Investigation on the reactivity of nucleophilic radiohalogens with arylboronic acids in water: access to an efficient single-step method for the radioiodination and astatination of antibodies

Abstract

Easy access to radioiodinated and 211At-labelled bio(macro)molecules is essential to develop new strategies in nuclear imaging and targeted radionuclide therapy of cancers. Yet, the labelling of complex molecules with heavy...

Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution

“…This is suitable for both astatination and iodination of BPA. Our findings suggest that deboronation is one of the most efficient routes for the astatination of aryl compounds and antibodies, as concluded in the previous studies conducted using copper catalysts 6 – 8 .…”

“…They prepared an [ 211 At] PARP inhibitor in high radiochemical yields by using the corresponding boronic ester precursor and [ 211 At]NaAt in the presence of Cu(pyridine) 4 OTf in a 4:1 mixture of methanol and acetonitrile. This method could be successfully applied for the astatination of antibodies and small molecules 8 .…”

Overview of the Most Promising Radionuclides for Targeted Alpha Therapy: The “Hopeful Eight”

“…N -succinimidyl-3-[ 211 At]astatobenzoate ([ 211 At]SAB) was largely studied as prosthetic group for conjugation to lysine residues and was also derived with a maleimide function for coupling to cystein. The main reported approaches are the use of aryltrialkylstannane derivatives [ 111 , 112 ], boron clusters [ 110 ] and iodonium salts [ 113 ] or labeling of pre-modified antibodies with aryltrialkylstannane function [ 114 , 115 ], clickable moieties [ 116 ] and boronic acid functionalization [ 117 ]. Additional details about astatine chemistry are available in several complete reviews [ 88 , 118 , 119 ].…”

An expanded halogen bonding scale using astatine

“…[21][22][23] Practical interests notably lie in the improvement of the radiolabelling strategy for these applications. [24][25][26][27][28] For example, an At-mediated XB can be assumed to explain, in particular, the efficient radiolabelling of bis-(nido-carboranylmethyl)benzene derivatives, 29 the latter having been considered as pendant groups for attaching 211 At to carrier biomolecules. Therefore, we proposed to investigate on a more extended and diversified chemical sample the various features (structural, thermodynamic) of XBs involving astatine.…”