In this study, our goal was to synthesize novel aryl tacrine derivatives and assess their potential as anticancer, antibacterial agents, and enzyme inhibitors. We adopted a two‐step approach, ...initiating with the synthesis of dibromotacrine derivatives 3 and 4 through the Friedlander reaction. These intermediates underwent further transformation into diarylated tacrine derivatives 3a–e and 4a–e using a Suzuki–Miyaura cross‐coupling reaction. Thorough characterization of these novel diarylated tacrines was achieved using various spectroscopic techniques. Our findings highlighted the potent anticancer effects of these innovative compounds across a range of cancer cell lines, including lung, gynecologic, bone, colon, and breast cancers, while demonstrating low cytotoxicity against normal cells. Notably, these compounds surpassed the control drug, 5‐Fluorouracil, in terms of antiproliferative activity in numerous cancer cell lines. Moreover, our investigation included an analysis of the inhibitory properties of these novel compounds against various microorganisms and cytosolic carbonic anhydrase enzymes. The results suggest their potential for further exploration as cancer‐specific, enzyme inhibitory, and antibacterial therapeutic agents. Notably, four compounds, namely, 5,7‐bis(4‐(methylthio)phenyl)tacrine (3d), 5,7‐bis(4‐(trifluoromethoxy)phenyl)tacrine (3e), 2,4‐bis(4‐(trifluoromethoxy)phenyl)‐7,8,9,10‐tetrahydro‐6H‐cycloheptabquinolin‐11‐amine (4e), and 6,8‐dibromotacrine (3), emerged as the most promising candidates for preclinical studies.
The novel aryl substituted tacrine were efficiently synthesized and their anticancer potentials were highlighted in this study. Their inducing apoptosis, cell migration, and mitochondrial membrane potentials were screened.
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FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SBCE, SBMB, UL, UM, UPUK
Quinoline-based BODIPY AIEgen dyes were synthesized and the structures were elucidated by
1
H,
13
C,
19
F NMR, FT-IR spectroscopy and mass spectrometry methods. Their photophysical properties were ...investigated. The dyes showed fluorescence quantum yield in the range of 0.16–1.29% in MeOH. It was found that the presence of methoxy group and tetrazole moiety led to blue and red spectral shift, respectively, of the UV absorption maxima of these dyes compared to their chloroquinoline analog. Stokes shifts of the dyes were in the range of 637–955 cm
–1
. Aggregation-induced emission behavior of the dyes was investigated in EtOH–H
2
O mixture so that the dyes exhibited 1.6- to 2.3-fold fluorescence enhancement.
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DOBA, EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, IZUM, KILJ, KISLJ, MFDPS, NLZOH, NUK, OBVAL, OILJ, PILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UILJ, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
•Photophysical and theoretical properties of tetrazolo1,5-aquinolone –BODIPY are investigated.•The synthesized dyes display AIE activity in water-ethanol mixtures.•The dye bearing single methoxy ...group displays the highest quantum yield.•Viscosity sensitivity in common organic solvents is observed for most of the dyes.
Novel tetrazolo1,5-a quinoline-based BODIPY dyes (6b-d) were synthesized and characterized by photophysical and theoretical methods. Except for 6c, fluorescence quantum yield of the dyes increased parallelly with the solvent viscosity due to hindrance of free rotation at meso position. Fluorescence quantum yield of 6c is higher than 6d, although the number of electron-donating groups of the former is less than that of the latter. The fluorophores exhibited apparent responses in the fluorescence intensities with increasing water ratio in ethanol owing to their aggregation-induced emission (AIE) characteristics. In a separate study, NBO analysis and DFT calculations were also performed for dyes 6a-d. Various quantum chemical parameters from frontier orbital energies to polarizability were calculated and discussed in detail. The theoretical calculations showed that compound 6d is the most stable. These results demonstrate that tetrazolo1,5-a quinoline-based fluorophores would have potential application in water detection systems.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
•Effective synthesis of arylated BODIPY dyes via bromination and Suzuki Coupling.•The electron density of π-conjugated groups at different positions led to blue or red shifted spectra.•The electron ...accepting at meso and donating groups at C3/C5 of dyes lead red shifted spectra.•The electron donating at meso and accepting groups at C3/C5 of dyes lead blue shifted spectra.•The lowest HOMO-LUMO band gap by binding -SCH3 at C-3/C-5 of BODIPY.
In this study, a series of symmetrically arylated BODIPY dyes were synthesized using a pre-functionalization method, and their structures were characterized by several spectroscopic methods. The relationship between the aryl substitution pattern and the photophysical and electrochemical properties of the dyes was investigated using experimental and computational methods. It was found that electron-donating π-conjugated groups at the meso position and electron-accepting π-conjugated groups at the C3/C5 position led to blue-shifted spectra, while the opposite substitution pattern resulted in red-shifted spectra. Additionally, inductive electron-donating alkyl groups at the meso position produced a blue spectral shift and an alkyl group at the meso position significantly increased the fluorescence quantum yield compared to the arylated counterparts. Computational investigations revealed that a thioanisyl group at the C3/C5 position resulted in a significantly narrow band gap. These results provide valuable insights into the design and development of new BODIPY dyes with tailored properties for various applications.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UILJ, UL, UM, UPCLJ, UPUK, ZAGLJ, ZRSKP
Trout is the most widely cultivated and traded fish species in Turkey and many European countries, and a total of 471686 tons of production was realized in Turkey’s seas and inland waters in 2021. In ...addition to its nutritive value, this fish takes a crucial position in the aquaculture sector due to its continuous and intensive production. In this study, innovative bioactive protein hydrolysates (PH) produced from sprat were used as a coating to increase the quality and shelf life of trout fillets stored at +4 ˚C. The yields of traditional hydrolysate (TH) and ultrasound-assisted hydrolysate (UH) were 8.66% and 12.63%, respectively. Protein values of TH and UH were 75.88 and 74.45%, respectively. Three fillet groups were prepared from trout: uncoated control group (C), traditional enzymatic protein hydrolysate coated group (THC), and ultrasound-assisted enzymatic protein hydrolysate coated group (UHC). TVB-N value, which was 12.96 mg/100g in fresh trout, exceeded the consumable limit with 38.52 mg/100g on the 9th day of storage in the C. This value reached 32.92 mg/100g and 33.62 mg/100g on the 12th day for THC and UHC, respectively. At the beginning of storage, 0.21 mg MA/kg TBA reached the consumable limit with 7.72 mg MA/kg in the C on the 9th day, while THC and UHC remained within the limit with 6.67 mg MA/kg and 6.79 mg MA/kg, respectively. Total aerobic mesophilic bacteria (TAMB) and total aerobic psychrophilic bacteria (TAPB) counts on day 0 of storage were 2.13 log cfu/g and 1.66 log cfu/g, respectively. These values were calculated as 6.90, 5.20, 5.04, 6.95, 3.48, and 3.22 log cfu/g for C, THC, and UHC on the 12th day of storage, respectively. The application of ultrasound during the production of protein hydrolysate significantly increased the yield and hydrolysis degree of UH compared to TH. The lipid ratio of UH was also found to be significantly lower than TH. In these respects, the application of ultrasound has provided an advantage. Although both coatings have provided significant protection compared to the C, generally similar results were obtained between the THC and UHC. PH coatings delayed the chemical, physical, and microbial spoilage of trout fillets and extended the storage period. The results showed that PH can be used as a coating on fish fillets stored in cold conditions.
Alabalık ülkemizde ve birçok Avrupa ülkesinde yetiştiriciliği ve ticareti en fazla yapılan balık türüdür ve 2021 yılında ülkemiz denizleri ve içsularında toplam 471686 tonluk üretimi gerçekleştirilmiştir. Besleyici değerinin yanısıra sürekli ve yoğun üretiminden dolayı bu balık su ürünleri sektöründe önemli bir yere sahiptir. Bu çalışmada +4 ˚C’de depolanan alabalık filetolarının kalite ve raf ömrünü uzatmak amacıyla çaçadan üretilen yenilikçi biyoaktif protein hidrolizatları (PH) kaplama olarak kullanılmıştır. Geleneksel hidrolizat (TH) ve ultrason destekli hidrolizat (UH) verimleri sırasıyla %8.66 ve %12.63 olarak hesaplanmıştır. TH ve UH’a ait protein değerleri sırasıyla %75.88 ve %74.45 olarak belirlenmiştir. Kaplamasız kontrol grubu (K), geleneksel enzimatik protein hidrolizatı ile kaplanmış grup (GHKS) ve ultrases destekli enzimatik protein hidrolizatı ile kaplanmış grup (UHKS) olmak üzere 3 fileto grubu hazırlanmıştır. Taze alabalıkta 12,96 mg/100g olan TVB-N değeri K grubunda depolamanın 9. gününde 38,52 mg/100g ile tüketilebilirlik sınırını aşmıştır. Bu değer GHKS ve UHKS için 12. günde sırasıyla 32,92 mg/100g ve 33,62 mg/100g’a ulaşmıştır. Depolamanın başında 0,21 mg MA/kg TBA değeri 9. günde K grubunda 7,72 mg MA/kg ile tüketilebilirlik sınırına ulaşırken GHKS ve UHKS de sırasıyla 6,67 mg MA/kg ve 6,79 mg MA/kg ile sınırın içerisinde kalmıştır. Depolamanın 0. gününde toplam aerobik mezofilik bakteri (TAMB) ve toplam aerobik psikrofilik bakteri (TAPB) sayıları sırasıyla 2,13 log kob/g ve 1,66 log kob/g olarak bulunmuştur. Bu değerler depolamanın 12. gününde K, GHKS ve UHKS için sırasıyla 6,90, 5,20, 5,04 ve 6,95, 3,48 ile 3,22 log kob/g olarak hesaplanmıştır. PH kaplamalar alabalık filetolarında kimyasal, fiziksel ve mikrobiyal bozulmayı geciktirerek depolama süresini uzatmıştır. Elde edilen sonuçlar PH’ın, soğuk koşullarda depolanan balık filetolarında kaplama olarak kullanılabileceğini göstermiştir.
