A dual-functional rhodamine B and azo-salicylaldehyde derivative for the simultaneous detection of copper and hypochlorite: synthesis, biological applications and theoretical insights
- Title
- A dual-functional rhodamine B and azo-salicylaldehyde derivative for the simultaneous detection of copper and hypochlorite: synthesis, biological applications and theoretical insights
- Creator
- Vishnu S.; Das A.K.; Bylappa Y.; Nag A.; Dolai M.
- Description
- A multifunctional rhodamine derivative containing azo-salicylaldehyde (BBS) was designed and synthesized as a colorimetric and fluorescence turn-on probe for the selective detection of copper cations (Cu2+) and hypochlorite anions (OCl?) in aqueous media. In the presence of Cu2+, the probe BBS exhibited turn-on absorption and fluorescence change at 554 nm and 585 nm, respectively. The binding mechanism of BBS with Cu2+ induces the opening of a spirolactam ring in the rhodamine moiety by the formation of a metal-ligand complex, achieving 10-fold enhancement in fluorescence and quantum yield, along with a binding constant of 1 104 M?1 and a detection limit of 2.61 ?M. Addition of OCl? enhanced the absorbance and fluorescence intensities at 520 nm and 575 nm, respectively. The probe BBS underwent hypochlorite-mediated oxidation, followed by hydrolysis, resulting in the formation of rhodamine B itself, which is detectable by the naked eye via the color and fluorescence enhancement by 11-fold with a high quantum yield and a detection limit of 1.96 ?M. For practical applications, sensor BBS can be used to detect Cu2+ in water samples and on cotton swabs. For biological applications, the interaction of the BBS-Cu(ii) complex with transport proteins such as bovine serum albumin (BSA) and ct-DNA was investigated through UV-vis and fluorescence titration experiments. Additionally, the structural optimization of BBS and the BBS-Cu(ii) complex was demonstrated using DFT, and the interactions of the BBS-Cu(ii) complex with BSA and ct-DNA were analysed through theoretical docking studies. Bioimaging studies were conducted by capturing fluorescence images of BBS with Cu2+ and OCl? in a physiological medium containing living plant tissue using green gram seeds. 2024 The Royal Society of Chemistry.
- Source
- Analytical Methods, Vol-16, No. 47, pp. 8164-8178.
- Date
- 2024-01-01
- Publisher
- Royal Society of Chemistry
- Coverage
- Vishnu S., Department of Chemistry, Christ University, Hosur Road, Karnataka, Bangalore, 560029, India; Das A.K., Department of Chemistry, Christ University, Hosur Road, Karnataka, Bangalore, 560029, India; Bylappa Y., Department of Life Science, Christ University, Hosur Road, Karnataka, Bangalore, 560029, India; Nag A., Department of Life Science, Christ University, Hosur Road, Karnataka, Bangalore, 560029, India; Dolai M., Department of Chemistry, Prabhat Kumar College, Purba Medinipur, WB, Contai, 721404, India
- Rights
- Restricted Access
- Relation
- ISSN: 17599660; PubMed ID: 39508779
- Format
- Online
- Language
- English
- Type
- Article
Collection
Citation
Vishnu S.; Das A.K.; Bylappa Y.; Nag A.; Dolai M., “A dual-functional rhodamine B and azo-salicylaldehyde derivative for the simultaneous detection of copper and hypochlorite: synthesis, biological applications and theoretical insights,” CHRIST (Deemed To Be University) Institutional Repository, accessed February 24, 2025, https://archives.christuniversity.in/items/show/12853.