Computational choreography: dissecting the dance of hydrogen bonding and π–π stacking in the fluorescence discrimination mechanism of ciprofloxacin with supramolecular assembly

Abstract

The detailed binding insight between the fluorophore and analyte plays a pivotal role in the design of an efficient chemosensor for water pollution. In this study, we designed a picolinic acid-functionalized calix[4]pyrrole ligand (PCACP). When testing out the fluorescence study with selected antibiotics, we observed remarkable enhancement of fluorescence spectra in the presence of ciprofloxacin, singling out the PCACP_Ciprofloxacin complex. The detailed binding mechanism is explored via computational methods including molecular docking and dynamics, DFT (density functional theory) and NBO (Natural Bonding Orbital) analysis. The result of this study provides the comprehensive insight into the involvement of functionalized group of PCACP and ciprofloxacin antibiotic. The results of the computational findings are further explored through NMR complexation study, which corroborate the computational findings. With the limit of detection calculated at 18 µM, we carried out the water sample analysis, which shows promising results. The outcome of this research provides a new, effortless fluorescence approach to monitor the presence of ciprofloxacin in water.

In the presence of the ciprofloxacin antibiotic, the fluorescence spectra of PCACP experience remarkable enhancements. This complexation phenomenon is studied through different computational and experimental methods.

Communicated by Ramaswamy H. Sarma

Keywords:

• Fluorescence sensing
• density functional theory
• host–guest interaction

Acknowledgment

The authors would like to acknowledge Chemistry Research Laboratory (CRL)-MUIS, Ganpat University for providing with infrastructure to carry out research work and Gujarat University for providing access to the spectrofluorometer and related resources. Authors are thankful to Dr. Alan Liska for providing the access to the computing and storage facilities owned by parties and projects corresponding to the National Grid Infrastructure Meta Centrum under the programme of ‘Projects of Large Research, Development, and Innovations Infrastructures’ (CESNETLM2015042) Czech Republic

Author contributions

Jaymin Parikh: Investigation, Formal Analysis, Writing - Original Draft, Data Curation. Keyur Bhatt: Supervision, Conceptualization, Resources, Validation. Krunal Modi: Methodology, Resources, Data Curation, Validation. Ajay Desai: Resources. Nihal Patel: Visualization, Data Curation. Chirag Patel: Software. Ravibhai Bhola: Writing - Editing.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The authors declare that no funds, grants, or other support were received during the preparation of this manuscript.