Carbohydrate assisted fluorescence turn-on gluco–imino–anthracenyl conjugate as a Hg(<scp>ii</scp>) sensor in milk and blood serum milieu

Mitra, Atanu; Mittal, Ankit; Rao, Chebrolu P.

doi:10.1039/c0cc04967k

Cited by 50 publications

(14 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From these titrations, it was evident that L can respond towards Zn 2+ even in the presence of 30 equivalents of Na + , K + , Ca 2+ , Mg 2+ , and 5 equivalents of other ions in the same group, namely Cd 2+ and Hg 2+ . However, when the aromatic portion of L is changed from the naphthyl to the anthracenyl, the resulting conjugate selectively senses Hg 2+ and not Zn 2+ or Cd 2+ as shown by our research group recently 8. The composition of the complex formed between L and Zn 2+ (2:1) has been established based on the signal observed at m / z 729 (Figure 2 b; see SI 07 in the Supporting Information), which corresponds to the [( L ) 2 Zn] complex and the presence of zinc has been delineated by the observed isotope peak pattern.…”

Section: Methodsmentioning

confidence: 52%

A Zinc‐Sensing Glucose‐Based Naphthyl Imino Conjugate as a Detecting Agent for Inorganic and Organic Phosphates, Including DNA

Mitra

Hinge

Mittal

et al. 2011

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Owing to the importance of zinc and phosphate in biology and human health, [1] sensing such species is always important and continues to intrigue chemists to emerge with better receptor designs.[2] Our recent report on sensing of Zn 2 + in blood serum milieu by a calixarene derivative [2h] prompted us to employ biologically benign receptor systems and to investigate if these receptors can also extend their sensitivity towards anions (especially phosphates). In this regard, water-soluble and biologically benign [3] carbohydrate-based fluorescent sensors [4] would be of great relevance to explore their in vitro and in vivo applications. Among the derivatives of phosphate, adenosine-mono/di/triphosphate (AMP, ADP, ATP), DNA, and their hydrolytic species are important.[5] Therefore, it is essential to monitor the presence of phosphate related species in solution.[6] If a receptor can sense both the zinc and the phosphate group, it would be doubly advantageous.[5e] Therefore, herein we investigate the primary detection of Zn 2 + by switch-on fluorescence using 1-(d-glucopyranosyl-2'-deoxy-2'-iminomethyl)-2-hydroxynaphthalene conjugate L and the successive detection of phosphates by the corresponding zinc complex through fluorescence quenching (switch-off). To demonstrate the bio-suitability of L, titrations were carried out using nucleotides and DNA. To our knowledge, this is the first carbohydrate-based receptor system shown to be sensitive towards a cation followed by an anion, including biomolecular systems.Conjugate L has been synthesized by a one-pot condensation of the neutralized C2-deoxy-C2-amino-glucose with 2-hydroxy-1-naphthaldehyde and his structure has been characterized (see SI 01 in the Supporting Information).[7] Conjugate L has been crystallized in a non-centrosymmetric triclinic system by layering methanol on to a concentrated solution in DMSO and the structure was determined by single crystal XRD (for crystal and metric data see SI 02 in the Supporting Information). Conjugate L exhibits a preformed ONO core that is suitable for metal ion binding (Scheme 1). An intramolecular hydrogen bond present between the phenolic O4 À H···N1-imino orients the naphthyl moiety almost perpendicular to the mean plane of the carbohydrate moiety (see SI 02b in the Supporting Information). In the lattice, molecules form columns by interacting through two strong hydrogen bonds per each L and also by exhibiting hydrophobic p-p interactions with a centroid to centroid distance of 4.878 . The columnar structure formed in the lattice clearly exhibits hydrophobic (6 ) and hydrophilic (7 ) regions alternatively (see SI 02c in the Supporting Information).The selectivity of L has been demonstrated by titration against seven biologically and ecologically relevant metal ions, such as, Na + , K + , Ca 2 + , Mg 2 + , Zn 2 + , Cd 2 + , and Hg 2 + in methanol using fluorescence spectroscopy. In dry methanol, L exhibits approximately a 140-fold enhancement in the emission intensity against Zn 2 + , while none of the alkali and al...

show abstract

Section: Methodsmentioning

confidence: 52%

A Zinc‐Sensing Glucose‐Based Naphthyl Imino Conjugate as a Detecting Agent for Inorganic and Organic Phosphates, Including DNA

Mitra

Hinge

Mittal

et al. 2011

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

“…The reversible sensing mechanism for the chemosensor was drastically distinct that disconnected the binding of Hg 2+ ion at a thiol atom and alkyne moiety in the rhodamine scaffold (35). Another example of using EDTA as a reversing reagent was a gluco-imino-anthracenyl derivative-based chemosensor, in which the EDTA could disable the binding of Hg 2+ ion in the complex at imine and aromatic moieties (36). The sensor also presented high selectivity in the presence of several biological samples (e.g., blood serum and milk) and ecologically relevant metal ions.…”

Section: Current Development Of Fluorogenic Chemosensorsmentioning

confidence: 98%

Synthesis of Fluorogenic Chemosensors for Hg²⁺Detection Using Naphthalimide Derivatives

Lee

Jang

Den

et al. 2014

ACS Symposium Series

View full text Add to dashboard Cite

Mercury ions are considered as severe environmental pollutants as they are widely spread in the atmosphere and surface water from either natural or anthropogenic activities. Current practices in detecting the ions involve sophisticated and costly analytical techniques including atomic absorption spectrometry, atomic emission spectrometry and inductively coupled plasma/mass spectrometry. Fluorogenic chemosensors, on the other hand, offer the unique advantages of high selectivity, high sensitivity, long lifetime and relatively low costs. This study focuses on reviewing current development of fluorogenic chemosensors in mercury ions detection, based on the use of naphthalimide or non-naphthalimide derivatives. The design principles as well as photophysical properties for the fluorogenic chemosensors are discussed. This study concludes with future perspectives of chemosensor design, including employment of C=N isomerization mechanism for fluorescence improvement and utilization of crown ether for improved recognition of mercury ions.

show abstract

“…Consequently, developing simple and practical Hg 2+ chemosensors in aqueous media is still a challenge. [28][29][30] In this regard, a molecular system based on carbohydrates would be of great advantage. Recently, we reported novel water soluble [31][32][33][34][35][36][37] dyes as colorimetric cyanide chemosensors in water and at room temperature.…”

Section: Introductionmentioning

confidence: 99%

A water soluble fluorescent BODIPY dye with azathia-crown ether functionality for mercury chemosensing in environmental media

Isaad

Achari

2013

Analyst

View full text Add to dashboard Cite

A novel mercury chemosensor based on water soluble fluorescent BODIPY probe with an azathia-crown ether moiety has been synthesised through condensation of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene as a fluorophore coupled at the 3-position to an azathia macrocycle via an ethenylphenyl linker. Spectroscopic properties and complex formation with several metal ions are investigated in aqueous organic solvent and in water via colorimetric and fluorometric titrations. The binding ratio of chemosensor to Hg(2+) complex was determined to be 1 : 1 according to a Job plot. Hg(2+) binding in chemosensor was 8.19 × 10(3) M(-1). The fluorescence and colorimetric spectroscopic experiments in this study demonstrated that chemosensor can be used as a fluorescent and colorimetric probe for detecting Hg(2+) in water.

show abstract

Carbohydrate assisted fluorescence turn-on gluco–imino–anthracenyl conjugate as a Hg(ii) sensor in milk and blood serum milieu

Cited by 50 publications

References 38 publications

A Zinc‐Sensing Glucose‐Based Naphthyl Imino Conjugate as a Detecting Agent for Inorganic and Organic Phosphates, Including DNA

A Zinc‐Sensing Glucose‐Based Naphthyl Imino Conjugate as a Detecting Agent for Inorganic and Organic Phosphates, Including DNA

Synthesis of Fluorogenic Chemosensors for Hg²⁺Detection Using Naphthalimide Derivatives

A water soluble fluorescent BODIPY dye with azathia-crown ether functionality for mercury chemosensing in environmental media

Contact Info

Product

Resources

About

Carbohydrate assisted fluorescence turn-on gluco–imino–anthracenyl conjugate as a Hg(ii) sensor in milk and blood serum milieu

Cited by 50 publications

References 38 publications

A Zinc‐Sensing Glucose‐Based Naphthyl Imino Conjugate as a Detecting Agent for Inorganic and Organic Phosphates, Including DNA

A Zinc‐Sensing Glucose‐Based Naphthyl Imino Conjugate as a Detecting Agent for Inorganic and Organic Phosphates, Including DNA

Synthesis of Fluorogenic Chemosensors for Hg2+Detection Using Naphthalimide Derivatives

A water soluble fluorescent BODIPY dye with azathia-crown ether functionality for mercury chemosensing in environmental media

Contact Info

Product

Resources

About

Synthesis of Fluorogenic Chemosensors for Hg²⁺Detection Using Naphthalimide Derivatives