Programmed cell death (PCD) associated with the stilbene motif of arotinoids: discovery of novel apoptosis inducer agents possessing activity on multidrug resistant tumor cells
Considering that the stereochemistry of the C9–C10 alkenyl portion of natural 9- cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid 4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the cis...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2000-12, Vol.10 (23), p.2669-2673 |
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| creator | Simoni, Daniele Roberti, Marinella Paolo Invidiata, Francesco Rondanin, Riccardo Baruchello, Riccardo Malagutti, Cinzia Mazzali, Angelica Rossi, Marcello Grimaudo, Stefania Dusonchet, Luisa Meli, Maria Raimondi, Maria Valeria D'Alessandro, Natale Tolomeo, Manlio |
| description | Considering that the stereochemistry of the C9–C10 alkenyl portion of natural 9-
cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid
4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the
cis or
trans configuration of the alkenyl portion. The compounds were evaluated in vitro for their cytotoxic and apoptotic activities. We discovered that the
cis-TTNPB
9c possesses apoptotic activity comparable with that of the retinoid
4. Moreover, the amino arotinoid
16c showed potent apoptotic activity in HL60 promyelocytic leukemia cells. Interestingly,
16c proved to be a particularly potent apoptosis-inducing agent active in multidrug resistant (MDR) cell lines. Therefore, to the best of our knowledge,
16c may represent the first known aminoarotinoid endowed with potent apoptotic activity in MDR cells. Taken together, these results seem to point out that the
cis-stilbene motif of arotinoids may be at least an important feature in conferring cytotoxic and apoptotic activity to this class of compounds. |
| doi_str_mv | 10.1016/S0960-894X(00)00547-3 |
| format | Article |
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cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid
4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the
cis or
trans configuration of the alkenyl portion. The compounds were evaluated in vitro for their cytotoxic and apoptotic activities. We discovered that the
cis-TTNPB
9c possesses apoptotic activity comparable with that of the retinoid
4. Moreover, the amino arotinoid
16c showed potent apoptotic activity in HL60 promyelocytic leukemia cells. Interestingly,
16c proved to be a particularly potent apoptosis-inducing agent active in multidrug resistant (MDR) cell lines. Therefore, to the best of our knowledge,
16c may represent the first known aminoarotinoid endowed with potent apoptotic activity in MDR cells. Taken together, these results seem to point out that the
cis-stilbene motif of arotinoids may be at least an important feature in conferring cytotoxic and apoptotic activity to this class of compounds.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/S0960-894X(00)00547-3</identifier><identifier>PMID: 11128648</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Apoptosis - drug effects ; Biological and medical sciences ; Drug Resistance, Multiple ; General aspects ; HL-60 Cells ; Humans ; K562 Cells ; Medical sciences ; Pharmacology. Drug treatments ; Retinoids - chemistry ; Retinoids - pharmacology ; Stilbenes - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2000-12, Vol.10 (23), p.2669-2673</ispartof><rights>2000 Elsevier Science Ltd</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-97f0eedb06a08543b03025a2b68153814b5402057627af8a536b3086819fb01e3</citedby><cites>FETCH-LOGICAL-c389t-97f0eedb06a08543b03025a2b68153814b5402057627af8a536b3086819fb01e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X00005473$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=805226$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11128648$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Simoni, Daniele</creatorcontrib><creatorcontrib>Roberti, Marinella</creatorcontrib><creatorcontrib>Paolo Invidiata, Francesco</creatorcontrib><creatorcontrib>Rondanin, Riccardo</creatorcontrib><creatorcontrib>Baruchello, Riccardo</creatorcontrib><creatorcontrib>Malagutti, Cinzia</creatorcontrib><creatorcontrib>Mazzali, Angelica</creatorcontrib><creatorcontrib>Rossi, Marcello</creatorcontrib><creatorcontrib>Grimaudo, Stefania</creatorcontrib><creatorcontrib>Dusonchet, Luisa</creatorcontrib><creatorcontrib>Meli, Maria</creatorcontrib><creatorcontrib>Raimondi, Maria Valeria</creatorcontrib><creatorcontrib>D'Alessandro, Natale</creatorcontrib><creatorcontrib>Tolomeo, Manlio</creatorcontrib><title>Programmed cell death (PCD) associated with the stilbene motif of arotinoids: discovery of novel apoptosis inducer agents possessing activity on multidrug resistant tumor cells</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Considering that the stereochemistry of the C9–C10 alkenyl portion of natural 9-
cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid
4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the
cis or
trans configuration of the alkenyl portion. The compounds were evaluated in vitro for their cytotoxic and apoptotic activities. We discovered that the
cis-TTNPB
9c possesses apoptotic activity comparable with that of the retinoid
4. Moreover, the amino arotinoid
16c showed potent apoptotic activity in HL60 promyelocytic leukemia cells. Interestingly,
16c proved to be a particularly potent apoptosis-inducing agent active in multidrug resistant (MDR) cell lines. Therefore, to the best of our knowledge,
16c may represent the first known aminoarotinoid endowed with potent apoptotic activity in MDR cells. Taken together, these results seem to point out that the
cis-stilbene motif of arotinoids may be at least an important feature in conferring cytotoxic and apoptotic activity to this class of compounds.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis - drug effects</subject><subject>Biological and medical sciences</subject><subject>Drug Resistance, Multiple</subject><subject>General aspects</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>K562 Cells</subject><subject>Medical sciences</subject><subject>Pharmacology. 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Drug treatments</topic><topic>Retinoids - chemistry</topic><topic>Retinoids - pharmacology</topic><topic>Stilbenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Simoni, Daniele</creatorcontrib><creatorcontrib>Roberti, Marinella</creatorcontrib><creatorcontrib>Paolo Invidiata, Francesco</creatorcontrib><creatorcontrib>Rondanin, Riccardo</creatorcontrib><creatorcontrib>Baruchello, Riccardo</creatorcontrib><creatorcontrib>Malagutti, Cinzia</creatorcontrib><creatorcontrib>Mazzali, Angelica</creatorcontrib><creatorcontrib>Rossi, Marcello</creatorcontrib><creatorcontrib>Grimaudo, Stefania</creatorcontrib><creatorcontrib>Dusonchet, Luisa</creatorcontrib><creatorcontrib>Meli, Maria</creatorcontrib><creatorcontrib>Raimondi, Maria Valeria</creatorcontrib><creatorcontrib>D'Alessandro, Natale</creatorcontrib><creatorcontrib>Tolomeo, Manlio</creatorcontrib><collection>Pascal-Francis</collection><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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Simoni, Daniele</au><au>Roberti, Marinella</au><au>Paolo Invidiata, Francesco</au><au>Rondanin, Riccardo</au><au>Baruchello, Riccardo</au><au>Malagutti, Cinzia</au><au>Mazzali, Angelica</au><au>Rossi, Marcello</au><au>Grimaudo, Stefania</au><au>Dusonchet, Luisa</au><au>Meli, Maria</au><au>Raimondi, Maria Valeria</au><au>D'Alessandro, Natale</au><au>Tolomeo, Manlio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Programmed cell death (PCD) associated with the stilbene motif of arotinoids: discovery of novel apoptosis inducer agents possessing activity on multidrug resistant tumor cells</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2000-12-04</date><risdate>2000</risdate><volume>10</volume><issue>23</issue><spage>2669</spage><epage>2673</epage><pages>2669-2673</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Considering that the stereochemistry of the C9–C10 alkenyl portion of natural 9-
cis-RA, as the one of the olefinic moiety of the previously described isoxazole retinoid
4, seems of particular importance for their apoptotic activity, we prepared a novel class of TTNPB analogues bearing both the
cis or
trans configuration of the alkenyl portion. The compounds were evaluated in vitro for their cytotoxic and apoptotic activities. We discovered that the
cis-TTNPB
9c possesses apoptotic activity comparable with that of the retinoid
4. Moreover, the amino arotinoid
16c showed potent apoptotic activity in HL60 promyelocytic leukemia cells. Interestingly,
16c proved to be a particularly potent apoptosis-inducing agent active in multidrug resistant (MDR) cell lines. Therefore, to the best of our knowledge,
16c may represent the first known aminoarotinoid endowed with potent apoptotic activity in MDR cells. Taken together, these results seem to point out that the
cis-stilbene motif of arotinoids may be at least an important feature in conferring cytotoxic and apoptotic activity to this class of compounds.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>11128648</pmid><doi>10.1016/S0960-894X(00)00547-3</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2000-12, Vol.10 (23), p.2669-2673 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72507783 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Antineoplastic agents Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Apoptosis - drug effects Biological and medical sciences Drug Resistance, Multiple General aspects HL-60 Cells Humans K562 Cells Medical sciences Pharmacology. Drug treatments Retinoids - chemistry Retinoids - pharmacology Stilbenes - pharmacology |
| title | Programmed cell death (PCD) associated with the stilbene motif of arotinoids: discovery of novel apoptosis inducer agents possessing activity on multidrug resistant tumor cells |
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