The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum
Bisnaphthalimidopropyl derivatives (BNIPSpd, BNIPDaoct, BNIPDanon, BNIPDadec, BNIPDpta and BNIPDeta) were synthesised in yields ranging from 50% to 70% and their cytotoxicity against colon cancer cells (Caco-2) and the parasite Leishmania infantum determined using the MTT assay. Cytotoxicity within...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007, Vol.15 (1), p.541-545 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Oliveira, João Ralton, Lynda Tavares, Joana Codeiro-da-Silva, Anabela Bestwick, Charles S. McPherson, Anne Thoo Lin, Paul Kong |
| description | Bisnaphthalimidopropyl derivatives (BNIPSpd, BNIPDaoct, BNIPDanon, BNIPDadec, BNIPDpta and BNIPDeta) were synthesised in yields ranging from 50% to 70% and their cytotoxicity against colon cancer cells (Caco-2) and the parasite
Leishmania infantum determined using the MTT assay. Cytotoxicity within Caco-2 cells was manifested with IC
50 values between 0.3 and 22
μM. Compounds with the central longer alkyl chains exhibited the highest cytotoxicity. Against
L. infantum, IC
50 values were encompassed within a narrower concentration range of 0.47–1.54
μM. In the parasites, the presence of nitrogen in the central chain and the length of the central alkyl chains did not especially enhance cytotoxicity. This may be due to the way these compounds are transported in the cells. |
| doi_str_mv | 10.1016/j.bmc.2006.09.031 |
| format | Article |
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Leishmania infantum determined using the MTT assay. Cytotoxicity within Caco-2 cells was manifested with IC
50 values between 0.3 and 22
μM. Compounds with the central longer alkyl chains exhibited the highest cytotoxicity. Against
L. infantum, IC
50 values were encompassed within a narrower concentration range of 0.47–1.54
μM. In the parasites, the presence of nitrogen in the central chain and the length of the central alkyl chains did not especially enhance cytotoxicity. This may be due to the way these compounds are transported in the cells.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2006.09.031</identifier><identifier>PMID: 17010616</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Animals ; Anticancer ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antiparasitic activity ; Antiparasitic Agents - chemical synthesis ; Antiparasitic Agents - chemistry ; Antiparasitic Agents - pharmacology ; Bisnaphthalimidopropyl ; Caco-2 Cells ; Cell Proliferation - drug effects ; Colonic Neoplasms - drug therapy ; Drug Screening Assays, Antitumor ; Humans ; Leishmania infantum ; Leishmania infantum - drug effects ; Molecular Structure ; Parasitic Sensitivity Tests ; Polyamines ; Polyamines - chemical synthesis ; Polyamines - chemistry ; Polyamines - pharmacology ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry, 2007, Vol.15 (1), p.541-545</ispartof><rights>2006 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c448t-121d1c88ed87337354b145967ad77eb166bdfc7db50266e58c21b686c0f1f5433</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2006.09.031$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,4025,27928,27929,27930,46000</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17010616$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Oliveira, João</creatorcontrib><creatorcontrib>Ralton, Lynda</creatorcontrib><creatorcontrib>Tavares, Joana</creatorcontrib><creatorcontrib>Codeiro-da-Silva, Anabela</creatorcontrib><creatorcontrib>Bestwick, Charles S.</creatorcontrib><creatorcontrib>McPherson, Anne</creatorcontrib><creatorcontrib>Thoo Lin, Paul Kong</creatorcontrib><title>The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Bisnaphthalimidopropyl derivatives (BNIPSpd, BNIPDaoct, BNIPDanon, BNIPDadec, BNIPDpta and BNIPDeta) were synthesised in yields ranging from 50% to 70% and their cytotoxicity against colon cancer cells (Caco-2) and the parasite
Leishmania infantum determined using the MTT assay. Cytotoxicity within Caco-2 cells was manifested with IC
50 values between 0.3 and 22
μM. Compounds with the central longer alkyl chains exhibited the highest cytotoxicity. Against
L. infantum, IC
50 values were encompassed within a narrower concentration range of 0.47–1.54
μM. In the parasites, the presence of nitrogen in the central chain and the length of the central alkyl chains did not especially enhance cytotoxicity. This may be due to the way these compounds are transported in the cells.</description><subject>Animals</subject><subject>Anticancer</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiparasitic activity</subject><subject>Antiparasitic Agents - chemical synthesis</subject><subject>Antiparasitic Agents - chemistry</subject><subject>Antiparasitic Agents - pharmacology</subject><subject>Bisnaphthalimidopropyl</subject><subject>Caco-2 Cells</subject><subject>Cell Proliferation - drug effects</subject><subject>Colonic Neoplasms - drug therapy</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Leishmania infantum</subject><subject>Leishmania infantum - drug effects</subject><subject>Molecular Structure</subject><subject>Parasitic Sensitivity Tests</subject><subject>Polyamines</subject><subject>Polyamines - chemical synthesis</subject><subject>Polyamines - chemistry</subject><subject>Polyamines - pharmacology</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkb2u1DAQRiME4i4XHoAGuaJLsBPHcUSFrviTVqK51JZjT8isEjvYzoo8Da-KV7sSHVTj4sw34zlF8ZrRilEm3p2qYTFVTamoaF_Rhj0pDowLXjZNz54WB9oLWVLZi7viRYwnSmnNe_a8uGMdZVQwcSh-P05A4u7SBBEj0c6S_CToyBlT8MTsySf_Cw2mncS0WYRI_EgGjE6vU5r0jAtavwa_7jNZ_bzrBR0QCwHPOuE58_qHRhcTMX72jhjtDARiYJ6vA1cddMQE5AgYp0U71HmBUbu0LS-LZ6OeI7y61fvi-6ePjw9fyuO3z18fPhxLw7lMJauZZUZKsLJrmq5p-cB424tO266DgQkx2NF0dmhpLQS00tRsEFIYOrKx5U1zX7y95uaP_NwgJrVgvKyoHfgtKiGbtuWi_S_I-qaTPeUZZFfQBB9jgFGtARcddsWouuhTJ5X1qYs-RXuV9eWeN7fwbVjA_u24-crA-ysA-RZnhKCiQcj3tBjAJGU9_iP-D3FqryQ</recordid><startdate>2007</startdate><enddate>2007</enddate><creator>Oliveira, João</creator><creator>Ralton, Lynda</creator><creator>Tavares, Joana</creator><creator>Codeiro-da-Silva, Anabela</creator><creator>Bestwick, Charles S.</creator><creator>McPherson, Anne</creator><creator>Thoo Lin, Paul Kong</creator><general>Elsevier Ltd</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>2007</creationdate><title>The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum</title><author>Oliveira, João ; Ralton, Lynda ; Tavares, Joana ; Codeiro-da-Silva, Anabela ; Bestwick, Charles S. ; McPherson, Anne ; Thoo Lin, Paul Kong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c448t-121d1c88ed87337354b145967ad77eb166bdfc7db50266e58c21b686c0f1f5433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Animals</topic><topic>Anticancer</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiparasitic activity</topic><topic>Antiparasitic Agents - chemical synthesis</topic><topic>Antiparasitic Agents - chemistry</topic><topic>Antiparasitic Agents - pharmacology</topic><topic>Bisnaphthalimidopropyl</topic><topic>Caco-2 Cells</topic><topic>Cell Proliferation - drug effects</topic><topic>Colonic Neoplasms - drug therapy</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Leishmania infantum</topic><topic>Leishmania infantum - drug effects</topic><topic>Molecular Structure</topic><topic>Parasitic Sensitivity Tests</topic><topic>Polyamines</topic><topic>Polyamines - chemical synthesis</topic><topic>Polyamines - chemistry</topic><topic>Polyamines - pharmacology</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Oliveira, João</creatorcontrib><creatorcontrib>Ralton, Lynda</creatorcontrib><creatorcontrib>Tavares, Joana</creatorcontrib><creatorcontrib>Codeiro-da-Silva, Anabela</creatorcontrib><creatorcontrib>Bestwick, Charles S.</creatorcontrib><creatorcontrib>McPherson, Anne</creatorcontrib><creatorcontrib>Thoo Lin, Paul Kong</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Oliveira, João</au><au>Ralton, Lynda</au><au>Tavares, Joana</au><au>Codeiro-da-Silva, Anabela</au><au>Bestwick, Charles S.</au><au>McPherson, Anne</au><au>Thoo Lin, Paul Kong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2007</date><risdate>2007</risdate><volume>15</volume><issue>1</issue><spage>541</spage><epage>545</epage><pages>541-545</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Bisnaphthalimidopropyl derivatives (BNIPSpd, BNIPDaoct, BNIPDanon, BNIPDadec, BNIPDpta and BNIPDeta) were synthesised in yields ranging from 50% to 70% and their cytotoxicity against colon cancer cells (Caco-2) and the parasite
Leishmania infantum determined using the MTT assay. Cytotoxicity within Caco-2 cells was manifested with IC
50 values between 0.3 and 22
μM. Compounds with the central longer alkyl chains exhibited the highest cytotoxicity. Against
L. infantum, IC
50 values were encompassed within a narrower concentration range of 0.47–1.54
μM. In the parasites, the presence of nitrogen in the central chain and the length of the central alkyl chains did not especially enhance cytotoxicity. This may be due to the way these compounds are transported in the cells.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>17010616</pmid><doi>10.1016/j.bmc.2006.09.031</doi><tpages>5</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2007, Vol.15 (1), p.541-545 |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Animals Anticancer Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiparasitic activity Antiparasitic Agents - chemical synthesis Antiparasitic Agents - chemistry Antiparasitic Agents - pharmacology Bisnaphthalimidopropyl Caco-2 Cells Cell Proliferation - drug effects Colonic Neoplasms - drug therapy Drug Screening Assays, Antitumor Humans Leishmania infantum Leishmania infantum - drug effects Molecular Structure Parasitic Sensitivity Tests Polyamines Polyamines - chemical synthesis Polyamines - chemistry Polyamines - pharmacology Stereoisomerism Structure-Activity Relationship |
| title | The synthesis and the in vitro cytotoxicity studies of bisnaphthalimidopropyl polyamine derivatives against colon cancer cells and parasite Leishmania infantum |
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