Sensors and Actuators B 252 (2017) 257–267 Contents lists available at ScienceDirect Sensors and Actuators B: Chemical jo ur nal home page: www.elsevier.com/locate/snb Macrocycle aza-crown chromogenic reagent to Al 3+ and fluorescence sensor for Zn 2+ and Al 3+ along with live cell application and logic operation Anup Kumar Bhanja a , Chiranjit Patra a , Sudipa Mondal a , Snehasish Mishra b , Krishna Das Saha b , Chittaranjan Sinha a,∗ a Department of Chemistry, Jadavpur University, Kolkata 700 032, India b Cancer Biology & Inflammatory Disorder Division, CSIR-Indian Institute of Chemical Biology, Kolkata 700 032, India a r t i c l e i n f o Article history: Received 21 December 2016 Received in revised form 27 May 2017 Accepted 30 May 2017 Available online 3 June 2017 Keywords: 15-C-4 sensor Differently selective Zn 2+ and Al 3+ LOD Logic gate Cell imaging MTT Assay a b s t r a c t 1-Hydroxy-diaza-15-Crown-4 (HL) is a macrocycle and is a chromogenic sensor (red;  abs , 505 nm) to Al 3+ in DMSO-water medium. The probe is an effective turn-on fluorescent reagent at two different emission wavelengths ( em ) for Al 3+ at 580 nm and Zn 2+ at 505 nm. The limit of detections (LOD) are 1.2 M (Al 3+ ) and 21 nM (Zn 2+ ). HL is stable in the pH range, 2–12 and maximum turn-on response to Zn 2+ and Al 3+ is observed at pH, 9. The composition of the complexes has been supported by Job’s plot, Mass spectral measurement and 1 H NMR titration. Fluorescence selectivity of HL has been used in the analysis of intracellular Al 3+ and Zn 2+ in SCC084 (Human Oral carcinoma) cell lines by cell imaging processes. The MTT assay reports that the probe, HL is non-toxic upto 150 g/ml. HL uses a combination of OR and NOT gates for input, Zn 2+ or Al 3+ as signals and for two inputs (Zn 2+ and Al 3+ ). © 2017 Elsevier B.V. All rights reserved. 1. Introduction A tremendous effort has now been invested in the design of fluorescence chemosensors particularly for selective and sensitive probing of biologically and environmentally important metal ions. Chemosensors can selectively recognize and signal the presence of specific ions/molecules through the naked eye and through spec- troscopic instruments. The optical responses of chemosensors have received significant attention for last two decades [1–3]. Because of high sensitivity, selectivity, simplicity, real-time analysis, cost- effective, rapid and facile process the spectroscopic tools become applicable as analytical apparatus in the environmental, medical, and biochemical fields as well as in industry [4]. In general, a typ- ical optical sensitive molecular probe contains a receptor/ligand unit integrated or attached through a spacer to a signaling unit (transducer) (Scheme 1). The receptor/ligand unit can bind the ion/molecule with a concomitant change in one or more properties of the system, such as color (colorimetric probes) or fluorescence intensity (fluorescence probes), that arise from the complexa- tion, hydrolysis/substitution, or oxidation/ring transformation. In ∗ Corresponding author. E-mail addresses: krishna@iicb.res.in (K.D. Saha), c r sinha@yahoo.com (C. Sinha). order to achieve high selectivity, the receptor/ligand is required to have the strongest affinity with the ion of interest. The fluo- rescent chemosensors have attracted considerable attention due to convenient use and real application in biological systems [5,6]. Metal-specific fluorescence probes are of increasing importance in understanding the neurobiology and general cell biology of metal ions. In fact, a great number of chemosensors have been designed for monitoring heavy toxic metal ions [7]. Schiff bases, a particular class of chelating molecules, have been widely used as chemical probes due to their facile synthesis, stability in wide pH range, solubility in polar and mixed polar media, and good photophys- ical properties [8–13]. The Schiff bases serve as N,O bidentate monoanionic chelating agent and have been extensively investi- gated for more than a century and employed in different aspects including magneto-chemistry, non-linear optics, photo-physical studies, catalysis, materials chemistry, chemical analysis, bioinor- ganic chemistry. Use of iminephenolato function as chemosensor for ions (cations and anions) has been explored recently [8–13] for chemometric identification of several ions by absorption and fluorescence spectroscopic routes. Majority of chemosensors are single-ion selective while multi-ion responsive systems are of great interest because they can differentiate and detect analyte of inter- est in the presence of interfering ions [14,15] and are essentially important in the developing of multifaceted molecular logic gates, http://dx.doi.org/10.1016/j.snb.2017.05.178 0925-4005/© 2017 Elsevier B.V. All rights reserved.