Organic arsenicals as efficient and highly specific linkers for protein/peptide-polymer conjugation

Journal of the American Chemical Society
Paul WilsonThomas P Davis

Abstract

The entropy-driven affinity of trivalent (in)organic arsenicals for closely spaced dithiols has been exploited to develop a novel route to peptide/protein-polymer conjugation. A trivalent arsenous acid (As(III)) derivative (1) obtained from p-arsanilic acid (As(V)) was shown to readily undergo conjugation to the therapeutic peptide salmon calcitonin (sCT) via bridging of the Cys(1)-Cys(7) disulfide, which was verified by RP-HPLC and MALDI-ToF-MS. Conjugation was shown to proceed rapidly (t < 2 min) in situ and stoichiometrically through sequential reduction-conjugation protocols, therefore exhibiting conjugation efficiencies equivalent to those reported for the current leading disulfide-bond targeting strategies. Furthermore, using bovine serum albumin as a model protein, the trivalent organic arsenical 1 was found to demonstrate enhanced specificity for disulfide-bond bridging in the presence of free cysteine residues relative to established maleimide functional reagents. This specificity represents a shift toward potential orthogonality, by clearly distinguishing between the reactivity of mono- and disulfide-derived (vicinal or neighbors-through-space) dithiols. Finally, p-arsanilic acid was transformed into an initiator for ...Continue Reading

References

Jan 2, 1992·Nature·M J Gething, J Sambrook
Apr 1, 1984·Fundamental and Applied Toxicology : Official Journal of the Society of Toxicology·H V AposhianE Stine
Feb 1, 1994·Chemico-biological Interactions·M DelnomdedieuD J Thomas
Sep 1, 1993·Chemical Research in Toxicology·M DelnomdedieuD J Thomas
May 1, 1996·Bioconjugate Chemistry·M MorpurgoJ M Harris
Apr 8, 2000·Trends in Cell Biology·A R FrandC A Kaiser
Oct 2, 2002·FEBS Letters·Barry P Rosen
May 9, 2003·Cancer Chemotherapy and Pharmacology·Hatice DuzkaleSrdan Verstovsek
Dec 9, 2004·Journal of the American Chemical Society·Neel S JoshiMatthew B Francis
Dec 30, 2004·Angewandte Chemie·Nicholas C LloydRon S Ronimus
Nov 4, 2005·Angewandte Chemie·Christopher T WalshGregory J Gatto
Jan 26, 2006·Journal of the American Chemical Society·S David Tilley, Matthew B Francis
Apr 25, 2006·Nature Chemical Biology·Sunil ShaunakSteve Brocchini
Jan 1, 1947·The Biochemical Journal·V P Whittaker
Feb 24, 2007·Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences·Guang-Biao ZhouZhu Chen
Apr 5, 2007·Nature Protocols·Steve BrocchiniSunil Shaunak
May 16, 2007·Journal of the American Chemical Society·Cyrille BoyerChristopher Barner-Kowollik
Jul 13, 2007·Cancer Treatment Reviews·Pierre J Dilda, Philip J Hogg
Jun 12, 2008·Free Radical Biology & Medicine·Christine C Winterbourn, Mark B Hampton
Oct 31, 2008·Talanta·Badal Kumar Mandal, Kazuo T Suzuki
Aug 15, 2009·Journal of the Royal Society of Medicine·K J Williams
Aug 27, 2009·Chemical Communications : Chem Comm·Mathew W JonesDavid M Haddleton
Jan 14, 2010·Journal of the American Chemical Society·Hitoshi BanCarlos F Barbas
Jan 23, 2010·Journal of the American Chemical Society·Mark E B SmithJames R Baker
Jul 1, 1946·The Biochemical Journal·L A STOCKEN, R H S THOMPSON
Apr 13, 2010·Journal of Environmental Monitoring : JEM·Chris NewcombeJörg Feldmann
May 18, 2010·Blood Reviews·Ashkan Emadi, Steven D Gore
Jul 28, 2010·Toxicological Sciences : an Official Journal of the Society of Toxicology·David J Thomas
Nov 13, 2010·Current Opinion in Chemical Biology·Gregory N Grover, Heather D Maynard
Jan 14, 2011·Chemical Communications : Chem Comm·Rebecca M BroyerHeather D Maynard
Jan 29, 2011·Bioconjugate Chemistry·Felix F SchumacherJames R Baker
Feb 17, 2011·Journal of the American Chemical Society·Danielle ParkPhilip J Hogg
May 14, 2011·Macromolecular Rapid Communications·Peter J RothThomas P Davis
Aug 26, 2011·Bioconjugate Chemistry·Aaron D Baldwin, Kristi L Kiick
Dec 23, 2011·Journal of the American Chemical Society·Mathew W JonesDavid M Haddleton
Feb 22, 2012·Current Opinion in Chemical Biology·Jian-Xiang LiuZhu Chen
Apr 13, 2012·Journal of the American Chemical Society·Mathew W JonesDavid M Haddleton

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Citations

Aug 1, 2015·Chemical Reviews·Athina AnastasakiDavid M Haddleton
Jan 23, 2016·Nature Chemistry·Chi ZhangBradley L Pentelute
Mar 8, 2016·Macromolecules·Maltish M LorenzoHeather D Maynard
Jul 14, 2017·Chemical Communications : Chem Comm·Charlotte FootmanPaul Wilson
Feb 20, 2018·Chemistry : a European Journal·Kenji Watanabe, Takashi Ohshima
Apr 26, 2016·Chemical Communications : Chem Comm·Danielle J LloydDavid M Haddleton
Sep 12, 2017·Chemical Communications : Chem Comm·Christoph NitscheGottfried Otting
Apr 1, 2018·Angewandte Chemie·Glen R JonesDavid M Haddleton
Nov 7, 2018·Angewandte Chemie·Chi ZhangBradley L Pentelute
Oct 26, 2016·Chemistry : a European Journal·Seah Ling KuanTanja Weil
Jun 17, 2020·Organic & Biomolecular Chemistry·Neelesh C ReddyVishal Rai
Nov 14, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Yanxiong PanZhongyu Yang
Aug 2, 2017·Angewandte Chemie·Ronald A GlabonjatKevin A Francesconi
Jan 1, 2016·Chemical Science·Maximillian T W LeeVijay Chudasama
May 29, 2018·Macromolecular Rapid Communications·Joji TanakaPaul Wilson
May 13, 2021·Organic & Biomolecular Chemistry·Heather C HayesYu-Hsuan Tsai
Mar 8, 2018·Biomacromolecules·Nabil BensabehVirgil Percec
Aug 25, 2021·Bioconjugate Chemistry·Kuan-Lin WuHan Xiao
May 4, 2018·Biomacromolecules·Yanjing Wang, Chi Wu

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