Highly efficient technetium-99m labeling procedure based on the conjugation of N-[N-(3-diphenylphosphinopropionyl)glycyl]cysteine ligand with poly(ethylene glycol)

Bioconjugate Chemistry
Roberta VisentinUlderico Mazzi

Abstract

The PN(2)S N-(N-(3-diphenylphosphinopropionyl)glycyl)cysteine ligand was conjugated to methoxy-poly(ethylene glycol)-amino (mPEG-NH(2)) 5 and 20 kDa to yield PN(2)S(Trt)-PEG(5000) 1 and PN(2)S(Trt)-PEG(20000) 2, and then detritylated to PN(2)S-PEG(5000) 4 and PN(2)S-PEG(20000) 5. When an acidic solution of (99m)TcO(4)(-) is added to 4 or 5 in solid form, a quantitative yield in a single labeled species, (99m)Tc-labeled PN(2)S-PEG(5000) 9 and (99m)Tc-labeled PN(2)S-PEG(20000) 10, respectively, is obtained. The reaction occurs in less than 15 min at room temperature for 4 and 35 degrees C for 5. This labeling procedure avoids the use of an external reducing agent, and it is based on the amphiphilic properties of PN(2)S-PEGs. Once in water, 4 and 5 self-assemble in micelles, which catalyze the metal reduction by means of an electron pair transfer from the phosphorus to technetium. The [(99m)TcO](3+) species is then coordinated, and at micelle level, both the (P)ON(2)S and the PN(2)S coordinations are possible, as demonstrated by reacting (99m)Tc-gluconate and ReOCl(3)(PPh(3))(2) with 4 and 5 and with the oxidized analogous (P)ON(2)S-PEG(5000) 6. Compounds 9 and 10 exhibited a high stability both in vitro and in vivo. Biodistributi...Continue Reading

Citations

Aug 21, 2010·Pharmaceutical Research·Chris OerlemansWim E Hennink
Mar 30, 2012·Chemical Society Reviews·Petr Stěpnička
Jul 26, 2005·Il Farmaco·Cinzia BersaniFrancesco Maria Veronese
Feb 26, 2016·Chemical Society Reviews·Yi YanChuanbing Tang
Sep 10, 2008·BioDrugs : Clinical Immunotherapeutics, Biopharmaceuticals and Gene Therapy·Francesco M Veronese, Anna Mero
Sep 19, 2020·Journal of Biomaterials Science. Polymer Edition·Deepa Yadav, Hitesh Kumar Dewangan
Oct 26, 2005·Drug Discovery Today·Francesco M Veronese, Gianfranco Pasut

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