Review of the Syntheses and Activities of Some Sulfur-Containing Drugs

Ferro, Criscieli Taynara Barce; Santos, Beatriz F. dos; Silva, Caren Daniele Galeano da; Brand, George; Silva, Caren D. G. da; Domingues, Nélson

doi:10.2174/1570179417666200212113412

Cited by 44 publications

(22 citation statements)

References 98 publications

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“…It has been also suggested that biotin’s sulfur atom forms S–N interactions through delocalization of the π-electron system of the ureido group, thus increasing the basicity and nucleophilicity of the ureido nitrogen atoms . Sulfur’s application to drug design − remains uncommon; even adoption of covalent inhibitors targeting the reactive SH group of cysteines has been slow despite the success of such drugs …”

Section: Sulfur: the Ugly Duckling Of Acceptorsmentioning

confidence: 99%

Biotin’s Lessons in Drug Design

McConnell

2021

J. Med. Chem.

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At the heart of drug design is the discovery of molecules that bind with high affinity to their drug targets. Biotin forms the strongest known noncovalent ligand–protein interactions with avidin and streptavidin, achieving femtomolar and picomolar affinities, respectively. This is made even more exceptional because biotin achieves this with a meagre molecular weight of 240 Da. Surprisingly, the approaches by which biotin achieves this are not in the standard repertoire of current medicinal chemistry practice. Biotin’s biggest lesson is the importance of nonclassical H-bonds in protein–ligand complexes. Most of biotin’s affinity stems from its flexible valeric acid side chain that forms CH−π, CH–O, and classical H-bonds with the lipophilic region of the binding pocket. Biotin also utilizes an oxyanion hole, a sulfur-centered H-bond, and water solvation in the bound state to achieve its potency. The facets and advantages of biotin’s approach to binding should be more widely adopted in drug design.

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Section: Sulfur: the Ugly Duckling Of Acceptorsmentioning

confidence: 99%

Biotin’s Lessons in Drug Design

McConnell

2021

J. Med. Chem.

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“…In addition to organic endoperoxides, a great variety of sulfur‐containing compounds have attracted wide attention in human cancer treatment because of its redox‐active properties 329,330 . The classic one is phenethyl isothiocyanate ( 86 ; Figure 9B), which was reported to be involved in inhibition of GPx, formation of GSH adducts, and production of ROS arising from complex III of the mitochondrial ETC 238 .…”

Section: Paradoxical Strategies In Ros‐based Cancer Therapymentioning

confidence: 99%

Small molecules regulating reactive oxygen species homeostasis for cancer therapy

Zhang

Duan

Song

et al. 2020

Medicinal Research Reviews

124

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Elevated intracellular reactive oxygen species (ROS) and antioxidant defense systems have been recognized as one of the hallmarks of cancer cells. Compared with normal cells, cancer cells exhibit increased ROS to maintain their malignant phenotypes and are more dependent on the “redox adaptation” mechanism. Thus, there are two apparently contradictory but virtually complementary therapeutic strategies for the regulation of ROS to prevent or treat cancer. The first strategy, that is, chemoprevention, is to prevent or reduce intracellular ROS either by suppressing ROS production pathways or by employing antioxidants to enhance ROS clearance, which protects normal cells from malignant transformation and inhibits the early stage of tumorigenesis. The second strategy is the ROS‐mediated anticancer therapy, which stimulates intracellular ROS to a toxicity threshold to activate ROS‐induced cell death pathways. Therefore, targeting the regulation of intracellular ROS‐related pathways by small‐molecule candidates is considered to be a promising treatment for tumors. We herein first briefly introduce the source and regulation of ROS, and then focus on small molecules that regulate ROS‐related pathways and show efficacy in cancer therapy from the perspective of pharmacophores. Finally, we discuss several challenges in developing cancer therapeutic agents based on ROS regulation and propose the direction of future development.

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“…Aryl sulfides, as a ubiquitous structural motif in functional molecules, plays a unique role in pharmaceutical ( Le Grand et al, 2008 ; Ilardi et al, 2014 ; Xiao et al, 2019 ; Golosov et al, 2021 ; Mourtas et al, 2020 ; Hai et al, 2021 ; Liu and Jiang, 2013 ; Barce Ferro et al, 2020 ) and material science ( Figure 1 ). ( Boyd 2016 ; Lu et al, 2017 ; Zhang et al, 2018 ; Hou et al, 2022 ) Hence, the development of efficient methods for the construction of C-S bond has attracted considerable attentions from chemical researchers.…”

Section: Introductionmentioning

confidence: 99%

Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation

Mao

Zhao²,

Luo³

et al. 2022

Front. Chem.

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A photo-induced C-S radical cross-coupling of aryl iodides and disulfides under transition-metal and external photosensitizer free conditions for the synthesis of aryl sulfides at room temperature has been presented, which features mild reaction conditions, broad substrate scope, high efficiency, and good functional group compatibility. The developed methodology could be readily applied to forge C-S bond in the field of pharmaceutical and material science.

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Review of the Syntheses and Activities of Some Sulfur-Containing Drugs

Cited by 44 publications

References 98 publications

Biotin’s Lessons in Drug Design

Biotin’s Lessons in Drug Design

Small molecules regulating reactive oxygen species homeostasis for cancer therapy

Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation

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