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1.
Spectrochim Acta A Mol Biomol Spectrosc ; 303: 123110, 2023 Dec 15.
Article in English | MEDLINE | ID: mdl-37499469

ABSTRACT

In present work a pyrene-dansyl dyad functionalized chemoreceptor, DPNS is unveiled towards ultrasensitive chromo-fluorogenic detection of heavy and transition metal ions (HTMs) like Cu2+ and pernicious CN-. It demonstrated distinct chromogenic responses; colorless to faint yellow (Cu2+), intense yellow (CN-) from contaminant aqueous sources. Cu2+ instigated alteration in DPNS fluorescence from feeble emission to sparkling green with LOD: 37.75 × 10-9 M, cyan emission for CN- having LOD 61.51 × 10-8M. In particular, chemical scaffold of DPNS consists of -C = N, O = S = O donor entitities that escalates overall polarity thereby providing an excellent binding pocket for simultaneous Cu2+ and CN- recognition with distinct photophysical signaling. Impressively, presence of two fluorophoric moieties triggers FRET, CHEF phenomenon. The conceivable host:guest interactive pathway is manifested by LMCT- FRET-PET-CHEF, C = N isomerization for Cu2+ and ICT-H-bonding for CN-. An exquisite experimental and theoretical corroboration further strengthened the recognition phenomenon. In addition owing to pyrene excimer formation, DPNS exhibits AIEE with increasing water fraction. Notably, DPNS could successfully undergo intracellular tracking of Cu2+ in Tecoma Stans, Peperomia Pellucida. DPNS•••Cu2+ adduct displayed significant intercalative DNA binding activity rationalized by spectral investigation, competitive EB binding, viscosity study. The overall findings, excellent properties endows DPNS a potential contender towards discriminative detection of Cu2+ and CN- like toxic industrial contaminants.


Subject(s)
Fluorescence Resonance Energy Transfer , Fluorescent Dyes , Fluorescent Dyes/chemistry , Diagnostic Imaging , Water , DNA , Pyrenes
2.
Chem Asian J ; 16(24): 4108-4121, 2021 Dec 13.
Article in English | MEDLINE | ID: mdl-34706155

ABSTRACT

Chiral polyheterocycles are one of the most frequently encountered scaffolds in natural products and in current drugs repertoire. A carbohydrate-based diversity oriented synthetic (DOS) approach has been employed for gaining access to many structurally diverse and stereochemically complex rigid polyheterocyclic molecules with multiple chiral hydroxyl groups to enhance aqueous solubility. Inexpensive chiral pool of D-Glucose has been judiciously exploited to get access of complex chiral polyheterocyclic structures using inexpensive, common achiral reagents and domino-Knoevenagel hetero-Diels-Alder (DKHDA) reaction as one of the key synthetic tools. Stereochemistry of newly generated stereocenters of polycyclic structures are unambiguously determined through NMR and X-ray crystallographic study. A chemoinformatic comparison (PCA and PMI) with 40 branded blockbuster drugs showed that newly generated polyheterocycles have good three-dimensional scaffold diversity and most of these pass the Lipinski filter of drug-likeness.

3.
Dalton Trans ; 48(13): 4375-4386, 2019 Mar 26.
Article in English | MEDLINE | ID: mdl-30864567

ABSTRACT

Herein, a hydrazine-based chromogenic, fluorogenic and electrochemical chemosensor BCC [1,5-bis(4-cyanophenyl) carbonohydrazide] was premeditated and synthesized through a simple one-step synthetic procedure for the selective detection of toxic anions, such as F-, in a DMSO-ACN medium and cations, such as Hg2+ and Cu2+, in a MeOH-water medium. The detection limit for F- was reckoned to be 0.5 ppm, and for Hg2+ and Cu2+, it was 0.8 ppm and 50 nM, respectively. The chemosensor exhibited a distinct change in colour from colourless to dark blue in the presence of F-, and upon the addition of Hg2+ and Cu2+, the BCC turned from colourless to light blue and purple accordingly. Moreover, turn-on fluorescence response transpired by the attenuation of PET signified the selective sensing of analytes with a zero-order rate constant. Sophisticated analytical experiments, such as ESI-MS, UV-Vis, photoluminescence, cyclic voltammetry, FTIR, and 1H-NMR, along with the theoretical calculations corroborated the probable sensing pathways. The reversible colorimetric response of BCC towards F- and H+ can be advantageous in the design of electronic circuits derived from Boolean algebra. The complexation ability of the sensor with toxic Hg2+- and Cu2+-like ions made it an efficient material to remove these metal ions from real water sources polluted with these toxic elemental ions. Furthermore, the in vitro studies were accomplished using the Bauhinia acuminate pollen cell to check the cell penetrability of the sensor molecule.


Subject(s)
Coloring Agents/chemistry , Copper/analysis , Fluorides/analysis , Mercury/analysis , Urea/chemistry , Water Pollutants, Chemical/analysis , Anions , Biosensing Techniques/methods , Cations, Divalent , Cell Line , Colorimetry/methods , Copper/isolation & purification , Electrochemical Techniques/methods , Limit of Detection , Mercury/isolation & purification , Models, Molecular , Optical Imaging/methods , Spectrometry, Fluorescence/methods , Water Pollutants, Chemical/isolation & purification
4.
Dalton Trans ; 47(4): 1082-1091, 2018 Jan 23.
Article in English | MEDLINE | ID: mdl-29261204

ABSTRACT

A dual-channel chromogenic and fluorogenic fused-aromatic-system-based chemoreceptor (2-(benzo[d]thiazol-2-yl)-1-((pyren-8-yl)methylene)hydrazine) (TyM) was designed for ditopic sensitivity towards heavy and transition metal ions (HTMs), such as Cu2+, in an aqueous medium and lethal CN- in a semi-aqueous medium. The chemoreceptor displayed proclivity towards the targeted analytes with a distinct optical response (yellow to colourless in the case of Cu2+ and yellow to bright red for CN-). TyM formed a 2 : 1 adduct with Cu2+ with a detection limit of 40 nM. A 1 : 1 binding stoichiometry was confirmed with the chemoreceptor TyM with CN- in sub-nano molar limit of detection. In addition to sophisticated spectroscopic analysis, such as UV-vis, fluorescence, FTIR, 1H-NMR, 13C-NMR, ESI-MS, and HRMS, the plausible mechanistic course of sensing was also established from a theoretical perspective. The reversible UV-vis response of the chemoreceptor TyM towards CN- and H+ can mimic different molecular logic functions and therefore can be exploited for designing several complex electronic circuits principally based on Boolean Algebra. In vitro fluorescence imaging in male microspores of seed plants (Bohonia Nigalandra) and Monilia Albicans (diploid fungus) with TyM and Cu2+ confirmed the permeability of the chemoreceptor TyM at the cellular level as well as its ability to investigate transition metals, such as Cu2+, in biological samples.

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