Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate
Bioactive peptides are promising therapeutic agents due to their antimicrobial and anticancer activities, although their lack of selectivity often limits clinical applications. This study demonstrates the optimal synthetic route for conjugating folic acid (FA) with the bioactive peptide Lunatin-1, a...
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MDPI AG
2025-02-01
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| Series: | Organics |
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| Online Access: | https://www.mdpi.com/2673-401X/6/1/8 |
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| author | Amanda Neves de Souza Adriano Monteiro de Castro Pimenta Rodrigo Moreira Verly |
| author_facet | Amanda Neves de Souza Adriano Monteiro de Castro Pimenta Rodrigo Moreira Verly |
| author_sort | Amanda Neves de Souza |
| collection | DOAJ |
| description | Bioactive peptides are promising therapeutic agents due to their antimicrobial and anticancer activities, although their lack of selectivity often limits clinical applications. This study demonstrates the optimal synthetic route for conjugating folic acid (FA) with the bioactive peptide Lunatin-1, aiming to improve selectivity for neoplastic cells. The synthesis combines solid-phase peptide synthesis (SPPS) and Cu(I)-catalyzed cycloaddition to link folic acid to Lunatin-1 via a triazole ring. Using the model tripeptide FIG-<sub>NH2</sub>, key intermediates and the final product were characterized by high-performance liquid chromatography (HPLC), mass spectrometry (MALDI-ToF), Fourier-transform infrared spectroscopy (FTIR), and nuclear magnetic resonance (NMR). Reaction yields and purity were optimized with FIG-<sub>NH2</sub>, providing a reproducible synthesis pathway. Additionally, the results confirmed successful conjugation, with the FA-Trz-Luna product exhibiting molecular integrity and structural stability, as validated by spectral analyses. This study highlights a potential synthesis route for peptide-folate conjugates to be used as selective and multifunctional therapeutic agents, laying the groundwork for biological evaluations of their cytotoxicity and antimicrobial properties. |
| format | Article |
| id | doaj-art-22ffcf1367b64e05b0f37941648fb13b |
| institution | DOAJ |
| issn | 2673-401X |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Organics |
| spelling | doaj-art-22ffcf1367b64e05b0f37941648fb13b2025-08-20T02:42:28ZengMDPI AGOrganics2673-401X2025-02-0161810.3390/org6010008Synthesis and Characterization of the Conjugated Peptide Lunatin-FolateAmanda Neves de Souza0Adriano Monteiro de Castro Pimenta1Rodrigo Moreira Verly2Departamento de Química, Faculdade de Ciências Exatas, Universidade Federal dos Vales do Jequitinhonha e Mucuri (UFVJM)—Campus JK, Diamantina 39100-000, MG, BrazilDepartamento de Bioquímica e Imunologia, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, MG, BrazilDepartamento de Química, Faculdade de Ciências Exatas, Universidade Federal dos Vales do Jequitinhonha e Mucuri (UFVJM)—Campus JK, Diamantina 39100-000, MG, BrazilBioactive peptides are promising therapeutic agents due to their antimicrobial and anticancer activities, although their lack of selectivity often limits clinical applications. This study demonstrates the optimal synthetic route for conjugating folic acid (FA) with the bioactive peptide Lunatin-1, aiming to improve selectivity for neoplastic cells. The synthesis combines solid-phase peptide synthesis (SPPS) and Cu(I)-catalyzed cycloaddition to link folic acid to Lunatin-1 via a triazole ring. Using the model tripeptide FIG-<sub>NH2</sub>, key intermediates and the final product were characterized by high-performance liquid chromatography (HPLC), mass spectrometry (MALDI-ToF), Fourier-transform infrared spectroscopy (FTIR), and nuclear magnetic resonance (NMR). Reaction yields and purity were optimized with FIG-<sub>NH2</sub>, providing a reproducible synthesis pathway. Additionally, the results confirmed successful conjugation, with the FA-Trz-Luna product exhibiting molecular integrity and structural stability, as validated by spectral analyses. This study highlights a potential synthesis route for peptide-folate conjugates to be used as selective and multifunctional therapeutic agents, laying the groundwork for biological evaluations of their cytotoxicity and antimicrobial properties.https://www.mdpi.com/2673-401X/6/1/8Lunatin-1antimicrobial peptideCu-catalyzed azide?alkyne cycloadditionpeptide–drug conjugate |
| spellingShingle | Amanda Neves de Souza Adriano Monteiro de Castro Pimenta Rodrigo Moreira Verly Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate Organics Lunatin-1 antimicrobial peptide Cu-catalyzed azide?alkyne cycloaddition peptide–drug conjugate |
| title | Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate |
| title_full | Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate |
| title_fullStr | Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate |
| title_full_unstemmed | Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate |
| title_short | Synthesis and Characterization of the Conjugated Peptide Lunatin-Folate |
| title_sort | synthesis and characterization of the conjugated peptide lunatin folate |
| topic | Lunatin-1 antimicrobial peptide Cu-catalyzed azide?alkyne cycloaddition peptide–drug conjugate |
| url | https://www.mdpi.com/2673-401X/6/1/8 |
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