Non-peptidic cell-penetrating agents: synthesis of oligomeric chiral bicyclic guanidinium vectors
| العنوان: | Non-peptidic cell-penetrating agents: synthesis of oligomeric chiral bicyclic guanidinium vectors |
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| المؤلفون: | Julián Valero, Pilar Castreño, Michiel Luc Maria Van Gool, Pilar Prados, Ruth Pérez-Fernández, Jorge Sánchez-Quesada, Javier de Mendoza |
| المصدر: | Valero Moreno, J, Van Gool, M, Pérez-Fernández, R, Castreño, P, Sánchez-Quesada, J, Prados, P & de Mendoza, J 2012, ' Non-peptidic cell-penetrating agents: synthesis of oligomeric chiral bicyclic guanidinium vectors. ', Organic & Biomolecular Chemistry, vol. 10, pp. 5417-5430 . https://doi.org/10.1039/C2OB25467KTest |
| بيانات النشر: | Royal Society of Chemistry (RSC), 2012. |
| سنة النشر: | 2012 |
| مصطلحات موضوعية: | Cell Membrane Permeability, Stereochemistry, Cell, Trimer, Chemistry Techniques, Synthetic, Random hexamer, Biochemistry, Bridged Bicyclo Compounds, chemistry.chemical_compound, Tetramer, Thioether, Polyamines, medicine, Humans, Disulfides, Sulfhydryl Compounds, Histone octamer, Physical and Theoretical Chemistry, Guanidine, Bicyclic molecule, Organic Chemistry, Polyelectrolytes, Polyelectrolyte, medicine.anatomical_structure, chemistry, HeLa Cells |
| الوصف: | Polycationic oligo(chiral bicyclic guanidines) constitute useful non-peptidic penetrating agents for cell uptake and protein surface recognition. We report herein improved and selective procedures for the preparation of oligoguanidinium scaffolds linked through thioether bonds, with similar or different groups and functions at both ends of the chain. Two synthetic strategies were developed to obtain these compounds in relatively good yields from a common thioacetate precursor: generation of a disulfide intermediate or thiolate formation. Thus, tetraguanidinium intermediates 8 and 22 are best synthesized by the disulfide route, whereas hexamer 29, octamer 31, and trimer 37 arise from a combination of both the disulfide and the thioacetate routes. Finally, tetramer 28 can be readily obtained from either strategy. |
| تدمد: | 1477-0539 1477-0520 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::81f868f9237a618427e7b128665fb118Test https://doi.org/10.1039/c2ob25467kTest |
| حقوق: | RESTRICTED |
| رقم الانضمام: | edsair.doi.dedup.....81f868f9237a618427e7b128665fb118 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14770539 14770520 |
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