An organometallic substitute for the radioactive Bolton–Hunter reagent

Savignac, Monique; Sasaki, André; Potìer, Pierre; Jaouen, Gérard

doi:10.1039/c39910000615

Cited by 12 publications

(12 citation statements)

References 17 publications

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“…The cytotoxicity of dicobalt hexacarbonyl alkyne compounds involving alkynes functionalized with peptides, 136,137 proteins, 138 therapeutic drugs, 139,140 steroids, 141 corticoids and androgens, 142 and estrogens 143 have been evaluated. In one such complex derivatized with aspirin, high cytotoxicities were obtained on a number of different cancer cell lines.…”

Section: ■ Metal−carbenes and Other Ligand Typesmentioning

confidence: 99%

Challenges and Opportunities in the Development of Organometallic Anticancer Drugs

2012

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This review provides an introduction into the fascinating area of organometallic anticancer compounds. Although the subject dates back many years, it has witnessed considerable growth only in the past decade. A brief overview of the subject together with recent pertinent examples is provided. The properties of organometallic compounds that lend themselves to medical applications, the main current approaches used, and possible avenues for future research are identified.

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Section: ■ Metal−carbenes and Other Ligand Typesmentioning

confidence: 99%

Challenges and Opportunities in the Development of Organometallic Anticancer Drugs

2012

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“…135−137 Alternatively, stable cobalt and molybdenum carbonyl complexes of OSu-activated hex-4ynoic acid were prepared and reacted with mono-and dipeptides to give formation of the OM conjugates in respectable yields of 30−53%. 138 OM moieties that are functionalized with (an) aldehyde(s) are conveniently conjugated to the amino functionality of peptides by formation of a Schiff base or imine. Since the imine is readily hydrolyzed, leading to the initial reaction components, these moieties were reduced to secondary amino groups by use of NaBH 4 (at 0 °C).…”

Section: Direct Conjugation To the N-terminus In Solutionmentioning

confidence: 99%

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

2016

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Peptides are important biological molecular entities in biomedical research. They can be prepared in a large variety of shapes, with a host of chemical functions, and tailored for specific applications. Organometallic medicinal chemistry is a relatively young field that explores biomedical and bioanalytical applications of organometallic complexes, that is, metal compounds with at least one direct, covalent metal-carbon bond. The conjugation of peptides to such medicinally active organometallic moieties started only about 20 years ago, and it has been very beneficial for the development of bioorganometallic chemistry in general. Similarly, the biomedical properties of peptides have been altered by their conjugation to organometallic (OM) moieties. In this review, synthetic methods by which OM moieties can be conjugated to peptides via a carbon-metal bond are described, and selected medicinal applications of such conjugates are discussed. Inorganic coordination complexes between metal ions and peptides are excluded from this review. Also, the labeling of peptides with radiometals and applications of radiolabeled peptides will not be treated herein. First, modifications of the peptide backbone (either N- or C-terminally, or both) with organometallic moieties will be described, including the insertion of OM moieties as part of the peptide backbone. Then side-chain modifications will be reported, among them the most recent strategies for chemoselective arene metalation on peptides. Finally, approaches by which multiple metalation can be achieved are explored. In each section, selected examples of biological applications are highlighted.

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“…assays is chemoselectivity: [12,18] No doubt is to remain about Iodinated aromatic compounds were previously used as the number of attached organometallics nor their site of radio-labels for amino acids [22] and monoclonal antiattachment to the biomolecule Ϫ which may even be, for bodies [23] and as such were successfully employed in solid example, a large enzyme [10,11,13] or peptide hormone like se-support peptide synthesis. [24] In this study, alternativelycretin.…”

Section: Introductionmentioning

confidence: 99%

A Two-Step Palladium-Catalyzed Coupling Scheme for the Synthesis of Ferrocene-Labeled Amino Acids

Brosch

Weyhermüller

Metzler‐Nolte³

2000

Eur. J. Inorg. Chem.

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This work describes a Pd‐catalyzed coupling of ferrocene alkyne derivatives to iodo amino acids. Ferrocene carboxylic acid propargyl amides were easily obtained in high yield. The crystal structures of the propargyl amine derivative 3 and the 1,1‐diethylpropargylamine derivative 4 have been determined by X‐ray diffraction. Pd‐catalyzed coupling to p‐iodoanilide amino acids gave the corresponding ferrocene‐labeled amino acid derivatives, which were easily purified by diethyl ether extraction in the case of the 1,1‐diethyl derivatives 8. The coupling reaction did not require anhydrous solvents and tolerated a variety of functional groups present in peptides such as alcohols (8a, Ser), thioethers (8d, Met), disulfide bonds (cystine, 12) esters (as in the N‐labeled Leu derivative 10) and of course amides. A minor by‐product of the coupling reaction, namely the homo‐dimer bis(ferrocene carboxylic acid propargylamide) 9, was identified in the crude reaction mixtures by mass spectrometry and independently synthesized by oxidative coupling (Glaser and Eglington) of 3. All new compounds were completely characterized spectroscopically, including 15N‐ and 2D NMR spectroscopy, Mössbauer spectroscopy and electrochemistry. This work introduces a versatile procedure for a selective functionalization of amino acids with organometallics at the C‐terminus which is expected to be of general applicability to peptide chemistry.

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An organometallic substitute for the radioactive Bolton–Hunter reagent

Cited by 12 publications

References 17 publications

Challenges and Opportunities in the Development of Organometallic Anticancer Drugs

Challenges and Opportunities in the Development of Organometallic Anticancer Drugs

Organometallic–Peptide Bioconjugates: Synthetic Strategies and Medicinal Applications

A Two-Step Palladium-Catalyzed Coupling Scheme for the Synthesis of Ferrocene-Labeled Amino Acids

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