(<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines
(<i>E</i>)-1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid (2<i>E</i>,6<i>E</i>)-2,6-bis(3,4-dimethoxybenzylidene)acetone and ethyl hydrazinob...
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MDPI AG
2020-01-01
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| Online Access: | https://www.mdpi.com/1422-8599/2020/1/M1114 |
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| author | Dimitris Matiadis Barbara Mavroidi Angeliki Panagiotopoulou Constantinos Methenitis Maria Pelecanou Marina Sagnou |
| author_facet | Dimitris Matiadis Barbara Mavroidi Angeliki Panagiotopoulou Constantinos Methenitis Maria Pelecanou Marina Sagnou |
| author_sort | Dimitris Matiadis |
| collection | DOAJ |
| description | (<i>E</i>)-1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid (2<i>E</i>,6<i>E</i>)-2,6-bis(3,4-dimethoxybenzylidene)acetone and ethyl hydrazinobenzoate in high yield and purity (>95% by High-performance liquid chromatography (HPLC)). The compound has been fully characterized by <sup>1</sup>H, <sup>13</sup>C NMR, FTIR, UV-Vis and HRMS and its activity was evaluated in terms of its potential interaction with DNA as well as its cytotoxicity against resistant and non-resistant tumor cells. Both DNA thermal denaturation and DNA viscosity measurements revealed that a significant intercalation binding takes place upon treatment of the DNA with the synthesized pyrazoline, causing an increase in melting temperature by 3.53 ± 0.11 °C and considerable DNA lengthening and viscosity increase. However, neither re-sensitisation of Doxorubicin (DO X)-resistant breast cancer and multidrug resistance (MDR) reversal nor synergistic activity with DOX by potentially increasing the DOX cell killing ability was observed. |
| first_indexed | 2024-04-13T05:16:45Z |
| format | Article |
| id | doaj.art-889b12d9b5e04c939a9a4f0dc2d81b8e |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-04-13T05:16:45Z |
| publishDate | 2020-01-01 |
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| spelling | doaj.art-889b12d9b5e04c939a9a4f0dc2d81b8e2022-12-22T03:00:52ZengMDPI AGMolbank1422-85992020-01-0120201M111410.3390/M1114M1114(<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell LinesDimitris Matiadis0Barbara Mavroidi1Angeliki Panagiotopoulou2Constantinos Methenitis3Maria Pelecanou4Marina Sagnou5National Center for Scientific Research “Demokritos”, Institute of Biosciences & Applications, 153 10 Athens, GreeceNational Center for Scientific Research “Demokritos”, Institute of Biosciences & Applications, 153 10 Athens, GreeceNational Center for Scientific Research “Demokritos”, Institute of Biosciences & Applications, 153 10 Athens, GreeceNational and Kapodistrian University of Athens, Department of Chemistry, 157 84 Athens, GreeceNational Center for Scientific Research “Demokritos”, Institute of Biosciences & Applications, 153 10 Athens, GreeceNational Center for Scientific Research “Demokritos”, Institute of Biosciences & Applications, 153 10 Athens, Greece(<i>E</i>)-1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid (2<i>E</i>,6<i>E</i>)-2,6-bis(3,4-dimethoxybenzylidene)acetone and ethyl hydrazinobenzoate in high yield and purity (>95% by High-performance liquid chromatography (HPLC)). The compound has been fully characterized by <sup>1</sup>H, <sup>13</sup>C NMR, FTIR, UV-Vis and HRMS and its activity was evaluated in terms of its potential interaction with DNA as well as its cytotoxicity against resistant and non-resistant tumor cells. Both DNA thermal denaturation and DNA viscosity measurements revealed that a significant intercalation binding takes place upon treatment of the DNA with the synthesized pyrazoline, causing an increase in melting temperature by 3.53 ± 0.11 °C and considerable DNA lengthening and viscosity increase. However, neither re-sensitisation of Doxorubicin (DO X)-resistant breast cancer and multidrug resistance (MDR) reversal nor synergistic activity with DOX by potentially increasing the DOX cell killing ability was observed.https://www.mdpi.com/1422-8599/2020/1/M1114pyrazolinescurcuminoidsnitrogen heterocyclescytotoxicdna bindingmdr reversal |
| spellingShingle | Dimitris Matiadis Barbara Mavroidi Angeliki Panagiotopoulou Constantinos Methenitis Maria Pelecanou Marina Sagnou (<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines Molbank pyrazolines curcuminoids nitrogen heterocycles cytotoxic dna binding mdr reversal |
| title | (<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines |
| title_full | (<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines |
| title_fullStr | (<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines |
| title_full_unstemmed | (<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines |
| title_short | (<i>E</i>)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines |
| title_sort | i e i 1 4 ethoxycarbonylphenyl 5 3 4 dimethoxyphenyl 3 3 4 dimethoxystyryl 2 pyrazoline synthesis characterization dna interaction and evaluation of activity against drug resistant cell lines |
| topic | pyrazolines curcuminoids nitrogen heterocycles cytotoxic dna binding mdr reversal |
| url | https://www.mdpi.com/1422-8599/2020/1/M1114 |
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