Synthesis of the first poly(diaminosulfide)s and an investigation of their applications as drug delivery vehicles.

Macromolecules
Jun YooNed B Bowden

Abstract

This paper reports the first examples of poly(diaminosulfide)s that were synthesized by the reaction of a sulfur transfer reagent and several secondary diamines. The diaminosulfide group has the general structure of R(2)N-S-NR(2) and, although it has been used in the synthesis of small molecules, it has never been utilized in the synthesis of macromolecules until this report. A series of poly(diaminosulfide)s were synthesized at elevated temperatures, and the molecular weights of the polymers were as high as 12,400 g mol(-1) with conversions for the polymerization reaction up to 99%. The rate constants for the transamination reactions that lead to the polymers were measured in several solvents to provide an understanding the reaction conditions necessary to polymerize the monomers. The degradation of diaminosulfides were studied in D(2)O, C(6)D(6), CD(3)OD, CDCl(3), and DMSO-d(6)/D(2)O to demonstrate that they were very stable in organic solvents but degraded within hours under aqueous conditions. These results clearly demonstrated that diaminosulfides are very stable in organic solvents under ambient conditions. Poly(diaminosulfide)s have sufficient stabilities to be useful for many applications. The ability of these polymers ...Continue Reading

References

Feb 15, 2001·Accounts of Chemical Research·T M Trnka, R H Grubbs
Dec 26, 2001·Chemical Reviews·K Matyjaszewski, J Xia
Feb 27, 2003·Journal of the American Chemical Society·Tina M TrnkaRobert H Grubbs
May 6, 2003·Angewandte Chemie·Stephen J Connon, Siegfried Blechert
Sep 10, 2004·Journal of the American Chemical Society·John C SworenKenneth B Wagener
Sep 28, 2004·Science·Daniel G AndersonRobert Langer
Nov 8, 2005·Inorganic Chemistry·Adrian B ChaplinPaul J Dyson
Apr 7, 2006·Organic Letters·Tianzhi Zhang, Eric V Anslyn
May 19, 2006·Organic Letters·Chih-Hsin ChenMing-Chang P Yeh
May 26, 2006·Angewandte Chemie·Yves Chauvin
Jan 19, 2008·Journal of Controlled Release : Official Journal of the Controlled Release Society·Jordy LutenWim E Hennink
Mar 31, 2009·Journal of Agricultural and Food Chemistry·Ranfeng SunQingmin Wang
Jun 19, 2009·Current Drug Delivery·Benjamin Thierry
Jun 27, 2009·Accounts of Chemical Research·Megan E FoxJean M J Fréchet
Jul 21, 2009·Biomaterials·Mei OuSung Wan Kim
Nov 4, 2009·Journal of Medicinal Chemistry·Coco N KapandaDidier M Lambert
Apr 13, 2010·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·M Wang, M Thanou
Aug 20, 2010·Journal of the American Chemical Society·Huan MengAndre E Nel
Oct 7, 2010·Journal of the American Chemical Society·Frank A LeibfarthCraig J Hawker
Oct 12, 2010·Molecular Pharmaceutics·Christopher R DrakeAndrew D Miller
Nov 30, 2010·Therapeutic Delivery·Mohanad MossalamCarol S Lim
Dec 3, 2010·Nature Chemistry·Frank A LeibfarthCraig J Hawker
Jan 25, 2011·Current Medicinal Chemistry·Y MalamA M Seifalian
Apr 26, 2011·Current Drug Discovery Technologies·Samuli HirsjärviJean-Pierre Benoit
Oct 2, 1998·Angewandte Chemie·Thomas WeskampWolfgang A Herrmann

❮ Previous
Next ❯

Citations

Sep 12, 2015·Journal of Controlled Release : Official Journal of the Controlled Release Society·Sean M GearyAliasger K Salem
May 29, 2020·Macromolecular Rapid Communications·Hatice Mutlu, Patrick Theato
Jan 3, 2020·Biomacromolecules·Emad I WafaAliasger K Salem

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antibodies: Agglutination

Antibody-mediated agglutination is the clumping of cells in the presence of antibody, which binds multiple cells together. This enhances the clearance of pathogens. Find the latest research on antibody-mediated agglutination here.