<i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin
An amphiphilic derivative of chitosan containing quaternary ammonium and myristoyl groups, herein named as ammonium myristoyl chitosan (DMCat), was synthesized by reacting glycidyltrimethylammonium chloride (GTMAC) and myristoyl chitosan (DMCh). The success of the modification was confirmed using Fo...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-11-01
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| Series: | Pharmaceutics |
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| Online Access: | https://www.mdpi.com/1999-4923/10/4/245 |
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| author | Daniella S. Silva Danilo M. dos Santos Andreia Almeida Leonardo Marchiori Sérgio P. Campana-Filho Sidney J. L. Ribeiro Bruno Sarmento |
| author_facet | Daniella S. Silva Danilo M. dos Santos Andreia Almeida Leonardo Marchiori Sérgio P. Campana-Filho Sidney J. L. Ribeiro Bruno Sarmento |
| author_sort | Daniella S. Silva |
| collection | DOAJ |
| description | An amphiphilic derivative of chitosan containing quaternary ammonium and myristoyl groups, herein named as ammonium myristoyl chitosan (DMCat), was synthesized by reacting glycidyltrimethylammonium chloride (GTMAC) and myristoyl chitosan (DMCh). The success of the modification was confirmed using Fourier-transform infrared spectroscopy (FTIR) and <sup>1</sup>H nuclear magnetic resonance (NMR) spectroscopy. The average degrees of alkylation and quaternization (<inline-formula> <math display="inline"> <semantics> <mrow> <mover accent="true"> <mrow> <mi>D</mi> <mi>Q</mi> </mrow> <mo stretchy="true">¯</mo> </mover> </mrow> </semantics> </math> </inline-formula>) were determined by using <sup>1</sup>H NMR and conductometric titration. The zeta potential of the micelles was higher than 28 mV while its average size and encapsulation efficiency ranged from 280 nm to 375 nm and 68% to 100%, respectively. The in vitro cytotoxicity of the unloaded and curcumin (CUR)-loaded micelles was tested against Caco-2 and HT29-MTX intestinal epithelial cell lines. The results showed no cytotoxic effect from loaded and unloaded micelles as compared to free CUR. In the permeability test, it was observed that both types of micelles, i.e., DMCh and DMCat, improved CUR permeability. Additionally, higher permeability was verified for both systems in Caco-2/HT29-MTX:Raji B because of the mucoadhesive character of chitosan and its ability to open tight junctions. The results indicated that DMCat micelles, due to the physico-chemical, improved characteristics may be a promising carrier to encapsulate CUR aiming cancer therapy. |
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| id | doaj.art-bfa19cf9e4b24ae6ac08d9523c6f8a57 |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-04-13T00:30:22Z |
| publishDate | 2018-11-01 |
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| series | Pharmaceutics |
| spelling | doaj.art-bfa19cf9e4b24ae6ac08d9523c6f8a572022-12-22T03:10:29ZengMDPI AGPharmaceutics1999-49232018-11-0110424510.3390/pharmaceutics10040245pharmaceutics10040245<i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer CurcuminDaniella S. Silva0Danilo M. dos Santos1Andreia Almeida2Leonardo Marchiori3Sérgio P. Campana-Filho4Sidney J. L. Ribeiro5Bruno Sarmento6Institute of Chemistry, São Paulo State University—UNESP, Araraquara 4800-900, BrazilEmbrapa Instrumentação, Rua XV de Novembro 1452, São Carlos 13560-970, BrazilInstitute for Research and Innovation in Health (i3S), Rua Alfredo Allen, 208, 4200-393 Porto, PortugalInstitute of Chemistry, São Paulo State University—UNESP, Araraquara 4800-900, BrazilSao Carlos Institute of Chemistry, University of Sao Paulo—USP, Av. Trabalhador São-Carlense, 400, São Carlos 13566-590, BrazilInstitute of Chemistry, São Paulo State University—UNESP, Araraquara 4800-900, BrazilInstitute for Research and Innovation in Health (i3S), Rua Alfredo Allen, 208, 4200-393 Porto, PortugalAn amphiphilic derivative of chitosan containing quaternary ammonium and myristoyl groups, herein named as ammonium myristoyl chitosan (DMCat), was synthesized by reacting glycidyltrimethylammonium chloride (GTMAC) and myristoyl chitosan (DMCh). The success of the modification was confirmed using Fourier-transform infrared spectroscopy (FTIR) and <sup>1</sup>H nuclear magnetic resonance (NMR) spectroscopy. The average degrees of alkylation and quaternization (<inline-formula> <math display="inline"> <semantics> <mrow> <mover accent="true"> <mrow> <mi>D</mi> <mi>Q</mi> </mrow> <mo stretchy="true">¯</mo> </mover> </mrow> </semantics> </math> </inline-formula>) were determined by using <sup>1</sup>H NMR and conductometric titration. The zeta potential of the micelles was higher than 28 mV while its average size and encapsulation efficiency ranged from 280 nm to 375 nm and 68% to 100%, respectively. The in vitro cytotoxicity of the unloaded and curcumin (CUR)-loaded micelles was tested against Caco-2 and HT29-MTX intestinal epithelial cell lines. The results showed no cytotoxic effect from loaded and unloaded micelles as compared to free CUR. In the permeability test, it was observed that both types of micelles, i.e., DMCh and DMCat, improved CUR permeability. Additionally, higher permeability was verified for both systems in Caco-2/HT29-MTX:Raji B because of the mucoadhesive character of chitosan and its ability to open tight junctions. The results indicated that DMCat micelles, due to the physico-chemical, improved characteristics may be a promising carrier to encapsulate CUR aiming cancer therapy.https://www.mdpi.com/1999-4923/10/4/245chitosan derivativesamphiphilic polymerspolymeric micellesquaternizationcurcuminintestinal delivery |
| spellingShingle | Daniella S. Silva Danilo M. dos Santos Andreia Almeida Leonardo Marchiori Sérgio P. Campana-Filho Sidney J. L. Ribeiro Bruno Sarmento <i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin Pharmaceutics chitosan derivatives amphiphilic polymers polymeric micelles quaternization curcumin intestinal delivery |
| title | <i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin |
| title_full | <i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin |
| title_fullStr | <i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin |
| title_full_unstemmed | <i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin |
| title_short | <i>N</i>-(2-Hydroxy)-propyl-3-trimethylammonium, <i>O</i>-Mysristoyl Chitosan Enhances the Solubility and Intestinal Permeability of Anticancer Curcumin |
| title_sort | i n i 2 hydroxy propyl 3 trimethylammonium i o i mysristoyl chitosan enhances the solubility and intestinal permeability of anticancer curcumin |
| topic | chitosan derivatives amphiphilic polymers polymeric micelles quaternization curcumin intestinal delivery |
| url | https://www.mdpi.com/1999-4923/10/4/245 |
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