Selenium- and tellurium-containing fluorescent molecular probes for the detection of biologically important analytes
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- Selenium- and tellurium-containing fluorescent molecular probes for the detection of biologically important analytes
- Sudesh T. Manjare; Kim Y.; Churchill D.G.
- ACCOUNTS OF CHEMICAL RESEARCH, v.47, no.10, pp.2985 - 2998
- AMER CHEMICAL SOC
- As scientists in recent decades have discovered,
selenium is an important trace element in life. The
element is now known to play an important role in biology as
an enzymatic antioxidant. In this case, it sits at the active site
and converts biological hydrogen peroxides to water. Mimicking
this reaction, chemists have synthesized several organoselenium
compounds that undergo redox transformations. As such, these
types of compounds are important in the future of both medicinal
and materials chemistry. One main challenge for organochalcogen
chemists has been to synthesize molecular probes that
are soluble in water where a selenium or tellurium center can
best modify electronics of the molecule based on a chemical oxidation
or reduction event.
In this Account, we discuss chemists’ recent efforts to create chalcogen-based chemosensors through synthetic means and current
photophysical understanding. Our work has focused on small chromophoric or fluorophoric molecules, in which we incorporate
discrete organochalcogen atoms (e.g., R-Se-R, R-Te-R) in predesigned sites. These synthetic molecules, involving rational synthetic
pathways, allow us to chemoselectively oxidize compounds and to study the level of analyte selectivity by way of their optical
responses. All the reports we discussed here deal with well-def ined and small synthetic molecular systems.
With a large number of reports published over the last few years, many have notably originated from the laboratory of K. Han (P. R.
China). This growing body of research has given chemists new ideas for the previously untenable reversible reactive oxygen species
detection. While reversibility of the probe is technically important from the stand-point of the chalcogen center, facile regenerability
of the probe using a secondary analyte to recover the initial probe is a very promising avenue. This is because (bio)chalcogen chemistry
is extremely rich and bioinspired and continues to yield important developments across many scientific fields. Organochalcogen
(R-E-R) chemistry in such chemical recognition and supramolecular pursuits is a fundamental tool to allow chemists to explore stable
organic-based probe modalities of interest to develop better spectroscopic tools for (neuro)biological applications.
Chalcogen donor sites also provide sites where metals can coordinate, and facile oxidation may extend to the sulfone analogues
(R-EO2-R) or beyond. Consequently, chemists can then make use of reliable reversible chemical probing platforms based on the chemical
redox properties valence state switching principally from 2 to 4 (and back to 2) of selenium and tellurium atoms. The main organic
molecular skeletons have involved chemical frames including boron-dipyrromethene (BODIPY) systems, extended cyanine groups,
naphthalimide, rhodamine, and fluorescein cores, and isoselenazolone, pyrene, coumarin, benzoselenadiazole, and selenoguanine systems.
Our group has tested many such molecular probe systems in cellular milieu and under a series of conditions and competitive
environments. We have found that the most important analytes have been reactive oxygen species (ROS) such as superoxide and
hypochlorite. Reactive nitrogen species (RNS) such as peroxynitrite are also potential targets. In addition, we have also considered Fenton
chemistry systems. Our research and that of others shows that the action of ROS is often reversible with H2S or biothiols such as
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