Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring
We chemically linked corosolic and asiatic acids and a synthetic polyoxygenated analogue of ursolic acid via an alkyl linker to the cationic mitochondrial targeting compound F16 (4-(1H-indole-3-ylvinyl)-<i>N</i>-methylpyridinium iodide). The conjugates were tested for cytotoxic activity...
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MDPI AG
2023-11-01
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| author | Anna Spivak Darya Nedopekina Eldar Davletshin |
| author_facet | Anna Spivak Darya Nedopekina Eldar Davletshin |
| author_sort | Anna Spivak |
| collection | DOAJ |
| description | We chemically linked corosolic and asiatic acids and a synthetic polyoxygenated analogue of ursolic acid via an alkyl linker to the cationic mitochondrial targeting compound F16 (4-(1H-indole-3-ylvinyl)-<i>N</i>-methylpyridinium iodide). The conjugates were tested for cytotoxic activity against two human lung adenocarcinoma cell lines, H1299 and A549, and non-cancerous mouse embryonic fibroblast cells. The results showed that conjugation of polyoxygenated triterpene acids with the terminal cationic fragment F16 in the C-28 side chain enhanced cytotoxicity (30–35 fold) compared to the original natural ursolic acid. However, the presence of hydroxyl or acetyl functions in the A-ring of F16 conjugates of corosolic or asiatic acids resulted in a significant decrease in cytotoxicity compared to their structural analogue, the F16 derivative of ursolic acid. |
| format | Article |
| id | doaj-art-c23b210734b14ca79ca596123273ae47 |
| institution | DOAJ |
| issn | 2673-4583 |
| language | English |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
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| series | Chemistry Proceedings |
| spelling | doaj-art-c23b210734b14ca79ca596123273ae472025-08-20T02:56:06ZengMDPI AGChemistry Proceedings2673-45832023-11-011414310.3390/ecsoc-27-16177Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ringAnna Spivak0Darya Nedopekina1Eldar Davletshin2Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, RussiaInstitute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, RussiaInstitute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, RussiaWe chemically linked corosolic and asiatic acids and a synthetic polyoxygenated analogue of ursolic acid via an alkyl linker to the cationic mitochondrial targeting compound F16 (4-(1H-indole-3-ylvinyl)-<i>N</i>-methylpyridinium iodide). The conjugates were tested for cytotoxic activity against two human lung adenocarcinoma cell lines, H1299 and A549, and non-cancerous mouse embryonic fibroblast cells. The results showed that conjugation of polyoxygenated triterpene acids with the terminal cationic fragment F16 in the C-28 side chain enhanced cytotoxicity (30–35 fold) compared to the original natural ursolic acid. However, the presence of hydroxyl or acetyl functions in the A-ring of F16 conjugates of corosolic or asiatic acids resulted in a significant decrease in cytotoxicity compared to their structural analogue, the F16 derivative of ursolic acid.https://www.mdpi.com/2673-4583/14/1/43ursolic acidconjugatespolyhydroxylated A-ringdelocalized lypophilic cationsF16anti-cancer agents |
| spellingShingle | Anna Spivak Darya Nedopekina Eldar Davletshin Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring Chemistry Proceedings ursolic acid conjugates polyhydroxylated A-ring delocalized lypophilic cations F16 anti-cancer agents |
| title | Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring |
| title_full | Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring |
| title_fullStr | Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring |
| title_full_unstemmed | Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring |
| title_short | Synthesis and Cytotoxic Activity of Conjugates of Mitochondrial-Directed Cationic Compound F16 with Ursane-Structure Triterpenic Acids Containing a Polyhydroxylated A-ring |
| title_sort | synthesis and cytotoxic activity of conjugates of mitochondrial directed cationic compound f16 with ursane structure triterpenic acids containing a polyhydroxylated a ring |
| topic | ursolic acid conjugates polyhydroxylated A-ring delocalized lypophilic cations F16 anti-cancer agents |
| url | https://www.mdpi.com/2673-4583/14/1/43 |
| work_keys_str_mv | AT annaspivak synthesisandcytotoxicactivityofconjugatesofmitochondrialdirectedcationiccompoundf16withursanestructuretriterpenicacidscontainingapolyhydroxylatedaring AT daryanedopekina synthesisandcytotoxicactivityofconjugatesofmitochondrialdirectedcationiccompoundf16withursanestructuretriterpenicacidscontainingapolyhydroxylatedaring AT eldardavletshin synthesisandcytotoxicactivityofconjugatesofmitochondrialdirectedcationiccompoundf16withursanestructuretriterpenicacidscontainingapolyhydroxylatedaring |