An optimized chitosan/alginate-based microencapsulation of lime peel essential oil and its application as an antibacterial textile.

A functional textile immobilized by microcapsules of the lime peel essential oils of C. aurantifolia (LPEO) was prepared and characterized. A varied amount of Chitosan/Alginate (CH/AG) ratios, followed by a mass of LPEO and concentration of sodium tripolyphosphate (STPP) crosslinker, was optimized sequentially to coacervate LPEO using a Tween 80 emulsifier. An antibacterial assay against both Gram-positive and Gram-negative bacteria was further evaluated for the embedded microcapsules. The LPEO (0.2 g) was effectively coacervated by CH/AG (5:3) crosslinked by 2% of STTP to give a yield, oil content (OC), and encapsulation efficiency (EE) of 53.45 ± 2.16%, 65.08 ± 2.60% and 85.04 ± 0.70% respectively. A rough spherical shape of LPEO microcapsules was homogeneously observed with an average particle size of 0.757 mm. An Avrami's kinetic model revealed the release mechanism of the core following zero-order kinetics (k = 1.11 ± 0.13 × 10-9 s-1, Ea = 70.21 kJ/mol). The LPEO microcapsules demonstrated good thermal stability up to 122 °C and maintained 38% OC at ambient temperature for four weeks. A 70.34 ± 4.16% of the LPEO microcapsules were successfully overlaid onto the gauze with citric acid binder and sodium phosphate catalyst. Overall, the immobilized microcapsules exhibited strong inhibition against S. aureus and moderate against S. epidermidis, E. coli, and K. pneumonia.

Structure-Activity Relationship Study and Design Strategies of Hydantoin, Thiazolidinedione, and Rhodanine-Based Kinase Inhibitors: A Two-Decade Review.

Cancer is one of the most prominent causes of the rapidly growing mortality numbers worldwide. Cancer originates from normal cells that have acquired the capability to alter their molecular, biochemical, and cellular traits. The alteration of cell signaling enzymes, such as kinases, can initiate and amplify cancer progression. As a curative method, the targeted therapy utilized small molecules' capability to inhibit kinase's cellular function. This review provides a brief history (1999-2023) of Small Molecule Kinase Inhibitors (SMKIs) discovery with their molecular perspective. Furthermore, this current review also addresses the application and the development of hydantoin, thiazolidinedione, and rhodanine-based derivatives as kinase inhibitors toward several subclasses (EGFR, PI3K, VEGFR, Pim, c-Met, CDK, IGFR, and ERK) accompanied by their structure-activity relationship study and their molecular interactions. The present work summarizes and compiles all the important structural information essential for developing hydantoin, thiazolidinedione, and rhodanine-based kinase inhibitors to improve their potency in the future.

Synthesis of a Cyclooctapeptide, Cyclopurpuracin, and Evaluation of Its Antimicrobial Activity.

Cyclopurpuracin is a cyclooctapeptide isolated from the methanol extract of Annona purpurea seeds with a sequence of cyclo-Gly-Phe-Ile-Gly-Ser-Pro-Val-Pro. In our previous study, the cyclisation of linear cyclopurpuracin was problematic; however, the reversed version was successfully cyclised even though the NMR spectra revealed the presence of a mixture of conformers. Herein, we report the successful synthesis of cyclopurpuracin using a combination of solid- and solution-phase synthetic methods. Initially, two precursors of cyclopurpuracin were prepared, precursor linear A (NH2-Gly-Phe-Ile-Gly-Ser(t-Bu)-Pro-Val-Pro-OH) and precursor linear B (NH-Pro-Gly-Phe-Ile-Gly-Ser(t-Bu)-Pro-Val-OH, and various coupling reagents and solvents were trialled to achieve successful synthesis. The final product was obtained when precursors A and B were cyclised using the PyBOP/NaCl method, resulting in a cyclic product with overall yields of 3.2% and 3.6%, respectively. The synthetic products were characterised by HR-ToF-MS, 1H-NMR, and 13C-NMR, showing similar NMR profiles to the isolated product from nature and no conformer mixture. The antimicrobial activity of cyclopurpuracin was also evaluated for the first time against S. aureus, E. coli, and C. albicans, showing weak activity with MIC values of 1000 µg/mL for both synthetic products, whereas the reversed cyclopurpuracin was more effective with an MIC of 500 µg/mL.

Microencapsulation of Citrus aurantifolia essential oil with the optimized CaCl2 crosslinker and its antibacterial study for cosmetic textiles.

A functional fabric immobilized by the microcapsules of C. aurantifolia lime essential oil (LO) was prepared and characterized. A varied amount of CaCl2 crosslinker was optimized to coacervate LO using alginate-gelatin biopolymers and Tween 80 emulsifier. A further evaluation of the immobilized LO microcapsules for the antibacterial effect against both Gram-positive and Gram-negative bacteria was conducted. The optimized alginate/gelatin-based microcapsules were effectively crosslinked by 15% CaCl2 with an yield, oil content (OC), and encapsulation efficiency (EE) of 39.91 ± 3.10%, 78.33 ± 7.53%, and 90.27 ± 5.84%, respectively. A spherical shape of LO microcapsules was homogeneously found with an average particle size of 1.394 µm. A first-order kinetics mechanism for the release of LO out of the microcapsules was modeled by Avrami's kinetic equation (k = 1.60 ± 3.68 × 10-5 s-1). The LO microcapsules demonstrated good thermal stability up to 100 °C and maintained 51.07% OC and 43.56% EE at ambient temperature for three weeks. Using a pad dry method and citric acid binder, LO microcapsules were successfully immobilized on a cloth with a % add on 30.60 ± 1.80%. The LO microcapsules and the immobilized one exhibited a moderate ZoI of bacterial growth for Gram-positive S. aureus and S. epidermidis as well as Gram-negative E. coli and K. pneumonia. Further washing test toward the functional fabric showed that the LO microcapsules incorporated into the fabric were resistant to five cycles of normal washing with a mass reduction of 22.01 ± 1.69%.

A new highly selective "off-on" typical chemosensor of Al3+, 1-((Z)-((E)-(3,5-dichloro-2-hydroxybenzylidene)hydrazono)methyl) naphthalene-2-ol, an experimental and in silico study.

A new promising fluorescent chemosensor based on a 2-hydroxynaphthaldehyde skeleton was successfully synthesized through double imine formation as a yellow solid with an overall chemical yield of 63%. The compound showed UV/Visible maxima of at 394 nm in DMSO. Based on spectroscopic data of FTIR, ToF-HRMS, 1H-NMR, and 13C-NMR, the product was characterized as 1-((Z)-((E)-(3,5-dichloro-2-hydroxybenzilydine)hydrazono)methyl)naphthalene-2-ol. Upon experimental study, the compound was confirmed as a highly selective and reversible off-on typical chemosensor against Al3+ with an emission quantum yield of 0.203 ± 0.009. The Job's plot analysis revealed that a highly stable 1:1 complex was formed with an association constant of 8.73 × 105 M-1. A pH-dependent study showed that the sensor was potentially applicable at physiological conditions (pH 7-8) in a mixture of DMSO : H2O (99 : 1, v/v). The LoD and LoQ of the chemosensor towards Al3+ in DMSO were found to be 0.04 and 0.14 µM respectively. Based on DFT and TD-DFT calculation (B3LYP hybrid method/basis set of 6-311+G(d,p)), the sensing mechanism of the chemosensor to the ion was discovered as inhibition of excited-state intramolecular proton transfer (ESIPT).

Microencapsulation of lime (Citrus aurantifolia) oil for antibacterial finishing of cotton fabric.

Functional cotton fabric incorporated with antibacterial microcapsules of lime (C. aurantifolia) essential oil (LO) was prepared. The coacervation method, employing two biopolymers of alginate and gelatin as the shells, was preferentially selected to produce the LO microcapsules, whereas immobilization of the LO microcapsules onto the fabric was done using the pad-dry-cure method using various concentrations of citric acid binder. The antibacterial inhibition zone of the functional fabric was subsequently analysed using the Kirby Bauer method. The LO microcapsules were produced with a yield, encapsulation efficiency (EE), and oil content (OC) of 47 ± 4%, 84 ± 11%, and 58 ± 4%, respectively. The homogenous spherical and soft microcapsules (1.554 µm) bonded effectively by 4% citric acid onto the surface of the fabric and detached back by only 3% after 15 cycles of washing. Overall, the optimized functional fabric exhibited the highest antibacterial activities among others against typical skin bacteria, such as S. aureus, E. coli, K. pneumoniae, and S. epidermidis, and thus it can be potentially applied to obtain antibacterial functional textile.

Azobenzene photoisomerization quantum yields in methanol redetermined.

The quantum yields of azobenzene photoisomerization in methanol solution were redetermined using newly obtained molar absorption coefficients of its cis- and trans-isomers. The results differ substantially from those published previously, especially in the range of the nπ* absorption band. Besides actinometry, these findings are relevant for applications of azobenzene derivatives in optical switching.

The absorption spectrum of cis-azobenzene.

Azobenzene is a prototypical photochromic molecule existing in two isomeric forms, which has numerous photochemical applications that rely on a precise knowledge of the molar absorption coefficients (ε). Careful analysis revealed that the previously reported absorption spectra of the "pure" isomers were in fact mutually contaminated by small amounts of the other isomer. Therefore, the absorption spectra of both trans- and cis-azobenzene in methanol were re-determined at temperatures of 5-45 °C. The thermodynamically more stable trans-azobenzene was prepared by warming the solution in the dark. To obtain the spectrum of cis-azobenzene three methods were used, which gave consistent results within the limits of error. The method based on the subtraction of derivative spectra coupled with a global analysis of the spectra recorded during thermal cis-trans isomerization is shown to give slightly more reliable results than the method using isomeric ratios determined by 1H-NMR. The described methods are readily generalizable to other azobenzene derivatives and to other photochromic systems. The practical implication of the re-determined ε values is demonstrated by a very high precision of spectrophotometric species analysis in azobenzene isomeric mixtures. The new ε values imply that the previously reported quantum yields must be revised.

The internal heavy-atom effect on 3-phenylselanyl and 3-phenyltellanyl BODIPY derivatives studied by transient absorption spectroscopy.

Three monosubstituted 3-phenylselanyl and 3-phenyltellanyl BODIPY derivatives were synthesized and their spectroscopic properties were characterized and compared to those of iodine and chlorine-atoms containing analogues as well as an unsubstituted BODIPY derivative. The fluorescence quantum yields were found to decrease, whereas the intersystem crossing quantum yields (ΦISC), determined by transient spectroscopy, increased in the order of the H → Cl → Se/I → Te substitution. The maximum ΦISC, found for the 3-phenyltellanyl derivative, was 59%. The results are interpreted in terms of the internal heavy-atom effect of the substituents.

Fluorescein analogues as photoremovable protecting groups absorbing at ∼520 nm.

A new photoremovable protecting group, (6-hydroxy-3-oxo-3H-xanthen-9-yl)methyl (1), with a molar absorption coefficient ε of ∼4 × 10(4) m(-1) cm(-1) at ∼520 nm for the release of carboxylates or phosphates is reported. Three derivatives of 1 (diethyl phosphate, acetate, and bromide) were isolated as complexes with DDQ and shown to release the ligands with quantum yields ≤2.4% in aqueous solution.