An efficient fluorescent Al(3+) receptor, N-(2-hydroxy-1-naphthalene)-N'-(2-(2-hydroxy-1-naphthalene)amino-ethyl)-ethane-1,2-diamine (L) has been synthesized by the condensation reaction between 2-hydroxy naphthaldehyde and diethylenetriamine. High selectivity and affinity of L towards Al(3+) in ethanol (EtOH) as well as in HEPES buffer at pH 7.4, makes it suitable to detect intracellular Al(3+) with fluorescence microscopy. Metal ions, viz. Li(+), Na(+), K(+), Mg(2+), Ca(2+), Mn(2+), Co(2+), Ni(2+), Cu(2+), Zn(2+), Ag(+), Cd(2+), Hg(2+) and Pb(2+) do not interfere. The lowest detection limit for Al(3+) is 3.0 × 10(-7) M and 1.0 × 10(-7) M in EtOH and HEPES buffer respectively.
Rhodamine-diformyl p-cresol conjugate (L) has been developed as a novel Al(3+)-selective fluorometric and colorimetric sensor based on the FRET mechanism for the first time. L can selectively detect Al(3+) through time-dependent PET-CHEF and FRET processes. This phenomenon is nicely reflected from (1)H NMR, fluorescence lifetime, and fluorescence cell imaging studies. The probe can detect Al(3+) as low as 5 × 10(-9) M in HEPES-buffered EtOH:water (0.1 M, 4:1, v/v, pH 7.4). The probe shows pH-dependent emission properties viz. an intense red emission (585 nm) at acidic pH and an intense green fluorescence (535 nm) at basic pH. Thus, L can also be used as a pH sensor via tunable wavelength.
2-((Naphthalen-6-yl)methylthio)ethanol (HL) was prepared by one pot synthesis using 2-mercaptoethanol and 2-bromomethylnaphthalene. It was found to be a highly selective fluorescent sensor for Al(3+) in the physiological pH (pH 7.0-8.0). It could sense Al(3+) bound to cells through fluorescence microscopy. Metal ions like Mn(2+), Fe(3+), Co(2+), Ni(2+), Cu(2+), Zn(2+), Ag(+), Cd(2+), Hg(2+), Cr(3+) and Pb(2+) did not interfere. No interference was also observed with anions like Cl(-), Br(-), F(-), SO(4)(2-), NO(3)(-), CO(3)(2-), HPO(4)(2-) and SCN(-). Experimentally observed structural and spectroscopic features of HL and its Al(3+) complex have been substantiated by computational calculations using density functional theory (DFT) and time dependent density functional theory (TDDFT).
Adenosine is known as an endogenous purine nucleoside and it modulates a wide variety of physiological responses by interacting with adenosine receptors. Among the four adenosine receptor subtypes, the A3 receptor is of major interest in this study as it is overexpressed in some cancer cell lines. Herein, we have highlighted the strategy of designing the hA3 receptor targeted novel benzothiazolylquinoline scaffolds. The radioligand binding data of the reported compounds are rationalized with the molecular docking results. Compound 6a showed best potency and selectivity at hA3 among other adenosine receptors.
Two novel fluorescent probes based on anthracene (AAC) and naphthalene (ANC) have been synthesised and characterised. Both the AAC and ANC derivative show green fluorescence at basic pH, but at acidic pH AAC is non-fluorescent, while ANC emits red light. This is attributed primarily to the FRET on-off processes. ANC has better pH discrimination abilities than AAC and can be used to distinguish between different pH environments inside a living cell for the first time.13 C NMR spectra have been recorded using Bruker Advance 400 (100 MHz) and 500 (125 MHz) instruments in CDCl 3 or DMSO-d 6 .
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