Glycolipids from Sargassum filipendula, a Natural Alternative for Overcoming ABC Transporter-Mediated MDR in Cancer.
ABCB1
ABCC1
Sargassum filipendula
cancer
glycolipids
multidrug resistance
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Nov 2023
Nov 2023
Historique:
received:
19
07
2023
accepted:
25
09
2023
medline:
29
11
2023
pubmed:
25
9
2023
entrez:
25
9
2023
Statut:
ppublish
Résumé
Chemotherapy is a widely used strategy to treat cancer, a disease that causes millions of deaths each year. However, its efficacy is reduced by the overexpression of ABC transporters, which are proteins that expel the drugs used in chemotherapy and involved in the multidrug resistance (MDR). Glycolipids have been identified as potential inhibitors of ABC transporters. Algae of the genus Sargassum contain high levels of glycolipids, making them a promising therapeutic alternative against the MDR phenotype. Sargassum filipendula glycolipids were obtained by exhaustive maceration with chloroform/methanol, purified by column and thin layer chromatography, and then characterized by FTIR, NMR, and LC-MS. Cell viability by PI labeling and inhibition of ABC transporters were analyzed by flow cytometry. Assessment of resistance reversal was determined by MTT assay. Ten sulfoquinovosylglycerol-type compounds were found, and six of them are reported for the first time. In particular, moiety 4 (GL-4) showed strong and moderate inhibitory activity against ABCC1 and ABCB1 transporters respectively. Treatment of GL-4 in combination with the antineoplastic drug vincristine sensitized Lucena-1 cell model to drug and reversed the MDR phenotype. This is the first report of glycolipids isolated from S. filipendula capable of inhibiting ABC transporters and thus overcoming acquired drug resistance.
Identifiants
pubmed: 37747792
doi: 10.1002/cbdv.202301058
doi:
Substances chimiques
ATP-Binding Cassette Transporters
0
Forssman glycolipid
60267-39-2
Antineoplastic Agents
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301058Subventions
Organisme : Universidad de Antioquia
Organisme : Institute of Chemistry of the University of Antioquia
Organisme : CODI of the Universidad de Antioquia
ID : 2019-25210
Organisme : Glycobiology Laboratory/IBCCF/UFRJ
Organisme : CNPq
Organisme : FAPERJ
Organisme : Cancer Foundation/Brazil
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
Références
D. Hanahan, R. A. Weinberg, Cell 2011, 144, 646-674.
“World Health Organization,” can be found under https://www.who.int/news-room/fact-sheets/detail/cancer/, 2022 (accessed 13 June 2023).
National Cancer Institute, “Cancer Basics,” can be found under https://www.cancer.gov/about-cancer/treatment/types, 2022 (accessed 13 June 2023).
E. Dickens, S. Ahmed, Surg. 2021, 39, 215-220.
S.-T. Pan, Z.-L. Li, Z.-X. He, J.-X. Qiu, S.-F. Zhou, Clin. Exp. Pharmacol. Physiol. 2016, 43, 723-737.
L. W. Elmore, S. F. Greer, E. C. Daniels, C. C. Saxe, M. H. Melner, G. M. Krawiec, W. G. Cance, W. C. Phelps, Ca-Cancer J. Clin. 2021, 71, 107-139.
Janice Ann Gabriel, The Biology of Cancer, England 2007, 130-132.
D. J. Hutschison, Adv. Cancer Res. 1963, 7, 235-250.
M. Rebucci, C. Michiels, Biochem. Pharmacol. 2013, 85, 1219-1226.
M. Bar-Zeev, Y. D. Livney, Y. G. Assaraf, Drug Resist. Updat. Rev. Comment. Antimicrob. Anticancer Chemother. 2017, 31, 15-30.
C.-P. Wu, C.-H. Hsieh, Y.-S. Wu, Mol. Pharm. 2011, 8, 1996-2011.
L. N. Abdullah, E. K.-H. Chow, Clin. Transl. Med. 2013, 2, 3.
P. Borst, R. Evers, M. Kool, J. Wijnholds, J. Natl. Cancer Inst. 2000, 92, 1295-1302.
P. M. Jones, A. M. George, Cell. Mol. Life Sci. 2004, 61, 682-699.
M. P. Ween, M. A. Armstrong, M. K. Oehler, C. Ricciardelli, Crit. Rev. Oncol. Hematol. 2015, 96, 220-256.
M. Dean, A. Rzhetsky, R. Allikmets, Genome Res. 2001, 11, 1156-1166.
R. L. Juliano, V. Ling, Biochim. Biophys. Acta 1976, 455, 152-162.
S. P. Cole, G. Bhardwaj, J. H. Gerlach, J. E. Mackie, C. E. Grant, K. C. Almquist, A. J. Stewart, E. U. Kurz, A. M. Duncan, R. G. Deeley, Science 1992, 258, 1650-1654.
R. Silva, V. Vilas-Boas, H. Carmo, R. J. Dinis-Oliveira, F. Carvalho, M. de Lourdes Bastos, F. Remião, Pharmacol. Ther. 2015, 149, 1-123.
S. P. C. Cole, Annu. Rev. Pharmacol. Toxicol. 2014, 54, 95-117.
H. Cui, A. J. Zhang, M. Chen, J. J. Liu, Curr. Drug Targets 2015, 16, 1356-1371.
Y. Xiao, W.-S. Ji, W.-K. Jin, P. Wen, L.-H. Shan, Z.-R. Hou, X.-H. Li, X.-L. Zhou, Y.-J. Liu, J.-B. Xu, F. Gao, Bioorg. Chem. 2023, 131, 106329.
M. L. Amin, Drug Target Insights 2013, 7, 27-34.
A. Palmeira, E. Sousa, M. H. Vasconcelos, M. M. Pinto, Curr. Med. Chem. 2012, 19, 1946-2025.
K. M. da Costa, E. J. Salustiano, R. do C. Valente, L. Freire-de-Lima, L. Mendonça-Previato, J. O. Previato, Molecules 2021, 26, 3510.
K. M. da Costa, R. C. Valente, E. J. Salustiano, L. B. Gentile, L. Freire-de-Lima, L. Mendonça-Previato, J. O. Previato, Front. Microbiol. 2018, 9, 205.
J. Castañeda-Gómez, D. Rosas-Ramírez, S. Cruz-Morales, M. Fragoso-Serrano, R. Pereda-Miranda, Rev. Bras. Farmacogn. 2017, 27, 434-439.
S. Cruz-Morales, J. Castañeda-Gómez, G. Figueroa-González, A. D. Mendoza-García, A. Lorence, R. Pereda-Miranda, J. Nat. Prod. 2012, 75, 1603-1611.
S. Cruz-Morales, J. Castañeda-Gómez, D. Rosas-Ramírez, M. Fragoso-Serrano, G. Figueroa-González, A. Lorence, R. Pereda-Miranda, J. Nat. Prod. 2016, 79, 3093-3104.
E. Bautista, M. Fragoso-Serrano, R. Pereda-Miranda, J. Nat. Prod. 2015, 78, 168-172.
G. Figueroa-González, N. Jacobo-Herrera, A. Zentella-Dehesa, R. Pereda-Miranda, J. Nat. Prod. 2012, 75, 93-97.
L. Mattio, C. Payri, Bot. Rev. 2011, 77, 31-70.
S. R. Yende, U. N. Harle, B. B. Chaugule, Pharmacogn. Rev. 2014, 8, 1-7.
M. I. Rushdi, I. A. M. Abdel-Rahman, H. Saber, E. Z. Attia, W. M. Abdelraheem, H. A. Madkour, H. M. Hassan, A. H. Elmaidomy, U. R. Abdelmohsen, RSC Adv. 2020, 10, 24951-24972.
S. Logvinov, N. Gerasimenko, A. Esipov, V. A. Denisenko, J. Phycol. 2015, 51, 1066-1074.
V. M. Dembitsky, O. A. Rozentsvet, E. E. Pechenkina, Phytochemistry 1990, 29, 3417-3421.
S. I. Alzarea, A. H. Elmaidomy, H. Saber, A. Musa, M. M. Al-Sanea, E. M. Mostafa, O. M. Hendawy, K. A. Youssif, A. S. Alanazi, M. Alharbi, A. M. Sayed, U. R. Abdelmohsen, Antibiot. 2021, 10, 4.
Z. Hossain, H. Kurihara, M. Hosokawa, K. Takahashi, In Vitro Cell. Dev. Biol. Anim. 2005, 41, 154-159.
C.-J. Tsai, B. Sun Pan, J. Agric. Food Chem. 2012, 60, 8404-8410.
D. A. Abdelrheem, A. A. Rahman, K. N. M. Elsayed, H. R. Abd El-Mageed, H. S. Mohamed, S. A. Ahmed, J. Mol. Struct. 2021, 1225, 129245.
J. Santos, F. Guihéneuf, G. Fleming, F. Chow, D. Stengel, Algal Res. 2019, 41, 101572.
N. M. Sanina, S. N. Goncharova, E. Y. Kostetsky, Phytochemistry 2004, 65, 721-730.
N. M. Sanina, S. N. Goncharova, E. Y. Kostetsky, Phytochemistry 2008, 69, 1517-1527.
N. M. Sanina, E. Y. Kostetsky, V. L. Shnyrov, A. V Tsybulsky, O. D. Novikova, O. Y. Portniagina, N. S. Vorobieva, A. N. Mazeika, M. V Bogdanov, Biochimie 2012, 94, 1048-1056.
S. E. Fomenko, N. F. Kushnerova, V. G. Sprygin, E. S. Drugova, L. N. Lesnikova, V. Y. Merzlyakov, T. V Momot, Russ. J. Plant Physiol. 2019, 66, 942-949.
Z. Cui, Y. S. Li, H. B. Liu, D. Yuan, B. R. Lu, J. Asian Nat. Prod. Res. 2001, 3, 117-122.
Y. H. Kim, E.-H. Kim, C. Lee, M.-H. Kim, J.-R. Rho, Lipids 2007, 42, 395-399.
M. P. Rahelivao, M. Gruner, H. Andriamanantoanina, I. Bauer, H.-J. Knölker, Nat. Products Bioprospect. 2015, 5, 223-235.
E. Plouguerné, L. M. de Souza, G. L. Sassaki, C. Hellio, R. Trepos, B. A. P. da Gama, R. C. Pereira, E. Barreto-Bergter, Front. Mar. Sci. 2020, 7, 116.
A.-C. Ma, Z. Chen, T. Wang, N. Song, Q. Yan, Y.-C. Fang, H.-S. Guan, H.-B. Liu, J. Agric. Food Chem. 2014, 62, 11157-11162.
E. Plouguerné, E. Ioannou, P. Georgantea, C. Vagias, V. Roussis, C. Hellio, E. Kraffe, V. Stiger-Pouvreau, Mar. Biotechnol. (NY). 2010, 12, 52-61.
E. Plouguerné, L. M. de Souza, G. L. Sassaki, J. F. Cavalcanti, M. T. Villela Romanos, B. A. P. da Gama, R. C. Pereira, E. Barreto-Bergter, Mar. Drugs 2013, 11, 4628-4640.
K. Fitch, C. Kemker, “Algae, Phytoplankton and Chlorophyll. Fundamentals of Environmental Measurements,” can be found under https://www.fondriest.com/environmental-measurements/parameters/water-quality/algae-phytoplankton-and-chlorophyll, 2014 (accessed 24 May 2023).
Y. M. Qian, W. C. Song, H. Cui, S. P. Cole, R. G. Deeley, J. Biol. Chem. 2001, 276, 6404-6411.
F. J. Sharom, Essays Biochem. 2011, 50, 161-178.
S. V Ambudkar, C. Kimchi-Sarfaty, Z. E. Sauna, M. M. Gottesman, Oncogene 2003, 22, 7468-7485.
M. A. A. Ibrahim, K. A. A. Abdeljawaad, A. H. M. Abdelrahman, L. A. Jaragh-Alhadad, H. F. Oraby, E. B. Elkaeed, G. A. H. Mekhemer, G. A. Gabr, A. M. Shawky, P. A. Sidhom, M. E. S. Soliman, M. F. Moustafa, P. W. Paré, M.-E. F. Hegazy, Molecules 2022, 27, 10.
T. W. Loo, D. M. Clarke, Biochem. Biophys. Res. Commun. 2005, 329, 419-422.
S. Mollazadeh, A. Sahebkar, F. Hadizadeh, J. Behravan, S. Arabzadeh, Life Sci. 2018, 214, 118-123.
E. J. Salustiano, K. M. da Costa, L. Freire-de-Lima, L. Mendonça-Previato, J. O. Previato, J. Biol. Chem. 2020, 295, 6457-6471.
K. M. da Costa, R. do C. Valente, L. M. da Fonseca, L. Freire-de-Lima, J. O. Previato, L. Mendonça-Previato, Pathog. (Basel, Switzerland) 2022, 11, 988.
K. M. da Costa, L. Freire-de-Lima, L. M. da Fonseca, J. O. Previato, L. Mendonça-Previato, R. do C. Valente, Int. J. Mol. Sci. 2023, 24.
J. M. L. Folch, M. P. Lees, G. H. A. Stanley, J. Biol. Chem. 1957, 226, 497-509.
N. Daflon-Yunes, F. E. Pinto-Silva, R. S. Vidal, B. F. Novis, T. Berguetti, R. R. S. Lopes, C. Polycarpo, V. M. Rumjanek, Mol. Cell. Biochem. 2013, 383, 123-135.