Selective arylthiolane deprotection by singlet oxygen: a promising tool for sensors and prodrugs

2015 ◽  
Vol 51 (15) ◽  
pp. 3196-3199 ◽  
Author(s):  
Brian M. Lamb ◽  
Carlos F. Barbas III
Keyword(s):  
Reactive Oxygen Species ◽  
Singlet Oxygen ◽  
Small Molecule ◽  
Reactive Oxygen ◽  
Fluorescent Sensors ◽  
Oxygen Species ◽  
Protecting Group ◽  
Biologically Relevant ◽  
Promising Tool ◽  
Gating Mechanism

A routine thioketal protecting group reacts rapidly and selectively with singlet oxygen to reveal ketone products in good (aryl 1,3-dithiolane) to excellent (aryl 1,3-oxathiolane) yields. Arylthiolanes are stable to biologically relevant reactive oxygen species and can be used as a light-activated gating mechanism for activating fluorescent sensors or small molecule prodrugs.

Small-Molecule-Based Fluorescent Sensors for Selective Detection of Reactive Oxygen Species in Biological Systems

2019 ◽  
Vol 88 (1) ◽  
pp. 605-633 ◽  
Author(s):  
Xiaoyu Bai ◽  
Kenneth King-Hei Ng ◽  
Jun Jacob Hu ◽  
Sen Ye ◽  
Dan Yang
Keyword(s):  
Reactive Oxygen Species ◽  
Small Molecule ◽  
Redox Regulation ◽  
Biological Systems ◽  
Reactive Oxygen ◽  
Fluorescent Sensors ◽  
Ros Generation ◽  
Oxygen Species ◽  
Redox Biology ◽  
Health And Disease

Reactive oxygen species (ROS) encompass a collection of intricately linked chemical entities characterized by individually distinct physicochemical properties and biological reactivities. Although excessive ROS generation is well known to underpin disease development, it has become increasingly evident that ROS also play central roles in redox regulation and normal physiology. A major challenge in uncovering the relevant biological mechanisms and deconvoluting the apparently paradoxical roles of distinct ROS in human health and disease lies in the selective and sensitive detection of these transient species in the complex biological milieu. Small-molecule-based fluorescent sensors enable molecular imaging of ROS with great spatial and temporal resolution and have thus been appreciated as excellent tools for aiding discoveries in modern redox biology. We review a selection of state-of-the-art sensors with demonstrated utility in biological systems. By providing a systematic overview based on underlying chemical sensing mechanisms, we wish to highlight the strengths and weaknesses in prior sensor works and propose some guiding principles for the development of future probes.

UV-Vis Spectrophotometrical and Analytical Methodology for the Determination of Singlet Oxygen in New Antibacterials Drugs

2007 ◽  
Vol 2 ◽  
pp. 117739010700200 ◽  
Author(s):  
Tamara Zoltan ◽  
Franklin Vargas ◽  
Carla Izzo
Keyword(s):  
Reactive Oxygen Species ◽  
Singlet Oxygen ◽  
Nalidixic Acid ◽  
Reactive Oxygen ◽  
Oxygen Species ◽  
Inexpensive Method ◽  
Analytical Methodology ◽  
First Time

We have determined and quantified spectrophotometrically the capacity of producing reactive oxygen species (ROS) as 1O2 during the photolysis with UV-A light of 5 new synthesized naphthyl ester derivates of well-known quinolone antibacterials (nalidixic acid (1), cinoxacin (2), norfloxacin (3), ciprofloxacin (4) and enoxacin (5)). The ability of the naphthyl ester derivatives (6-10) to generate singlet oxygen were detecting and for the first time quantified by the histidine assay, a sensitive, fast and inexpensive method. The following tendency of generation of singlet oxygen was observed: compounds 7 >10 > 6 > 8 > 9 >> parent drugs 1-5.

scholarly journals Reactivity of Several Reactive Oxygen Species (ROS) with the Sesquiterpene Cacalol

2008 ◽  
Vol 3 (4) ◽  
pp. 1934578X0800300
Author(s):  
Manuel Jiménez-Estrada ◽  
Ricardo Reyes-Chilpa ◽  
Arturo Navarro-Ocaña ◽  
Daniel Arrieta-Báez
Keyword(s):  
Reactive Oxygen Species ◽  
Hydroxyl Radical ◽  
Singlet Oxygen ◽  
Furan Ring ◽  
Reactive Oxygen ◽  
Antioxidant Effect ◽  
Oxygen Species ◽  
Site Reaction ◽  
Hexanedioic Acid ◽  
Antioxidant Effects

To analyze the antioxidant effects of cacalol we determined its reactivity with different reactive oxygen species (ROS). Cacalol gave rise to cacalone by a specific site reaction with a hydroxyl radical. Singlet oxygen reacted only with the double bond of the furan ring, causing its rupture. On the other hand, ozone reacted with all double bonds in cacalol affording 2-methyl-hexanedioic acid as an end product. No reaction was observed with either superoxide or hydrogen peroxide. The potential antioxidant effect of cacalol as a scavenger of hydroxyl radical and singlet oxygen could be related to its function in the plant roots.

scholarly journals Reactivity of graphene oxide with reactive oxygen species (hydroxyl radical, singlet oxygen, and superoxide anion)

2019 ◽  
Vol 6 (12) ◽  
pp. 3734-3744 ◽  
Author(s):  
Hsin-Se Hsieh ◽  
Richard G. Zepp
Keyword(s):  
Reactive Oxygen Species ◽  
Graphene Oxide ◽  
Hydroxyl Radical ◽  
Singlet Oxygen ◽  
Superoxide Anion ◽  
Reactive Oxygen ◽  
Toxic Effects ◽  
Oxygen Species ◽  
Ecological Risks

Increases in the production and applications of graphene oxide (GO), coupled with reports of its toxic effects, are raising concerns about its health and ecological risks.

scholarly journals Discovery of Small-Molecule Enhancers of Reactive Oxygen Species That are Nontoxic or Cause Genotype-Selective Cell Death

2013 ◽  
Vol 8 (5) ◽  
pp. 923-929 ◽  
Author(s):  
Drew J. Adams ◽  
Zarko V. Boskovic ◽  
Jimmy R. Theriault ◽  
Alex J. Wang ◽  
Andrew M. Stern ◽  
...  
Keyword(s):  
Reactive Oxygen Species ◽  
Cell Death ◽  
Small Molecule ◽  
Reactive Oxygen ◽  
Oxygen Species ◽  
Small Molecule Enhancers
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