Analysis of iodinated peptides by LC-DAD/ESI ion trap mass spectrometry

Vergote, Valentijn; Bodé, Samuel; Peremans, Kathelijne; Vanbree, Henri; Baert, Bram; Slegers, Guido; Burvenich, Christian; Spiegeleer, Bart De

doi:10.1016/j.jchromb.2006.11.028

Cited by 25 publications

(13 citation statements)

References 21 publications

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“…High radiochemical purities were not reached using either the Iodogen ® or Iodobeads ® methods. These results may confirm earlier observations [23] that iodination of the selected peptide using solid phase oxidants (Iodobeads ® and Iodogen ® ) resulted in lower yield compared with CAT in solution. A third methodology involving gentle oxidation through enzymatic reactions was therefore evaluated.…”

Section: Discussionsupporting

confidence: 91%

“…Until now, only a few analytical characterizations have been performed on iodinated peptides. Vergote et al [22,23] reported the analyses and separation of different radioiodinated species of Obestatin labelled using current oxidative method of iodination. To avoid separation of the formed different radioiodinated species, which can be difficult to achieve, it is better to find the best labelling conditions to encourage the production of a single species, the mono-iodinated form.…”

Section: Introductionmentioning

confidence: 99%

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Selective mono-radioiodination and characterization of a Cell-Penetrating Peptide: L-Tyr-Maurocalcine

Ahmadi¹,

Bacot²,

Poillot³

et al. 2014

Radiochimica Acta

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Mono-and poly-iodinated peptides form frequently during radioiodination procedures. However, the formation of a single species in its mono-iodinated form is essential for quantitative studies such as determination of tissue concentration or image quantification. Therefore, the aim of the present study was to define the optimal experimental conditions in order to exclusively obtain the mono-iodinated form of L-maurocalcine (L-MCa). L-MCa is an animal venom toxin which was shown to act as a cellpenetrating peptide. In order to apply the current direct radioiodination technique using oxidative agents including chloramine T, Iodo-Gen ® or lactoperoxidase, an analogue of this peptide containing a tyrosine residue (Tyr-L-MCa) was synthesized and was shown to fold/oxidize properly.The enzymatic approach using lactoperoxidase/H 2 O 2 was found to be the best method for radioiodination of Tyr-LMCa. MALDI-TOF mass spectrometry analyses were then used for identification of the chromatographic eluting components of the reaction mixtures. We observed that the production of different radioiodinated species depended upon the reaction conditions. Our results successfully described the experimental conditions of peptide radioiodination allowing the exclusive production of the mono-iodinated form with high radiochemical purity and without the need for a purification step. Mono-radioiodination of L-Tyr-MCa will be crucial for future quantitative studies, investigating the mechanism of cell penetration and in vivo biodistribution.

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Section: Discussionsupporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Selective mono-radioiodination and characterization of a Cell-Penetrating Peptide: L-Tyr-Maurocalcine

Ahmadi¹,

Bacot²,

Poillot³

et al. 2014

Radiochimica Acta

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“…37,39 Briefly, a 1 g/l peptide solution was prepared by dissolving about 1 mg in phosphate buffer (pH 7.4, 130 mM). A Iodo-Gen® coated tube was previously rinsed with 1 ml phosphate buffer.…”

Section: Methodsmentioning

confidence: 99%

Variation of the Net Charge, Lipophilicity, and Side Chain Flexibility in Dmt¹-DALDA: Effect on Opioid Activity and Biodistribution

et al. 2012

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The influence of the side chain charges of the second and fourth amino acid residues in the peptidic μ opioid lead agonist Dmt-D-Arg-Phe-Lys-NH2 ([Dmt1]-DALDA) was examined. Additionally, to increase the overall lipophilicity of [Dmt1]-DALDA and to investigate the Phe3 side chain flexibility, the final amide bond was N-methylated and Phe3 was replaced by a constrained aminobenzazepine analogue. The in vitro receptor binding and activity of the peptides, as well as their in vivo transport (brain in- and efflux and tissue biodistribution) and antinociceptive properties after peripheral administration (i.p. and s.c.) in mice were determined. The structural modifications result in significant shifts of receptor binding, activity and transport properties. Strikingly, while [Dmt1]-DALDA and its N-methyl analogue, Dmt-D-Arg-Phe-NMeLys-NH2, showed a long-lasting antinociceptive effect (>7h), the peptides with D-Cit2 generate potent antinociception more rapidly (maximal effect at 1h post-injection) but also lose their analgesic activity faster, when compared to [Dmt1]-DALDA and [Dmt1,NMeLys4]-DALDA.

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“…Peptides were labeled by the Iodogen method to assess their BBB transport behavior [55,58,59]. Briefly, a 1 g/L peptide solution was prepared by dissolving about 1 mg in phosphate buffer (pH 7.4, 130 mM).…”

Section: Radiolabeling Of Enkephalin Analogsmentioning

confidence: 99%

Blood–brain transfer and antinociception of linear and cyclic N-methyl-guanidine and thiourea-enkephalins

et al. 2015

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Analysis of iodinated peptides by LC-DAD/ESI ion trap mass spectrometry

Cited by 25 publications

References 21 publications

Selective mono-radioiodination and characterization of a Cell-Penetrating Peptide: L-Tyr-Maurocalcine

Selective mono-radioiodination and characterization of a Cell-Penetrating Peptide: L-Tyr-Maurocalcine

Variation of the Net Charge, Lipophilicity, and Side Chain Flexibility in Dmt¹-DALDA: Effect on Opioid Activity and Biodistribution

Blood–brain transfer and antinociception of linear and cyclic N-methyl-guanidine and thiourea-enkephalins

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Analysis of iodinated peptides by LC-DAD/ESI ion trap mass spectrometry

Cited by 25 publications

References 21 publications

Selective mono-radioiodination and characterization of a Cell-Penetrating Peptide: L-Tyr-Maurocalcine

Selective mono-radioiodination and characterization of a Cell-Penetrating Peptide: L-Tyr-Maurocalcine

Variation of the Net Charge, Lipophilicity, and Side Chain Flexibility in Dmt1-DALDA: Effect on Opioid Activity and Biodistribution

Blood–brain transfer and antinociception of linear and cyclic N-methyl-guanidine and thiourea-enkephalins

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Variation of the Net Charge, Lipophilicity, and Side Chain Flexibility in Dmt¹-DALDA: Effect on Opioid Activity and Biodistribution