Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry
Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietino...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_14203049_v23_n6_p_Pertino |
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todo:paper_14203049_v23_n6_p_Pertino2023-10-03T16:13:15Z Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry Pertino, M.W. Petrera, E. Edith Alché, L. Schmeda-Hirschmann, G. Antiviral Click chemistry Cytotoxicity Hybrid molecules Terpenes antineoplastic agent antivirus agent terpene animal carbon nuclear magnetic resonance chemistry click chemistry drug effect drug screening electrospray mass spectrometry human Human alphaherpesvirus 1 mouse preclinical study proton nuclear magnetic resonance RAW 264.7 cell line synthesis tumor cell line Animals Antineoplastic Agents Antiviral Agents Carbon-13 Magnetic Resonance Spectroscopy Cell Line, Tumor Click Chemistry Drug Evaluation, Preclinical Drug Screening Assays, Antitumor Herpesvirus 1, Human Humans Mice Proton Magnetic Resonance Spectroscopy RAW 264.7 Cells Spectrometry, Mass, Electrospray Ionization Terpenes Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds. © 2018 by the authors. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14203049_v23_n6_p_Pertino |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Antiviral Click chemistry Cytotoxicity Hybrid molecules Terpenes antineoplastic agent antivirus agent terpene animal carbon nuclear magnetic resonance chemistry click chemistry drug effect drug screening electrospray mass spectrometry human Human alphaherpesvirus 1 mouse preclinical study proton nuclear magnetic resonance RAW 264.7 cell line synthesis tumor cell line Animals Antineoplastic Agents Antiviral Agents Carbon-13 Magnetic Resonance Spectroscopy Cell Line, Tumor Click Chemistry Drug Evaluation, Preclinical Drug Screening Assays, Antitumor Herpesvirus 1, Human Humans Mice Proton Magnetic Resonance Spectroscopy RAW 264.7 Cells Spectrometry, Mass, Electrospray Ionization Terpenes |
| spellingShingle |
Antiviral Click chemistry Cytotoxicity Hybrid molecules Terpenes antineoplastic agent antivirus agent terpene animal carbon nuclear magnetic resonance chemistry click chemistry drug effect drug screening electrospray mass spectrometry human Human alphaherpesvirus 1 mouse preclinical study proton nuclear magnetic resonance RAW 264.7 cell line synthesis tumor cell line Animals Antineoplastic Agents Antiviral Agents Carbon-13 Magnetic Resonance Spectroscopy Cell Line, Tumor Click Chemistry Drug Evaluation, Preclinical Drug Screening Assays, Antitumor Herpesvirus 1, Human Humans Mice Proton Magnetic Resonance Spectroscopy RAW 264.7 Cells Spectrometry, Mass, Electrospray Ionization Terpenes Pertino, M.W. Petrera, E. Edith Alché, L. Schmeda-Hirschmann, G. Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry |
| topic_facet |
Antiviral Click chemistry Cytotoxicity Hybrid molecules Terpenes antineoplastic agent antivirus agent terpene animal carbon nuclear magnetic resonance chemistry click chemistry drug effect drug screening electrospray mass spectrometry human Human alphaherpesvirus 1 mouse preclinical study proton nuclear magnetic resonance RAW 264.7 cell line synthesis tumor cell line Animals Antineoplastic Agents Antiviral Agents Carbon-13 Magnetic Resonance Spectroscopy Cell Line, Tumor Click Chemistry Drug Evaluation, Preclinical Drug Screening Assays, Antitumor Herpesvirus 1, Human Humans Mice Proton Magnetic Resonance Spectroscopy RAW 264.7 Cells Spectrometry, Mass, Electrospray Ionization Terpenes |
| description |
Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds. © 2018 by the authors. |
| format |
JOUR |
| author |
Pertino, M.W. Petrera, E. Edith Alché, L. Schmeda-Hirschmann, G. |
| author_facet |
Pertino, M.W. Petrera, E. Edith Alché, L. Schmeda-Hirschmann, G. |
| author_sort |
Pertino, M.W. |
| title |
Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry |
| title_short |
Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry |
| title_full |
Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry |
| title_fullStr |
Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry |
| title_full_unstemmed |
Synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry |
| title_sort |
synthesis, antiviral and cytotoxic activity of novel terpenyl hybrid molecules prepared by click chemistry |
| url |
http://hdl.handle.net/20.500.12110/paper_14203049_v23_n6_p_Pertino |
| work_keys_str_mv |
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| _version_ |
1807319876607410176 |