Schrittweise Festphasensynthese von zwei‐ und dreikernigen Metallkomplexen

Heinze, Katja; Toro, Juan D. Bueno

doi:10.1002/ange.200351849

Cited by 11 publications

(17 citation statements)

References 21 publications

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“…[29][30][31][32][33][34][35][36] More recently, labeling of DNA with ferrocene has been reported. [37][38][39][40][41] The solid-phase synthesis of Mo carbonyl complexes have also been reported; without biomolecules [42][43][44] and with [Leu 5 ]-enkephalin. [45] We have previously prepared metallocene-peptide conjugates with tri-to pentapeptides for antibacterial testing.…”

Section: Discussionmentioning

confidence: 99%

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

et al. 2006

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This work shows how the introduction of an organometallic group enhances and modifies the specificity of biologically active peptides. Ferrocene was chosen as an organometallic group because it has been shown to alter the pharmacodynamic profile of bioactive compounds. A comparison with the isosteric cobaltocenium group allows one to explore the influence of charge and redox potential on the biological activity of the conjugates. Arginine and tryptophan containing peptides H-WRWRWR-NH(2) and H-RWRWRW-NH(2) and the metallocene peptide bioconjugates [M]-C(O)-RWRWR-NH(2) and [M]-C(O)-WRWRW-NH(2), where [M]=[Co(Cp)(C(5)H(4))](+), [Fe(Cp)(C(5)H(4))] were prepared by solid-phase peptide synthesis (SPPS). They were purified by HPLC, characterized by ESIMS and NMR spectroscopy, and tested for antibacterial properties against Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus using the minimum inhibitory concentration (MIC) test. In most cases, no metal-specific activity could be observed. However, the conjugate [Fe(Cp)(C(5)H(4))-C(O)-WRWRW-NH(2)] 6 was found to be particularly effective against the Gram-positive S. aureus. The activity of this metallocene-pentapeptide conjugate (7.1 microM) was even better than the 20 amino acid naturally occurring pilosulin 2, which was used as a positive control. Unlike all other compounds tested, which were most active against the Gram-negative E. coli strain, the ferrocene conjugate 6 was the only compound in this series that was most active against Gram-positive bacteria. Given the health concerns resulting from multidrug resistant S. aureus strains, the incorporation of metallocenes may provide a novel line of attack.

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Section: Discussionmentioning

confidence: 99%

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

et al. 2006

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“…[2] Organometallic compounds, however, have only recently been synthesised by this method, [4Ϫ17] and the solid-phase synthesis of oligometallic complexes, in particular, remains a challenge. [5,17] This is probably due to the fact that the cisely determined by the reaction sequence and is retained under the applied reaction conditions as shown by IR, NMR and UV/Vis spectroscopic analysis of the cleaved soluble products. Additionally, the same complex library has been prepared by conventional solution-phase synthesis to allow evaluation of the advantages and disadvantages of the solidphase synthesis method.…”

Section: Introductionmentioning

confidence: 99%

Solid‐ and Solution‐Phase Synthesis of a Library of Mixed‐Metal Complexes

Heinze

Toro

2004

Eur J Inorg Chem

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A solid-phase synthesis protocol has been developed for the stepwise assembly of mixed-metal dinuclear complexes built from chromium, molybdenum and tungsten and a directional bridging ligand. Complexes with all nine possible metal combinations have been prepared on polystyrene/divinylbenzene copolymer employing a metal-complex-compatible silyl ether linker. Release of the metal complexes from the polymeric support is accomplished by fluoridolysis under mild conditions. The metal sequence in these complexes is pre-

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“…For rather sensitive organometallic complexes a silyl ether linker between the polymer and the first ligand has been successfully employed. [42][43][44][45][46] This linker type has been used in organic solid-phase synthesis of sensitive compounds, for example, oligosaccharides and prostaglandins. [47][48][49] The feasible and mild cleavage of silyl ethers by using fluoride ions was also attractive especially for sensitive organometallic complexes (low-valent, soft transition metals).…”

Section: Sps Of Transition-metal Complexes: Formation Of Coordinativementioning

confidence: 99%

“…Thus mononuclear M 0 (M = Cr, Mo, W) and Mo II complexes fulfil the conditions required for SPS of oligonuclear metal complexes and the SPS of oligonuclear complexes was addressed. [44,46] For this approach the bifunctional diimine isonitrile ligand 17 a (for mixed-metal carbonyl complexes) and 1,10-phenanthroline-5,6-dione (17 b; for platinum(II) complexes, vide infra) were employed (Scheme 11). Ligand 17 a is capable of coordinating two metal-carbonyl units, one through the isonitrile group and another one by the diimine chelate and is, therefore, an ideal directional bridging ligand.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…[44,46] Coordination of a M 1 (CO) 3 fragment (M 1 = Cr, Mo or W) to 13-PS is followed by addition of the bridging ligand 17 a, which binds to M 1 in a monodentate fashion through its isonitrile functionality (Scheme 12, 18-PS). Repeating this procedure employing a M Up to four M(CO) n units can be precisely arranged in this manner; however, poor solubility of the products prohibits further chain elongation.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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Solid‐Phase Synthesis of Transition‐Metal Complexes

Heinze

Beckmann

Hempel

2008

Chemistry A European J

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This overview highlights recent progress in the field of selective construction of linear, oligonuclear transition-metal complexes by using solid-phase synthesis procedures. Two general protocols have been identified: formation of coordinative bonds between metal centres and bridging ligands and formation of covalent bonds between preformed kinetically inert transition-metal-containing building blocks in the chain growth step. Currently available suitable building blocks for the second approach are based on ferrocene units, bis(terpyridine)-ruthenium(II) moieties or metal porphyrins.

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Schrittweise Festphasensynthese von zwei‐ und dreikernigen Metallkomplexen

Cited by 11 publications

References 21 publications

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

Solid‐Phase Synthesis, Characterization, and Antibacterial Activities of Metallocene–Peptide Bioconjugates

Solid‐ and Solution‐Phase Synthesis of a Library of Mixed‐Metal Complexes

Solid‐Phase Synthesis of Transition‐Metal Complexes

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