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Issue 21, 2013
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Efficient cysteine labelling of peptides with N-succinimidyl 4-[18F]fluorobenzoate: stability study and in vivo biodistribution in rats by positron emission tomography (PET)

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Abstract

A rapid and high-yielding cysteine labelling of peptides has been observed with the specific labelling agent for amines, N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB). Interestingly, conjugation of the 4-fluorobenzoyl (FB) moiety is selectively achieved through a cysteine (Cys) thiol of the peptides with high yield (>80%) in short time (<5 min), while for a Cys amino acid derivative, a slow process has been observed. The large reactivity of these peptides for the conjugation reaction is rationalised on the basis of electrostatic interactions between the sulfhydril and the guanidinium groups of the amino acid side chains. Moreover, the stability of these novel conjugates and the biodistribution of the radiolabelled dodecapeptide by positron emission tomography (PET) in rats has been examined.

Graphical abstract: Efficient cysteine labelling of peptides with N-succinimidyl 4-[18F]fluorobenzoate: stability study and in vivo biodistribution in rats by positron emission tomography (PET)

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Publication details

The article was received on 12 Feb 2013, accepted on 13 Mar 2013 and first published on 14 Mar 2013


Article type: Paper
DOI: 10.1039/C3RA40754C
Citation: RSC Adv., 2013,3, 8028-8036
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    Efficient cysteine labelling of peptides with N-succinimidyl 4-[18F]fluorobenzoate: stability study and in vivo biodistribution in rats by positron emission tomography (PET)

    S. Rojas, P. Nolis, J. D. Gispert, J. Spengler, F. Albericio, J. R. Herance and S. Abad, RSC Adv., 2013, 3, 8028
    DOI: 10.1039/C3RA40754C

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