Super/hyperhalogen aromatic heterocyclic compounds

Reddy, G. Naaresh; Giri, Santanab

doi:10.1039/c6ra08625j

Cited by 23 publications

(16 citation statements)

References 36 publications

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“…These two ligands are five-membered aromatic compounds with electron-withdrawing character.T he reported values of the vertical detachmente nergy (VDE) of C 2 HBN 2 F 3 and C 2 HBN 2 (CN) 3 at the B3LYP/6-31 + G(d,p) level of theory are 2.4 eV and 4.3 eV,r espectively. [13] From the VDE data, it is clear that C 2 HBN 2 F 3 is not as uperhalogen,b ut C 2 HBN 2 (CN) 3 shows potentials uperhalogen nature. To confirm the superhalogen property of the latter,w er ecomputed the VDE at the MP2 level of theory using the def2-TZVPP basis set.…”

Section: Resultsmentioning

confidence: 96%

“…These two ligands are derived from the heterocyclic molecule imidazole (C 3 N 2 H 4 ). It is interesting to note that although the imidazole molecule has a negative electron affinity, the corresponding ligand derivatives show positive electron affinity. Moreover, C 2 HBN 2 (CN) 3 is itself a superhalogen.…”

Section: Introductionmentioning

confidence: 99%

“…According to Gutsev and Boldyrev, [9] superhalogensh ave the general formula MX k + 1 ,w here Mi sametal atom, Xi sahalogen atom,a nd k is the valence of the metal M. However,i th as been found that severalo rganic and magnetic superhalogens [10,11] do not obey this general formula. The superhalogensa re mostly inorganic in nature.Recently,Jena et al [12] and Giri et al [13] have designed aromatic heterocyclics uperhalogens.Although several types of superhalogens have been reported in the literature in the last two decades, examples of Zintl-based superhalogensa re very few.T his may be due to the unique structural features of the Zintl moiety,w hich is not conducive to the design of superhalogens.…”

Section: Introductionmentioning

confidence: 99%

“…In this work, we have taken aw ell-knownG roup 14 Zintl ion, Ge 9 4À , [24] and coupled it with two different organic heterocyclic ligands,n amely C 2 HBN 2 F 3 and C 2 HBN 2 (CN) 3 ,t of orm organo-Zintlc omplexes.T hese two ligandsa re derived from the heterocyclicm olecule imidazole (C 3 N 2 H 4 ). It is interesting to note that although the imidazole molecule has an egative electron affinity, [13] the corresponding ligandd erivatives show positive electron affinity.M oreover, C 2 HBN 2 (CN) 3 is itself as uperhalogen.T hus,i ti se xpected that the newly designed deltahedral organo-Zintlc omplexw ill also have superhalogen properties.…”

Section: Introductionmentioning

confidence: 99%

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Deltahedral Organo‐Zintl Superhalogens

Reddy

Parida

Chakraborty³

et al. 2018

Chemistry A European J

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Zintl ions constitute a special type of naked anionic clusters, mainly consisting of Group 13, 14, and 15 elements of the Periodic Table. Due to the presence of multiple negative ions, the chemistry of Zintl ions is unique. They not only form Zintl phases with alkali and alkaline-earth metal cations, but also form organo-Zintl clusters with distinct properties. By first-principles calculations based on density functional theory, we have designed a new deltahedral organo-Zintl cluster with Ge as the core and aromatic heterocyclic compounds as ligands. Calculations on such complexes show that they form a special class of system known as a superhalogen (SH), with a high vertical detachment energy of 4.9 eV. The density of states (DOS), partial DOS, and different molecular orbitals give additional information about the bonding features of the complexes.

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Deltahedral Organo‐Zintl Superhalogens

Reddy

Parida

Chakraborty³

et al. 2018

Chemistry A European J

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“…We also replaced boron with carbon in the bodipy group for docking of BD-CsA. Although the substitution of boron with carbon has been used by others (Naaresh Reddy and Giri, 2016;Verwilst et al, 2017;Zhao et al, 2017;Bonacorso et al, 2018) and by us ( Fig. 10), the interaction of boron compared with carbon in the BD-CsA with residues in the drug-binding pocket of P-gp might be different.…”

Section: Development Of Abcb1 Fluorescent Substrate Probementioning

confidence: 99%

Synthesis and Characterization of Bodipy-FL-Cyclosporine A as a Substrate for Multidrug Resistance-Linked P-Glycoprotein (ABCB1)

et al. 2019

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Generation of fluorescent conjugates of small molecules and existing drugs has facilitated their use in addressing cellular functions and pharmacological analysis. These compounds interact with several proteins as substrates or inhibitors, thus allowing the development of unique fluorescence‐based methods to study in vivo localization and the molecular mechanisms. Pglycoprotein (P‐gp) is an ATP‐binding cassette transporter that effluxes most anti‐cancer drugs from cells, contributing to the development of drug resistance in cancer cells. P‐gp, which exports toxic metabolites and xenobiotics, is expressed on the surface of epithelial cells of the intestine, kidney, liver, placenta, adrenal gland and endothelial cells at blood‐brain barrier. With the aim of developing an effective probe to study drug‐transport by P‐gp in various model systems including cultured cells, mice and zebra fish, we synthesized a BODIPY‐FL conjugate of cyclosporine A (BD‐CsA). After synthesis and characterization of its chemical purity, BD‐CsA was compared with the currently available 7‐nitrobenz‐2‐oxa‐1,3‐diazol‐4‐yl (NBD)‐CsA probe in terms of its usage as a substrate of human and mouse P‐gp. Using a BacMam baculovirus HeLa cell expression system and a flow cytometry‐based transport assay, we found that BD‐CsA is recognized as a substrate by both human and mouse P‐gp. The rate of efflux of BD‐CsA by human P‐gp is similar to that of NBD‐CsA (T1/2 of 5.0 min and 3.0 min for BD‐CsA and NBD‐CsA, respectively). In flow cytometry assays, the fluorescence intensity of BD‐CsA was almost 10‐times higher than that of NBD‐CsA due to the high fluorescence quantum yield of the BODIPY fluorophore, allowing us to use significantly lower concentrations of BD‐CsA to achieve the same fluorescence levels. The transport of BD‐CsA was inhibited by the P‐gp inhibitor tariquidar, with similar IC50 values as for NBD‐CsA transport (21.6 nM for BD‐CsA and 25.8 nM for NBD‐CsA). We also observed that both BD‐CsA and NBD‐CsA partially inhibited the ATPase activity of P‐gp. In silico docking of BD‐CsA and NBD‐CsA to the homology model of human P‐gp indicates that both probes bind in the drug‐binding pocket of Pgp with similar docking scores. Thus, we demonstrate that BD‐CsA is a sensitive and efficient fluorescent substrate of P‐gp that can be used to study the transporter's function in both in vitro and in vivo settings. Support or Funding Information This research was funded by the Intramural Research Program of the National Institutes of Health, the National Cancer Institute, Center for Cancer Research This abstract is from the Experimental Biology 2019 Meeting. There is no full text article associated with this abstract published in The FASEB Journal.

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Intensiv farbige Bor‐dotierte Thiazolthiazole durch reduktive Dimerisierung von Borisothiocyanaten

et al. 2021

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Die Reduktion von (CAAC)BBr2(NCS) (CAAC=cyclisches Alkyl(amino)carben) in der Gegenwart einer Lewis‐Base L liefert dreifach koordinierte (CAAC)LB(NCS)‐Borylene, die eine reversible (E)/(Z)‐Isomerisierung eingehen. Die gleiche Reduktion in Abwesenheit von L führt zu intensiv blauen, bis(CAAC)‐stabilisierten, Bor‐dotierten, aromatischen Thiazolthiazolen, die aus der Dimerisierung zweifach koordinierter (CAAC)B(NCS)‐Borylenintermediate resultieren.

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Super/hyperhalogen aromatic heterocyclic compounds

Abstract: Aromatic heterocyclic molecules with negative electron affinity values can be transformed to highly oxidizing super/hyperhalogens based on a systematic in silico approach.

Cited by 23 publications

References 36 publications

Deltahedral Organo‐Zintl Superhalogens

Deltahedral Organo‐Zintl Superhalogens

Synthesis and Characterization of Bodipy-FL-Cyclosporine A as a Substrate for Multidrug Resistance-Linked P-Glycoprotein (ABCB1)

Intensiv farbige Bor‐dotierte Thiazolthiazole durch reduktive Dimerisierung von Borisothiocyanaten

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