02754nas a2200193 4500008004100000022001400041245011400055210006900169260011000238300001400348490000700362520194900369100002402318700002402342700002102366700002102387700002202408856013002430 2011 eng d a1144-054600aAntioxidant and anticancer activities of supramolecularly controlled magnetostructural halo-oximes of lawsone0 aAntioxidant and anticancer activities of supramolecularly contro aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcMAY a1615-16230 v353 a

Crystal engineering based on halogen bonding together with host-guest interactions of water molecules via H-bonding, stabilizing supramolecular architecture in chloro 1, bromo 2 and iodo 3 oximes of lawsone, is discussed. 1 and 2 crystallize in orthorhombic, non-centrosymmetric space group Pna2(1) while 3 crystallizes in monoclinic P2(1)/n space group. Non-covalent competitive interactions of asymmetric solvation and halogen bonding can have a large influence on the spin distribution in 1, 2 and 3 derivatives of spin carrier lawsone live polymer as revealed by single crystal X-ray and EPR studies. The significant C3-Cl/Br center dot center dot center dot O, C3-Cl/Br center dot center dot center dot H, O-H center dot center dot center dot O-C, C-H center dot center dot center dot pi and pi center dot center dot center dot pi interactions have been identified in the molecular assemblies leading to net magnetostructures of halo-oximes. Dimer-of-dimer-type tetrameric radical assembly of 3 and interacting bi- and monoradical chain on 2(1) axis in 1 and 2 have been identified. The proton-coupled electron transfers possibly govern the antioxidant nature in halooximes of spin carrier lawsone in terms of oxygen reduction to water molecules. Such activity is found to be directly proportional to the spin (radical) concentrations in 1 to 3 and increases in order 1 < 2 < 3 according to halogen bonding effect. The antioxidant chemical DPPH assays for scavenging of such free radicals result in similar trend of increasing order like 1 < 2 < 3, but the chemical in vitro as well as ex vivo SOD antioxidant activities and biological anticancer activity on MCF-7, Hela and HL-60 cell lines show the increasing order 3 < 2 < 1 according to H-bonding effect. This probably could be attributed to the conversion of superoxide radical ions into H(2)O(2), which leads to greater oxidative stress leading to apoptosis.

1 aZaware, Santosh, B.1 aGonnade, Rajesh, G.1 aSrinivas, Darbha1 aKhan, Ayesha, A.1 aRane, Sandhya, Y. uhttps://library.ncl.res.in/content/antioxidant-and-anticancer-activities-supramolecularly-controlled-magnetostructural-halo-002009nas a2200277 4500008004100000022001400041245011400055210006900169260007300238300001200311490000900323520098100332653002201313653004401335653002301379653004001402653001601442100002201458700001801480700002401498700002101522700002001543700002101563700001801584856012901602 2011 eng d a0022-286000aAzide derivatized anticancer agents of vitamin K-3: X-ray structural, DSC, resonance spectral and API studies0 aAzide derivatized anticancer agents of vitamin K3 Xray structura aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcDEC a288-2960 v10063 a

Compound 1 [1-imino (acetyl hydrazino)-Vitamin K-3], displays valence tautomerically related electronic isomers as Form land Form II. Form I exhibits 2D packing fragment with 1D ribbon chains of N-H center dot center dot center dot O hydrogen bonds and shows EPR silent features. While Form II is EPR active and exhibits biradical nature with double quantum transitions at g = 2.0040. H-1 NMR of compound 2, [1-imino (hydrazino carboxylate)-Vitamin K-3] and Form II exhibit pi delocalization via resonance assisted H-bonding [RAHB] effect compared to Form I. Molecular interactions in Form I and II are visualized by DSC. The electronic structures of compounds 1 and 2 have been correlated to their API values by measuring anticancer activities, mitochondrial potentials and DNA shearing patterns. Form II and compound 2 indicate mitochondria mediated apoptosis (similar to 75% cell death) while Form I causes 35% cell death. (C) 2011 Elsevier B.V. All rights reserved.

10aAnticancer agents10aAPI (Active Pharmaceutical Ingredients)10aElectronic isomers10aRAHB (resonance assisted H-bonding)10aVitamin K-31 aBadave, Kirti, D.1 aPatil, Yogesh1 aGonnade, Rajesh, G.1 aSrinivas, Darbha1 aDasgupta, Rajan1 aKhan, Ayesha, A.1 aRane, Sandhya uhttps://library.ncl.res.in/content/azide-derivatized-anticancer-agents-vitamin-k-3-x-ray-structural-dsc-resonance-spectral-002789nas a2200217 4500008004100000022001400041245014400055210006900199260007100268300001200339490000700351520192500358100002102283700002302304700002302327700002102350700002602371700002402397700002602421856012402447 2011 eng d a0020-166900aSynthesis, electronic structure, DNA and protein binding, DNA cleavage, and anticancer activity of fluorophore-labeled copper(II) complexes0 aSynthesis electronic structure DNA and protein binding DNA cleav a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcJAN a545-5580 v503 a

Two mononuclear fluorophore-labeled copper(II) complexes [Cu(nip)(acac)](+) (2) and [Cu(nip)(2)](2+) (3), where fluorophore is 2-(naphthalen-1-yl)-1H-imidazo[4,5-f][1,10]phenanthroline (nip) (1) and acac is acetylacetone, have been synthesized aid characterized by various techniques. The ligand 1 and complex 2 are structurally characterized by single-crystal X-ray diffraction. The coordination geometries around the copper are square planar in solid as well as solution state as evidenced by electron paramagnetic resonance (EPR) spectroscopy. The density functional calculations carried out on 1-3 have shown that electron-rich regions in the highest occupied orbital are localized on the naphthalene end partly on the phenanthroline moiety. Both complexes 2 and 3 in dimethyl sulfoxide (DMSO) exhibit near square planar structure around the metal ion in their ground state. Time-dependent density functional theory (TD-DFT) calculations reveal that Cu(II) ion in complex 2 shows tetrahedral coordination around the metal while 3 retains its square planar geometry in the lowest excited state. The interaction of complexes with calf-thymus DNA (CT DNA) has been explored by using absorption, emission, thermal denaturation, and viscosity studies, and the intercalating mode of DNA binding has been proposed. The complexes cleave DNA oxidatively without any exogenous additives. The protein binding ability has been monitored by quenching of tryptophan emission in the presence of complexes using bovine serum albumin (BSA) as model protein. The compounds showed dynamic quenching behavior. Further, the anticancer activity of the complexes on MCF-7 (human breast cancer), HeLa (human cervical cancer), HL-60 (human promyelocytic leukemia), and MCF-12A (normal epithelial) cell lines has been studied. It has been observed that 3 exhibits higher cytotoxicity than 2, and the cells undergo apoptotic cell death.

1 aBhat, Satish, S.1 aKumbhar, Anupa, A.1 aHeptullah, Hussain1 aKhan, Ayesha, A.1 aGobre, Vivekanand, V.1 aGejji, Shridhar, P.1 aPuranik, Vedavati, G. uhttps://library.ncl.res.in/content/synthesis-electronic-structure-dna-and-protein-binding-dna-cleavage-and-anticancer-001651nas a2200253 4500008004100000022001400041245011400055210006900169260011000238300001200348490000700360520067200367100002201039700002301061700002101084700002101105700002501126700002401151700002601175700002301201700002401224700002201248856012701270 2014 eng d a1144-054600aCu(II) conjugation along the transformation of a vitamin K-3 derivative to a dinaphthoquinone methide radical0 aCuII conjugation along the transformation of a vitamin K3 deriva aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcJAN a277-2840 v383 a

1,1'-Methide-bi-vitamin K-3 (B) has been isolated as a dinaphthoquinone methide radical (DNQM) by the transformation of 1-imino(acetylhydrazino)-vitamin K-3 (A). The transformation follows a biomimetic activation pathway mediated via Cu(II) ion catalyzed oxidative coupling. Single crystal X-ray and electron spin resonance (ESR) experiments combined with density functional calculations elucidate the ``resonance structure'' of the DNQM radical (B). Fluorescence investigations reveal that DNQM facilitates interaction with the cysteine residue. As compared to the parent substrate, B shows a depletion in the level of GSH, triggering apoptosis in HeLa cells.

1 aBadave, Kirti, D.1 aPatil, Shalaka, S.1 aKhan, Ayesha, A.1 aSrinivas, Darbha1 aButcher, Raymond, J.1 aGonnade, Rajesh, G.1 aPuranik, Vedavati, G.1 aPinjari, Rahul, V.1 aGejji, Shridhar, P.1 aRane, Sandhya, Y. uhttps://library.ncl.res.in/content/cuii-conjugation-along-transformation-vitamin-k-3-derivative-dinaphthoquinone-methide-002832nas a2200289 4500008004100000022001400041245013800055210006900193260007300262300001000335490000900345520178500354653002402139653002402163653000902187653002302196653001902219100001702238700002102255700002102276700002102297700002302318700001902341700002602360700002702386856012902413 2014 eng d a0022-286000aMolecular structures and biological evaluation of 2-chloro-3-(n-alkylamino)-1,4-napthoquinone derivatives as potent antifungal agents0 aMolecular structures and biological evaluation of 2chloro3nalkyl aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcFEB a68-740 v10593 a

Derivatives of 2-chloro-3-(n-alkylamino)-1,4-naphthoquinone (1-alkyl: methyl; L-1, ethyl; L-2, propyl; L-3 and butyl; L-4) have been synthesized and characterized by elemental analysis, FT-IR, H-1 NMR, UV-visible spectroscopy, LC-MS and single crystal X-ray diffraction studies. Antifungal activity of L-1 to L-4 has been evaluated against Candida tropicalis, Candida albicans and Cladosporium herbarum. The intramolecular hydrogen bonding affects the N-H vibrational frequency in L-2 (3273 cm(-1)). The single crystal X-ray structure reveal that L-1 and L-3 crystallizes in triclinic P-1, whereas L-2 crystallizes in orthorhombic Pca2(1), space group. An extensive intra and intermolecular hydrogen bonding interactions were observed in L-1 to L-3 which leads to molecular association. Intramolecular N-H center dot center dot center dot O hydrogen bonding were observed in L-1 to L-3. Moreover pi-pi stacking interactions were observed between the quinonoid rings of L-1 and L-3, however no such interactions were observed in L-2. An electrochemical study showed molecular association of L-1 to L-4 in DMSO solution. Compounds L-1 to L-4 were found to be potent antifungal agents against all the three strains, especially against C. tropicalis. Amongst these promising antifungal candidates, L-1 showed better activity compared to the clinically administered antifungal drug Amphotericin B and Nitrofurantoin with MIC = 1.25 mu g ml(-1) and MIC = 0.025 mu g ml(-1) respectively against C. albicans. Structure and activity relationship (SAR) study suggest a LogP value of similar to 2.0 and the cyclic voltammetry studies reveals additional chemical processes for L-1, which exhibits maximum activity against all fungal strains. (C) 2013 Elsevier B.V. All rights reserved.

10aAminonaphthoquinone10aAntifungal activity10aLogP10aNaphthosemiquinone10api-pi stacking1 aPawar, Omkar1 aPatekar, Ashwini1 aKhan, Ayesha, A.1 aKathawate, Laxmi1 aHaram, Santosh, K.1 aMarkad, Ganesh1 aPuranik, Vedavati, G.1 aSalunke-Gawali, Sunita uhttps://library.ncl.res.in/content/molecular-structures-and-biological-evaluation-2-chloro-3-n-alkylamino-14-napthoquinone-001591nas a2200193 4500008004100000022001400041245012600055210006900181260007100250300001200321490000700333520081400340100001901154700002301173700002101196700002301217700002601240856013101266 2014 eng d a1043-180200aMonitoring cellular uptake and cytotoxicity of copper(II) complex using a fluorescent anthracene thiosemicarbazone ligand0 aMonitoring cellular uptake and cytotoxicity of copperII complex  a1155 16TH ST, NW, WASHINGTON, DC 20036 USAbAMER CHEMICAL SOCcJAN a102-1140 v253 a

The thiosemicarbazone derivative of anthracene (ATSC, anthracene thiosemicarbazone I) and its copper(II) complex (CuATSC, 2) were synthesized and characterized by spectroscopic, electrochemical, and crystallographic techniques. Interaction of 1 and 2 with calf thymus (CT) DNA was explored using absorption and emission spectral methods, and viscosity measurements reveal a partial-intercalation binding mode. Their protein binding ability was monitored by the quenching of tryptophan emission using bovine serum albumin (BSA) as a model protein. Furthermore, their cellular uptake, in vitro cytotoxicity testing on the HeLa cell line, and flow cytometric analysis were carried out to ascertain the mode of cell death. Cell cycle analysis indicated that 1 and 2 cause cell cycle arrest in sub-G1 phase.

1 aKate, Anup, N.1 aKumbhar, Anupa, A.1 aKhan, Ayesha, A.1 aJoshi, Pranaya, V.1 aPuranik, Vedavati, G. uhttps://library.ncl.res.in/content/monitoring-cellular-uptake-and-cytotoxicity-copperii-complex-using-fluorescent-anthracene-002765nas a2200217 4500008004100000022001400041245016600055210006900221260011000290300001200400490000600412520183400418100002602252700002702278700002102305700003102326700001902357700002102376700001902397856013102416 2016 eng d a2050-750X00aInverse high internal phase emulsion polymerization (i-HIPE) of GMMA, HEMA and GDMA for the preparation of superporous hydrogels as a tissue engineering scaffold0 aInverse high internal phase emulsion polymerization iHIPE of GMM aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcNOV a450-4600 v43 a

A series of novel superporous hydrogels for regenerative medicine were prepared by oil-in-water (o/w) or inverse high internal phase emulsion (i-HIPE) copolymerization of glycerol monomethacrylate (GMMA), 2-hydroxy ethyl methacrylate (HEMA) and glycerol dimethacrylate (GDMA) as a cross-linker using a non toxic solvent and a redox initiator system at the physiological temperature (37 degrees C). The monomer GMMA was synthesized from glycidyl methacrylate (GMA) by an alternative facile method using Amberlyst-15. The described i-HIPEs showed a significantly wider stability window. The polyHIPE hydrogels were characterized by FTIR, BET method for surface area, mercury porosimetry, SEM, DSC, TGA, XRD, compressive strain and strain recovery. The swelling ratio of the hydrogels and their degradation in 0.007 M NaOH and lipase B (Candida antarctica) solutions were determined gravimetrically and the rate of degradation was explained in terms of the molecular structure of the hydrogels. The morphological studies showed that the pore diameter varied between 20 and 30 mu m and the pore throats (interconnecting windows) diameter was in the range of 4-8 mu m. The described polyHIPE hydrogels were found to have an open cell morphology and interconnected pore architecture, which are important characteristics for scaffold applications. The initial cytotoxicity study performed according to ISO-10993-5 indicated cytocompatibility (97% cell viability) and the subsequent cell seeding and proliferation study exhibited 55-88% cell viability (increased monotonously from GHG-1 to GHG-5), which could be attributed to modulation of the physical and chemical properties of the hydrogels. The described super porous hydrogels are considered as potential candidates for scaffold materials in tissue engineering applications.

1 aNalawade, Archana, C.1 aGhorpade, Ravindra, V.1 aShadbar, Sadiqua1 aQureshi, Mohammed, Shadbar1 aChavan, Nayaku1 aKhan, Ayesha, A.1 aPonrathnam, S. uhttps://library.ncl.res.in/content/inverse-high-internal-phase-emulsion-polymerization-i-hipe-gmma-hema-and-gdma-preparation-001559nas a2200193 4500008004100000022001400041245012400055210006900179260000800248300001400256490000700270520084900277100002401126700002501150700002401175700002101199700002501220856012001245 2018 eng d a1144-054600aX-ray crystal structures and anti-breast cancer property of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acids0 aXray crystal structures and antibreast cancer property of 3tertb cJAN a1078-10860 v423 a

Diastereomeric `2RS, 4R'-2-arylthiazolidine-4-carboxylic acids (ATCAs) were synthesized and their resolution to chiraly pure N-BOC derivatives was attempted by column chromatography. The absolute stereochemistry of the resolved compounds was ascertained by X-ray single crystal structures. Further application of the synthesized compounds was studied for their in vitro anti-breast cancer activity against MCF7 cell line using DOX as a standard by MTT assay method. Cell morphology analysis was carried out by fluorescence microscopy. The compounds containing `2S' absolute configuration in thiazolidine ring and presence of 2-NO2, 2,6-Cl groups on `2R'-aryl substituent showed significant antibreast cancer activity where some of the compounds were found to be more active than DOX in terms of induced apoptosis mode of MCF7 cell death.

1 aJagtap, Rohidas, M.1 aThorat, Shridhar, H.1 aGonnade, Rajesh, G.1 aKhan, Ayesha, A.1 aPardeshi, Satish, K. uhttps://library.ncl.res.in/content/x-ray-crystal-structures-and-anti-breast-cancer-property-3-tert-butoxycarbonyl-2