Grace James P, Bowden Ned B
Department of Chemistry, University of Iowa, W425 Chemistry Building, Iowa City, Iowa 52242, United States.
ACS Omega. 2021 Jun 28;6(27):17741-17747. doi: 10.1021/acsomega.1c02585. eCollection 2021 Jul 13.
Heterosubstituted disulfides are an understudied class of molecules that have been used in biological studies, but they have not been investigated for their ability to release hydrogen sulfide (HS). The synthesis of two sets of chemicals with the diaminodisulfide (NSSN) and dialkoxydisulfide (OSSO) functional groups was reported. These chemicals were synthesized from commercially available sulfur monochloride or a simple disulfur transfer reagent. Both the diaminodisulfide and dialkoxydisulfide functional groups were found to have rapid rates of HS release in the presence of excess thiol. The release of HS was complete with 10 min, and the only byproducts were conversion of the thiols into disulfides and the amines or alcohols originally used in the synthesis of the diaminodisulfide or dialkoxydisulfide functional groups. These results will allow the design of HS releasing chemicals that also release natural, biocompatible alcohols or amines. Chemicals with the diaminodisulfide and dialkoxydisulfide functional groups may find applications in medicine where a controlled, burst release of HS is needed.
杂取代二硫化物是一类研究较少的分子，已用于生物学研究，但尚未对其释放硫化氢（HS）的能力进行研究。报道了两组含有二氨基二硫化物（NSSN）和二烷氧基二硫化物（OSSO）官能团的化合物的合成。这些化合物由市售的一氯化硫或一种简单的二硫转移试剂合成。发现二氨基二硫化物和二烷氧基二硫化物官能团在存在过量硫醇的情况下都具有快速释放HS的速率。HS在10分钟内完全释放，唯一的副产物是硫醇转化为二硫化物以及最初用于合成二氨基二硫化物或二烷氧基二硫化物官能团的胺或醇。这些结果将有助于设计出还能释放天然、生物相容性醇或胺的HS释放化合物。含有二氨基二硫化物和二烷氧基二硫化物官能团的化合物可能在需要可控、突发释放HS的医学领域找到应用。
