The Use of Solid‐Phase Synthesis Techniques for the Preparation of Peptide–Metal Complex Conjugates

Abstract

This microreview summarizes recent reports on the preparation of metal complex peptide conjugates by solid‐phase synthesis methods. Procedures for such conjugates are in many cases different from standard solid‐phase peptide synthesis protocols. Specific advantages of general strategies, the synthesis of peptide–ligand conjugates and complexation with excess metal ions on solid support or the incorporation of previously prepared metal complex amino acid derivatives are discussed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Somatostatin Subtype-2 Receptor-Targeted Metal-Based Anticancer Complexes

“…25 In recent years, several coordination or organometallic complexes have also been conjugated to carrier molecules such as receptor-binding peptides or known delivery peptides to improve both cellular uptake to cancer cells and cytotoxic activity of the metal-based drug. 26,27,28,29,30,31,32,33 Herein we report on the use of conjugates between octreotide and several metal complexes as new chemotherapeutic agents. In particular, the synthesis of hybrid compounds between the dicarba analogue of octreotide (2) and platinum(II), ruthenium(II) and osmium(II) metal complexes has been accomplished by efficient solid-phase procedures (compounds 3-6 in Chart 1).…”

Microwave-assisted solid-phase synthesis, cellular uptake, and cytotoxicity studies of cymantrene–peptide bioconjugates

“…It would thus be particularly interesting if metal-based markers could also directly be attached to such carrier peptides during the automated solid-phase synthesis protocol with minimal side reactions and purification steps. While redox-active sandwich complexes have been quite frequently used in the labelling of peptides [6][7][8][9][10][11][12][13][14], other functional groups have received somewhat less attention [15][16][17][18][19][20][21][22][23][24]. In addition, most of these functionalities were introduced by manual coupling.…”

Synthesis, characterization, X-ray crystallography, and cytotoxicity of a cymantrene keto carboxylic acid for IR labelling of bioactive peptides on a solid support

“…Especially metallocenes have been at the focus of intense research efforts, since, for example, the Fe II/III redox couple as in ferrocene allows for an easy electrochemical quantification of the labelled peptide [1][2][3][4][5][6][7][8][9]. Substantially less work has however been carried out based on other properties of organometallic compounds [10][11][12][13][14][15][16][17][18][19][20][21][22]. We are particularly interested in the attachment of IR spectroscopic labels to peptides for biological imaging applications with scanning near-field IR microscopy (SNIM) [23].…”