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Biscoumarin derivatives: Synthesis, crystal structure, theoretical studies and induced apoptosis activity on bladder urothelial cancer cell
•Five new biscoumarin derivatives (1–5) were synthesized.•Their anti-cancer activities on two human bladder urothelial cell lines were evaluated.•The cell cycle analysis and apoptosis change of the compounds were also observed.•The HB energies of compounds 1–5 were calculated. In this study, five ne...
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Published in: | Journal of molecular structure 2015-03, Vol.1084, p.200-206 |
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container_title | Journal of molecular structure |
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creator | Xin, Jia-jia Li, Jing Zhang, Zi-dan Hu, Xing-bin Li, Ming-kai |
description | •Five new biscoumarin derivatives (1–5) were synthesized.•Their anti-cancer activities on two human bladder urothelial cell lines were evaluated.•The cell cycle analysis and apoptosis change of the compounds were also observed.•The HB energies of compounds 1–5 were calculated.
In this study, five new biscoumarin derivatives (1–5) were synthesized and compound 4 inhibited the proliferation of the bladder urothelial cells (J82 cell line) obviously after 48h treatment at different concentration (1, 5 and 10μmol/L), and J82 cells were predominantly induced to apoptotic cell death after compound 4 treatment. Morphologic changes of bladder urothelial cancer cells were also observed under transmission electron microscopy (TEM) after compound 4 treatment. In addition, compound 4 had much less toxicity to human umbilical vein endothelial cells. To explore the possible anti-cancer mechanism of compound 4, two classical intramolecular OH⋯O hydrogen bonds (HBs) in their structures and the corresponding HB energies were performed with the density functional theory (DFT) [B3LYP/6-31G∗] method. Anti-bladder cancer activity of compound 4 is possible due to the intramolecular weakest HB energies. |
doi_str_mv | 10.1016/j.molstruc.2014.12.024 |
format | article |
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In this study, five new biscoumarin derivatives (1–5) were synthesized and compound 4 inhibited the proliferation of the bladder urothelial cells (J82 cell line) obviously after 48h treatment at different concentration (1, 5 and 10μmol/L), and J82 cells were predominantly induced to apoptotic cell death after compound 4 treatment. Morphologic changes of bladder urothelial cancer cells were also observed under transmission electron microscopy (TEM) after compound 4 treatment. In addition, compound 4 had much less toxicity to human umbilical vein endothelial cells. To explore the possible anti-cancer mechanism of compound 4, two classical intramolecular OH⋯O hydrogen bonds (HBs) in their structures and the corresponding HB energies were performed with the density functional theory (DFT) [B3LYP/6-31G∗] method. Anti-bladder cancer activity of compound 4 is possible due to the intramolecular weakest HB energies.</description><identifier>ISSN: 0022-2860</identifier><identifier>EISSN: 1872-8014</identifier><identifier>DOI: 10.1016/j.molstruc.2014.12.024</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>Apoptosis ; Biscoumarin ; Bladder ; Bladder urothelial cancer ; Cancer ; Chemotherapy ; Crystal ; Derivatives ; Endothelial cells ; Molecular structure ; Toxicity ; Veins</subject><ispartof>Journal of molecular structure, 2015-03, Vol.1084, p.200-206</ispartof><rights>2014 Elsevier B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c345t-1b18a2e9ffdffbf246de28b19b95294985659993dd497645b6e33314f85343163</citedby><cites>FETCH-LOGICAL-c345t-1b18a2e9ffdffbf246de28b19b95294985659993dd497645b6e33314f85343163</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Xin, Jia-jia</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><creatorcontrib>Zhang, Zi-dan</creatorcontrib><creatorcontrib>Hu, Xing-bin</creatorcontrib><creatorcontrib>Li, Ming-kai</creatorcontrib><title>Biscoumarin derivatives: Synthesis, crystal structure, theoretical studies and induced apoptosis activity on bladder urothelial cancer cell</title><title>Journal of molecular structure</title><description>•Five new biscoumarin derivatives (1–5) were synthesized.•Their anti-cancer activities on two human bladder urothelial cell lines were evaluated.•The cell cycle analysis and apoptosis change of the compounds were also observed.•The HB energies of compounds 1–5 were calculated.
In this study, five new biscoumarin derivatives (1–5) were synthesized and compound 4 inhibited the proliferation of the bladder urothelial cells (J82 cell line) obviously after 48h treatment at different concentration (1, 5 and 10μmol/L), and J82 cells were predominantly induced to apoptotic cell death after compound 4 treatment. Morphologic changes of bladder urothelial cancer cells were also observed under transmission electron microscopy (TEM) after compound 4 treatment. In addition, compound 4 had much less toxicity to human umbilical vein endothelial cells. To explore the possible anti-cancer mechanism of compound 4, two classical intramolecular OH⋯O hydrogen bonds (HBs) in their structures and the corresponding HB energies were performed with the density functional theory (DFT) [B3LYP/6-31G∗] method. Anti-bladder cancer activity of compound 4 is possible due to the intramolecular weakest HB energies.</description><subject>Apoptosis</subject><subject>Biscoumarin</subject><subject>Bladder</subject><subject>Bladder urothelial cancer</subject><subject>Cancer</subject><subject>Chemotherapy</subject><subject>Crystal</subject><subject>Derivatives</subject><subject>Endothelial cells</subject><subject>Molecular structure</subject><subject>Toxicity</subject><subject>Veins</subject><issn>0022-2860</issn><issn>1872-8014</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkMtu3DAMRYWiBTKd9hcCLbuIHb2sWF2lDfICAmTRdi3IEo1q4LEmkjzAfEN-OkwmXXdF4JL3kjyEnHLWcsb1-abdpqnUvPhWMK5aLlom1Aey4v2FaHqUPpIVY0I0otfshHwuZcMY42hekeefsfi0bF2OMw2Q497VuIfynf46zPUvlFjOqM-HUt1E35bUJcMZxVbKUKN_k5cQoVA3BxrnsHgI1O3SriZ0U-cxMNYDTTMdJhdwCV1ywoApotm72aPiYZq-kE-jmwp8fa9r8ufm-vfVXfPweHt_9eOh8VJ1teED750AM45hHIdRKB1A9AM3g-mEUabvdGeMkSEoc6FVN2iQUnI19p1Ukmu5Jt-OubucnhYo1W4RAh7gZkhLsVxrg6QkTq-JPo76nErJMNpdjgjrYDmzr_Ttxv6jb1_pWy4s0kfj5dEI-Mg-QrbFR8BXQ8zgqw0p_i_iBQw2lTM</recordid><startdate>20150315</startdate><enddate>20150315</enddate><creator>Xin, Jia-jia</creator><creator>Li, Jing</creator><creator>Zhang, Zi-dan</creator><creator>Hu, Xing-bin</creator><creator>Li, Ming-kai</creator><general>Elsevier B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20150315</creationdate><title>Biscoumarin derivatives: Synthesis, crystal structure, theoretical studies and induced apoptosis activity on bladder urothelial cancer cell</title><author>Xin, Jia-jia ; Li, Jing ; Zhang, Zi-dan ; Hu, Xing-bin ; Li, Ming-kai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c345t-1b18a2e9ffdffbf246de28b19b95294985659993dd497645b6e33314f85343163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Apoptosis</topic><topic>Biscoumarin</topic><topic>Bladder</topic><topic>Bladder urothelial cancer</topic><topic>Cancer</topic><topic>Chemotherapy</topic><topic>Crystal</topic><topic>Derivatives</topic><topic>Endothelial cells</topic><topic>Molecular structure</topic><topic>Toxicity</topic><topic>Veins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xin, Jia-jia</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><creatorcontrib>Zhang, Zi-dan</creatorcontrib><creatorcontrib>Hu, Xing-bin</creatorcontrib><creatorcontrib>Li, Ming-kai</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of molecular structure</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xin, Jia-jia</au><au>Li, Jing</au><au>Zhang, Zi-dan</au><au>Hu, Xing-bin</au><au>Li, Ming-kai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biscoumarin derivatives: Synthesis, crystal structure, theoretical studies and induced apoptosis activity on bladder urothelial cancer cell</atitle><jtitle>Journal of molecular structure</jtitle><date>2015-03-15</date><risdate>2015</risdate><volume>1084</volume><spage>200</spage><epage>206</epage><pages>200-206</pages><issn>0022-2860</issn><eissn>1872-8014</eissn><abstract>•Five new biscoumarin derivatives (1–5) were synthesized.•Their anti-cancer activities on two human bladder urothelial cell lines were evaluated.•The cell cycle analysis and apoptosis change of the compounds were also observed.•The HB energies of compounds 1–5 were calculated.
In this study, five new biscoumarin derivatives (1–5) were synthesized and compound 4 inhibited the proliferation of the bladder urothelial cells (J82 cell line) obviously after 48h treatment at different concentration (1, 5 and 10μmol/L), and J82 cells were predominantly induced to apoptotic cell death after compound 4 treatment. Morphologic changes of bladder urothelial cancer cells were also observed under transmission electron microscopy (TEM) after compound 4 treatment. In addition, compound 4 had much less toxicity to human umbilical vein endothelial cells. To explore the possible anti-cancer mechanism of compound 4, two classical intramolecular OH⋯O hydrogen bonds (HBs) in their structures and the corresponding HB energies were performed with the density functional theory (DFT) [B3LYP/6-31G∗] method. Anti-bladder cancer activity of compound 4 is possible due to the intramolecular weakest HB energies.</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.molstruc.2014.12.024</doi><tpages>7</tpages></addata></record> |
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subjects | Apoptosis Biscoumarin Bladder Bladder urothelial cancer Cancer Chemotherapy Crystal Derivatives Endothelial cells Molecular structure Toxicity Veins |
title | Biscoumarin derivatives: Synthesis, crystal structure, theoretical studies and induced apoptosis activity on bladder urothelial cancer cell |
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