Amino acid-based H2S donors: N-thiocarboxyanhydrides that release H2S with innocuous byproducts.

A library of N-thiocarboxyanhydrides (NTAs) derived from natural amino acids with benign byproducts and controlled H2S-release kinetics is reported. Minimal acute in vitro toxicity was observed in multiple cell lines, while longer-term toxicity in cancer cells was observed, with slow-releasing donors exhibiting the greatest cytotoxic effects.

[1]  John B. Matson,et al.  Tuning small molecule release from polymer micelles: Varying H2S release through cross linking in the micelle core. , 2020, European polymer journal.

[2]  Qian Du,et al.  Insights into the Mechanism of Thiol Triggered COS/H2S Release from N-Dithiasuccinoyl Amines. , 2020, The Journal of organic chemistry.

[3]  John B. Matson,et al.  The evolving landscape for cellular nitric oxide and hydrogen sulfide delivery systems: A new era of customized medications. , 2020, Biochemical pharmacology.

[4]  Christopher H. Hendon,et al.  Dithiasuccinoyl-Caged Amines Enables COS/H2S Release Lacking Electrophilic Byproducts. , 2019, Chemistry.

[5]  John B. Matson,et al.  The Benefits of Macromolecular/Supramolecular Approaches in H2S Delivery: A Review of Polymeric and Self-Assembled H2S Donors. , 2019, Antioxidants & redox signaling.

[6]  Michael D. Pluth,et al.  Development and Application of Carbonyl Sulfide-Based Donors for H2S Delivery. , 2019, Accounts of chemical research.

[7]  John B. Matson,et al.  Functional N-Substituted N-Thiocarboxyanhydrides as Modular Tools for Constructing H2S Donor Conjugates. , 2019, ACS chemical biology.

[8]  M. Xian,et al.  Strategies for the Design of Donors and Precursors of Reactive Sulfur Species. , 2019, Chemistry.

[9]  F. Ercole,et al.  Recent advances in the delivery of hydrogen sulfide via a macromolecular approach , 2018 .

[10]  P. Klán,et al.  Visible to NIR Light Photoactivation of Hydrogen Sulfide for Biological Targeting. , 2018, Organic letters.

[11]  K. Kashfi.  The dichotomous role of H2S in cancer cell biology? Déjà vu all over again. , 2018, Biochemical pharmacology.

[12]  B. Wang,et al.  Toward Hydrogen Sulfide Based Therapeutics: Critical Drug Delivery and Developability Issues , 2018, Medicinal research reviews.

[13]  John B. Matson,et al.  A review of hydrogen sulfide (H2S) donors: Chemistry and potential therapeutic applications , 2017, Biochemical pharmacology.

[14]  D. Saini,et al.  Visible-Light-Triggered Uncaging of Carbonyl Sulfide for Hydrogen Sulfide (H2S) Release. , 2017, Organic letters.

[15]  Michael D. Pluth,et al.  Inhibition of Mitochondrial Bioenergetics by Esterase-Triggered COS/H2S Donors. , 2017, ACS chemical biology.

[16]  Zhao-yu,et al.  Emerging Roles of Carbonyl Sulfide in Chemical Biology: Sulfide Transporter or Gasotransmitter? , 2017 .

[17]  Michael D. Pluth,et al.  Light-Activated COS/H2S Donation from Photocaged Thiocarbamates. , 2017, Organic letters.

[18]  D. Lefer,et al.  Protective Actions of H2S in Acute Myocardial Infarction and Heart Failure. , 2017, Comprehensive Physiology.

[19]  John B. Matson,et al.  Gasotransmitter delivery via self‐assembling peptides: Treating diseases with natural signaling gases , 2017, Advanced drug delivery reviews.

[20]  H. Chakrapani,et al.  Esterase Activated Carbonyl Sulfide/Hydrogen Sulfide (H2S) Donors. , 2017, Organic letters.

[21]  J. Wallace,et al.  ATB-346, a novel hydrogen sulfide-releasing anti-inflammatory drug, induces apoptosis of human melanoma cells and inhibits melanoma development in vivo. , 2016, Pharmacological research.

[22]  Michael D. Pluth,et al.  Hydrogen Sulfide Donors Activated by Reactive Oxygen Species , 2016 .

[23]  John B. Matson,et al.  Therapeutic Delivery of H2S via COS: Small Molecule and Polymeric Donors with Benign Byproducts , 2016, Journal of the American Chemical Society.

[24]  W. Durante.  Hydrogen Sulfide Therapy in Diabetes-Accelerated Atherosclerosis: A Whiff of Success , 2016, Diabetes.

[25]  J. Wallace,et al.  H2S-releasing drugs: anti-inflammatory, cytoprotective and chemopreventative potential. , 2015, Nitric oxide : biology and chemistry.

[26]  Rui Wang.  Gasotransmitters: growing pains and joys. , 2014, Trends in biochemical sciences.

[27]  D. Lefer,et al.  Emergence of hydrogen sulfide as an endogenous gaseous signaling molecule in cardiovascular disease. , 2014, Circulation research.

[28]  K. Olson,et al.  Passive loss of hydrogen sulfide in biological experiments. , 2012, Analytical biochemistry.

[29]  Ming-Jie Wang,et al.  Hydrogen sulfide induces human colon cancer cell proliferation: Role of Akt, ERK and p21 , 2010, Cell biology international.

[30]  P. Moore,et al.  Actions and interactions of nitric oxide, carbon monoxide and hydrogen sulphide in the cardiovascular system and in inflammation--a tale of three gases! , 2009, Pharmacology & therapeutics.

[31]  T. Monks,et al.  The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers. , 2002, Current drug metabolism.