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DINDULKAR, S. D.,BHATNAGAR, I.,GAWADE, R. L.,PURANIK, V. G.,KIM, S. K.,ANH, D. H.,PARTHIBAN, P.,JEONG, Y. T. Springer Science + Business Media 2014 Journal of chemical sciences Vol.126 No.3
A series of fifteen diversified N-benzylpiperidin-4-one oximes were synthesized and characterized by their NMR spectral data. Additionally, single-crystal XRD analysis was performed for the representative symmetrically and unsymmetrically substituted molecules. All the synthesized oximes from unsymmetrical ketones existed as E-isomer as witnessed by their NMR and XRD data. Among the synthesized target compounds that evaluated for their in vitro cytotoxicity against human cervical carcinoma (HeLa) cells, five compounds were potent with IC50 < 17 mu M. 1-Benzyl-2,6-bis(4-isopropylphenyl)-3-methylpiperidin-4-one oxime 3c with an IC50 of 13.88 mu M was found to be the best active compound as depicted by the microscopic analysis.
Dindulkar, Someshwar D.,Jeong, Daham,Cho, Eunae,Kim, Dongjin,Jung, Seunho The Royal Society of Chemistry 2016 GREEN CHEMISTRY Vol.18 No.12
<P>As a novel biosourced saccharide catalyst, microbial cyclosophoraose, a cyclic beta-(1,2) glucan, was used for the synthesis of therapeutically important versatile indolyl 4H-chromenes via a one pot three-component Knoevenagel-Michael addition-cyclization reaction of salicylaldehyde, 1,3-cyclohexanedione/ dimedone, and indoles in water under neutral conditions. A possible reaction mechanism through molecular complexation is suggested based on 2D ROESY NMR spectroscopic analysis. Moreover, green chemistry metric calculations were carried out for a model reaction, indicating the satisfactory greener approach of this method, with a low E-factor (0.18) and high atom economy (AE = 91.20%). The key features of this protocol are based on two critical factors where the first is to use a novel eco-friendly supramolecular carbohydrate catalyst and the second is its fine green properties such as compatibility with various substituted reactants, recyclability of the catalyst, chromatography-free purification, high product selectivity, and clean conversion with moderate to excellent yields in an aqueous medium.</P>
Kim, H.,Dindulkar, S.D.,Jeong, D.,Park, S.,Jun, B.H.,Cho, E.,Jung, S. Korean Society of Industrial and Engineering Chemi 2016 Journal of industrial and engineering chemistry Vol.44 No.-
<P>A new pentacosadiynoyl cyclosophoraose (P-Cys) was synthesized using a biosourced cyclooligosac-charide with intrinsic complexation capacity. NOESY analysis revealed that switchable molecular behavior of pentacosadiynoyl moiety attached to P-Cys was dependent on the external lipophilicity. Both encapsulation by cyclosophoraose and switchable emulsification by pentacosadiynoyl moiety in P-Cys make it possible to finely formulate a nanoemulsion state for an external hydrophobic guest molecule like Sudan III. Various physicochemical properties of the emulsions of P-Cys were investigated using TEM and DLS. The results indicate that P-Cys is a useful potential platform for the encapsulating emulsification of bioactive molecules for cosmetic and pharmaceutical applications. (C) 2016 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.</P>
김환희,Someshwar D Dindulkar,정다함,박세연,전봉현,조은애,정선호 한국공업화학회 2016 Journal of Industrial and Engineering Chemistry Vol.44 No.-
A new pentacosadiynoyl cyclosophoraose (P-Cys) was synthesized using a biosourced cyclooligosac-charide with intrinsic complexation capacity. NOESY analysis revealed that switchable molecularbehavior of pentacosadiynoyl moiety attached to P-Cys was dependent on the external lipophilicity. Bothencapsulation by cyclosophoraose and switchable emulsification by pentacosadiynoyl moiety in P-Cysmake it possible tofinely formulate a nanoemulsion state for an external hydrophobic guest moleculelike Sudan III. Various physicochemical properties of the emulsions of P-Cys were investigated using TEMand DLS. The results indicate that P-Cys is a useful potential platform for the encapsulating emulsificationof bioactive molecules for cosmetic and pharmaceutical applications.
Biosourced cyclosophoraose-driven acceleration of click reaction in H<sub>2</sub>O
Cho, Eunae,Jeong, Daham,Dindulkar, Someshwar D.,Jung, Seunho THE KOREAN SOCIETY OF INDUSTRIAL AND ENGINEERING 2018 JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY -S Vol.59 No.-
<P><B>Abstract</B></P> <P>Here, we report biosourced cyclosophoraose (CyS)-promoted click reaction of organic azides and alkynes in water, where CyS, rhizobial cyclic β-1,2 glucan molecules containing 17–23 glucoses, dramatically decreased the reaction time from hours to minutes <I>via</I> the solubilization of aromatic alkynes. This catalytic system was successfully applied to the copper-mediated Huisgen 1,3-dipolar cycloaddition reaction using <I>in situ</I>-generated azide. The developed strategy yielded 1,4-disubstituted-1,2,3-triazoles after a short reaction time without bases from a room-temperature aqueous medium, and the products were purified simply by precipitation without requiring further column purifications.</P> <P><B>Highlights</B></P> <P> <UL> <LI> A facile synthetic strategy of 1,4-disubstituted-1,2,3-triazoles in H<SUB>2</SUB>O is reported. </LI> <LI> Cyclosophoraoses purified from <I>Rhizobium</I> species promoted the click reaction of azide and alkyne in water. </LI> <LI> The supramolecular catalytic system provides a simple, workup-free, and green catalytic platform for aqueous click reaction. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
Biosourced cyclosophoraose-driven acceleration of click reaction in H2O
조은애,정다함,Someshwar D Dindulkar,정선호 한국공업화학회 2018 Journal of Industrial and Engineering Chemistry Vol.59 No.-
Here, we report biosourced cyclosophoraose (CyS)-promoted click reaction of organic azides and alkynes in water, where CyS, rhizobial cyclic β-1,2 glucan molecules containing 17–23 glucoses, dramatically decreased the reaction time from hours to minutes via the solubilization of aromatic alkynes. This catalytic system was successfully applied to the copper-mediated Huisgen 1,3-dipolar cycloaddition reaction using in situ-generated azide. The developed strategy yielded 1,4-disubstituted-1,2,3-triazoles after a short reaction time without bases from a room-temperature aqueous medium, and the products were purified simply by precipitation without requiring further column purifications.
Choi, Jae Min,Park, Kyeonghui,Lee, Benel,Jeong, Daham,Dindulkar, Someshwar D,Choi, Youngjin,Cho, Eunae,Park, Seyeon,Yu, Jae-hyuk,Jung, Seunho Elsevier 2017 Carbohydrate polymers Vol.163 No.-
<P><B>Abstract</B></P> <P>Ciprofloxacin is a broad-spectrum fluoroquinolone antibiotic used to treat bacterial infections; however, its limited aqueous solubility inhibits its broader clinical uses. This study investigated the complexation effect of mono-6-deoxy-6-aminoethylamino-β-cyclodextrin on the aqueous solubility and bioavailability of ciprofloxacin. During complexation, the oval-shaped cavity induced by mono-aminoethylamine substitution on the primary rim of β-cyclodextrin, was considered to be a key factor according to NMR spectroscopy and molecular modeling studies. The ciprofloxacin with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin complex was characterized using FE-SEM, DSC, FT-IR, T1 relaxation, 2D NOESY, and DOSY NMR spectroscopy and molecular modeling studies. The solubility property of ciprofloxacin complexed with mono-6-deoxy-6-aminoethylamino-β-cyclodextrin was enhanced by seven-fold compared to that of pure ciprofloxacin. Furthermore antibacterial activity of that complex against methicillin-resistant <I>Staphylococcus aureus</I> was enhanced and it clearly showed the growth inhibition. The mono-6-deoxy-6-aminoethylamino-β-cyclodextrin has the potential to be utilized for other oblong guest molecules besides ciprofloxacin based on the novel induced elliptical cavity.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Mono-6-deoxy-6-aminoethylamino-β-cyclodextrin (Et-β-CD) was synthesized. </LI> <LI> Oval-shaped cavity within Et-β-CD was induced by mono aminoethylamine substitution. </LI> <LI> Ciprofloxacin (CIP)/Et-β-CD complex was thoroughly characterized. </LI> <LI> CIP/Et-β-CD complex effectively enhanced the bioavailability and solubility of CIP. </LI> </UL> </P>
최재민,Benel Lee,정다함,박경희,최은지,전용준,Someshwar D Dindulkar,조은애,도선희,이경호,이임순,박세연,전봉현,유재혁,정선호 한국공업화학회 2017 Journal of Industrial and Engineering Chemistry Vol.48 No.-
Hydroxypropyl cyclosophoraose-pullulan (HPCys-Pul) microspheres were designed as a novel hybridsystem of biocompatible pullulan matrice and pendant hydroxypropyl cyclosophoraoses with drugcomplexing ability. The HPCys-Pul microspheres were prepared by emulsion crosslinking method, andcharacterized using thermogravimetric analysis, Fourier transform infrared spectroscopy, scanningelectron microscopy, and solid state NMR spectroscopy. By virtue of hydroxypropyl cyclosophoraoses, thedeveloped microspheres can encapsulate 4.2-fold more naproxen than pullulan microspheres. Korsmeyer–Peppas model was introduced for describing release kinetics. In vivo naproxen releaseanalysis was carried out in Sprague-Dawley (SD) rats. From those results HPCys-Pul microsphere will be apromising platform for controlled drug delivery.