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Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

Structure and Nomenclature of Thiols and Sulfides

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...

Phase II Reactions: Miscellaneous Conjugation Reactions

Phase II Reactions: Miscellaneous Conjugation Reactions

Phase II biotransformations are detoxification mechanisms that conjugate xenobiotics with endogenous substances, neutralizing their toxicity.
A key example involves the conjugation of cyanide ions, which impair cellular respiration and alter hemoglobin into non-oxygen-carrying cyanmethemoglobin. To neutralize this threat, a sulfur atom from thiosulphate is transferred to the cyanide ion, catalyzed by the enzyme rhodanese, resulting in an inactive compound called thiocyanate. The production of...

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A Sensitive Visual Method for the Detection of Hydrogen Sulfide Producing Bacteria

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Pyranthiones/Pyrones: "Click and Release" Donors for Subcellular Hydrogen Sulfide Delivery and Labeling.

Wei Huang¹, Nipuni Gunawardhana¹, Yunlei Zhang¹

¹Department of Chemistry, Stony Brook University, 100 Nicolls Road, Stony Brook, NY 11790, United States.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|November 20, 2023

Summary

Researchers developed novel pyranthiones that efficiently release hydrogen sulfide (H₂S) using a click reaction. These compounds offer tunable kinetics for targeted delivery, addressing challenges in H₂S donor development for cellular signaling.

Keywords:

Click and release hydrogen sulfide labeling and live imaging pyrone/pyranthione subcellular delivery

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Published on: April 9, 2018

Area of Science:

Chemical Biology
Medicinal Chemistry
Biochemistry

Background:

Hydrogen sulfide (H₂S) is a crucial gasotransmitter involved in various disease signaling pathways.
Developing efficient and controllable H₂S donors for subcellular delivery remains a significant challenge.
Existing methods often lack tunable release kinetics or high efficiency for precise biological applications.

Purpose of the Study:

To design and synthesize novel H₂S donors with tunable release kinetics and high efficiency.
To explore a new click and release reaction for controlled gasotransmitter delivery.
To investigate the potential of these donors for subcellular and mitochondrial targeting.

Main Methods:

Developed a click and release reaction utilizing pyrone/pyranthiones and bicyclononyne (BCN).
Investigated reaction kinetics, comparing pyranthiones and pyrones, and assessed biorthogonality.
Synthesized substituted pyranthiones and evaluated their H₂S release efficiency in vitro and in living cells.

Main Results:

The pyrone/pyranthiones and BCN reaction releases CO₂/COS with efficient second-order rate constants.
Pyranthiones exhibited faster reaction rates than pyrones, demonstrating enhanced performance.
Synthesized pyranthiones provided tunable H₂S release kinetics and high in vitro release efficiency, enabling mitochondrial targeting.

Conclusions:

A novel click and release strategy using pyranthiones offers a promising platform for developing H₂S donors.
These pyranthiones demonstrate tunable release kinetics and high efficiency, suitable for various cellular dynamics.
The developed compounds show potential for targeted H₂S and COS delivery, particularly to mitochondria.