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  1. Wan M. Khairul, Foong, Y.D., Lee, O.J., Lim, S.K.J., Daud, A.I., Rahamathullah, R., et al.
    ASM Science Journal, 2018;11(101):124-135.
    MyJurnal
    A new class of liquid crystalline acetylide-imine system was successfully synthesized, characterized
    and deposited on indium tin oxide (ITO) coated substrate via electrochemical deposition
    method for potential organic film application. The relationship between liquid crystal
    molecular structure, phase transition temperature and electrical performance was evaluated.
    The mesomorphic properties were identified via polarized optic microscopy (POM) which displayed
    fan-shaped texture of smectic A phase and their corresponding transition enthalpies
    are in concurrence with DSC and TGA studies. The findings from the conductivity analysis
    revealed that the fabricated film exhibits good electrical performance where it displayed
    linear current-voltage relationship of I-V curve. Therefore, this proposed type of molecular
    framework has given an ideal indication to act as transporting material for application in
    optoelectronic devices.
  2. Khairul WM, Hashim F, Rahamathullah R, Mohammed M, Aisyah Razali S, Ahmad Tajudin Tuan Johari S, et al.
    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.
  3. 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.
  4. 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.

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