Searching for new derivatives of neocryptolepine: synthesis, antiproliferative, antimicrobial and antifungal activities
A series of novel amino acid and dipeptide derivatives of neocryptolepine were synthesized and tested for their antimicrobial, antifungal and antiproliferative activity in vitro against cancer cell lines (KB, A549, MCF-7, LoVo) and normal mice fibroblast cells (BALB/3T3). Biological evaluation revea...
Gespeichert in:
| Veröffentlicht in: | European journal of medicinal chemistry 2014-05, Vol.78, p.304-313 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 313 |
|---|---|
| container_issue | |
| container_start_page | 304 |
| container_title | European journal of medicinal chemistry |
| container_volume | 78 |
| creator | Sidoryk, Katarzyna Jaromin, Anna Edward, Jessica A Świtalska, Marta Stefańska, Joanna Cmoch, Piotr Zagrodzka, Joanna Szczepek, Wojciech Peczyńska-Czoch, Wanda Wietrzyk, Joanna Kozubek, Arkadiusz Zarnowski, Robert Andes, David R Kaczmarek, Łukasz |
| description | A series of novel amino acid and dipeptide derivatives of neocryptolepine were synthesized and tested for their antimicrobial, antifungal and antiproliferative activity in vitro against cancer cell lines (KB, A549, MCF-7, LoVo) and normal mice fibroblast cells (BALB/3T3). Biological evaluation revealed that almost all of the new compounds displayed high antiproliferative activity against the tested cells and moderate to potent antibacterial activities. Interestingly, these compounds were active against Candida albicans biofilms at doses significantly lower than those required against free-floating planktonic fungal cells. The most promising compounds are derivatives with glycine and L-proline as a substituent both at 2 and at 9 position of 5H-indolo[2,3-b]quinoline. In general, these new compounds (2a, 3a, 6a and 7a) showed the highest dual action against cancer lines and infectious pathogenic microbes in vitro. |
| doi_str_mv | 10.1016/j.ejmech.2014.03.060 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1516400605</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1516400605</sourcerecordid><originalsourceid>FETCH-LOGICAL-c307t-5c37a5b5a6ef3c851becca0dd347df850cac114d016ac2db374b7273388e8173</originalsourceid><addsrcrecordid>eNo9kElPwzAQhS0EoqXwDxDKkQMJ49iOI24IsUmVONC75TiT1lE27LRV_z3uAqfRPL03y0fILYWEAs0e6wTrFs0qSYHyBFgCGZyRKZVZHrNU8HMyhTRlsUgZn5Ar72sAEBnAJZmkPMszoHJKtt-onVnZbhlVvYs63EYlOrvRo92gj_oqSL1xu2HsGxxsh0-R33XjCr31D5HuRju4vrEVukPiKLXWuL6wugldeVCqdbfctyaY7GjRX5OLSjceb051RhZvr4uXj3j-9f758jyPDQM5xsIwqUUhdIYVM7mgBRqjoSwZl2WVCzDaUMrLAESbtCyY5IVMJWN5jjmVbEbuj2PDlT9r9KNqrTfYNDq8tfaKCppxCOREsPKjNdzuvcNKDc622u0UBbUnrmp1JK72xBUwFXIhdnfasC5aLP9Df4jZLz_3gfE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1516400605</pqid></control><display><type>article</type><title>Searching for new derivatives of neocryptolepine: synthesis, antiproliferative, antimicrobial and antifungal activities</title><source>MEDLINE</source><source>ScienceDirect Journals (5 years ago - present)</source><creator>Sidoryk, Katarzyna ; Jaromin, Anna ; Edward, Jessica A ; Świtalska, Marta ; Stefańska, Joanna ; Cmoch, Piotr ; Zagrodzka, Joanna ; Szczepek, Wojciech ; Peczyńska-Czoch, Wanda ; Wietrzyk, Joanna ; Kozubek, Arkadiusz ; Zarnowski, Robert ; Andes, David R ; Kaczmarek, Łukasz</creator><creatorcontrib>Sidoryk, Katarzyna ; Jaromin, Anna ; Edward, Jessica A ; Świtalska, Marta ; Stefańska, Joanna ; Cmoch, Piotr ; Zagrodzka, Joanna ; Szczepek, Wojciech ; Peczyńska-Czoch, Wanda ; Wietrzyk, Joanna ; Kozubek, Arkadiusz ; Zarnowski, Robert ; Andes, David R ; Kaczmarek, Łukasz</creatorcontrib><description>A series of novel amino acid and dipeptide derivatives of neocryptolepine were synthesized and tested for their antimicrobial, antifungal and antiproliferative activity in vitro against cancer cell lines (KB, A549, MCF-7, LoVo) and normal mice fibroblast cells (BALB/3T3). Biological evaluation revealed that almost all of the new compounds displayed high antiproliferative activity against the tested cells and moderate to potent antibacterial activities. Interestingly, these compounds were active against Candida albicans biofilms at doses significantly lower than those required against free-floating planktonic fungal cells. The most promising compounds are derivatives with glycine and L-proline as a substituent both at 2 and at 9 position of 5H-indolo[2,3-b]quinoline. In general, these new compounds (2a, 3a, 6a and 7a) showed the highest dual action against cancer lines and infectious pathogenic microbes in vitro.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2014.03.060</identifier><identifier>PMID: 24686017</identifier><language>eng</language><publisher>France</publisher><subject>Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Alkaloids - pharmacology ; Animals ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; BALB 3T3 Cells ; Biofilms - drug effects ; Candida albicans - drug effects ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Fibroblasts - drug effects ; Humans ; MCF-7 Cells ; Mice ; Mice, Inbred BALB C ; Microbial Sensitivity Tests ; Molecular Structure ; Quinolines - chemical synthesis ; Quinolines - chemistry ; Quinolines - pharmacology ; Structure-Activity Relationship</subject><ispartof>European journal of medicinal chemistry, 2014-05, Vol.78, p.304-313</ispartof><rights>Copyright © 2014 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c307t-5c37a5b5a6ef3c851becca0dd347df850cac114d016ac2db374b7273388e8173</citedby><cites>FETCH-LOGICAL-c307t-5c37a5b5a6ef3c851becca0dd347df850cac114d016ac2db374b7273388e8173</cites><orcidid>0000-0001-8222-8380</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24686017$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sidoryk, Katarzyna</creatorcontrib><creatorcontrib>Jaromin, Anna</creatorcontrib><creatorcontrib>Edward, Jessica A</creatorcontrib><creatorcontrib>Świtalska, Marta</creatorcontrib><creatorcontrib>Stefańska, Joanna</creatorcontrib><creatorcontrib>Cmoch, Piotr</creatorcontrib><creatorcontrib>Zagrodzka, Joanna</creatorcontrib><creatorcontrib>Szczepek, Wojciech</creatorcontrib><creatorcontrib>Peczyńska-Czoch, Wanda</creatorcontrib><creatorcontrib>Wietrzyk, Joanna</creatorcontrib><creatorcontrib>Kozubek, Arkadiusz</creatorcontrib><creatorcontrib>Zarnowski, Robert</creatorcontrib><creatorcontrib>Andes, David R</creatorcontrib><creatorcontrib>Kaczmarek, Łukasz</creatorcontrib><title>Searching for new derivatives of neocryptolepine: synthesis, antiproliferative, antimicrobial and antifungal activities</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of novel amino acid and dipeptide derivatives of neocryptolepine were synthesized and tested for their antimicrobial, antifungal and antiproliferative activity in vitro against cancer cell lines (KB, A549, MCF-7, LoVo) and normal mice fibroblast cells (BALB/3T3). Biological evaluation revealed that almost all of the new compounds displayed high antiproliferative activity against the tested cells and moderate to potent antibacterial activities. Interestingly, these compounds were active against Candida albicans biofilms at doses significantly lower than those required against free-floating planktonic fungal cells. The most promising compounds are derivatives with glycine and L-proline as a substituent both at 2 and at 9 position of 5H-indolo[2,3-b]quinoline. In general, these new compounds (2a, 3a, 6a and 7a) showed the highest dual action against cancer lines and infectious pathogenic microbes in vitro.</description><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>BALB 3T3 Cells</subject><subject>Biofilms - drug effects</subject><subject>Candida albicans - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Fibroblasts - drug effects</subject><subject>Humans</subject><subject>MCF-7 Cells</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Quinolines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kElPwzAQhS0EoqXwDxDKkQMJ49iOI24IsUmVONC75TiT1lE27LRV_z3uAqfRPL03y0fILYWEAs0e6wTrFs0qSYHyBFgCGZyRKZVZHrNU8HMyhTRlsUgZn5Ar72sAEBnAJZmkPMszoHJKtt-onVnZbhlVvYs63EYlOrvRo92gj_oqSL1xu2HsGxxsh0-R33XjCr31D5HuRju4vrEVukPiKLXWuL6wugldeVCqdbfctyaY7GjRX5OLSjceb051RhZvr4uXj3j-9f758jyPDQM5xsIwqUUhdIYVM7mgBRqjoSwZl2WVCzDaUMrLAESbtCyY5IVMJWN5jjmVbEbuj2PDlT9r9KNqrTfYNDq8tfaKCppxCOREsPKjNdzuvcNKDc622u0UBbUnrmp1JK72xBUwFXIhdnfasC5aLP9Df4jZLz_3gfE</recordid><startdate>20140506</startdate><enddate>20140506</enddate><creator>Sidoryk, Katarzyna</creator><creator>Jaromin, Anna</creator><creator>Edward, Jessica A</creator><creator>Świtalska, Marta</creator><creator>Stefańska, Joanna</creator><creator>Cmoch, Piotr</creator><creator>Zagrodzka, Joanna</creator><creator>Szczepek, Wojciech</creator><creator>Peczyńska-Czoch, Wanda</creator><creator>Wietrzyk, Joanna</creator><creator>Kozubek, Arkadiusz</creator><creator>Zarnowski, Robert</creator><creator>Andes, David R</creator><creator>Kaczmarek, Łukasz</creator><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>7X8</scope><orcidid>https://orcid.org/0000-0001-8222-8380</orcidid></search><sort><creationdate>20140506</creationdate><title>Searching for new derivatives of neocryptolepine: synthesis, antiproliferative, antimicrobial and antifungal activities</title><author>Sidoryk, Katarzyna ; Jaromin, Anna ; Edward, Jessica A ; Świtalska, Marta ; Stefańska, Joanna ; Cmoch, Piotr ; Zagrodzka, Joanna ; Szczepek, Wojciech ; Peczyńska-Czoch, Wanda ; Wietrzyk, Joanna ; Kozubek, Arkadiusz ; Zarnowski, Robert ; Andes, David R ; Kaczmarek, Łukasz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c307t-5c37a5b5a6ef3c851becca0dd347df850cac114d016ac2db374b7273388e8173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - pharmacology</topic><topic>Animals</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>BALB 3T3 Cells</topic><topic>Biofilms - drug effects</topic><topic>Candida albicans - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Fibroblasts - drug effects</topic><topic>Humans</topic><topic>MCF-7 Cells</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - chemistry</topic><topic>Quinolines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sidoryk, Katarzyna</creatorcontrib><creatorcontrib>Jaromin, Anna</creatorcontrib><creatorcontrib>Edward, Jessica A</creatorcontrib><creatorcontrib>Świtalska, Marta</creatorcontrib><creatorcontrib>Stefańska, Joanna</creatorcontrib><creatorcontrib>Cmoch, Piotr</creatorcontrib><creatorcontrib>Zagrodzka, Joanna</creatorcontrib><creatorcontrib>Szczepek, Wojciech</creatorcontrib><creatorcontrib>Peczyńska-Czoch, Wanda</creatorcontrib><creatorcontrib>Wietrzyk, Joanna</creatorcontrib><creatorcontrib>Kozubek, Arkadiusz</creatorcontrib><creatorcontrib>Zarnowski, Robert</creatorcontrib><creatorcontrib>Andes, David R</creatorcontrib><creatorcontrib>Kaczmarek, Łukasz</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sidoryk, Katarzyna</au><au>Jaromin, Anna</au><au>Edward, Jessica A</au><au>Świtalska, Marta</au><au>Stefańska, Joanna</au><au>Cmoch, Piotr</au><au>Zagrodzka, Joanna</au><au>Szczepek, Wojciech</au><au>Peczyńska-Czoch, Wanda</au><au>Wietrzyk, Joanna</au><au>Kozubek, Arkadiusz</au><au>Zarnowski, Robert</au><au>Andes, David R</au><au>Kaczmarek, Łukasz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Searching for new derivatives of neocryptolepine: synthesis, antiproliferative, antimicrobial and antifungal activities</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2014-05-06</date><risdate>2014</risdate><volume>78</volume><spage>304</spage><epage>313</epage><pages>304-313</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>A series of novel amino acid and dipeptide derivatives of neocryptolepine were synthesized and tested for their antimicrobial, antifungal and antiproliferative activity in vitro against cancer cell lines (KB, A549, MCF-7, LoVo) and normal mice fibroblast cells (BALB/3T3). Biological evaluation revealed that almost all of the new compounds displayed high antiproliferative activity against the tested cells and moderate to potent antibacterial activities. Interestingly, these compounds were active against Candida albicans biofilms at doses significantly lower than those required against free-floating planktonic fungal cells. The most promising compounds are derivatives with glycine and L-proline as a substituent both at 2 and at 9 position of 5H-indolo[2,3-b]quinoline. In general, these new compounds (2a, 3a, 6a and 7a) showed the highest dual action against cancer lines and infectious pathogenic microbes in vitro.</abstract><cop>France</cop><pmid>24686017</pmid><doi>10.1016/j.ejmech.2014.03.060</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-8222-8380</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2014-05, Vol.78, p.304-313 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1516400605 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Alkaloids - chemical synthesis Alkaloids - chemistry Alkaloids - pharmacology Animals Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology BALB 3T3 Cells Biofilms - drug effects Candida albicans - drug effects Cell Line, Tumor Cell Proliferation - drug effects Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Fibroblasts - drug effects Humans MCF-7 Cells Mice Mice, Inbred BALB C Microbial Sensitivity Tests Molecular Structure Quinolines - chemical synthesis Quinolines - chemistry Quinolines - pharmacology Structure-Activity Relationship |
| title | Searching for new derivatives of neocryptolepine: synthesis, antiproliferative, antimicrobial and antifungal activities |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T16%3A35%3A54IST&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=Searching%20for%20new%20derivatives%20of%20neocryptolepine:%20synthesis,%20antiproliferative,%20antimicrobial%20and%20antifungal%20activities&rft.jtitle=European%20journal%20of%20medicinal%20chemistry&rft.au=Sidoryk,%20Katarzyna&rft.date=2014-05-06&rft.volume=78&rft.spage=304&rft.epage=313&rft.pages=304-313&rft.issn=0223-5234&rft.eissn=1768-3254&rft_id=info:doi/10.1016/j.ejmech.2014.03.060&rft_dat=%3Cproquest_cross%3E1516400605%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=1516400605&rft_id=info:pmid/24686017&rfr_iscdi=true |