PMID: 11906259Mar 22, 2002Paper

Chemical synthesis of Escherichia coli ST(h) analogues by regioselective disulfide bond formation: biological evaluation of an (111)In-DOTA-Phe(19)-ST(h) analogue for specific targeting of human colon cancers

Bioconjugate Chemistry
H GaliW A Volkert

Abstract

New human Escherichia coli heat-stable peptide (ST(h)) analogues containing a DOTA chelating group were synthesized by sequential and selective formation of disulfides bonds in the peptide. This synthetic approach utilizes three orthogonal thiol-protecting groups, Trt, Acm, and t-Bu, to form three disulfide bonds by successive reactions using 2-PDS, iodine, and silyl chloride-sulfoxide systems. The DOTA-ST(h) conjugates exhibiting high guanylin/guanylate cyclase-C (GC-C) receptor binding affinities were obtained with >98% purity. In vitro competitive binding assays, employing T-84 human colon cancer cells, demonstrated the IC(50) values of <2 nM for GC-C receptor binding suggesting that the new synthetic ST(h) analogues are biologically active. In vitro stability studies of the (111)In-DOTA-Phe(19)-ST(h) conjugate incubated in human serum at 37 degrees C under 5% CO(2) atmosphere revealed that this conjugate is extremely stable with no observable decomposition at 24 h postincubation. HPLC analysis of mouse urine at 1 h pi of the (111)In-DOTA-Phe(19)-ST(h) conjugate showed only about 15% decomposition suggesting that the (111)In-DOTA-Phe(19)-ST(h) conjugate is highly stable, even under in vivo conditions. In vivo pharmacokinetic...Continue Reading

References

May 1, 1995·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·L R Forte, M G Currie
Apr 1, 1994·Endocrine Reviews·J G Drewett, D L Garbers
Dec 26, 2001·Chemical Reviews·W A Volkert, T J Hoffman

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Citations

May 28, 2005·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·E BucD Pezet
Sep 25, 2003·Bioorganic & Medicinal Chemistry Letters·Roger LégerDominique Bridon
Mar 3, 2007·Bioconjugate Chemistry·Byunghee Yoo, Mark D Pagel
Sep 10, 2014·Amino Acids·Elaheh JamasbiMohammed Akhter Hossain
Dec 17, 2003·Kidney International·Stephen L CarrithersRichard N Greenberg
Aug 24, 2013·Journal of Biomolecular Structure & Dynamics·Philipp R WeiglmeierPaul Rösch
Jul 11, 2008·Biopolymers·Xiaobing TianEric Wickstrom

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