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Facile synthesis of MDTPA and BMDTPA: Design and synthesis of novel DTPA-peptide conjugates for radiolabelling

Surfraz, M. Bashir-Uddin, Blower, Philip J., Biagini, Stefano C. G. (2007) Facile synthesis of MDTPA and BMDTPA: Design and synthesis of novel DTPA-peptide conjugates for radiolabelling. In: European Journal of Nuclear Medicine and Molecular Imaging. 34 (S2). S190-S190. Springer (doi:10.1007/s00259-007-0540-0) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided) (KAR id:13256)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided.
Official URL:
http://dx.doi.org/10.1007/s00259-007-0540-0

Abstract

Aim: In-111 radiolabelling of monoclonal antibodies was achieved by using 3,6-bis(carboxymethyl)-9-{[(2-maleimidoethyl)carbamoyl]-methyl}-3,6,9-triazaundecanedioic acid (MDTPA), synthesised in 12 steps. 1.We designed and investigated a new synthetic route of MDTPA to investigate In-radiolabelling of a cysteine derivatised nanogastrin peptide. We also targeted the synthesis of 1,9-bis{[(2-maleimidoethyl)-carbamoyl]methyl}-3,6,9-tris(carboxymethyl)-3,6,9-triaza-undecanoic acid (BMDTPA) from which the corresponding DTPA-N,N”-bis(amide) peptide conjugate can potentially chelate Gd(III), Y(III), Cu(II) and Zn(II) and therefore open avenues towards novel peptide/antibody based MRI and PET contrasting agents.

2.Methods: 2-aminoethylmaleimide, synthesised in 3 steps, was reacted with DTPA anhydride to obtain MDTPA and/or BMDTPA. Then nanogastrin peptide was treated separately with both MDTPA and BMDTPA and cold Indium labelling of the corresponding peptide conjugates were characterised by RP HPLC-MS. Results: The coupling of 2-aminoethylmaleimide, synthesised in 3 steps (70% overall yield) with DTPA anhydride afforded both MDTPA and BMDTPA in 5% and 72% yield respectively after RP HPLC purification. Nanogastrin-MDTPA coupling afforded the corresponding peptide conjugate, which successfully labelled with Indium (analysed by HPLC-MS). Application of BMDTPA as a spacer in the synthesis of a bis-HYNICnanogastrin conjugate followed by Tc-99m radiolabelling will also be presented.

Conclusions:The novel 4-step short synthesis of both MDTPA and BMDTPA was accomplished thus making both compounds more accessible to functionalise peptides and antibodies of interest for a wide range of applications.

Item Type: Conference or workshop item (Other)
DOI/Identification number: 10.1007/s00259-007-0540-0
Additional information: Meeting abstract.
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Divisions > Division of Natural Sciences > Physics and Astronomy
Depositing User: Stefano Biagini
Date Deposited: 05 Oct 2009 17:28 UTC
Last Modified: 16 Nov 2021 09:51 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/13256 (The current URI for this page, for reference purposes)

University of Kent Author Information

Surfraz, M. Bashir-Uddin.

Creator's ORCID:
CReDIT Contributor Roles:

Blower, Philip J..

Creator's ORCID:
CReDIT Contributor Roles:

Biagini, Stefano C. G..

Creator's ORCID: https://orcid.org/0000-0002-4713-5127
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