Antimicrobial Platform against Multidrug‐Resistant Microorganisms

Abd‐El‐Aziz

Agatemor

Etkin

et al. 2017

Macromolecular Bioscience

View full text Add to dashboard Cite

New macromolecules such as dendrimers are increasingly needed to drive breakthroughs in diverse areas, for example, healthcare. Here, the authors report hybrid antimicrobial dendrimers synthesized by functionalizing organometallic dendrimers with quaternary ammonium groups or 2-mercaptobenzothiazole. The functionalization tunes the glass transition temperature and antimicrobial activities of the dendrimers. Electron paramagnetic resonance spectroscopy reveals that the dendrimers form free radicals, which have significant implications for catalysis and biology. In vitro antimicrobial assays indicate that the dendrimers are potent antimicrobial agents with activity against multidrug-resistant pathogens such as methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium as well as other microorganisms. The functionalization increases the activity, especially in the quaternary ammonium group-functionalized dendrimers. Importantly, the activities are selective because human epidermal keratinocytes cells and BJ fibroblast cells exposed to the dendrimers are viable after 24 h.

show abstract

Exploring Structure–Activity Relationships in Synthetic Antimicrobial Peptides (synAMPs) by a Ferrocene Scan

Cited by 15 publications

References 43 publications

Recent Advances and Trends in Chemical CPP–Drug Conjugation Techniques

Recent Advances and Trends in Chemical CPP–Drug Conjugation Techniques

The Road from Host-Defense Peptides to a New Generation of Antimicrobial Drugs

Quaternized and Thiazole‐Functionalized Free Radical‐Generating Organometallic Dendrimers as Antimicrobial Platform against Multidrug‐Resistant Microorganisms

Contact Info

Product

Resources

About