Alternative isolation protocol for desulfo and zwitterionic cylindrospermopsin alkaloids and comparison of their toxicity in hepG2 cells

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dc.contributorLaboratório de Desenvolvimento e Inovaçãopt_BR
dc.contributor.authorBlanco, Carlos Andrey Gonzálezpt_BR
dc.contributor.authorDörr, Felipe Augustopt_BR
dc.contributor.authorAlbuquerque, Renatapt_BR
dc.contributor.authorOnuki, Janicept_BR
dc.contributor.authorPinto, Ernanipt_BR
dc.date.accessioned2020-08-03T19:20:50Z-
dc.date.available2020-08-03T19:20:50Z-
dc.date.issued2020-
dc.identifier.citationBlanco CAG, Dörr FA, Albuquerque R, Onuki J, Pinto E. Alternative isolation protocol for desulfo and zwitterionic cylindrospermopsin alkaloids and comparison of their toxicity in hepG2 cells. Molecules. 2020 Jul;25(13)3027. doi:10.3390/molecules25133027.pt_BR
dc.identifier.issn1420-3049-
dc.identifier.urihttps://repositorio.butantan.gov.br/handle/butantan/3096-
dc.description.abstractThe term cylindrospermopsins (CYNs) refers to a structurally related class of cyanobacterial metabolites comprised of a tricyclic guanidine group and a hydroxymethyluracil moiety. Most reports in environmental aquatic samples refer to cylindrospermopsin (CYN), and reports on other CYN alkaloids are scarce, due, in part, to a lack of versatile isolation protocols. Thus, using commercially available solid phase extraction (SPE) cartridges, we optimized an isolation protocol for the complete recovery of CYN, 7-deoxy-cylindrospermopsin (7D-CYN) and 7-deoxy-desulfo-cylindrospermopsin (7D-desulfo-CYN) from the same aliquot. The isolation protocol was adaptable depending on the nature of the sample (solid biomass, culture broth or environmental water sample) and tolerates up to 4 L of dense culture broth or 400 mg of lyophilized biomass. To quantitate the CYN alkaloids, we validated an LC-DAD-MS2 method, which takes advantage of the UV absorption of the uracil group (λ 262 nm). Using electrospray ionization (ESI) in a positive ion mode, the high-resolution MS1 data confirms the presence of the protonated alkaloids, and the MS2 fragment assignment is reported as complementary proof of the molecular structure of the CYNs. We isolated three CYN alkaloids with different water solubility using the same lyophilized sample, with a purity that ranged from 95% to 99%. The biological activity of the purified CYNs, along with a synthetic degradation product of CYN (desulfo-cylindrospermopsin), was evaluated by assessing necrosis and apoptosis in vitro using flow cytometry. CYN’s lethal potency in HepG2 cells was greater than the other analogs, due to the presence of all four functional groups: guanidine, uracil, C-7 hydroxyl and the sulfate residuept_BR
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorshipUniversidade de São Paulo (USP)pt_BR
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)pt_BR
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
dc.format.extent3027pt_BR
dc.languageengpt_BR
dc.publisherMDPIpt_BR
dc.relation.ispartofMoleculespt_BR
dc.rightsOpen Accesspt_BR
dc.titleAlternative isolation protocol for desulfo and zwitterionic cylindrospermopsin alkaloids and comparison of their toxicity in hepG2 cellspt_BR
dc.typeArticlept_BR
dc.identifier.doi10.3390/molecules25133027pt_BR
dc.identifier.urlhttps://doi.org/10.3390/molecules25133027pt_BR
dc.contributor.externalUniversidade de São Paulo (USP)pt_BR
dc.contributor.externalOrganismo de Investigación Judicial (OIJ)pt_BR
dc.publisher.cityBaselpt_BR
dc.identifier.citationvolume25pt_BR
dc.identifier.citationissue13pt_BR
dc.subject.keywordLC-MS2pt_BR
dc.subject.keywordLC-DADpt_BR
dc.subject.keywordcylindrospermopsinpt_BR
dc.subject.keyword7-deoxy-cylindrospermopsinpt_BR
dc.subject.keyword7-deoxy-desulfo-cylindrospermopsinpt_BR
dc.subject.keywordcyanotoxinspt_BR
dc.subject.keywordHepG2 cellspt_BR
dc.subject.keywordbiomasspt_BR
dc.subject.keywordculture brothpt_BR
dc.relation.ispartofabbreviatedMoleculespt_BR
dc.identifier.citationabntv. 25, n. 13, 3027, jul. 2020pt_BR
dc.identifier.citationvancouver2020 Jul;25(13)3027pt_BR
dc.publisher.countrySwitzerlandpt_BR
dc.contributor.butantanBlanco, Carlos Andrey González|:Aluno|:Laboratório de Desenvolvimento e Inovação|:PrimeiroAutorpt_BR
dc.contributor.butantanOnuki, Janice|:Pesquisador|:Laboratório de Desenvolvimento e Inovaçãopt_BR
dc.sponsorship.butantanFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)¦¦2014/50420-9pt_BR
dc.sponsorship.butantanUniversidade de São Paulo (USP)¦¦1979pt_BR
dc.sponsorship.butantanCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)¦¦23038.001401/2018-92pt_BR
dc.sponsorship.butantanConselho Nacional de Desenvolvimento Científico e Tecnológico(CNPq)¦¦311048/2016-1pt_BR
dc.sponsorship.butantanConselho Nacional de Desenvolvimento Científico e Tecnológico(CNPq)¦¦439065/2018-6pt_BR
dc.identifier.bvsccBR78.1pt_BR
dc.identifier.bvsdbIBProdpt_BR
item.openairetypeArticle-
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item.grantfulltextembargo_29990101-
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