Click-chemistry strategy for labeling antibodies with copper-64 via a cross-bridged tetraazamacrocyclic chelator scaffold.

Bioconjugate Chemistry
Amit KumarXiankai Sun

Abstract

We report a click-chemistry based modular strategy for antibody labeling with (64)Cu (t1/2 = 12.7 h; β(+) 0.656 MeV, 17.4%; β(-) 0.573 MeV, 39%; EC 43%) under ambient condition utilizing a cross-bridged tetraazamacrocyclic (CB-TE2A) analogue, which otherwise requires harsh conditions that make the CB-TE2A analogues under-utilized for protein labeling despite the fact that they form kinetically inert copper complexes with high in vivo stability. Our strategy involves prelabeling a CB-TE2A based scaffold (CB-TE2A-1C) with (64)Cu and its subsequent reaction with an antibody via the tetrazine-norbornene mediated click chemistry. The effectiveness of this strategy was demonstrated by labeling two monoclonal antibodies, an anti-PSMA antibody (YPSMA-1) and a chimeric anti-phosphatidylserine antibody (Bavituximab). The immunoreactivity of the antibodies remained unchanged after the tetrazine modification and click-chemistry (64)Cu labeling. To further demonstrate the practicality of the modular (64)Cu labeling strategy, we tested positron emission tomography (PET) imaging of tumor with the (64)Cu-labeled bavituximab in a mouse xenograft model. The tumor visualization and uptake of the labeled antibody exhibited the versatility of the c...Continue Reading

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Citations

Jun 2, 2016·Bioconjugate Chemistry·Amit KumarXiankai Sun
Oct 28, 2016·Bioconjugate Chemistry·Jan-Philip MeyerBrian M Zeglis
Mar 13, 2018·Medicinal Research Reviews·Anna A RybczynskaAren van Waarde
Jan 18, 2018·Journal of Labelled Compounds & Radiopharmaceuticals·Eduardo Aluicio-SarduyJonathan W Engle
Apr 4, 2021·International Journal of Molecular Sciences·Christophe Van de WieleMaes Alex
Mar 12, 2016·Bioconjugate Chemistry·Antoinette CordovaMilton L Brown
Mar 24, 2020·Chemical Reviews·Weijun WeiWeibo Cai
Jun 20, 2018·ACS Applied Materials & Interfaces·Djamila KechkecheBenoit Dubertret

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