02936nas a2200313   4500008004100000022001400041245013900055210006900194260007300263300001200336490000900348520175800357653002402115653001602139653002802155653005502183653001202238653003102250100002102281700002202302700002302324700001702347700002002364700002602384700002602410700002802436700002702464856013102491       2014                        eng d  a0022-286000aReaction between lawsone and aminophenol derivatives: synthesis, characterization, molecular structures and antiproliferative activity0 aReaction between lawsone and aminophenol derivatives synthesis c  aPO BOX 211, 1000 AE AMSTERDAM, NETHERLANDSbELSEVIER SCIENCE BVcOCT  a397-4050 v10753 a<p>Reaction between two bioreductive reactants lawsone (2-hydroxy-1,4-napthoquinone) and derivatives 2-aminophenol without catalyst is reported. The reaction between lawsone and 4-chloro-2-aminophenol leads to formation of red colored major product 1A:[2-[(5-chloro-hydroxyphenyl)amino]naphthalene-1,4-dione] and fluorescent orange colored minor compound 1B:[10-chloro-benzo[alpha]phenoxazine-5-one]. Molecular structure of 1A and 1B were determined by single crystal X-ray diffraction. Two mechanisms were proposed to the formation of red 1A and 1B. `Ortho-para' tautomeric equilibrium was observed in DMSO-d(6) solution in 1A, which was revealed by H-1, C-13 NMR and LC-MS studies. Molecules of 1A formed dimers via N-H center dot center dot center dot O interaction and polymeric chain of dimers was formed by OH center dot center dot center dot O interactions. Cl center dot center dot center dot Cl interactions were observed between the polymeric chains of dimers in 1A. Molecules of 1B show Cl center dot center dot center dot N interaction. Antiproliferative properties is studied for 1A-5A compounds (obtained by the reaction of lawsone with 2-amino-4-methylpheno1;2A, 2-aminopheno1;3A, 3-aminophenol;4A and 4-aminophenol;5A) and evaluated against two cancer cell lines, THP1 (human monocytic leukemia cells) and COLO205 (colorectal adenocarcinoma) and one normal cell line, HEK293T (human embryonic kidney). The values of 50% inhibitory concentration (IC50) of compounds 1A-5A was determined using XTT assay. The cytotoxic effects of compounds 2A and 3A were observed against COLO205 and compounds 4A and 5A on THP1 were observed to be higher in comparison to their effect on HEK293T cell lines. (C) 2014 Elsevier B.V. All rights reserved.</p>10aAminonaphthoquinone10aAminophenol10aBenzo[alpha]phenoxazine10aCl center dot center dot center dot N interactions10aLawsone10api-pi stacking interaction1 aKathawate, Laxmi1 aJoshi, Pranya, V.1 aDash, Tapan, Kumar1 aPal, Sanjima1 aNikalje, Milind1 aWeyhermueller, Thomas1 aPuranik, Vedavati, G.1 aKonkimalla, Badireenath1 aSalunke-Gawali, Sunita  uhttps://library.ncl.res.in/content/reaction-between-lawsone-and-aminophenol-derivatives-synthesis-characterization-molecular-002237nas a2200229   4500008004100000022001400041245010600055210006900161260011000230300001600340490000600356520134200362100001701704700002801721700002101749700002001770700002401790700002601814700002601840700002701866856011401893       2015                        eng d  a2046-206900aTargeting a chemorefractory COLO205 (BRAF V600E) cell line using substituted benzo[alpha]phenoxazines0 aTargeting a chemorefractory COLO205 BRAF V600E cell line using s  aTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLANDbROYAL SOC CHEMISTRYcSEP  a82549-825630 v53 a<p>Mutational activations of the oncogene BRAF (especially BRAF V600E) result in a poor prognosis for colon cancer patients and are associated with chemoresistance rendering them refractory to treatment. The development of novel bioactive compounds with specific targeting abilities under such conditions is an urgent need in drug discovery. In this report we synthesize and characterize three fluorescent benzo[alpha]phenoxazine compounds (10R-benzo[alpha]phenoxazine-5-one, 1B; R = Cl, 2B; R = CH3, 3B; R = H) and their anticancer activities are evaluated in a COLO205 cell line. All three compounds with a log P value around 2 were cell permeable. However, 2B and 3B showed specific cytotoxicity in a malignant COLO205 cell line with a BRAF mutation (V600E) in comparison to a non-malignant wild-type BRAF HEK293T cell line. From further cell-based assays (cell cycle analysis, DNA fragmentation and caspase activation), we conclude that 2B and 3B treatment-induced selective cell death by inducing cell cycle arrest at the G0/G1 phase and caspase-mediated apoptosis (activation of the intrinsic and extrinsic pathways) are present only in BRAF V600E COLO205 cells. Further studies in the drug discovery pipeline might help develop these benzo[alpha]phenoxazines as promising chemotherapeutics for such refractory mutated cancers.</p>1 aPal, Sanjima1 aKonkimalla, Badireenath1 aKathawate, Laxmi1 aRao, Soniya, S.1 aGejji, Shridhar, P.1 aPuranik, Vedavati, G.1 aWeyhermueller, Thomas1 aSalunke-Gawali, Sunita  uhttps://library.ncl.res.in/content/targeting-chemorefractory-colo205-braf-v600e-cell-line-using-substituted-0