Fluorescein dye derivative: Synthesis,characterization, quantum chemical and promising antimicrobial activity studies |
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| Authors: | Navjot Sandhu Satish Kumar Pandey Ram Kumar Tittal Kamlesh Kumar Ashish Pratap Singh Rajesh K. Yadav Rahul Shrivastava Atul Pratap Singh |
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| Affiliation: | 1. Department of Chemistry, Chandigarh University, Mohali, India;2. Department of Biotechnology, School of Life Sciences, Mizoram University (Central University), Aizawl, India;3. Department of Chemistry, National Institute of Technology, Kurukshetra, India;4. Materials Science and Sensors Applications, CSIR-Central Scientific Instruments Organization, Chandigarh, India;5. Division of Material Groups, Bhabha Atomic Research Centre, Mumbai, India;6. Department of Applied Science (Chemistry), Madan Mohan Malaviya University of Technology, Gorakhpur, India;7. Department of Chemistry, Manipal University Jaipur, Jaipur, India |
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| Abstract: | The dimethyl sulfite as an alkylating as well as alkoxylating reagent is well known in synthetic organic as well as organometallic chemistry for a long time. Herein, we have utilized dimethyl sulfite as an alkylating reagent and reacted with fluorescein derivative, N-fluorescein-lactam-hydrazine ( B ). This reaction leads to the generation of tetramethylated fluorescein lactam hydrazine ( A ). The newly designed and synthesized molecule ( A ) has been characterized by 1H, 13C NMR and HRMS data. The antimicrobial activity of the synthesized alkylated fluorescein derivative has been tested against E. coli, P. aeruginosa, Salmonella typhimurium and S. aureus microbial agents. Time-kill assay results also confirmed that fluorescein derivative is a potent antimicrobial agent and revealed that the time-kill assay of fluorescein derivative is value-added than the well-known antibiotic. In addition, quantum chemical study was used to analyze its activity trend and correlated with the experimental data. The computed results of DFT revealed that the lipophilicity as well as the LUMO-HOMO band gap (ΔELUMO-HOMO = 4.75 eV) of compound A make it more suitable as an antimicrobial agent to match with in vitro antimicrobial experimental results. The MIC and MBC values of compound A were observed to be lower in contrast to fluorescein and ampicillin for all the tested bacterial strains, which were approximately 3- to 4-fold lower than MIC and MBC values of the later. Results obtained from the study clearly indicate that compound A has better antimicrobial and bactericidal activity in comparison to ampicillin and fluorescein. Synthesized compound can be a better substitute of traditionally used antibiotics, Ampicillin. |
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