DSC studies on the interaction of lipophilic cytarabine prodrugs with DMPC multilamellar vesicles
Cytarabine (1-β- d -arabinofuranosylcytosine, Ara-C), a pyrimidine nucleoside analogue, is used for the treatment of both acute and chronic myeloblastic leukemias and non-Hodgkin lymphoma. It has a very short plasma half-life and a very low oral bioavailability. To overcome these disadvantages, much...
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| Veröffentlicht in: | Journal of thermal analysis and calorimetry 2019-11, Vol.138 (4), p.2759-2767 |
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| container_title | Journal of thermal analysis and calorimetry |
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| creator | Berrio Escobar, Jhon Fernando Marquez Fernandez, Diana Margarita Giordani, Cristiano Castelli, Francesco Sarpietro, Maria Grazia |
| description | Cytarabine (1-β-
d
-arabinofuranosylcytosine, Ara-C), a pyrimidine nucleoside analogue, is used for the treatment of both acute and chronic myeloblastic leukemias and non-Hodgkin lymphoma. It has a very short plasma half-life and a very low oral bioavailability. To overcome these disadvantages, much effort has been focused on the design of cytarabine prodrugs. In this study, we have synthesized four different cytarabine prodrugs in order to increase the drug lipophilicity and the affinity of the prodrugs toward the biological membranes, as well as the lipophilic carriers. Differential scanning calorimetry was used to study the interaction of cytarabine and its prodrugs with multilamellar vesicles (MLVs) made of dimyristoylphosphatidylcholine (DMPC) and used as a model of biomembranes as well as a lipophilic carrier. The results showed that the 4-
N
-acetyl-2′,3′-5′-acetyl derivative and the prodrug with short chain fatty acids do not have a significant affinity with MLVs, whereas the prodrugs with long chain fatty acids have a stronger affinity with the MLVs with respect to cytarabine. The entity of the affinity depends on the fatty acids length. The increased affinity could be due to the fatty acid moieties which allow the molecule to insert among the phospholipid molecules. These results provide information on the interaction of these prodrugs with biomembranes and could be useful to design liposomes as carriers for the prodrugs. |
| doi_str_mv | 10.1007/s10973-019-08780-x |
| format | Article |
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d
-arabinofuranosylcytosine, Ara-C), a pyrimidine nucleoside analogue, is used for the treatment of both acute and chronic myeloblastic leukemias and non-Hodgkin lymphoma. It has a very short plasma half-life and a very low oral bioavailability. To overcome these disadvantages, much effort has been focused on the design of cytarabine prodrugs. In this study, we have synthesized four different cytarabine prodrugs in order to increase the drug lipophilicity and the affinity of the prodrugs toward the biological membranes, as well as the lipophilic carriers. Differential scanning calorimetry was used to study the interaction of cytarabine and its prodrugs with multilamellar vesicles (MLVs) made of dimyristoylphosphatidylcholine (DMPC) and used as a model of biomembranes as well as a lipophilic carrier. The results showed that the 4-
N
-acetyl-2′,3′-5′-acetyl derivative and the prodrug with short chain fatty acids do not have a significant affinity with MLVs, whereas the prodrugs with long chain fatty acids have a stronger affinity with the MLVs with respect to cytarabine. The entity of the affinity depends on the fatty acids length. The increased affinity could be due to the fatty acid moieties which allow the molecule to insert among the phospholipid molecules. These results provide information on the interaction of these prodrugs with biomembranes and could be useful to design liposomes as carriers for the prodrugs.</description><identifier>ISSN: 1388-6150</identifier><identifier>EISSN: 1588-2926</identifier><identifier>DOI: 10.1007/s10973-019-08780-x</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Affinity ; Analysis ; Analytical Chemistry ; Bioavailability ; Calorimetry ; Care and treatment ; Chemical compounds ; Chemistry ; Chemistry and Materials Science ; Cytarabine ; Drugs ; Fatty acids ; Fish oils ; Inorganic Chemistry ; Leukemia ; Lipophilicity ; Liposomes ; Measurement Science and Instrumentation ; Non-Hodgkin's lymphomas ; Phospholipids ; Physical Chemistry ; Polymer Sciences ; Pyrimidines ; Vesicles</subject><ispartof>Journal of thermal analysis and calorimetry, 2019-11, Vol.138 (4), p.2759-2767</ispartof><rights>Akadémiai Kiadó, Budapest, Hungary 2019</rights><rights>COPYRIGHT 2019 Springer</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-70a59b29ec54c738a582ad0e2557f31c723705d3cef7a7b057b73a33e58f77533</citedby><cites>FETCH-LOGICAL-c457t-70a59b29ec54c738a582ad0e2557f31c723705d3cef7a7b057b73a33e58f77533</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10973-019-08780-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10973-019-08780-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Berrio Escobar, Jhon Fernando</creatorcontrib><creatorcontrib>Marquez Fernandez, Diana Margarita</creatorcontrib><creatorcontrib>Giordani, Cristiano</creatorcontrib><creatorcontrib>Castelli, Francesco</creatorcontrib><creatorcontrib>Sarpietro, Maria Grazia</creatorcontrib><title>DSC studies on the interaction of lipophilic cytarabine prodrugs with DMPC multilamellar vesicles</title><title>Journal of thermal analysis and calorimetry</title><addtitle>J Therm Anal Calorim</addtitle><description>Cytarabine (1-β-
d
-arabinofuranosylcytosine, Ara-C), a pyrimidine nucleoside analogue, is used for the treatment of both acute and chronic myeloblastic leukemias and non-Hodgkin lymphoma. It has a very short plasma half-life and a very low oral bioavailability. To overcome these disadvantages, much effort has been focused on the design of cytarabine prodrugs. In this study, we have synthesized four different cytarabine prodrugs in order to increase the drug lipophilicity and the affinity of the prodrugs toward the biological membranes, as well as the lipophilic carriers. Differential scanning calorimetry was used to study the interaction of cytarabine and its prodrugs with multilamellar vesicles (MLVs) made of dimyristoylphosphatidylcholine (DMPC) and used as a model of biomembranes as well as a lipophilic carrier. The results showed that the 4-
N
-acetyl-2′,3′-5′-acetyl derivative and the prodrug with short chain fatty acids do not have a significant affinity with MLVs, whereas the prodrugs with long chain fatty acids have a stronger affinity with the MLVs with respect to cytarabine. The entity of the affinity depends on the fatty acids length. The increased affinity could be due to the fatty acid moieties which allow the molecule to insert among the phospholipid molecules. These results provide information on the interaction of these prodrugs with biomembranes and could be useful to design liposomes as carriers for the prodrugs.</description><subject>Affinity</subject><subject>Analysis</subject><subject>Analytical Chemistry</subject><subject>Bioavailability</subject><subject>Calorimetry</subject><subject>Care and treatment</subject><subject>Chemical compounds</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Cytarabine</subject><subject>Drugs</subject><subject>Fatty acids</subject><subject>Fish oils</subject><subject>Inorganic Chemistry</subject><subject>Leukemia</subject><subject>Lipophilicity</subject><subject>Liposomes</subject><subject>Measurement Science and Instrumentation</subject><subject>Non-Hodgkin's lymphomas</subject><subject>Phospholipids</subject><subject>Physical Chemistry</subject><subject>Polymer Sciences</subject><subject>Pyrimidines</subject><subject>Vesicles</subject><issn>1388-6150</issn><issn>1588-2926</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kV1PwyAUhhujiXP6B7wi8cqLzkMZpb008zPRaPy4Joyebiy0nUB1-_eiMzFLjOGCA3ke4PAmyTGFEQUQZ55CKVgKtEyhEAWkq51kQHlRpFmZ5buxZrHOKYf95MD7BQCUJdBBoi6eJ8SHvjLoSdeSMEdi2oBO6WDiuquJNctuOTfWaKLXQTk1NS2Spesq1888-TBhTi7uHyek6W0wVjVorXLkHb3RFv1hslcr6_HoZx4mr1eXL5Ob9O7h-nZyfpfqMRchFaB4Oc1K1HysBSsULzJVAWaci5pRLTImgFdMYy2UmAIXU8EUY8iLWgjO2DA52ZwbX_bWow9y0fWujVfKjNEcII8_9EvNlEVp2roLsdXGeC3Pc8gZiHE-jtToDyqOChujuxZrE_e3hNMtITIBV2Gmeu_l7fPTNpttWO067x3WculMo9xaUpBfacpNmjKmKb_TlKsosY3kI9zO0P1294_1CSwDoME</recordid><startdate>20191101</startdate><enddate>20191101</enddate><creator>Berrio Escobar, Jhon Fernando</creator><creator>Marquez Fernandez, Diana Margarita</creator><creator>Giordani, Cristiano</creator><creator>Castelli, Francesco</creator><creator>Sarpietro, Maria Grazia</creator><general>Springer International Publishing</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>ISR</scope></search><sort><creationdate>20191101</creationdate><title>DSC studies on the interaction of lipophilic cytarabine prodrugs with DMPC multilamellar vesicles</title><author>Berrio Escobar, Jhon Fernando ; Marquez Fernandez, Diana Margarita ; Giordani, Cristiano ; Castelli, Francesco ; Sarpietro, Maria Grazia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-70a59b29ec54c738a582ad0e2557f31c723705d3cef7a7b057b73a33e58f77533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Affinity</topic><topic>Analysis</topic><topic>Analytical Chemistry</topic><topic>Bioavailability</topic><topic>Calorimetry</topic><topic>Care and treatment</topic><topic>Chemical compounds</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Cytarabine</topic><topic>Drugs</topic><topic>Fatty acids</topic><topic>Fish oils</topic><topic>Inorganic Chemistry</topic><topic>Leukemia</topic><topic>Lipophilicity</topic><topic>Liposomes</topic><topic>Measurement Science and Instrumentation</topic><topic>Non-Hodgkin's lymphomas</topic><topic>Phospholipids</topic><topic>Physical Chemistry</topic><topic>Polymer Sciences</topic><topic>Pyrimidines</topic><topic>Vesicles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Berrio Escobar, Jhon Fernando</creatorcontrib><creatorcontrib>Marquez Fernandez, Diana Margarita</creatorcontrib><creatorcontrib>Giordani, Cristiano</creatorcontrib><creatorcontrib>Castelli, Francesco</creatorcontrib><creatorcontrib>Sarpietro, Maria Grazia</creatorcontrib><collection>CrossRef</collection><collection>Gale In Context: Science</collection><jtitle>Journal of thermal analysis and calorimetry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Berrio Escobar, Jhon Fernando</au><au>Marquez Fernandez, Diana Margarita</au><au>Giordani, Cristiano</au><au>Castelli, Francesco</au><au>Sarpietro, Maria Grazia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DSC studies on the interaction of lipophilic cytarabine prodrugs with DMPC multilamellar vesicles</atitle><jtitle>Journal of thermal analysis and calorimetry</jtitle><stitle>J Therm Anal Calorim</stitle><date>2019-11-01</date><risdate>2019</risdate><volume>138</volume><issue>4</issue><spage>2759</spage><epage>2767</epage><pages>2759-2767</pages><issn>1388-6150</issn><eissn>1588-2926</eissn><abstract>Cytarabine (1-β-
d
-arabinofuranosylcytosine, Ara-C), a pyrimidine nucleoside analogue, is used for the treatment of both acute and chronic myeloblastic leukemias and non-Hodgkin lymphoma. It has a very short plasma half-life and a very low oral bioavailability. To overcome these disadvantages, much effort has been focused on the design of cytarabine prodrugs. In this study, we have synthesized four different cytarabine prodrugs in order to increase the drug lipophilicity and the affinity of the prodrugs toward the biological membranes, as well as the lipophilic carriers. Differential scanning calorimetry was used to study the interaction of cytarabine and its prodrugs with multilamellar vesicles (MLVs) made of dimyristoylphosphatidylcholine (DMPC) and used as a model of biomembranes as well as a lipophilic carrier. The results showed that the 4-
N
-acetyl-2′,3′-5′-acetyl derivative and the prodrug with short chain fatty acids do not have a significant affinity with MLVs, whereas the prodrugs with long chain fatty acids have a stronger affinity with the MLVs with respect to cytarabine. The entity of the affinity depends on the fatty acids length. The increased affinity could be due to the fatty acid moieties which allow the molecule to insert among the phospholipid molecules. These results provide information on the interaction of these prodrugs with biomembranes and could be useful to design liposomes as carriers for the prodrugs.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><doi>10.1007/s10973-019-08780-x</doi><tpages>9</tpages></addata></record> |
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| subjects | Affinity Analysis Analytical Chemistry Bioavailability Calorimetry Care and treatment Chemical compounds Chemistry Chemistry and Materials Science Cytarabine Drugs Fatty acids Fish oils Inorganic Chemistry Leukemia Lipophilicity Liposomes Measurement Science and Instrumentation Non-Hodgkin's lymphomas Phospholipids Physical Chemistry Polymer Sciences Pyrimidines Vesicles |
| title | DSC studies on the interaction of lipophilic cytarabine prodrugs with DMPC multilamellar vesicles |
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