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Exploring ethynyl-based chalcones as green semiconductor materials for optical limiting interests

Khairul WM, Hashim F, Rahamathullah R, Mohammed M, Aisyah Razali S, Ahmad Tajudin Tuan Johari S, et al.

Spectrochim Acta A Mol Biomol Spectrosc, 2024 Mar 05;308:123776.
PMID: 38134650 DOI: 10.1016/j.saa.2023.123776

The fabrication of molecular electronics from non-toxic functional materials which eventually would potentially able to degrade or being breaking down into safe by-products have attracted much interests in recent years. Hence, in this study, the introduction of mixed highly functional substructures of chalcone (-CO-CH=CH-) and ethynylated (C≡C) as building blocks has shown ideal performance as solution-processed thin film candidatures. Two types of derivatives, (MM-3a) and (MM-3b) repectively, showed a substantial Stokes shifts at 75 nm and 116 nm, in which such emission exhibits an intramolecular charge transfer (ICT) state and fluoresce characteristics. The density functional theory (DFT) simulation shows that MM-3a and MM-3b exhibit low energy gaps of 3.70 eV and 2.81 eV, respectively. TD-DFT computations for molecular electrostatic potential (MEP) and frontier molecular orbitals (FMO) were also used to emphasise the structure-property relationship. A solution-processed thin film with a single layer of ITO/PEDOT:PSS/MM-3a-MM-3b/Au exhibited electroluminescence behaviour with orange and purple emissions when supplied with direct current (DC) voltages. To promote the safer application of the derivatives formed, ethynylated chalcone materials underwent toxicity studies toward Acanthamoeba sp. to determine their suitability as non-toxic molecules prior to the determination as safer materials in optical limiting interests. From the preliminary test, no IC50 value was obtained for both compounds via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay analysis and molecular docking analysis between MM-3a and MM-3b, with profilin protein exhibited weak bond interactions and attaining huge interaction distances.
Assessment on Functionalized Conjugated Acetylide and Its Designated Acetylide-Imine Moieties towards Acanthamoeba sp.: An in vitro Bioindicator Study

Manisekaran T, Wan M Khairul, Foong YD, Tuan Johari SAT, Hashim F, Rahamathullah R, et al.

Chemosphere, 2024 Sep 02.
PMID: 39233293 DOI: 10.1016/j.chemosphere.2024.143220

The demand for developing bioindicators to assess environmental pollution has increased significantly due to the awareness of potential threats of diseases. Herein, the eukaryotic ubiquitous microorganism Acanthamoeba sp. was used as a bioindicator to explore further the influence of functionalized organic molecules containing -C≡C- and -CH=N- moieties prior application in the potential electronic components. The acetylide and hybrid acetylide-imine derivatives (FYD3A, FYD4B, and FYD4C) were tested for their cytotoxicity potentials based on dose-response analysis, morphological observation, and mode of cell death assessment on Acanthamoeba sp. (environmental-isolate). The biological activities of optimized compounds were evaluated by HOMO-LUMO energy gap and MEP analysis. The determination of the IC50 value through the MTT assay showed functionalized organic molecules of FYD3A, FYD4B, and FYD4C, revealing the inhibition growth of Acanthamoeba sp. with IC50 values in the 3.515 - 3.845 μg/mL range. Morphological observation displayed encystment with cellular agglutination and overall cell shrinkage. AO/PI-stained moieties-treated Acanthamoeba sp. cells appeared with shades of red to orange in necrotic Acanthamoeba cells whilst green to yellow apoptotic Acanthamoeba cells when compared to entirely green fluorescence untreated cells. Moreover, the results of the mitochondrial membrane potential (MMP) assay demonstrate the integrity and functionality potential of the mitochondrial membrane in cells, where a decrease in the MMP assay is linked to apoptosis. This study confirmed that the functionalized organic molecule featuring acetylide and its designated acetylide-imine moieties exhibit cytotoxicity towards the Acanthamoeba sp. by apoptotic and necrotic mode of cell death. This indicates that seeping these derivatives as electronic components can lead to the leaching of hazardous chemicals and contribute to environmental pollution that negatively affects the ecosystem. This study proposes the selection of efficient systems and elements for functionalized organic molecules that are safe to be released into the environment.
Fulltext Marine microalgae co-cultured with floc-forming bacterium: Insight into growth and lipid productivity

Yee CS, Okomoda VT, Hashim F, Waiho K, Sheikh Abdullah SR, Alamanjo C, et al.

PeerJ, 2021;9:e11217.
PMID: 33981498 DOI: 10.7717/peerj.11217

This study investigated the effect of co-culturing microalgae with a floc-forming bacterium. Of the six microalgae isolated from a biofloc sample, only Thalassiosira weissflogii, Chlamydomonas sp. and Chlorella vulgaris were propagated successfully in Conway medium. Hence, these species were selected for the experiment comparing microalgae axenic culture and co-culture with the floc-forming bacterium, Bacillus infantis. Results obtained showed that the co-culture had higher microalgae biomass compared to the axenic culture. A similar trend was also observed concerning the lipid content of the microalgae-bacterium co-cultures. The cell number of B. infantis co-cultured with T. weissflogii increased during the exponential stage until the sixth day, but the other microalgae species experienced a significant early reduction in cell density of the bacteria at the exponential stage. This study represents the first attempt at co-culturing microalgae with B. infantis, a floc-forming bacterium, and observed increased biomass growth and lipid accumulation compared to the axenic culture.
Synthesis, Molecular Docking and Biological Activity Evaluation of Alkoxy Substituted Chalcone Derivatives: Potential Apoptosis Inducing Agent on MCF-7 Cells

Khairul WM, Hashim F, Mohammed M, Shah NSMN, Johari SATT, Rahamathullah R, et al.

Anticancer Agents Med Chem, 2021;21(13):1738-1750.
PMID: 33176667 DOI: 10.2174/1871520620999201110190709

INTRODUCTION: In this contribution, a series of alkoxy substituted chalcones were successfully designed, synthesized, spectroscopically characterized and evaluated for their cytotoxicity potential in inhibiting the growth of MCF-7 cells.
OBJECTIVE: In order to investigate the influence between electron density in conjugated π-systems and biological activities, different withdrawing substituents, namely Nitro (NO2), Cyano (C≡N) and trifluoromethyl (CF3) were introduced in the chalcone-based molecular system.
METHODS: All the derivatives were then tested on MCF-7 cell line using the fluorescence microscopy-based cytotoxicity analyses.
RESULTS: The preliminary findings showed that both -NO2 and -CF3 substituents revealed their potential to inhibit the growth of MCF-7 with IC;50 values of 14.75 and 13.75 μg/ml, respectively. In addition, the morphological changes of MCF-7 cells were observed in response to alkoxy substituted chalcone treatment through an induction of apoptosis pathway with cell blebbing, phosphatidylserine exposure and autophagic activity with acidification of lysosomal structure. Intermolecular interaction based on in silico investigation on nitro, trifluoromethyl and cyano based chalcones exhibited several types of interactions with tumor necrosis factor receptor (PDB: 1EXT) protein and high hydrogen bond in the molecule-receptor interaction have given significant impact towards their toxicity on MCF-7 cells.
CONCLUSION: Significantly, these types of chalcones exhibited ideal and high potential to be further developed as anti-cancer agents.
Fulltext Urinary levels of organophosphate flame retardants metabolites in a young population from Southern Taiwan and potential health effects

Chen FS, Chen CC, Tsai CC, Lu JH, You HL, Chen CM, et al.

Front Endocrinol (Lausanne), 2023;14:1173449.
PMID: 37334296 DOI: 10.3389/fendo.2023.1173449

BACKGROUND: Organophosphate flame retardants (OPFRs) are widely distributed in the environment and their metabolites are observed in urine, but little is known regarding OPFRs in a broad-spectrum young population from newborns to those aged 18 years.
OBJECTIVES: Investigate urinary levels of OPFRs and OPFR metabolites in Taiwanese infants, young children, schoolchildren, and adolescents within the general population.
METHODS: Different age groups of subjects (n=136) were recruited from southern Taiwan to detect 10 OPFR metabolites in urine samples. Associations between urinary OPFRs and their corresponding metabolites and potential health status were also examined.
RESULTS: The mean level of urinary Σ10 OPFR in this broad-spectrum young population is 2.25 μg/L (standard deviation (SD) of 1.91 μg/L). Σ10 OPFR metabolites in urine are 3.25 ± 2.84, 3.06 ± 2.21, 1.75 ± 1.10, and 2.32 ± 2.29 μg/L in the age groups comprising of newborns, 1-5 year-olds, 6-10 year-olds, and 11-18 year-olds, respectively, and borderline significant differences were found in the different age groups (p=0.125). The OPFR metabolites of TCEP, BCEP, DPHP, TBEP, DBEP, and BDCPP predominate in urine and comprise more than 90% of the total. TBEP was highly correlated with DBEP in this population (r=0.845, p<0.001). The estimated daily intake (EDI) of Σ5OPFRs (TDCPP, TCEP, TBEP, TNBP, and TPHP) was 2,230, 461, 130, and 184 ng/kg bw/day for newborns, 1-5 yr children, 6-10 yr children, and 11-17 yr adolescents, respectively. The EDI of Σ5OPFRs for newborns was 4.83-17.2 times higher than the other age groups. Urinary OPFR metabolites are significantly correlated with birth length and chest circumference in newborns.
CONCLUSION: To our knowledge, this is the first investigation of urinary OPFR metabolite levels in a broad-spectrum young population. There tended to be higher exposure rates in both newborns and pre-schoolers, though little is known about their exposure levels or factors leading to exposure in the young population. Further studies should clarify the exposure levels and factor relationships.