Development of hydrazide based fluorescence probe for detection of Al3+ ions and application in live cell image

https://doi.org/10.1016/j.jphotochem.2020.112921Get rights and content

Highlights

  • Hydrazide based fluorescence probe for detection of Al3+ ions.

  • Therotical calculations (DFT) were carried out for probe (SCH) and Al3+-SCH.

  • Life time decay were carried out.

  • SCH and Al3+-SCH used for cellular imaging sensor in MCF-7 cells

Abstract

Development of highly specific and susceptible sensors for aluminium (Al3+ ions) determination in water medium is still a remarkable task. Herein, a fluorescence probe (SCH) is derived from the condensation of salicyaldehyde and carbohydrazide in 2:1 M ratio and promising chemical sensing of Al3+ ions is investigated. Examinations of the emission features of SCH in CH3OH:H2O (1:2, v/v) solution showed excellent turn on behaviour of Al3+ ions, which is due to 1:1 complex formation between SCH and the Al3+ ions at ambient conditions. The lowest limit of detection was estimated by emission titration experiments and found to be 32 nM which is much more 1000-fold lower than that WHO suggested maximum tolerable concentration. The present probe SCH was highly specific for the detection of Al3+ ions over other potential interfering metal cations. Based on the reversible emission behaviour, an INHIBIT logic gate was assembled with EDTA and Al3+ ions as two inputs. In addition, prospective application of SCH as cellular imaging sensor of Al3+ ions in MCF-7 cells was monitored using optical fluorescence microscopic images and real water samples.

Introduction

In recent decade, development and design of super specific and highly susceptible chemosensors for determination of important metal ions has received significant consideration owing to their probable functions in environment and clinical biochemistry. The metal ions are released into the eco settings as results of human actions which preserve source in brutal effects for environment and human health [[1], [2], [3]]. Among the different metal ions, aluminium (Al3+) ions were considered as one of the hazardous metal ions [4,5]. Al3+ions were extensively related with our everyday life in the type of water purification, food packaging, pharmaceuticals, cooking utensils and etc [6,7]. The higher amounts of Al3+ ions in microorganism can cause a variety of physiological syndromes, including osteoporosis and Alzheimer’s disease [6]. Even though, the discriminating concern for biologically and environmentally appropriate moieties of Al3+ has stimulated vital to explore on the prospective impact of its poisonous outcomes [3,8]. Due to the toxic nature of the Al3+ ions, World Health Organization (WHO) has suggested the highest value of Al3+ concentration as 7.41 μM in drinking water [9]. Moreover, poor coordination ability and a lack of spectroscopic characteristics attributed to the quantification of Al3+ions compose still a most important challenge. Therefore, an important attention has been rewarded to develop the helpful method and to determine the concentration of Al3+ ions in water samples.

The various analytical procedures existing for sensitive detection of Al3+ ions such as atomic absorption spectroscopy, high performance liquid chromatography, electrochemical sensing, inductively coupled plasma mass spectrometry and etc [[10], [11], [12], [13]]. Conversely, the operation of these tactics are basically restricted by time consuming and tedious dealings occupies the usage of high cost instrumentation and not suitable for on time monitoring in live cell imaging [10]. Therefore, it is essential to expand the chemical compounds for choosy determination of Al3+ ions in physiological, analytical and environmental samples. Small organic molecule based chemosensors by fluorescence spectral technique has offered chemist’s admittance to a capable substitute device that specifically identifies particular analytes. In addition, optical spectral detection method offering excellent selectivity, high sensitivity, easy visualization, low technical complexity, rapid response and on-site tracking of bio-imaging in cancer cells [14].

Generally, Al3+ ions exhibit hard-acid behaviour, it has been established that Al3+ desires to bind a coordination sphere holding oxygen (O) and nitrogen (N) as hard-base donor sites. Schiff bases (imines, -C = N) were recognized as excellent ligands for the preparation of metal complexes. The composition of Schiff base contains N-O-rich coordination background which present hard-base behaviour for the binding of Al3+ ions (hard-acid) [7,10,15]. Particularly, Schiff base compounds integrated with a fluorescence molecule are elegant implements for the quantification of various metal ions [15,16]. In light of this objective, we have projected a novel Schiff-base probe (SCH), which was synthesized by simple condensation reaction of carbohydrazide with salicyaladehyde in 1:2 ratios.

In this paper, we reported a Schiff-base probe (SCH) synthesized by simple condensation reaction and fluorescence based “turn-on’’ probe for the detection of Al3+ in Methanol/water, which is due to chelation induced enhanced fluorescence (CHEF) process. The sensing mechanism was examined by different spectroscopic experiments and applied for quantification of Al3+ in semi-aqueous media. In addition, potential usage of SCH as intracellular detection of Al3+ ions in MCF-7 cells was also examined by fluorescence microscopy and further applied for environmental water samples.

Section snippets

Materials and methods

The metal salts were collected from Sigma-Aldrich and Loba Chemie and are of at least analytical reagent (AR grade) grade. The precursor’s salicylaldehyde and carbohydrazide utilized for the preparation of Schiff base probe (SCH) was purchased from Sigma-Aldrich. All the solvents were obtained from SD fine chemicals (AR grade) and used as received. Doubly distilled (DD water) water was used throughout the experiments.

Instruments

UV–vis absorption and steady state fluorescence spectral studies were

Results and discussion

The new probe SCH was synthesized by condensation of salicylaldehyde with carbohydrazide in ethanol in 2:1 ratio under reflux conditions (Scheme 1). The new probe SCH was characterized by various spectroscopic techniques like UV–vis, 1H NMR and 13C-NMR spectrometry. The crude product was recrystallized with ethanol and the structure of SCH was confirmed by single crystal X-ray crystallography. The characteristic IR bands of the probe SCH provide significant information of functional groups. A

Conclusion

In summary, a new type of fluorescent sensor probe SCH has been synthesized and characterised by various spectroscopic techniques and structure of probe SCH was confirmed through single crystal X-ray crystallography. The probe SCH showed strong fluorescent response towards Al3+ ions as compared to other metals. The selectivity toward Al3+ ions is due to chelation enhanced fluorescence in semi aqueous medium. Investigations of analytical results of SCH displayed that in existence of Al3+ ions,

CRediT authorship contribution statement

D. Anu: Formal analysis, Data curation, Validation, Writing - original draft, Funding acquisition. P. Naveen: Supervision, Visualization, Writing - original draft, Writing - review & editing, Project administration, Funding acquisition. R. Rajamanikandan: Formal analysis, Data curation, Validation, Writing - original draft. M. V. Kaveri: Supervision, Visualization, Writing - original draft, Writing - review & editing, Project administration, Funding acquisition.

Declaration of Competing Interest

The authors report no declarations of interest.

Acknowledgement

The author D. Anu greatly acknowledged UGC, New Delhi, India for UGC-BSR fellowship

(F. 25-1/2014-15(BSR)7-26/2007/(BSR) Dated: 05.11.2015).

References (43)

  • J.M.C. Pavon et al.

    Talanta

    (1990)
  • R. Manjunath et al.

    Spectrochim. Acta A. Mol. Biomol. Spectrosc.

    (2015)
  • V.K. Gupta et al.

    Talanta.

    (2007)
  • R. Rajamanikandan et al.

    Mater. Sci. Eng. C

    (2019)
  • Z.C. Liao et al.

    Dye. Pigment.

    (2013)
  • K. Kaur et al.

    Inorg. Chem. Com.

    (2012)
  • J. Lee et al.

    Dye. Pigment.

    (2013)
  • H.Y. Liu et al.

    Talanta

    (2016)
  • K. Ramki et al.

    J. Electroanal. Chem.

    (2020)
  • J. Gao et al.

    Spectrochim. Acta, Part A

    (2011)
  • Z. Li et al.

    Inorg. Chim. Acta Rev.

    (2020)
  • M. Beija et al.

    Chem. Soc. Rev.

    (2009)
  • J. Mao et al.

    Org. Lett.

    (2007)
  • A.P. De Silva et al.

    Chem. Rev.

    (1997)
  • F.S. Rojas et al.

    Analyst

    (1994)
  • S. Kim et al.

    Inorg. Chem.

    (2012)
  • S. Sen et al.

    Analyst.

    (2012)
  • T. Han et al.

    Chem. Commun.

    (2012)
  • A. Gupta et al.

    RSC Adv.

    (2016)
  • H. Lian et al.

    Talanta.

    (2004)
  • T.W. Lin et al.

    Anal. Chem.

    (2001)
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