Optical chemosensors for environmental monitoring of toxic metals related to Alzheimer\u27s disease

Alzheimer\u27s disease (AD) is the most common type of dementia and progresses from mild memory loss to severe decline in thinking, behavioral and social skills, which dramatically impairs a person\u27s ability to function independently. Genetics, some health disorders and lifestyle have all been connected to AD. Also, environmental factors are reported as contributors to this illness. The presence of heavy metals in air, water, food, soil and commercial products has increased tremendously. Accumulation of heavy metals in the body leads to serious malfunctioning of bodily organs, specifically the brain. For AD, a wide range of heavy metals have been reported to contribute to its onset and progression and the manifestation of its hallmarks. In this review, we focus on detection of highly toxic heavy metals such as mercury, cadmium, lead and arsenic in water. The presence of heavy metals in water is very troubling and regular monitoring is warranted. Optical chemosensors were designed and fabricated for determination of ultra-trace quantities of heavy metals in water. They have shown advantages when compared to other sensors, such as selectivity, low-detection limit, fast response time, and wide-range determination under optimal sensing conditions. Therefore, implementing optical chemosensors for monitoring levels of toxic metals in water represents an important contribution in fighting AD

Methyl 5′-Chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro-[chromene-2,2′-indoline]-6-carboxylate

Spiropyrans modified with reactive polyfunctional substituents are of great interest as building blocks for the creation of various smart systems with controllable properties for materials science and biomedicine. In this study, a new highly modified spiropyran of the indoline series, methyl 5′-chloro-8-formyl-5-hydroxy-1′,3′,3′-trimethyl-spiro[chromene-2,2′-indoline]-6-carboxylate, was obtained via the cyclocondensation reaction from 5-chloro-1,2,3,3-tetramethyl-3H-indolium perchlorate and methyl 3,5-diformyl-2,4-dihydroxy-benzoate. The molecular structure of the target compound was confirmed by 1H, 13C NMR, and IR spectroscopy, as well as LC/MS and elemental analysis. Photochemical studies revealed photochromic activity for the obtained spiropyran at room temperature. The photoinduced merocyanine form demonstrated an enhanced lifetime and fluorescent properties in the red region of the spectrum

Novel Indoline Spiropyrans Based on Human Hormones β-Estradiol and Estrone: Synthesis, Structure, Chromogenic and Cytotoxic Properties

The introduction of a switchable function into the structure of a bioactive compound can endow it with unique capabilities for regulating biological activity under the influence of various types of external stimuli, which makes such hybrid compounds promising objects for photopharmacology, targeted drug delivery and bio-imaging. This work is devoted to the synthesis and study of new spirocyclic derivatives of important human hormones—β-estradiol and estrone—possessing a wide range of biological activities. The obtained hybrid compounds represent an indoline spiropyrans family, a widely known class of organic photochromic compounds. The structure of the compounds was confirmed by 1H and 13C NMR, IR, HRMS and single-crystal X-ray analysis. The intermolecular interactions in the crystals of spiropyran (3) were defined by Hirshfeld surfaces and 2D fingerprint plots, which were successfully acquired from CrystalExplorer (v21.5). All target hybrids demonstrated pronounced activity in the visible region of the spectrum. The mechanisms of thermal isomerization processes of spiropyrans and their protonated merocyanine forms were studied by DFT methods, which revealed the energetic advantage of the protonation process with the formation of a β-cisoid CCCH conformer at the first stage and its further isomerization to more stable β-transoid forms. The proposed mechanism of acidochromic transformation was confirmed by the additional NMR study data that allowed for the detecting of the intermediate CCCH isomer. The study of the short-term cytotoxicity of new spirocyclic derivatives of estrogens and their 2-formyl-precursors was performed on the HeLa cell model. The precursors and spiropyrans differed in toxicity, suggesting their variable applicability in novel anti-cancer technologies