An anion induced multisignaling probe for Hg²⁺and its application for fish kidney and liver tissue imaging studies

Abstract

3',6'-Bis(diethylamino)-2-(pyridin-2-ylmethyl)spiro[isoindoline-1,9'-xanthen]-3-one () was synthesized for the selective fluorescence and colorimetric recognition of Hg(2+) at pH 6.0. In addition, was useful for imaging Hg(2+) in fish kidney and liver tissues using a fluorescence microscope. Spirolactam ring opening of for Hg(2+) recognition is strongly influenced by the nature of the mercury salt and found to be NO3(-)-induced. Other mercury salts such as HgCl2, Hg(CH3COO)2 and Hg(ClO4)2 failed to induce fluorescence and colorimetric response of under the same experimental conditions. For instance, the former salt does not exhibit spirolactam ring opening but forms a new ionic compound (H3L)2[Hg6Cl18]·2H2O (), whose structure has been elucidated by single crystal X-ray diffraction. This might be explained by (1) the higher covalent nature of Hg(2+) and, hence, the lower acidity of the metal center and its inability to induce the ring opening reaction, and (2) the bulky anion, in the case of Hg(ClO4)2, which is also ionic, faces steric hindrance to accommodate within the N(Et)2 group upon spirolactam ring opening.

Interaction of 2,6,7-Trihydroxy-Xanthene-3-Ones with Iron and Copper, and Biological Effect of the Most Active Derivative on Breast Cancer Cells and Erythrocytes

“…Some xanthone derivatives, which are developed as fluorescent metal probes, were previously reported to form colored complexes with several metals [18][19][20][21][22]. We also reported that the series of xanthones reported herein behaved as potent cytotoxic drugs against cervical, colorectal, hepatocellular and alveolar adenocarcinoma cell lines, with IC 50 values mostly in units or tens of µM concentrations [23].…”

Serendipitous Formation of a Cerium(IV)‐Mercury(II) Separated Ion Coordination Polymer#

“…In this example the chloridomercury array forms a more ordered grid around the copper cations, likely due to additional coordination of one nitrogen atom from the copper bound ligand to mercury. In addition, another interesting compound has a repeating [Hg 3 Cl 9 (H 3 L)] ⋅ 2H 2 O unit, where H 3 L=tri‐cationic N , N , N ′, N ′‐tetraethyl‐3‐oxo‐2‐(1‐pyridin‐2‐ylmethyl)‐2,3‐dihydrospiro[isoindole‐1,9′‐xanthene]‐3′,6′‐diammonium [47] . In this latter example, all Hg−Cl bonds are within the sum of the ionic radii (range: 2.334(3)–2.739(2) Å), and the chain is connected by four elongated Hg−Cl interactions (3.086(2)–3.3477(19) Å), with a degree of Cl … H interaction with the lattice water molecule.…”

9-(4'-dimethylaminophenyl)-2,6,7-trihydroxy-xanthene-3-one is a Potentially Novel Antiplatelet Drug which Antagonizes the Effect of Thromboxane A2

“…Two compounds, 9-[1-(2-methyl-4-methoxyphenyl)]-6-hydroxy-3H-xanthen-3one (Tokyo green) and another fluorescein derivate 9-[1-(4tert-butyl-2-methoxyphenyl)]-6-hydroxy-3H-xanthen-3-one (Granada green) are sensitive dyes for intracellular phosphate detection [8,9], 3',6'-bis(4-guanidinobenzoyloxy)-5-(N'-4-carboxylphenyl)thioureidospiro[isobenzofuran-1(3H), 9'- [9H]xanthen]-3-one is useful for the detection of plasminogen activator activity [10] and 3',6'-bis(diethylamino)-2-(pyridine-2-ylmethyl)spiro[isoindoline-1,9'-xanthen]-3-one is highly efficient for the recognition and determination of Hg 2+ . [11] Research has also been targeted to xanthene-9ones. Two of these compounds showed anticancer properties.…”