ArticleBeilstein journal of organic chemistry2012
Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups.
Article in Beilstein journal of organic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 71 citations in OpenAlex.
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- New nitazoxanide derivatives: design, synthesis, biological evaluation, and molecular docking studies as antibacterial and antimycobacterial agents.RSC medicinal chemistry · 2023Article
- Hydrogen Bonding Drives Helical Chirality via 10-Membered Rings in Dipeptide Conjugates of Ferrocene-1,1'-Diamine.International journal of molecular sciences · 2022Article
- The current research status and strategies employed to modify food-derived bioactive peptides.Frontiers in nutrition · 2022Review
- Hydrophobic-hydrophilic Alternation: An effective Pattern to de novo Designed Antimicrobial Peptides.Current pharmaceutical design · 2022Article
- Rational prioritization strategy allows the design of macrolide derivatives that overcome antibiotic resistance.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Solid-phase synthesis and evaluation of linear and cyclic ferrocenoyl/ruthenocenoyl water-soluble hexapeptides as potential antibacterial compounds.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2021Article
- Evaluation of Ruthenium(II)Molecules (Basel, Switzerland) · 2021Article
- A flat embedding method for transmission electron microscopy reveals an unknown mechanism of tetracycline.Communications biology · 2021Article
- Development of a Potent Antimicrobial Peptide With Photodynamic Activity.Frontiers in microbiology · 2021Article
- Comparison of Proteomic Responses as Global Approach to Antibiotic Mechanism of Action Elucidation.Antimicrobial agents and chemotherapy · 2020Article
- Assessing Membrane Fluidity and Visualizing Fluid Membrane Domains in Bacteria Using Fluorescent Membrane Dyes.Bio-protocol · 2018Article
- The novel antibiotic rhodomyrtone traps membrane proteins in vesicles with increased fluidity.PLoS pathogens · 2018Article
- Editorial: Antimicrobial Peptides - Interaction with Membrane Lipids and Proteins.Frontiers in cell and developmental biology · 2017Article
- Allicin Induces Thiol Stress in Bacteria through S-Allylmercapto Modification of Protein Cysteines.The Journal of biological chemistry · 2016Article
- Towards Profiles of Resistance Development and Toxicity for the Small Cationic Hexapeptide RWRWRW-NH2.Frontiers in cell and developmental biology · 2016Article
- An organometallic structure-activity relationship study reveals the essential role of a Re(CO)Chemical science · 2015Article
- Small cationic antimicrobial peptides delocalize peripheral membrane proteins.Proceedings of the National Academy of Sciences of the United States of America · 2014Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A series of small synthetic arginine and tryptophan containing peptides was prepared and analyzed for their antibacterial activity. The effect of N-terminal substitution with metallocenoyl groups such as ferrocene (FcCO) and ruthenocene (RcCO) was investigated. Antibacterial activity in different media, growth inhibition, and killing kinetics of the most active peptides were determined. The toxicity of selected derivatives was determined against erythrocytes and three human cancer cell lines. It was shown that the replacement of an N-terminal arginine residue with a metallocenoyl moiety modulates the activity of WRWRW-peptides against Gram-positive and Gram-negative bacteria. MIC values of 2-6 µM for RcCO-W(RW)(2) and 1-11 µM for (RW)(3) were determined. Interestingly, W(RW)(2)-peptides derivatized with ferrocene were significantly less active than those derivatized with ruthenocene which have similar structural but different electronic properties, suggesting a major influence of the latter. The high activities observed for the RcCO-W(RW)(2)- and (RW)(3)-peptides led to an investigation of the origin of activity of these peptides using several important activity-related parameters. Firstly, killing kinetics of the RcCO-W(RW)(2)-peptide versus killing kinetics of the (RW)(3) derivative showed faster reduction of the colony forming units for the RcCO-W(RW)(2)-peptide, although MIC values indicated higher activity for the (RW)(3)-peptide. This was confirmed by growth inhibition studies. Secondly, hemolysis studies revealed that both peptides did not lead to significant destruction of erythrocytes, even up to 500 µg/mL for (RW)(3) and 250 µg/mL for RcCO-W(RW)(2). In addition, toxicity against three human cancer cell lines (HepG2, HT29, MCF7) showed that the (RW)(3)-peptide had an IC(50) value of ~140 µM and the RcW(RW)(2) one of ~90 µM, indicating a potentially interesting therapeutic window. Both the killing kinetics and growth inhibition studies presented in this work point to a membrane-based mode of action for these two peptides, each having different kinetic parameters.
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