Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines
ABSTRACT: Glioblastoma is one of the most lethal tumors, displaying striking cellular heterogeneity and drug resistance. The prognosis of patients suffering from glioblastoma after 5 years is only 5%. In the present work, capsaicin analogues bearing modifications on the acyl chain with long-chain fa...
Published in: | Applied Microbiology and Biotechnology |
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Springer Berlin Heidelberg
2024
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Online Access: | http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10786984/ http://www.ncbi.nlm.nih.gov/pubmed/38217255 https://doi.org/10.1007/s00253-023-12856-y |
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ftpubmed:oai:pubmedcentral.nih.gov:10786984 2024-02-11T09:56:35+01:00 Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines Diaz-Vidal, Tania Armenta-Pérez, Vicente Paúl Rosales-Rivera, Luis Carlos Basulto-Padilla, Georgina Cristina Martínez-Pérez, Raúl Balam Mateos-Díaz, Juan Carlos Gutiérrez-Mercado, Yanet K. Canales-Aguirre, Alejandro A. Rodríguez, Jorge A. 2024-01-12 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10786984/ http://www.ncbi.nlm.nih.gov/pubmed/38217255 https://doi.org/10.1007/s00253-023-12856-y en eng Springer Berlin Heidelberg http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10786984/ http://www.ncbi.nlm.nih.gov/pubmed/38217255 http://dx.doi.org/10.1007/s00253-023-12856-y © The Author(s) 2024 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . Appl Microbiol Biotechnol Biotechnological Products and Process Engineering Text 2024 ftpubmed https://doi.org/10.1007/s00253-023-12856-y 2024-01-21T01:42:41Z ABSTRACT: Glioblastoma is one of the most lethal tumors, displaying striking cellular heterogeneity and drug resistance. The prognosis of patients suffering from glioblastoma after 5 years is only 5%. In the present work, capsaicin analogues bearing modifications on the acyl chain with long-chain fatty acids showed promising anti-tumoral activity by its cytotoxicity on U-87 and U-138 glioblastoma multiforme cells. The capsaicin analogues were enzymatically synthetized with cross-linked enzyme aggregates of lipase B from Candida antarctica (CALB). The catalytic performance of recombinant CALB-CLEAs was compared to their immobilized form on a hydrophobic support. After 72 h of reaction, the synthesis of capsaicin analogues from linoleic acid, docosahexaenoic acid, and punicic acid achieved a maximum conversion of 69.7, 8.3 and 30.3% with CALB-CLEAs, respectively. Similar values were obtained with commercial CALB, with conversion yields of 58.3, 24.2 and 22% for capsaicin analogues from linoleic acid, DHA and punicic acid, respectively. Olvanil and dohevanil had a significant cytotoxic effect on both U-87 and U-138 glioblastoma cells. Irrespective of the immobilization form, CALB is an efficient biocatalyst for the synthesis of anti-tumoral capsaicin derivatives. KEY POINTS: • This is the first report concerning the enzymatic synthesis of capsaicin analogues from docosahexaenoic acid and punicic acid with CALB-CLEAs. • The viability U-87 and U-138 glioblastoma cells was significantly affected after incubation with olvanil and dohevanil. • Capsaicin analogues from fatty acids obtained by CALB-CLEAs are promising candidates for therapeutic use as cytotoxic agents in glioblastoma cancer cells. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s00253-023-12856-y. Text Antarc* Antarctica PubMed Central (PMC) Applied Microbiology and Biotechnology 108 1 |
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Biotechnological Products and Process Engineering |
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Biotechnological Products and Process Engineering Diaz-Vidal, Tania Armenta-Pérez, Vicente Paúl Rosales-Rivera, Luis Carlos Basulto-Padilla, Georgina Cristina Martínez-Pérez, Raúl Balam Mateos-Díaz, Juan Carlos Gutiérrez-Mercado, Yanet K. Canales-Aguirre, Alejandro A. Rodríguez, Jorge A. Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines |
topic_facet |
Biotechnological Products and Process Engineering |
description |
ABSTRACT: Glioblastoma is one of the most lethal tumors, displaying striking cellular heterogeneity and drug resistance. The prognosis of patients suffering from glioblastoma after 5 years is only 5%. In the present work, capsaicin analogues bearing modifications on the acyl chain with long-chain fatty acids showed promising anti-tumoral activity by its cytotoxicity on U-87 and U-138 glioblastoma multiforme cells. The capsaicin analogues were enzymatically synthetized with cross-linked enzyme aggregates of lipase B from Candida antarctica (CALB). The catalytic performance of recombinant CALB-CLEAs was compared to their immobilized form on a hydrophobic support. After 72 h of reaction, the synthesis of capsaicin analogues from linoleic acid, docosahexaenoic acid, and punicic acid achieved a maximum conversion of 69.7, 8.3 and 30.3% with CALB-CLEAs, respectively. Similar values were obtained with commercial CALB, with conversion yields of 58.3, 24.2 and 22% for capsaicin analogues from linoleic acid, DHA and punicic acid, respectively. Olvanil and dohevanil had a significant cytotoxic effect on both U-87 and U-138 glioblastoma cells. Irrespective of the immobilization form, CALB is an efficient biocatalyst for the synthesis of anti-tumoral capsaicin derivatives. KEY POINTS: • This is the first report concerning the enzymatic synthesis of capsaicin analogues from docosahexaenoic acid and punicic acid with CALB-CLEAs. • The viability U-87 and U-138 glioblastoma cells was significantly affected after incubation with olvanil and dohevanil. • Capsaicin analogues from fatty acids obtained by CALB-CLEAs are promising candidates for therapeutic use as cytotoxic agents in glioblastoma cancer cells. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s00253-023-12856-y. |
format |
Text |
author |
Diaz-Vidal, Tania Armenta-Pérez, Vicente Paúl Rosales-Rivera, Luis Carlos Basulto-Padilla, Georgina Cristina Martínez-Pérez, Raúl Balam Mateos-Díaz, Juan Carlos Gutiérrez-Mercado, Yanet K. Canales-Aguirre, Alejandro A. Rodríguez, Jorge A. |
author_facet |
Diaz-Vidal, Tania Armenta-Pérez, Vicente Paúl Rosales-Rivera, Luis Carlos Basulto-Padilla, Georgina Cristina Martínez-Pérez, Raúl Balam Mateos-Díaz, Juan Carlos Gutiérrez-Mercado, Yanet K. Canales-Aguirre, Alejandro A. Rodríguez, Jorge A. |
author_sort |
Diaz-Vidal, Tania |
title |
Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines |
title_short |
Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines |
title_full |
Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines |
title_fullStr |
Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines |
title_full_unstemmed |
Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines |
title_sort |
long chain capsaicin analogues synthetized by calb-cleas show cytotoxicity on glioblastoma cell lines |
publisher |
Springer Berlin Heidelberg |
publishDate |
2024 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10786984/ http://www.ncbi.nlm.nih.gov/pubmed/38217255 https://doi.org/10.1007/s00253-023-12856-y |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Appl Microbiol Biotechnol |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10786984/ http://www.ncbi.nlm.nih.gov/pubmed/38217255 http://dx.doi.org/10.1007/s00253-023-12856-y |
op_rights |
© The Author(s) 2024 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
op_doi |
https://doi.org/10.1007/s00253-023-12856-y |
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Applied Microbiology and Biotechnology |
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108 |
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