Antimalarial, antiproliferative, and apoptotic activity of quinoline-chalcone and quinoline-pyrazoline hybrids. A dual action
A series of quinoline-chalcone (E) -1-[3 or 4-(7-chloroquinolin-4-ylamino) phenyl]-3-(phenyl substituted) prop-2-ene-1-one ( 4 , 5 ), and quinoline-pyrazoline hybrids 7-Chloro- N -[3 or 4-(4,5-dihydro-5-(phenyl-substituted)-1H-pyrazol-3-yl] phenyl) quinoline-4–amine ( 6 , 7 ) were synthesized with t...
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| Veröffentlicht in: | Medicinal chemistry research 2019-11, Vol.28 (11), p.2050-2066 |
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| creator | Charris, Jaime E. Monasterios, Melina C. Acosta, María E. Rodríguez, Miguel A. Gamboa, Neira D. Martínez, Gricelis P. Rojas, Héctor R. Mijares, Michael R. De Sanctis, Juan B. |
| description | A series of quinoline-chalcone
(E)
-1-[3 or 4-(7-chloroquinolin-4-ylamino) phenyl]-3-(phenyl substituted) prop-2-ene-1-one (
4
,
5
), and quinoline-pyrazoline hybrids 7-Chloro-
N
-[3 or 4-(4,5-dihydro-5-(phenyl-substituted)-1H-pyrazol-3-yl] phenyl) quinoline-4–amine (
6
,
7
) were synthesized with the aim of achieving an antimalarial and anticancer dual action. Most of the compounds showed significant inhibition (%>80) of β-hematin formation. The existing structures were tested in vivo as potential antimalarials in mice infected with
P. berghei
ANKA, chloroquine susceptible strain. Some of the compounds exhibited antimalarial activity comparable to that of chloroquine. Moreover, the compounds induce cell death on two human cancer cell lines (Jurkat E6.1 and HL60) without affecting the primary culture of human lymphocytes. Flow cytometry analysis confirmed the increase in apoptotic cell death after 24 h. Based on the structural analysis, these quinoline hybrids represent new compounds potentially useful for malaria end leukemia treatments. |
| doi_str_mv | 10.1007/s00044-019-02435-0 |
| format | Article |
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(E)
-1-[3 or 4-(7-chloroquinolin-4-ylamino) phenyl]-3-(phenyl substituted) prop-2-ene-1-one (
4
,
5
), and quinoline-pyrazoline hybrids 7-Chloro-
N
-[3 or 4-(4,5-dihydro-5-(phenyl-substituted)-1H-pyrazol-3-yl] phenyl) quinoline-4–amine (
6
,
7
) were synthesized with the aim of achieving an antimalarial and anticancer dual action. Most of the compounds showed significant inhibition (%>80) of β-hematin formation. The existing structures were tested in vivo as potential antimalarials in mice infected with
P. berghei
ANKA, chloroquine susceptible strain. Some of the compounds exhibited antimalarial activity comparable to that of chloroquine. Moreover, the compounds induce cell death on two human cancer cell lines (Jurkat E6.1 and HL60) without affecting the primary culture of human lymphocytes. Flow cytometry analysis confirmed the increase in apoptotic cell death after 24 h. Based on the structural analysis, these quinoline hybrids represent new compounds potentially useful for malaria end leukemia treatments.</description><identifier>ISSN: 1054-2523</identifier><identifier>EISSN: 1554-8120</identifier><identifier>DOI: 10.1007/s00044-019-02435-0</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Antimalarial activity ; Antimalarial agents ; Antiproliferatives ; Apoptosis ; Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Cell Biology ; Cell culture ; Cell death ; Chloroquine ; Flow cytometry ; Hybrids ; Lymphocytes ; Malaria ; Original Research ; Pharmacology/Toxicology ; Quinoline ; Structural analysis ; Substitutes ; Tumor cell lines</subject><ispartof>Medicinal chemistry research, 2019-11, Vol.28 (11), p.2050-2066</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2019</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-a5eaa9d2421736ee23f8c6a2121fcb20cb6aaf2943ab02d4e81fad8050ac6dcf3</citedby><cites>FETCH-LOGICAL-c319t-a5eaa9d2421736ee23f8c6a2121fcb20cb6aaf2943ab02d4e81fad8050ac6dcf3</cites><orcidid>0000-0001-6610-5516 ; 0000-0003-0090-7684 ; 0000-0002-5480-4608 ; 0000-0003-4335-3052 ; 0000-0003-0721-0046 ; 0000-0002-0055-2804 ; 0000-0002-8204-0174 ; 0000-0003-4404-2619 ; 0000-0002-9918-0413</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00044-019-02435-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00044-019-02435-0$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Charris, Jaime E.</creatorcontrib><creatorcontrib>Monasterios, Melina C.</creatorcontrib><creatorcontrib>Acosta, María E.</creatorcontrib><creatorcontrib>Rodríguez, Miguel A.</creatorcontrib><creatorcontrib>Gamboa, Neira D.</creatorcontrib><creatorcontrib>Martínez, Gricelis P.</creatorcontrib><creatorcontrib>Rojas, Héctor R.</creatorcontrib><creatorcontrib>Mijares, Michael R.</creatorcontrib><creatorcontrib>De Sanctis, Juan B.</creatorcontrib><title>Antimalarial, antiproliferative, and apoptotic activity of quinoline-chalcone and quinoline-pyrazoline hybrids. A dual action</title><title>Medicinal chemistry research</title><addtitle>Med Chem Res</addtitle><description>A series of quinoline-chalcone
(E)
-1-[3 or 4-(7-chloroquinolin-4-ylamino) phenyl]-3-(phenyl substituted) prop-2-ene-1-one (
4
,
5
), and quinoline-pyrazoline hybrids 7-Chloro-
N
-[3 or 4-(4,5-dihydro-5-(phenyl-substituted)-1H-pyrazol-3-yl] phenyl) quinoline-4–amine (
6
,
7
) were synthesized with the aim of achieving an antimalarial and anticancer dual action. Most of the compounds showed significant inhibition (%>80) of β-hematin formation. The existing structures were tested in vivo as potential antimalarials in mice infected with
P. berghei
ANKA, chloroquine susceptible strain. Some of the compounds exhibited antimalarial activity comparable to that of chloroquine. Moreover, the compounds induce cell death on two human cancer cell lines (Jurkat E6.1 and HL60) without affecting the primary culture of human lymphocytes. Flow cytometry analysis confirmed the increase in apoptotic cell death after 24 h. Based on the structural analysis, these quinoline hybrids represent new compounds potentially useful for malaria end leukemia treatments.</description><subject>Antimalarial activity</subject><subject>Antimalarial agents</subject><subject>Antiproliferatives</subject><subject>Apoptosis</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Cell Biology</subject><subject>Cell culture</subject><subject>Cell death</subject><subject>Chloroquine</subject><subject>Flow cytometry</subject><subject>Hybrids</subject><subject>Lymphocytes</subject><subject>Malaria</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><subject>Quinoline</subject><subject>Structural analysis</subject><subject>Substitutes</subject><subject>Tumor cell lines</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9UE1LxDAULKLguvoHPAW82vXlq9sel8UvELzoObymiZultt2kFSr4381uhb15eLzJMDOPTJJcU1hQgOVdAAAhUqBFCkxwmcJJMqNSijSnDE4jhoiZZPw8uQhhC8CXIOQs-Vk1vfvEGr3D-pZgfHW-rZ01Hnv3ZfZURbBru77tnSaoI-v6kbSW7AbXRGljUr3BWreNOYiPdDd6_D5AshlL76qwICtSDVgfctrmMjmzWAdz9bfnyfvD_dv6KX15fXxer15SzWnRpygNYlExweiSZ8YwbnOdIaOMWl0y0GWGaFkhOJbAKmFyarHKQQLqrNKWz5ObKTf-bTeY0KttO_gmnlSMA48jRRZVbFJp34bgjVWdj934UVFQ-5rVVLOKNatDzQqiiU-mEMXNh_HH6H9cv8_ngy0</recordid><startdate>20191101</startdate><enddate>20191101</enddate><creator>Charris, Jaime E.</creator><creator>Monasterios, Melina C.</creator><creator>Acosta, María E.</creator><creator>Rodríguez, Miguel A.</creator><creator>Gamboa, Neira D.</creator><creator>Martínez, Gricelis P.</creator><creator>Rojas, Héctor R.</creator><creator>Mijares, Michael R.</creator><creator>De Sanctis, Juan B.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-6610-5516</orcidid><orcidid>https://orcid.org/0000-0003-0090-7684</orcidid><orcidid>https://orcid.org/0000-0002-5480-4608</orcidid><orcidid>https://orcid.org/0000-0003-4335-3052</orcidid><orcidid>https://orcid.org/0000-0003-0721-0046</orcidid><orcidid>https://orcid.org/0000-0002-0055-2804</orcidid><orcidid>https://orcid.org/0000-0002-8204-0174</orcidid><orcidid>https://orcid.org/0000-0003-4404-2619</orcidid><orcidid>https://orcid.org/0000-0002-9918-0413</orcidid></search><sort><creationdate>20191101</creationdate><title>Antimalarial, antiproliferative, and apoptotic activity of quinoline-chalcone and quinoline-pyrazoline hybrids. A dual action</title><author>Charris, Jaime E. ; Monasterios, Melina C. ; Acosta, María E. ; Rodríguez, Miguel A. ; Gamboa, Neira D. ; Martínez, Gricelis P. ; Rojas, Héctor R. ; Mijares, Michael R. ; De Sanctis, Juan B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-a5eaa9d2421736ee23f8c6a2121fcb20cb6aaf2943ab02d4e81fad8050ac6dcf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antimalarial activity</topic><topic>Antimalarial agents</topic><topic>Antiproliferatives</topic><topic>Apoptosis</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Cell Biology</topic><topic>Cell culture</topic><topic>Cell death</topic><topic>Chloroquine</topic><topic>Flow cytometry</topic><topic>Hybrids</topic><topic>Lymphocytes</topic><topic>Malaria</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><topic>Quinoline</topic><topic>Structural analysis</topic><topic>Substitutes</topic><topic>Tumor cell lines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Charris, Jaime E.</creatorcontrib><creatorcontrib>Monasterios, Melina C.</creatorcontrib><creatorcontrib>Acosta, María E.</creatorcontrib><creatorcontrib>Rodríguez, Miguel A.</creatorcontrib><creatorcontrib>Gamboa, Neira D.</creatorcontrib><creatorcontrib>Martínez, Gricelis P.</creatorcontrib><creatorcontrib>Rojas, Héctor R.</creatorcontrib><creatorcontrib>Mijares, Michael R.</creatorcontrib><creatorcontrib>De Sanctis, Juan B.</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Charris, Jaime E.</au><au>Monasterios, Melina C.</au><au>Acosta, María E.</au><au>Rodríguez, Miguel A.</au><au>Gamboa, Neira D.</au><au>Martínez, Gricelis P.</au><au>Rojas, Héctor R.</au><au>Mijares, Michael R.</au><au>De Sanctis, Juan B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antimalarial, antiproliferative, and apoptotic activity of quinoline-chalcone and quinoline-pyrazoline hybrids. A dual action</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2019-11-01</date><risdate>2019</risdate><volume>28</volume><issue>11</issue><spage>2050</spage><epage>2066</epage><pages>2050-2066</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>A series of quinoline-chalcone
(E)
-1-[3 or 4-(7-chloroquinolin-4-ylamino) phenyl]-3-(phenyl substituted) prop-2-ene-1-one (
4
,
5
), and quinoline-pyrazoline hybrids 7-Chloro-
N
-[3 or 4-(4,5-dihydro-5-(phenyl-substituted)-1H-pyrazol-3-yl] phenyl) quinoline-4–amine (
6
,
7
) were synthesized with the aim of achieving an antimalarial and anticancer dual action. Most of the compounds showed significant inhibition (%>80) of β-hematin formation. The existing structures were tested in vivo as potential antimalarials in mice infected with
P. berghei
ANKA, chloroquine susceptible strain. Some of the compounds exhibited antimalarial activity comparable to that of chloroquine. Moreover, the compounds induce cell death on two human cancer cell lines (Jurkat E6.1 and HL60) without affecting the primary culture of human lymphocytes. Flow cytometry analysis confirmed the increase in apoptotic cell death after 24 h. Based on the structural analysis, these quinoline hybrids represent new compounds potentially useful for malaria end leukemia treatments.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s00044-019-02435-0</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0001-6610-5516</orcidid><orcidid>https://orcid.org/0000-0003-0090-7684</orcidid><orcidid>https://orcid.org/0000-0002-5480-4608</orcidid><orcidid>https://orcid.org/0000-0003-4335-3052</orcidid><orcidid>https://orcid.org/0000-0003-0721-0046</orcidid><orcidid>https://orcid.org/0000-0002-0055-2804</orcidid><orcidid>https://orcid.org/0000-0002-8204-0174</orcidid><orcidid>https://orcid.org/0000-0003-4404-2619</orcidid><orcidid>https://orcid.org/0000-0002-9918-0413</orcidid></addata></record> |
| fulltext | fulltext |
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| ispartof | Medicinal chemistry research, 2019-11, Vol.28 (11), p.2050-2066 |
| issn | 1054-2523 1554-8120 |
| language | eng |
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| source | Springer Nature - Complete Springer Journals |
| subjects | Antimalarial activity Antimalarial agents Antiproliferatives Apoptosis Biochemistry Biomedical and Life Sciences Biomedicine Cell Biology Cell culture Cell death Chloroquine Flow cytometry Hybrids Lymphocytes Malaria Original Research Pharmacology/Toxicology Quinoline Structural analysis Substitutes Tumor cell lines |
| title | Antimalarial, antiproliferative, and apoptotic activity of quinoline-chalcone and quinoline-pyrazoline hybrids. A dual action |
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