1415902-29-2

Upstream product

• 1415902-31-6 C₁₁H₁₁⁽¹⁸⁾FO₆S 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 
• 1415902-30-5 C₁₅H₁₉⁽¹⁸⁾FO₆S 
• 1679-64-7 Monomethyl terephthalate 
• 104141-93-7 terephthalic acid 1-tert-butyl ester 4-methyl ester 
• 1415902-25-8 sultone-benzoic acid tert-butyl ester 

Relevant academic research and scientific papers

NEW NUCLEOPHILE-REACTIVE SULFONATED COMPOUNDS FOR THE (RADIO)LABELLING OF (BIO)MOLECULES; PRECURSORS AND CONJUGATES THEREOF

The invention relates to nucleophile-reactive sulfonated compounds used as precursors to (radio)labelled (bio)molecules suitable mainly for medical applications. The aim of the invention is to provide novel prosthetic compounds or groups, the synthesis of which is straightforward, easy and automatable, enabling access to economical and effective, (radio)labelled, complex and fragile - especially water-soluble and more especially amine-containing- (bio)molecules. The aim is achieved by the invention, which involves precursors and compounds of respective formulae (Ip), (I). Said nucleophile-reactive sulfonated compounds are produced by pre-introduction of a nucleophilic compound R*, e.g. Fluorine- 18, through an unusal nucleophile-induced ring-opening reaction of the sultone (e.g. 1,3-propanesultone) moiety of the precursor. The invention also relates to the methods for producing the abovementioned precursors and compounds, as well as for the conjugation of these compounds with (bio)molecules, and to the drugs obtained through this method.

A novel sulfonated prosthetic group for [18F]-radiolabelling and imparting water solubility of biomolecules and cyanine fluorophores

Synthesis and some applications of a novel [18F]-fluorinated prosthetic group based on the promising sultone radiochemistry and suitable for the labelling of amine-containing (bio)chemical compounds are described. The combined sequential use of two easy and efficient conjugation reactions namely the fluoride ring-opening of a 1,3-propanesultone moiety and the aminolysis of an N-hydroxysuccinimidyl ester is the key component of this original radiolabelling strategy. The mild reaction conditions and the release of a free sulfonic acid moiety as a result of the [18F]-induced sultone ring-opening reaction, both make this [18F]-conjugation method suitable for the radiofluorination of fragile and hydrophobic biomolecules and fluorophores, particularly by making the separation of the targeted [ 18F]-tagged sulfonated compound from its starting precursor easier and thus faster. The ability of this unusual prosthetic group to readily introduce the radioisotope within complex (bio)molecular architectures has been demonstrated by (1) the preparation of the first [18F]-labelled cyanine 5.5 (Cy 5.5) dye, a suitable precursor for the construction of hybrid positron emission tomography/near-infrared fluorescence (PET/NIRF) imaging probes and (2) the radiolabelling of a biologically relevant peptide bearing a single lysine residue. The Royal Society of Chemistry 2013.