Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm

[Display omitted] •The (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm were prepared.•The structures of these compounds were determined using spectroscopic methods.•The crystal structures of four phosphazenes were established.•The antimicrobial and cytotoxic activities of the compound...

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Veröffentlicht in:Inorganica Chimica Acta 2019-09, Vol.495, p.118949, Article 118949
Hauptverfasser: Asmafiliz, Nuran, Berberoğlu, İpek, Özgür, Mehtap, Kılıç, Zeynel, Kayalak, Hande, Açık, Leyla, Türk, Mustafa, Hökelek, Tuncer
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container_title Inorganica Chimica Acta
container_volume 495
creator Asmafiliz, Nuran
Berberoğlu, İpek
Özgür, Mehtap
Kılıç, Zeynel
Kayalak, Hande
Açık, Leyla
Türk, Mustafa
Hökelek, Tuncer
description [Display omitted] •The (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm were prepared.•The structures of these compounds were determined using spectroscopic methods.•The crystal structures of four phosphazenes were established.•The antimicrobial and cytotoxic activities of the compounds were investigated.•The interactions between the compounds and pBR322 plasmid DNA were examined. In the present study, the partly and fully-substituted monospiro (4–6, 4a-6d), cis-dispiro (7–9), trans-dispiro (10–15) cyclotriphosphazenes were synthesized for the investigations of their chemical, stereogenic and biological properties. The cis/trans phosphazenes (7–12) have two stereogenic P centers. They are expected to be in meso and racemic forms. In addition, the structures of four compounds were evaluated using X-ray crystallographic data. Compound 13 was found to be a single enantiomer (RR) in the solid state, as also proved with its CD spectrum. The antibacterial and antifungal activities of the phosphazenes were elucidated for against Gram-positive (G+) and Gram-negative (G−) bacteria, and yeast strains, respectively.Of the compounds, 14 exhibits strong antimicrobial activity against most of the tested organisms, especially B. cereus and E. hirae. MBC and MFC values of compounds on different bacterial and fungal species ranged from 
doi_str_mv 10.1016/j.ica.2019.05.048
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The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm</title><source>Elsevier ScienceDirect Journals Complete - AutoHoldings</source><creator>Asmafiliz, Nuran ; Berberoğlu, İpek ; Özgür, Mehtap ; Kılıç, Zeynel ; Kayalak, Hande ; Açık, Leyla ; Türk, Mustafa ; Hökelek, Tuncer</creator><creatorcontrib>Asmafiliz, Nuran ; Berberoğlu, İpek ; Özgür, Mehtap ; Kılıç, Zeynel ; Kayalak, Hande ; Açık, Leyla ; Türk, Mustafa ; Hökelek, Tuncer</creatorcontrib><description>[Display omitted] •The (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm were prepared.•The structures of these compounds were determined using spectroscopic methods.•The crystal structures of four phosphazenes were established.•The antimicrobial and cytotoxic activities of the compounds were investigated.•The interactions between the compounds and pBR322 plasmid DNA were examined. In the present study, the partly and fully-substituted monospiro (4–6, 4a-6d), cis-dispiro (7–9), trans-dispiro (10–15) cyclotriphosphazenes were synthesized for the investigations of their chemical, stereogenic and biological properties. The cis/trans phosphazenes (7–12) have two stereogenic P centers. They are expected to be in meso and racemic forms. In addition, the structures of four compounds were evaluated using X-ray crystallographic data. Compound 13 was found to be a single enantiomer (RR) in the solid state, as also proved with its CD spectrum. The antibacterial and antifungal activities of the phosphazenes were elucidated for against Gram-positive (G+) and Gram-negative (G−) bacteria, and yeast strains, respectively.Of the compounds, 14 exhibits strong antimicrobial activity against most of the tested organisms, especially B. cereus and E. hirae. MBC and MFC values of compounds on different bacterial and fungal species ranged from &lt;9.8 µM to 2500 µM.Furthermore, the cytotoxic activities of 6, 4c, 10 and 14 were investigated against L929 fibroblast and DLD-1 cells, and 14 was the most cytotoxic compound against DLD-1.</description><identifier>ISSN: 0020-1693</identifier><identifier>EISSN: 1873-3255</identifier><identifier>DOI: 10.1016/j.ica.2019.05.048</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Antimicrobial activity ; Antimicrobial agents ; Biological properties ; Crystal structure ; Crystallography ; Cytotoxicity ; DNA cleavage ; Enantiomers ; Fungicides ; Monospiro and dispiroferrocenylphosphazenes ; Nitrogen compounds ; Organic chemistry ; Spectroscopy ; Yeast</subject><ispartof>Inorganica Chimica Acta, 2019-09, Vol.495, p.118949, Article 118949</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright Elsevier Science Ltd. 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The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm</title><title>Inorganica Chimica Acta</title><description>[Display omitted] •The (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm were prepared.•The structures of these compounds were determined using spectroscopic methods.•The crystal structures of four phosphazenes were established.•The antimicrobial and cytotoxic activities of the compounds were investigated.•The interactions between the compounds and pBR322 plasmid DNA were examined. In the present study, the partly and fully-substituted monospiro (4–6, 4a-6d), cis-dispiro (7–9), trans-dispiro (10–15) cyclotriphosphazenes were synthesized for the investigations of their chemical, stereogenic and biological properties. The cis/trans phosphazenes (7–12) have two stereogenic P centers. They are expected to be in meso and racemic forms. In addition, the structures of four compounds were evaluated using X-ray crystallographic data. Compound 13 was found to be a single enantiomer (RR) in the solid state, as also proved with its CD spectrum. The antibacterial and antifungal activities of the phosphazenes were elucidated for against Gram-positive (G+) and Gram-negative (G−) bacteria, and yeast strains, respectively.Of the compounds, 14 exhibits strong antimicrobial activity against most of the tested organisms, especially B. cereus and E. hirae. MBC and MFC values of compounds on different bacterial and fungal species ranged from &lt;9.8 µM to 2500 µM.Furthermore, the cytotoxic activities of 6, 4c, 10 and 14 were investigated against L929 fibroblast and DLD-1 cells, and 14 was the most cytotoxic compound against DLD-1.</description><subject>Antimicrobial activity</subject><subject>Antimicrobial agents</subject><subject>Biological properties</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Cytotoxicity</subject><subject>DNA cleavage</subject><subject>Enantiomers</subject><subject>Fungicides</subject><subject>Monospiro and dispiroferrocenylphosphazenes</subject><subject>Nitrogen compounds</subject><subject>Organic chemistry</subject><subject>Spectroscopy</subject><subject>Yeast</subject><issn>0020-1693</issn><issn>1873-3255</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kc2P0zAQxQMCibJw48LNEheQNlnbab7gtCqf0qr0sJwtZzLZTJXaWdtZaP963BYkTpwsS-_95s28JHkteCa4KK-2GYHOJBdNxouML-vHyULUVZ7msiieJAvOJU9F2eTPkufebznPeZkXi0evNoP102Dd7FNDwdk7NAzsbrKz6fx7ttEusGWZsdsBmUMNgazxzPZsnW_y1ViynxQG1lKHJuiATJuO7ayxf_8j3ekT6QjwexMG9OgvmQ9uhjA7PTIYtItgdHTQJ_xlpATaETjbUhQcmbAPNthfBOyY4YEC4UnXsY_ra0Ym2v8J93Z9tX7nJ3IW9jDa4Gg67akPaNCfMy9TGEYbR6A57Ec2oeniWKbd7kXytNejx5d_3ovkx-dPt6uv6c33L99W1zcpxKuGtGpaIXMOoPuqzRtoBMiKC7lcNm0HokbkouhbXXWyklxCzXtRFWXXQF1oXuv8Inlz5k7O3s_og9ra2Zk4UknZVEJUvORRJc6qeA7vHfZqcrTTbq8EV8fy1VbF8tWxfMULFcuPng9nD8b4D4ROeSA0gB05hKA6S_9x_wahMr2v</recordid><startdate>20190901</startdate><enddate>20190901</enddate><creator>Asmafiliz, Nuran</creator><creator>Berberoğlu, İpek</creator><creator>Özgür, Mehtap</creator><creator>Kılıç, Zeynel</creator><creator>Kayalak, Hande</creator><creator>Açık, Leyla</creator><creator>Türk, Mustafa</creator><creator>Hökelek, Tuncer</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20190901</creationdate><title>Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm</title><author>Asmafiliz, Nuran ; Berberoğlu, İpek ; Özgür, Mehtap ; Kılıç, Zeynel ; Kayalak, Hande ; Açık, Leyla ; Türk, Mustafa ; Hökelek, Tuncer</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-79b1230ccaf7b39c91c27012449bdc18ee015fba7d27202c80f1756d9c85a08a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antimicrobial activity</topic><topic>Antimicrobial agents</topic><topic>Biological properties</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Cytotoxicity</topic><topic>DNA cleavage</topic><topic>Enantiomers</topic><topic>Fungicides</topic><topic>Monospiro and dispiroferrocenylphosphazenes</topic><topic>Nitrogen compounds</topic><topic>Organic chemistry</topic><topic>Spectroscopy</topic><topic>Yeast</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Asmafiliz, Nuran</creatorcontrib><creatorcontrib>Berberoğlu, İpek</creatorcontrib><creatorcontrib>Özgür, Mehtap</creatorcontrib><creatorcontrib>Kılıç, Zeynel</creatorcontrib><creatorcontrib>Kayalak, Hande</creatorcontrib><creatorcontrib>Açık, Leyla</creatorcontrib><creatorcontrib>Türk, Mustafa</creatorcontrib><creatorcontrib>Hökelek, Tuncer</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Inorganica Chimica Acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Asmafiliz, Nuran</au><au>Berberoğlu, İpek</au><au>Özgür, Mehtap</au><au>Kılıç, Zeynel</au><au>Kayalak, Hande</au><au>Açık, Leyla</au><au>Türk, Mustafa</au><au>Hökelek, Tuncer</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm</atitle><jtitle>Inorganica Chimica Acta</jtitle><date>2019-09-01</date><risdate>2019</risdate><volume>495</volume><spage>118949</spage><pages>118949-</pages><artnum>118949</artnum><issn>0020-1693</issn><eissn>1873-3255</eissn><abstract>[Display omitted] •The (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm were prepared.•The structures of these compounds were determined using spectroscopic methods.•The crystal structures of four phosphazenes were established.•The antimicrobial and cytotoxic activities of the compounds were investigated.•The interactions between the compounds and pBR322 plasmid DNA were examined. In the present study, the partly and fully-substituted monospiro (4–6, 4a-6d), cis-dispiro (7–9), trans-dispiro (10–15) cyclotriphosphazenes were synthesized for the investigations of their chemical, stereogenic and biological properties. The cis/trans phosphazenes (7–12) have two stereogenic P centers. They are expected to be in meso and racemic forms. In addition, the structures of four compounds were evaluated using X-ray crystallographic data. Compound 13 was found to be a single enantiomer (RR) in the solid state, as also proved with its CD spectrum. The antibacterial and antifungal activities of the phosphazenes were elucidated for against Gram-positive (G+) and Gram-negative (G−) bacteria, and yeast strains, respectively.Of the compounds, 14 exhibits strong antimicrobial activity against most of the tested organisms, especially B. cereus and E. hirae. MBC and MFC values of compounds on different bacterial and fungal species ranged from &lt;9.8 µM to 2500 µM.Furthermore, the cytotoxic activities of 6, 4c, 10 and 14 were investigated against L929 fibroblast and DLD-1 cells, and 14 was the most cytotoxic compound against DLD-1.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.ica.2019.05.048</doi></addata></record>
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subjects Antimicrobial activity
Antimicrobial agents
Biological properties
Crystal structure
Crystallography
Cytotoxicity
DNA cleavage
Enantiomers
Fungicides
Monospiro and dispiroferrocenylphosphazenes
Nitrogen compounds
Organic chemistry
Spectroscopy
Yeast
title Phosphorus-nitrogen compounds: Part 46. The reactions of N3P3Cl6 with bidentate and monodentate ligands: The syntheses, structural characterizations, antimicrobial and cytotoxic activities, and DNA interactions of (N/N)spirocyclotriphosphazenes with 4-chlorobenzyl pendant arm
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