Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets
Two new tetralkylammonium‐OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two β‐d‐glucopyranose terminations, were synthesized. Their peculiar structural features, joining the biologically relevant sugar moieties, flat aromatic cores and positive charg...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2018-11, Vol.24 (64), p.16972-16976 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 16976 |
|---|---|
| container_issue | 64 |
| container_start_page | 16972 |
| container_title | Chemistry : a European journal |
| container_volume | 24 |
| creator | Mancuso, Aurora Barattucci, Anna Bonaccorsi, Paola Giannetto, Antonino La Ganga, Giuseppina Musarra‐Pizzo, Maria Salerno, Tania M. G. Santoro, Antonio Sciortino, Maria Teresa Puntoriero, Fausto Di Pietro, Maria Letizia |
| description | Two new tetralkylammonium‐OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two β‐d‐glucopyranose terminations, were synthesized. Their peculiar structural features, joining the biologically relevant sugar moieties, flat aromatic cores and positive charges, make these luminescent dyes soluble in aqueous media and able to strongly interact with DNA. As a result of UV/Vis spectral variations, DNA melting temperature measures, viscometric titrations and induced CD, we propose a partial insertion of the OPEs aromatic core into the helix, stabilized by glucose H‐bonding with the groups accessible from the grooves. This interaction leads to the quenching of the OPE luminescence due to guanine reduction. The biocompatibility of the monocationic OPE with healthy and cancer cells, and the reduction of proliferation in HEp‐2 cancer cells induced by the dicationic one, make this class of compounds promising for future biological applications.
Cooperation of biologically relevant sugar moieties, flat aromatic cores, and positive charges makes two new tetralkylammonium‐OPEs able to strongly interact with DNA, leading to the quenching of their luminescence due to guanine reduction (OPEs=oligo(phenylenethynylenes)). The new species are not cytotoxic on healthy cells (Vero), whereas the dicationic one is able to inhibit cancer cells (HEp‐2) proliferation. |
| doi_str_mv | 10.1002/chem.201803804 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2101913383</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2101913383</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3734-bd8a499e699ed4fe7d2917651cd128258c6f15f07f3403c373cc82509ef22af63</originalsourceid><addsrcrecordid>eNqFkLtPwzAQhy0EouWxMiJLLDCk-JGHzQbhUSQQC4wocp1zkyqNi50I5b_HVaFILAynO1nfffL9EDqhZEIJYZe6guWEESoIFyTeQWOaMBrxLE120ZjIOIvShMsROvB-QQiRKef7aMQJlSJldIzec-VmthpKpzrwWLUlzivl5mG2LX5p6rk9X1XQDg200FXDZvAXV_jVfipXetxVgG_B1_MWW4Nz1Wpw-KZvGuj8EdozqvFw_N0P0dv93Ws-jZ5eHh7z66dI84zH0awUKpYS0lBlbCArmaThBKpLygRLhE4NTQzJDI8JX-9oHZ6JBMOYMik_ROcb78rZjx58Vyxrr6FpVAu29wWj4WDKueABPfuDLmzv2vC7QPEkjYVI1sLJhtLOeu_AFCtXL5UbCkqKdfDFOvhiG3xYOP3W9rMllFv8J-kAyA3wWTcw_KMr8und86_8C3FpjlY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2135648856</pqid></control><display><type>article</type><title>Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets</title><source>MEDLINE</source><source>Wiley Journals</source><creator>Mancuso, Aurora ; Barattucci, Anna ; Bonaccorsi, Paola ; Giannetto, Antonino ; La Ganga, Giuseppina ; Musarra‐Pizzo, Maria ; Salerno, Tania M. G. ; Santoro, Antonio ; Sciortino, Maria Teresa ; Puntoriero, Fausto ; Di Pietro, Maria Letizia</creator><creatorcontrib>Mancuso, Aurora ; Barattucci, Anna ; Bonaccorsi, Paola ; Giannetto, Antonino ; La Ganga, Giuseppina ; Musarra‐Pizzo, Maria ; Salerno, Tania M. G. ; Santoro, Antonio ; Sciortino, Maria Teresa ; Puntoriero, Fausto ; Di Pietro, Maria Letizia</creatorcontrib><description>Two new tetralkylammonium‐OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two β‐d‐glucopyranose terminations, were synthesized. Their peculiar structural features, joining the biologically relevant sugar moieties, flat aromatic cores and positive charges, make these luminescent dyes soluble in aqueous media and able to strongly interact with DNA. As a result of UV/Vis spectral variations, DNA melting temperature measures, viscometric titrations and induced CD, we propose a partial insertion of the OPEs aromatic core into the helix, stabilized by glucose H‐bonding with the groups accessible from the grooves. This interaction leads to the quenching of the OPE luminescence due to guanine reduction. The biocompatibility of the monocationic OPE with healthy and cancer cells, and the reduction of proliferation in HEp‐2 cancer cells induced by the dicationic one, make this class of compounds promising for future biological applications.
Cooperation of biologically relevant sugar moieties, flat aromatic cores, and positive charges makes two new tetralkylammonium‐OPEs able to strongly interact with DNA, leading to the quenching of their luminescence due to guanine reduction (OPEs=oligo(phenylenethynylenes)). The new species are not cytotoxic on healthy cells (Vero), whereas the dicationic one is able to inhibit cancer cells (HEp‐2) proliferation.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201803804</identifier><identifier>PMID: 30198621</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Animals ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - metabolism ; Antineoplastic Agents - pharmacology ; Biocompatibility ; Cancer ; Carbohydrates ; Carbohydrates - chemistry ; Cell Line, Tumor ; Cell Proliferation ; Cercopithecus aethiops ; Chemistry ; Circular Dichroism ; Deoxyribonucleic acid ; DNA ; DNA - chemistry ; DNA - metabolism ; Drug Design ; Grooves ; Guanine ; Humans ; Kinetics ; luminescence quenching ; Melt temperature ; OPEs ; Polymers - chemistry ; Projectiles ; Reduction ; Spectrophotometry ; Sugar ; Transition Temperature ; Vero Cells</subject><ispartof>Chemistry : a European journal, 2018-11, Vol.24 (64), p.16972-16976</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3734-bd8a499e699ed4fe7d2917651cd128258c6f15f07f3403c373cc82509ef22af63</citedby><cites>FETCH-LOGICAL-c3734-bd8a499e699ed4fe7d2917651cd128258c6f15f07f3403c373cc82509ef22af63</cites><orcidid>0000-0002-2015-3747 ; 0000-0002-2415-5483 ; 0000-0001-8579-859X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201803804$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201803804$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30198621$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mancuso, Aurora</creatorcontrib><creatorcontrib>Barattucci, Anna</creatorcontrib><creatorcontrib>Bonaccorsi, Paola</creatorcontrib><creatorcontrib>Giannetto, Antonino</creatorcontrib><creatorcontrib>La Ganga, Giuseppina</creatorcontrib><creatorcontrib>Musarra‐Pizzo, Maria</creatorcontrib><creatorcontrib>Salerno, Tania M. G.</creatorcontrib><creatorcontrib>Santoro, Antonio</creatorcontrib><creatorcontrib>Sciortino, Maria Teresa</creatorcontrib><creatorcontrib>Puntoriero, Fausto</creatorcontrib><creatorcontrib>Di Pietro, Maria Letizia</creatorcontrib><title>Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Two new tetralkylammonium‐OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two β‐d‐glucopyranose terminations, were synthesized. Their peculiar structural features, joining the biologically relevant sugar moieties, flat aromatic cores and positive charges, make these luminescent dyes soluble in aqueous media and able to strongly interact with DNA. As a result of UV/Vis spectral variations, DNA melting temperature measures, viscometric titrations and induced CD, we propose a partial insertion of the OPEs aromatic core into the helix, stabilized by glucose H‐bonding with the groups accessible from the grooves. This interaction leads to the quenching of the OPE luminescence due to guanine reduction. The biocompatibility of the monocationic OPE with healthy and cancer cells, and the reduction of proliferation in HEp‐2 cancer cells induced by the dicationic one, make this class of compounds promising for future biological applications.
Cooperation of biologically relevant sugar moieties, flat aromatic cores, and positive charges makes two new tetralkylammonium‐OPEs able to strongly interact with DNA, leading to the quenching of their luminescence due to guanine reduction (OPEs=oligo(phenylenethynylenes)). The new species are not cytotoxic on healthy cells (Vero), whereas the dicationic one is able to inhibit cancer cells (HEp‐2) proliferation.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - metabolism</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biocompatibility</subject><subject>Cancer</subject><subject>Carbohydrates</subject><subject>Carbohydrates - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation</subject><subject>Cercopithecus aethiops</subject><subject>Chemistry</subject><subject>Circular Dichroism</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>DNA - chemistry</subject><subject>DNA - metabolism</subject><subject>Drug Design</subject><subject>Grooves</subject><subject>Guanine</subject><subject>Humans</subject><subject>Kinetics</subject><subject>luminescence quenching</subject><subject>Melt temperature</subject><subject>OPEs</subject><subject>Polymers - chemistry</subject><subject>Projectiles</subject><subject>Reduction</subject><subject>Spectrophotometry</subject><subject>Sugar</subject><subject>Transition Temperature</subject><subject>Vero Cells</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkLtPwzAQhy0EouWxMiJLLDCk-JGHzQbhUSQQC4wocp1zkyqNi50I5b_HVaFILAynO1nfffL9EDqhZEIJYZe6guWEESoIFyTeQWOaMBrxLE120ZjIOIvShMsROvB-QQiRKef7aMQJlSJldIzec-VmthpKpzrwWLUlzivl5mG2LX5p6rk9X1XQDg200FXDZvAXV_jVfipXetxVgG_B1_MWW4Nz1Wpw-KZvGuj8EdozqvFw_N0P0dv93Ws-jZ5eHh7z66dI84zH0awUKpYS0lBlbCArmaThBKpLygRLhE4NTQzJDI8JX-9oHZ6JBMOYMik_ROcb78rZjx58Vyxrr6FpVAu29wWj4WDKueABPfuDLmzv2vC7QPEkjYVI1sLJhtLOeu_AFCtXL5UbCkqKdfDFOvhiG3xYOP3W9rMllFv8J-kAyA3wWTcw_KMr8und86_8C3FpjlY</recordid><startdate>20181116</startdate><enddate>20181116</enddate><creator>Mancuso, Aurora</creator><creator>Barattucci, Anna</creator><creator>Bonaccorsi, Paola</creator><creator>Giannetto, Antonino</creator><creator>La Ganga, Giuseppina</creator><creator>Musarra‐Pizzo, Maria</creator><creator>Salerno, Tania M. G.</creator><creator>Santoro, Antonio</creator><creator>Sciortino, Maria Teresa</creator><creator>Puntoriero, Fausto</creator><creator>Di Pietro, Maria Letizia</creator><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2015-3747</orcidid><orcidid>https://orcid.org/0000-0002-2415-5483</orcidid><orcidid>https://orcid.org/0000-0001-8579-859X</orcidid></search><sort><creationdate>20181116</creationdate><title>Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets</title><author>Mancuso, Aurora ; Barattucci, Anna ; Bonaccorsi, Paola ; Giannetto, Antonino ; La Ganga, Giuseppina ; Musarra‐Pizzo, Maria ; Salerno, Tania M. G. ; Santoro, Antonio ; Sciortino, Maria Teresa ; Puntoriero, Fausto ; Di Pietro, Maria Letizia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3734-bd8a499e699ed4fe7d2917651cd128258c6f15f07f3403c373cc82509ef22af63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - metabolism</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biocompatibility</topic><topic>Cancer</topic><topic>Carbohydrates</topic><topic>Carbohydrates - chemistry</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation</topic><topic>Cercopithecus aethiops</topic><topic>Chemistry</topic><topic>Circular Dichroism</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>DNA - chemistry</topic><topic>DNA - metabolism</topic><topic>Drug Design</topic><topic>Grooves</topic><topic>Guanine</topic><topic>Humans</topic><topic>Kinetics</topic><topic>luminescence quenching</topic><topic>Melt temperature</topic><topic>OPEs</topic><topic>Polymers - chemistry</topic><topic>Projectiles</topic><topic>Reduction</topic><topic>Spectrophotometry</topic><topic>Sugar</topic><topic>Transition Temperature</topic><topic>Vero Cells</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mancuso, Aurora</creatorcontrib><creatorcontrib>Barattucci, Anna</creatorcontrib><creatorcontrib>Bonaccorsi, Paola</creatorcontrib><creatorcontrib>Giannetto, Antonino</creatorcontrib><creatorcontrib>La Ganga, Giuseppina</creatorcontrib><creatorcontrib>Musarra‐Pizzo, Maria</creatorcontrib><creatorcontrib>Salerno, Tania M. G.</creatorcontrib><creatorcontrib>Santoro, Antonio</creatorcontrib><creatorcontrib>Sciortino, Maria Teresa</creatorcontrib><creatorcontrib>Puntoriero, Fausto</creatorcontrib><creatorcontrib>Di Pietro, Maria Letizia</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mancuso, Aurora</au><au>Barattucci, Anna</au><au>Bonaccorsi, Paola</au><au>Giannetto, Antonino</au><au>La Ganga, Giuseppina</au><au>Musarra‐Pizzo, Maria</au><au>Salerno, Tania M. G.</au><au>Santoro, Antonio</au><au>Sciortino, Maria Teresa</au><au>Puntoriero, Fausto</au><au>Di Pietro, Maria Letizia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2018-11-16</date><risdate>2018</risdate><volume>24</volume><issue>64</issue><spage>16972</spage><epage>16976</epage><pages>16972-16976</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Two new tetralkylammonium‐OPEs, bearing one or two positively charged groups directly linked to the aromatic residues and two β‐d‐glucopyranose terminations, were synthesized. Their peculiar structural features, joining the biologically relevant sugar moieties, flat aromatic cores and positive charges, make these luminescent dyes soluble in aqueous media and able to strongly interact with DNA. As a result of UV/Vis spectral variations, DNA melting temperature measures, viscometric titrations and induced CD, we propose a partial insertion of the OPEs aromatic core into the helix, stabilized by glucose H‐bonding with the groups accessible from the grooves. This interaction leads to the quenching of the OPE luminescence due to guanine reduction. The biocompatibility of the monocationic OPE with healthy and cancer cells, and the reduction of proliferation in HEp‐2 cancer cells induced by the dicationic one, make this class of compounds promising for future biological applications.
Cooperation of biologically relevant sugar moieties, flat aromatic cores, and positive charges makes two new tetralkylammonium‐OPEs able to strongly interact with DNA, leading to the quenching of their luminescence due to guanine reduction (OPEs=oligo(phenylenethynylenes)). The new species are not cytotoxic on healthy cells (Vero), whereas the dicationic one is able to inhibit cancer cells (HEp‐2) proliferation.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30198621</pmid><doi>10.1002/chem.201803804</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-2015-3747</orcidid><orcidid>https://orcid.org/0000-0002-2415-5483</orcidid><orcidid>https://orcid.org/0000-0001-8579-859X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2018-11, Vol.24 (64), p.16972-16976 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2101913383 |
| source | MEDLINE; Wiley Journals |
| subjects | Animals Antineoplastic Agents - chemistry Antineoplastic Agents - metabolism Antineoplastic Agents - pharmacology Biocompatibility Cancer Carbohydrates Carbohydrates - chemistry Cell Line, Tumor Cell Proliferation Cercopithecus aethiops Chemistry Circular Dichroism Deoxyribonucleic acid DNA DNA - chemistry DNA - metabolism Drug Design Grooves Guanine Humans Kinetics luminescence quenching Melt temperature OPEs Polymers - chemistry Projectiles Reduction Spectrophotometry Sugar Transition Temperature Vero Cells |
| title | Carbohydrates and Charges on Oligo(phenylenethynylenes): Towards the Design of Cancer Bullets |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T07%3A31%3A52IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Carbohydrates%20and%20Charges%20on%20Oligo(phenylenethynylenes):%20Towards%20the%20Design%20of%20Cancer%20Bullets&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Mancuso,%20Aurora&rft.date=2018-11-16&rft.volume=24&rft.issue=64&rft.spage=16972&rft.epage=16976&rft.pages=16972-16976&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.201803804&rft_dat=%3Cproquest_cross%3E2101913383%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2135648856&rft_id=info:pmid/30198621&rfr_iscdi=true |