Bis(thio)carbohydrazone Luminogens with AIEE and ACQ Features and Their In Silico Investigations with SARS‐CoV‐2

Abstract

Herein, we report two novel multidentate luminogen proligands bis(3,5‐diiodosalicylidene) carbohydrazone (H4L1) and bis(3,5‐diiodosalicylidene) thiocarbohydrazone (H4L2), which are suitable candidates for biomedical applications. Though the thiocarbohydrazone H4L2 shows aggregation caused quenching (ACQ), the carbohydrazone H4L1 exhibits stronger fluorescence due to aggregation induced emission enhancement (AIEE). Molecular docking studies of H4L1 and H4L2 along with four similar (thio)carbohydrazones with the active sites of SARS‐CoV‐2 main protease 3CLpro reveals that the thiocarbohydrazones, in general, are showing better propensity compared to their oxygen analogues. Both the thiocarbohydrazones and the carbohydrazones, however, exhibit better binding potential at the active sites than that of some of the repurposed drugs such as chloroquine, hydroxychloroquine, lopinavir, ritonavir, darunavir and remdesivir. Also, the carbohydrazone H4L1 can be a better bioprobe compared to H4L2 as the former is found to have better binding potential with SARS‐CoV‐2 spike glycoprotein along with AIEE feature.

An all-rounder aminoguanidine based ligand, its unusual anionic zinc(ii) and cadmium(ii) coordination complexes and their biological implications

“…The positive or electron-deficient NH region is represented by the blue or cyan areas and is available for nucleophilic attack. 51 It is still highly instructive regarding areas where the ligand may come into contact with the electrophile.…”

Synthesis, SARS‐CoV‐2 3CL main protease inhibitor, anti‐inflammatory, and wound‐healing effects of a zinc(II)‐thiosemicarbazone complex

“…It was shown that some thiosemicarbazone compounds have antiviral effects on the SARS-CoV-2 as bioinformatically. [31][32][33] The effects of complex 2 on cell viability in BEAS-2B cells were measured by MTT cell viability test. As a result of the experiments, it was found that 2 had a proliferative effect at low doses.…”

“…It was shown that some thiosemicarbazone compounds have antiviral effects on the SARS‐CoV‐2 as bioinformatically. [ 31–33 ]…”

Aminoguanidine-based bioactive proligand as AIEE probe for anticancer and anticovid studies

“…18 Its applications range from improved bioimaging to the development of innovative biosensors and the deeper exploration of biomolecular interactions. 5,8 AIE luminogen's distinctive ability to enhance fluorescence upon aggregation offers a range of exciting possibilities for anticancer applications. 19–21 Also, the investigation of new luminescent probes capable of binding to SARS-CoV-2 holds immense potential for enhancing the sensitivity of coronavirus detection.…”

“…Compounds that demonstrate the AIE phenomenon possess significant potential as valuable assets in the battle against COVID-19. 8,28…”