Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery
An amphiphilic and bioactive calix[4]arene derivative 8 (CA) is designed and successfully synthesized from tert-butyl calix[4] arene 1 by sequential inverse F-C alkylation, nitration, O-alkylation, esterification, aminolysis, reduction, and acylation reaction. The blank micelles of FA-CA and doxorub...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2019-11-01
|
| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00732/full |
| _version_ | 1819209687665475584 |
|---|---|
| author | Lin An Lin An Jia-wei Wang Jia-wei Wang Jia-dong Liu Jia-dong Liu Zi-ming Zhao Zi-ming Zhao Yuan-jian Song |
| author_facet | Lin An Lin An Jia-wei Wang Jia-wei Wang Jia-dong Liu Jia-dong Liu Zi-ming Zhao Zi-ming Zhao Yuan-jian Song |
| author_sort | Lin An |
| collection | DOAJ |
| description | An amphiphilic and bioactive calix[4]arene derivative 8 (CA) is designed and successfully synthesized from tert-butyl calix[4] arene 1 by sequential inverse F-C alkylation, nitration, O-alkylation, esterification, aminolysis, reduction, and acylation reaction. The blank micelles of FA-CA and doxorubicin (DOX) loaded micelles FA-CA-DOX are prepared subsequently undergoing self-assembly and dialysis of CA and DSPE-PEG2000-FA. The drug release kinetics curve of the encapsulated-DOX micelle demonstrates a rapid release under mild conditions, indicating the good pH-responsive ability. Furthermore, the cytotoxicity of DOX-loaded micelle respect to the blank micelle against seven different human carcinoma (A549, HeLa, HepG2, HCT116, MCF-7, MDA-MB231, and SW480) cells has been also investigated. The results confirm the more significant inhibitory effect of DOX-loaded micelle than those of DOX and the blank micelles. The CDI calculations show a synergistic effect between blank micelles and DOX in inducing tumor cell death. In conclusion, FA-CA micelles reported in this work was a promising drug delivery vehicle for tumor targeting therapy. |
| first_indexed | 2024-12-23T05:59:15Z |
| format | Article |
| id | doaj.art-a5b38ab7647348ba9d457fc13a947733 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-23T05:59:15Z |
| publishDate | 2019-11-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-a5b38ab7647348ba9d457fc13a9477332022-12-21T17:57:42ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-11-01710.3389/fchem.2019.00732469477Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug DeliveryLin An0Lin An1Jia-wei Wang2Jia-wei Wang3Jia-dong Liu4Jia-dong Liu5Zi-ming Zhao6Zi-ming Zhao7Yuan-jian Song8College of Pharmacy, Xuzhou Medical University, Xuzhou, ChinaJiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, Xuzhou Medical University, Xuzhou, ChinaCollege of Pharmacy, Xuzhou Medical University, Xuzhou, ChinaJiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, Xuzhou Medical University, Xuzhou, ChinaCollege of Pharmacy, Xuzhou Medical University, Xuzhou, ChinaJiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, Xuzhou Medical University, Xuzhou, ChinaCollege of Pharmacy, Xuzhou Medical University, Xuzhou, ChinaJiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, Xuzhou Medical University, Xuzhou, ChinaDepartment of Genetics, Research Facility Center for Morphology, Xuzhou Medical University, Xuzhou, ChinaAn amphiphilic and bioactive calix[4]arene derivative 8 (CA) is designed and successfully synthesized from tert-butyl calix[4] arene 1 by sequential inverse F-C alkylation, nitration, O-alkylation, esterification, aminolysis, reduction, and acylation reaction. The blank micelles of FA-CA and doxorubicin (DOX) loaded micelles FA-CA-DOX are prepared subsequently undergoing self-assembly and dialysis of CA and DSPE-PEG2000-FA. The drug release kinetics curve of the encapsulated-DOX micelle demonstrates a rapid release under mild conditions, indicating the good pH-responsive ability. Furthermore, the cytotoxicity of DOX-loaded micelle respect to the blank micelle against seven different human carcinoma (A549, HeLa, HepG2, HCT116, MCF-7, MDA-MB231, and SW480) cells has been also investigated. The results confirm the more significant inhibitory effect of DOX-loaded micelle than those of DOX and the blank micelles. The CDI calculations show a synergistic effect between blank micelles and DOX in inducing tumor cell death. In conclusion, FA-CA micelles reported in this work was a promising drug delivery vehicle for tumor targeting therapy.https://www.frontiersin.org/article/10.3389/fchem.2019.00732/fullamphiphilic calixarenebioactive carrierdrug deliveryself-assemblydoxorubicin |
| spellingShingle | Lin An Lin An Jia-wei Wang Jia-wei Wang Jia-dong Liu Jia-dong Liu Zi-ming Zhao Zi-ming Zhao Yuan-jian Song Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery Frontiers in Chemistry amphiphilic calixarene bioactive carrier drug delivery self-assembly doxorubicin |
| title | Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery |
| title_full | Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery |
| title_fullStr | Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery |
| title_full_unstemmed | Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery |
| title_short | Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery |
| title_sort | design preparation and characterization of novel calix 4 arene bioactive carrier for antitumor drug delivery |
| topic | amphiphilic calixarene bioactive carrier drug delivery self-assembly doxorubicin |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00732/full |
| work_keys_str_mv | AT linan designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT linan designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT jiaweiwang designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT jiaweiwang designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT jiadongliu designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT jiadongliu designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT zimingzhao designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT zimingzhao designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery AT yuanjiansong designpreparationandcharacterizationofnovelcalix4arenebioactivecarrierforantitumordrugdelivery |