Antibacterial activities of ferrocenoyl- and cobaltocenium-peptide bioconjugates

Janine T. Chantson, Maria Vittoria Verga Falzacappa, Sergio Crovella, Nils Metzler-Nolte

Research output: Contribution to journalArticle

82 Citations (Scopus)

Abstract

The peptide and metallocene-peptide bioconjugates R-Arg-Arg-Phe-NH 2, R-Phe-Arg-Phe-NH 2 where R = H, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) + and R′-Gly-Trp-Arg-Arg-Phe-NH 2, R′-Trp-Arg-Arg-Phe- NH 2, where R′ = n-C 5H 11CO, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) +, and Arg = l-arginine, Gly = l-glycine, Phe = l-phenylalanine, Trp = l-tryptophan were prepared by solid phase peptide synthesis (SPPS). The compounds were purified by RP-HPLC and characterized by ESI-MS and NMR spectroscopy. Antibacterial properties of the compounds were determined by minimum inhibitory concentration (MIC) tests against Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus.

Original languageEnglish
Pages (from-to)4564-4572
Number of pages9
JournalJournal of Organometallic Chemistry
Volume690
Issue number21-22
DOIs
Publication statusPublished - Nov 1 2005

Fingerprint

Carbon Monoxide
Peptides
peptides
phenylalanyl-arginyl-phenylalanine
Arginine
pseudomonas
phenylalanine
staphylococcus
tryptophan
glycine
Escherichia
Escherichia coli
Solid-Phase Synthesis Techniques
Nuclear magnetic resonance spectroscopy
solid phases
Amino acids
Microbial Sensitivity Tests
Phenylalanine
Tryptophan
Glycine

Keywords

  • Antibacterial agents
  • Bioorganometallic chemistry
  • Cobaltocenium
  • Ferrocene
  • Peptides
  • Solid phase synthesis

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Materials Science (miscellaneous)
  • Materials Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Biochemistry

Cite this

Antibacterial activities of ferrocenoyl- and cobaltocenium-peptide bioconjugates. / Chantson, Janine T.; Falzacappa, Maria Vittoria Verga; Crovella, Sergio; Metzler-Nolte, Nils.

In: Journal of Organometallic Chemistry, Vol. 690, No. 21-22, 01.11.2005, p. 4564-4572.

Research output: Contribution to journalArticle

@article{a69fd632364c4c3489bf54c69256f724,
title = "Antibacterial activities of ferrocenoyl- and cobaltocenium-peptide bioconjugates",
abstract = "The peptide and metallocene-peptide bioconjugates R-Arg-Arg-Phe-NH 2, R-Phe-Arg-Phe-NH 2 where R = H, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) + and R′-Gly-Trp-Arg-Arg-Phe-NH 2, R′-Trp-Arg-Arg-Phe- NH 2, where R′ = n-C 5H 11CO, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) +, and Arg = l-arginine, Gly = l-glycine, Phe = l-phenylalanine, Trp = l-tryptophan were prepared by solid phase peptide synthesis (SPPS). The compounds were purified by RP-HPLC and characterized by ESI-MS and NMR spectroscopy. Antibacterial properties of the compounds were determined by minimum inhibitory concentration (MIC) tests against Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus.",
keywords = "Antibacterial agents, Bioorganometallic chemistry, Cobaltocenium, Ferrocene, Peptides, Solid phase synthesis",
author = "Chantson, {Janine T.} and Falzacappa, {Maria Vittoria Verga} and Sergio Crovella and Nils Metzler-Nolte",
year = "2005",
month = "11",
day = "1",
doi = "10.1016/j.jorganchem.2005.07.007",
language = "English",
volume = "690",
pages = "4564--4572",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",
number = "21-22",

}

TY - JOUR

T1 - Antibacterial activities of ferrocenoyl- and cobaltocenium-peptide bioconjugates

AU - Chantson, Janine T.

AU - Falzacappa, Maria Vittoria Verga

AU - Crovella, Sergio

AU - Metzler-Nolte, Nils

PY - 2005/11/1

Y1 - 2005/11/1

N2 - The peptide and metallocene-peptide bioconjugates R-Arg-Arg-Phe-NH 2, R-Phe-Arg-Phe-NH 2 where R = H, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) + and R′-Gly-Trp-Arg-Arg-Phe-NH 2, R′-Trp-Arg-Arg-Phe- NH 2, where R′ = n-C 5H 11CO, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) +, and Arg = l-arginine, Gly = l-glycine, Phe = l-phenylalanine, Trp = l-tryptophan were prepared by solid phase peptide synthesis (SPPS). The compounds were purified by RP-HPLC and characterized by ESI-MS and NMR spectroscopy. Antibacterial properties of the compounds were determined by minimum inhibitory concentration (MIC) tests against Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus.

AB - The peptide and metallocene-peptide bioconjugates R-Arg-Arg-Phe-NH 2, R-Phe-Arg-Phe-NH 2 where R = H, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) + and R′-Gly-Trp-Arg-Arg-Phe-NH 2, R′-Trp-Arg-Arg-Phe- NH 2, where R′ = n-C 5H 11CO, Fe(Cp)(C 5H 4-CO), Co(Cp)(C 5H 4-CO) +, and Arg = l-arginine, Gly = l-glycine, Phe = l-phenylalanine, Trp = l-tryptophan were prepared by solid phase peptide synthesis (SPPS). The compounds were purified by RP-HPLC and characterized by ESI-MS and NMR spectroscopy. Antibacterial properties of the compounds were determined by minimum inhibitory concentration (MIC) tests against Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus.

KW - Antibacterial agents

KW - Bioorganometallic chemistry

KW - Cobaltocenium

KW - Ferrocene

KW - Peptides

KW - Solid phase synthesis

UR - http://www.scopus.com/inward/record.url?scp=26644467705&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=26644467705&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2005.07.007

DO - 10.1016/j.jorganchem.2005.07.007

M3 - Article

AN - SCOPUS:26644467705

VL - 690

SP - 4564

EP - 4572

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 21-22

ER -