Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as Nanocarriers
Abstract A new class of non‐ionic dendritic amphiphiles has been developed from biobased chemicals, in particular glycerol‐based dendrons coupled to commercially available acids via the Steglich esterification process. These non‐ionic amphiphiles are functionalized with different hydrophobic segment...
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Wiley-VCH
2025-08-01
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| Online Access: | https://doi.org/10.1002/open.202400448 |
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| author | Pooja Kumari Christian Zoister Natalie Hanheiser Dr. Hesam Makki Dr. Boris Schade Dr. Mathias Dimde Katharina Achazi Dr. Sumit Kumar Prof. Dr. Rainer Haag Dr. Abhishek K. Singh |
| author_facet | Pooja Kumari Christian Zoister Natalie Hanheiser Dr. Hesam Makki Dr. Boris Schade Dr. Mathias Dimde Katharina Achazi Dr. Sumit Kumar Prof. Dr. Rainer Haag Dr. Abhishek K. Singh |
| author_sort | Pooja Kumari |
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| description | Abstract A new class of non‐ionic dendritic amphiphiles has been developed from biobased chemicals, in particular glycerol‐based dendrons coupled to commercially available acids via the Steglich esterification process. These non‐ionic amphiphiles are functionalized with different hydrophobic segments to investigate the contribution of the same towards their guest transport behaviour. Therefore, different alkyl chains i.e, C8 and C12, as well as two different aromatic units were introduced as a hydrophobic segments and G1‐oligo‐glycerol as a hydrophilic segment. Their physicochemical properties were characterized by different techniques such as dynamic light scattering and fluorescence measurements. The results show that these amphiphiles form a very uniform micellar supramolecular structures that is independent of the hydrophobic system. The critical micelle concentration for the prepared non‐ionic amphiphiles was found to be in the range of 0.3 to 1.8 mg/mL, which depend on the type of hydrophobic units. The encapsulation capacities of the amphiphiles were tested using Nile Red and Nimodipine as model dye and drug, respectively. The encapsulation studies showed a preference for C12‐ and pyrene‐based amphiphiles through relatively different mechanisms unraveled by molecular dynamics (MD) simulations. Further, the cytotoxicity and cellular uptake of these systems as well as the release profiles were investigated. |
| format | Article |
| id | doaj-art-eb3cbfa82d7c4b139735ad9215ee00e2 |
| institution | Kabale University |
| issn | 2191-1363 |
| language | English |
| publishDate | 2025-08-01 |
| publisher | Wiley-VCH |
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| series | ChemistryOpen |
| spelling | doaj-art-eb3cbfa82d7c4b139735ad9215ee00e22025-08-21T12:05:32ZengWiley-VCHChemistryOpen2191-13632025-08-01148n/an/a10.1002/open.202400448Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as NanocarriersPooja Kumari0Christian Zoister1Natalie Hanheiser2Dr. Hesam Makki3Dr. Boris Schade4Dr. Mathias Dimde5Katharina Achazi6Dr. Sumit Kumar7Prof. Dr. Rainer Haag8Dr. Abhishek K. Singh9Department of Chemistry Deenbandhu Chhoturam University of Science and Technology Murthal 131039 Sonipat IndiaInstitut für Chemie und Biochemie Organische Chemie Freie Universität Berlin Takustr. 3 14195 Berlin GermanyInstitut für Chemie und Biochemie Organische Chemie Freie Universität Berlin Takustr. 3 14195 Berlin GermanyDepartment of Chemistry and Materials Innovation Factory University of Liverpool L69 7ZD Liverpool U.K.Institut für Chemie und Biochemie Forschungszentrum fu“r Elektronenmikroskopie Freie Universität Berlin Fabeckstraße 36a 14195 Berlin GermanyInstitut für Chemie und Biochemie Forschungszentrum fu“r Elektronenmikroskopie Freie Universität Berlin Fabeckstraße 36a 14195 Berlin GermanyInstitut für Chemie und Biochemie Organische Chemie Freie Universität Berlin Takustr. 3 14195 Berlin GermanyDepartment of Chemistry Deenbandhu Chhoturam University of Science and Technology Murthal 131039 Sonipat IndiaInstitut für Chemie und Biochemie Organische Chemie Freie Universität Berlin Takustr. 3 14195 Berlin GermanyInstitut für Chemie und Biochemie Organische Chemie Freie Universität Berlin Takustr. 3 14195 Berlin GermanyAbstract A new class of non‐ionic dendritic amphiphiles has been developed from biobased chemicals, in particular glycerol‐based dendrons coupled to commercially available acids via the Steglich esterification process. These non‐ionic amphiphiles are functionalized with different hydrophobic segments to investigate the contribution of the same towards their guest transport behaviour. Therefore, different alkyl chains i.e, C8 and C12, as well as two different aromatic units were introduced as a hydrophobic segments and G1‐oligo‐glycerol as a hydrophilic segment. Their physicochemical properties were characterized by different techniques such as dynamic light scattering and fluorescence measurements. The results show that these amphiphiles form a very uniform micellar supramolecular structures that is independent of the hydrophobic system. The critical micelle concentration for the prepared non‐ionic amphiphiles was found to be in the range of 0.3 to 1.8 mg/mL, which depend on the type of hydrophobic units. The encapsulation capacities of the amphiphiles were tested using Nile Red and Nimodipine as model dye and drug, respectively. The encapsulation studies showed a preference for C12‐ and pyrene‐based amphiphiles through relatively different mechanisms unraveled by molecular dynamics (MD) simulations. Further, the cytotoxicity and cellular uptake of these systems as well as the release profiles were investigated.https://doi.org/10.1002/open.202400448Oligo-glycerol amphiphilesHydrophobicHydrophilicSupramolecular assembliesEncapsulation |
| spellingShingle | Pooja Kumari Christian Zoister Natalie Hanheiser Dr. Hesam Makki Dr. Boris Schade Dr. Mathias Dimde Katharina Achazi Dr. Sumit Kumar Prof. Dr. Rainer Haag Dr. Abhishek K. Singh Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as Nanocarriers ChemistryOpen Oligo-glycerol amphiphiles Hydrophobic Hydrophilic Supramolecular assemblies Encapsulation |
| title | Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as Nanocarriers |
| title_full | Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as Nanocarriers |
| title_fullStr | Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as Nanocarriers |
| title_full_unstemmed | Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as Nanocarriers |
| title_short | Synthesis of Dendritic Oligo‐Glycerol Amphiphiles with Different Hydrophobic Segments to Improve their Performance as Nanocarriers |
| title_sort | synthesis of dendritic oligo glycerol amphiphiles with different hydrophobic segments to improve their performance as nanocarriers |
| topic | Oligo-glycerol amphiphiles Hydrophobic Hydrophilic Supramolecular assemblies Encapsulation |
| url | https://doi.org/10.1002/open.202400448 |
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