Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma Stability
Peptide-based therapy is appealing in modern medicine owing to its high activity and excellent biocompatibility. Poor stability, leading to unacceptable bioavailability, severely constrains its clinical application. Here, we proposed a general supramolecular approach for improving the plasma resista...
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MDPI AG
2025-01-01
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| author | Keming Ren Junyi Chen Chunju Li |
| author_facet | Keming Ren Junyi Chen Chunju Li |
| author_sort | Keming Ren |
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| description | Peptide-based therapy is appealing in modern medicine owing to its high activity and excellent biocompatibility. Poor stability, leading to unacceptable bioavailability, severely constrains its clinical application. Here, we proposed a general supramolecular approach for improving the plasma resistance of a commercially available peptide agent, thymopentin. The <sup>1</sup>H NMR results indicated that the large-sized extended biphen[3]arene carboxylate (ExBP3C) can entirely encapsulate this peptide at its main chain with a binding stoichiometry of 1:1 and <i>K</i><sub>a</sub> value of (1.87 ± 0.15) × 10<sup>5</sup> M<sup>−1</sup>, which varied radically from recognizing specific amino acid residues by carboxylatopillar[5]arene (CP5A). Notably, host–guest complexation by ExBP3C could maintain 24.85% of the original thymopentin amount for 60 min in the presence of rat plasma, whereas free thymopentin, or co-dosed with CP5A and cucurbit[7]uril, underwent rapid degradation and became undetectable within just 30 min. In addition, cytotoxicity and hemolysis assays preliminary demonstrated that the employment of ExBP3C as a supplementary material was relatively nontoxic at a cellular level. |
| format | Article |
| id | doaj-art-4162f67b6ec245a08ee55b9d54e8efd6 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
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| series | Molecules |
| spelling | doaj-art-4162f67b6ec245a08ee55b9d54e8efd62025-01-24T13:43:33ZengMDPI AGMolecules1420-30492025-01-0130231410.3390/molecules30020314Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma StabilityKeming Ren0Junyi Chen1Chunju Li2Second Clinical Medical College, Heilongjiang University of Chinese Medicine, Harbin 150006, ChinaAcademy of Interdisciplinary Studies on Intelligent Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, ChinaAcademy of Interdisciplinary Studies on Intelligent Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, ChinaPeptide-based therapy is appealing in modern medicine owing to its high activity and excellent biocompatibility. Poor stability, leading to unacceptable bioavailability, severely constrains its clinical application. Here, we proposed a general supramolecular approach for improving the plasma resistance of a commercially available peptide agent, thymopentin. The <sup>1</sup>H NMR results indicated that the large-sized extended biphen[3]arene carboxylate (ExBP3C) can entirely encapsulate this peptide at its main chain with a binding stoichiometry of 1:1 and <i>K</i><sub>a</sub> value of (1.87 ± 0.15) × 10<sup>5</sup> M<sup>−1</sup>, which varied radically from recognizing specific amino acid residues by carboxylatopillar[5]arene (CP5A). Notably, host–guest complexation by ExBP3C could maintain 24.85% of the original thymopentin amount for 60 min in the presence of rat plasma, whereas free thymopentin, or co-dosed with CP5A and cucurbit[7]uril, underwent rapid degradation and became undetectable within just 30 min. In addition, cytotoxicity and hemolysis assays preliminary demonstrated that the employment of ExBP3C as a supplementary material was relatively nontoxic at a cellular level.https://www.mdpi.com/1420-3049/30/2/314peptide drugmacrocyclic hostmolecular recognitionplasma stability |
| spellingShingle | Keming Ren Junyi Chen Chunju Li Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma Stability Molecules peptide drug macrocyclic host molecular recognition plasma stability |
| title | Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma Stability |
| title_full | Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma Stability |
| title_fullStr | Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma Stability |
| title_full_unstemmed | Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma Stability |
| title_short | Entire Encapsulation of Thymopentin by Extended Biphen[3]arene Carboxylate for Improving Plasma Stability |
| title_sort | entire encapsulation of thymopentin by extended biphen 3 arene carboxylate for improving plasma stability |
| topic | peptide drug macrocyclic host molecular recognition plasma stability |
| url | https://www.mdpi.com/1420-3049/30/2/314 |
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