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Article ; Online: Recent Advances in Drug Discovery and Treatment of Neglected Diseases.

Lago, João H G / Domingues Passero, Luiz Felipe

2022 Volume 22, Issue 19, Page(s) 1593–1594

MeSH term(s)	Drug Discovery ; Humans ; Neglected Diseases/drug therapy
Language	English
Publishing date	2022-09-12
Publishing country	United Arab Emirates
Document type	Editorial
ZDB-ID	2064823-6
ISSN	1873-4294 ; 1568-0266
ISSN (online)	1873-4294
ISSN	1568-0266
DOI	10.2174/156802662219220728162323
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Article ; Online: Synthesis, characterization, and cytotoxic effects of new copper complexes using Schiff-base derivatives from natural sources.

Gomes, Rafael N / Silva, Matheus L / Gomes, Kaio S / Lago, João H G / Cerchiaro, Giselle

Journal of inorganic biochemistry

2023 Volume 250, Page(s) 112401

Abstract: Copper(II) complexes are interesting for cancer treatment due to their unique properties, including their redox potential, possible coordination structures with different ligands, the most diverse geometries, and different biomolecule reactivity. The ... ...

Abstract	Copper(II) complexes are interesting for cancer treatment due to their unique properties, including their redox potential, possible coordination structures with different ligands, the most diverse geometries, and different biomolecule reactivity. The present work synthesized new copper(II) complexes with Schiff-base (imine) type ligands using natural aldehydes such as cinnamaldehyde, vanillin, or ethyl vanillin. The ligands were obtained through the reaction of these aldehydes with the amines 1,3-diaminopropane, 2,2-dimethyl-1,3-propanediamine, or 1,3-diamino-2-propanol and characterized by
MeSH term(s)	Humans ; Copper/chemistry ; Neuroblastoma ; Magnetic Resonance Spectroscopy ; Acrolein/pharmacology ; Schiff Bases/chemistry ; Coordination Complexes/chemistry ; Ligands
Chemical Substances	Copper (789U1901C5) ; cinnamaldehyde (SR60A3XG0F) ; Acrolein (7864XYD3JJ) ; Schiff Bases ; Coordination Complexes ; Ligands
Language	English
Publishing date	2023-10-14
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	162843-4
ISSN	1873-3344 ; 0162-0134
ISSN (online)	1873-3344
ISSN	0162-0134
DOI	10.1016/j.jinorgbio.2023.112401
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Article ; Online: Selective cytotoxicity of ent-kaurene diterpenoids isolated from Baccharis lateralis and Baccharis retusa (Asteraceae).

Silva, Matheus L / Oliveira, Cyntia S / Dos Santos, Wagner J O / Oliveira, Vani X / Antar, Guilherme M / Lago, João H G / Cerchiaro, Giselle

Archiv der Pharmazie

2022 Volume 355, Issue 8, Page(s) e2200083

Abstract: This study presents the cytotoxic activity evaluation of the natural diterpenes ent-kaurenoic acid (1) and its 15β-hydroxy (2), 15β-senecioyloxy (3), and 15β-tiglinoyloxy (4) derivatives, isolated from Brazilian native plants, Baccharis retusa and B. ... ...

Abstract	This study presents the cytotoxic activity evaluation of the natural diterpenes ent-kaurenoic acid (1) and its 15β-hydroxy (2), 15β-senecioyloxy (3), and 15β-tiglinoyloxy (4) derivatives, isolated from Brazilian native plants, Baccharis retusa and B. lateralis (Asteraceae). Using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) colorimetric assay, it was observed that compound 1 displayed in vitro activity towards the aggressive MDA-MB-231 adenocarcinoma cell line and reduced toxicity against MCF-10A nontumorigenic epithelial cells, indicating expressive selectivity. On the contrary, compounds 2-4 exhibited reduced toxicity and selectivity in both tested cell lines. Based on the chemical structures of compounds 1-4, it is suggested that the presence of additional functional groups at the C-15 position-a hydroxyl group in compound 2 and isomeric isoprene units in compounds 3 and 4-might be responsible for the reduction in the potential/selectivity. In silico studies show, for compounds 1-4, good predictions regarding bioavailability and ADME (absorption, distribution, metabolism, and excretion) properties as well as no alerts for PAINS (pan-assay structures interference). In conclusion, ent-kaurenoic acid (1), a common diterpenoid isolated in high amounts from different plants belonging to the Baccharis genus, has been shown to be a promising cytotoxic agent against an aggressive adenocarcinoma cell line (MDA-MB-23) and, if well exploited, could be used as a scaffold in the development of molecular prototypes for the treatment of breast cancer.
MeSH term(s)	Adenocarcinoma ; Antineoplastic Agents/chemistry ; Baccharis/chemistry ; Diterpenes/pharmacology ; Diterpenes, Kaurane/chemistry ; Humans ; Structure-Activity Relationship
Chemical Substances	Antineoplastic Agents ; Diterpenes ; Diterpenes, Kaurane
Language	English
Publishing date	2022-05-12
Publishing country	Germany
Document type	Journal Article
ZDB-ID	6381-2
ISSN	1521-4184 ; 0365-6233 ; 1437-1014
ISSN (online)	1521-4184
ISSN	0365-6233 ; 1437-1014
DOI	10.1002/ardp.202200083
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Article ; Online: Integrative open workflow for confident annotation and molecular networking of metabolomics MSE/DIA data.

Katchborian-Neto, Albert / Alves, Matheus F / Bueno, Paula C P / de Jesus Nicácio, Karen / Ferreira, Miller S / Oliveira, Tiago B / Barbosa, Henrique / Murgu, Michael / de Paula Ladvocat, Ana C C / Dias, Danielle F / Soares, Marisi G / Lago, João H G / Chagas-Paula, Daniela A

Briefings in bioinformatics

2024 Volume 25, Issue 2

Abstract: Liquid chromatography coupled with high-resolution mass spectrometry data-independent acquisition (LC-HRMS/DIA), including MSE, enable comprehensive metabolomics analyses though they pose challenges for data processing with automatic annotation and ... ...

Abstract	Liquid chromatography coupled with high-resolution mass spectrometry data-independent acquisition (LC-HRMS/DIA), including MSE, enable comprehensive metabolomics analyses though they pose challenges for data processing with automatic annotation and molecular networking (MN) implementation. This motivated the present proposal, in which we introduce DIA-IntOpenStream, a new integrated workflow combining open-source software to streamline MSE data handling. It provides 'in-house' custom database construction, allows the conversion of raw MSE data to a universal format (.mzML) and leverages open software (MZmine 3 and MS-DIAL) all advantages for confident annotation and effective MN data interpretation. This pipeline significantly enhances the accessibility, reliability and reproducibility of complex MSE/DIA studies, overcoming previous limitations of proprietary software and non-universal MS data formats that restricted integrative analysis. We demonstrate the utility of DIA-IntOpenStream with two independent datasets: dataset 1 consists of new data from 60 plant extracts from the Ocotea genus; dataset 2 is a publicly available actinobacterial extract spiked with authentic standard for detailed comparative analysis with existing methods. This user-friendly pipeline enables broader adoption of cutting-edge MS tools and provides value to the scientific community. Overall, it holds promise for speeding up metabolite discoveries toward a more collaborative and open environment for research.
MeSH term(s)	Reproducibility of Results ; Workflow ; Metabolomics/methods ; Mass Spectrometry/methods ; Chromatography, Liquid/methods ; Software
Language	English
Publishing date	2024-02-07
Publishing country	England
Document type	Journal Article
ZDB-ID	2068142-2
ISSN	1477-4054 ; 1467-5463
ISSN (online)	1477-4054
ISSN	1467-5463
DOI	10.1093/bib/bbae013
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Article ; Online: Absolute Configuration and Antileishmanial Activity of (-)-Cyclocolorenone Isolated from

Monteiro, Jackson / Passero, Luiz Felipe D / Jesus, Jéssica A / Laurenti, Márcia D / Lago, João H G / Soares, Marisi G / Batista, Andrea N L / Batista, João M / Sartorelli, Patricia

Current topics in medicinal chemistry

2022 Volume 22, Issue 19, Page(s) 1626–1633

Abstract: Background: The fractionation of the n-hexane phase of the EtOH extract from the leaves of Duguetia lanceolata (Annonaceae) led to the identification of the sesquiterpene (-)-cyclocolorenone.: Objectives: Chemical characterization, including ... ...

Abstract	Background: The fractionation of the n-hexane phase of the EtOH extract from the leaves of Duguetia lanceolata (Annonaceae) led to the identification of the sesquiterpene (-)-cyclocolorenone. Objectives: Chemical characterization, including determination of the absolute stereochemistry, and in vitro evaluation of antileishmanial activity of the sesquiterpene (-)-cyclocolorenone, isolated from D. lanceolata, were carried out. Methods: (-)-Cyclocolorenone was isolated from D. lanceolata leaves using different chromatographic steps and its structure was defined by analysis of NMR and ESI-HRMS data. Additionally, the absolute configuration of (-)-cyclocolorenone was ambiguously assigned by means of vibrational circular dichroism (VCD). Antileishmanial activity of (-)-cyclocolorenone was evaluated on promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. The integrity of the cell membrane of L. (L.) amazonensis was analyzed using the SYTOX green probe. Results: (-)-(1R,6S,7R,10R)-Cyclocolorenone displayed activity against promastigotes and amastigotes forms of L. (L.) amazonensis with IC Conclusion: Obtained data suggested that (-)-cyclocolorenone, in which absolute configuration was determined, can be considered as a scaffold for the development of new drugs for the treatment of leishmaniasis.
MeSH term(s)	Animals ; Annonaceae ; Antiprotozoal Agents/chemistry ; Antiprotozoal Agents/pharmacology ; Mice ; Mice, Inbred BALB C ; Sesquiterpenes
Chemical Substances	Antiprotozoal Agents ; Sesquiterpenes ; cyclocolorenone (489-45-2)
Language	English
Publishing date	2022-07-24
Publishing country	United Arab Emirates
Document type	Journal Article
ZDB-ID	2064823-6
ISSN	1873-4294 ; 1568-0266
ISSN (online)	1873-4294
ISSN	1568-0266
DOI	10.2174/1568026622666220707095718
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Article: Petiveria alliacea, a plant used in Afro-Brazilian smoke rituals, triggers pulmonary inflammation in rats

Alves, Thiago Cagliumi / Girardi, Carlos Eduardo N / Hipólide, Debora C / Lago, João H.G / Prado, Carla M / Rodrigues, Eliana

Sociedade Brasileira de Farmacognosia Revista Brasileira de Farmacognosia. 2019 Sept., Oct., v. 29, no. 5

2019

Abstract: Petiveria alliacea L., Phytolaccaceae, a plant used in Afro-Brazilian religious smoke rituals is reported to have “harmonic properties” (anxiolytic effect) by ethnobotanical survey. In the present work, we analyzed the chemical composition of volatiles ... ...

Abstract	Petiveria alliacea L., Phytolaccaceae, a plant used in Afro-Brazilian religious smoke rituals is reported to have “harmonic properties” (anxiolytic effect) by ethnobotanical survey. In the present work, we analyzed the chemical composition of volatiles produced by leaves of P. alliacea, using headspace gas chromatography/mass spectrometry and its potential anxiolytic and toxic effects in smoke-exposed rats. Locomotor activity and anxiety-like behavior were allocated into groups, according to substance administration: acute (locomotor activity) or chronic (anxiety-like behavior) burning charcoal or to smoke from P. alliacea. Inflammatory cell counts in the bronchoalveolar lavage and morphometric analysis in airway were assessed. Animals exposed to P. alliacea smoke had no locomotor activity or elevated plus maze open arm exploration impairment, while lungs had lower number of macrophages in bronchoalveolar fluid and an increased number of mononuclear and polymorphonuclear cells in the peribronchovascular region. Chemical analysis of plant material allowed the identification of dimethylsulfide (18.7%), diethylsulfide (33.4%) and nerolidol (25.8%) as main volatile compounds. Taken together, prolonged exposure to P. alliacea smoke does not induce anxiolytic effects, but histological analyses indicate a possible pulmonary inflammatory response.
Keywords	burning ; charcoal ; chemical composition ; dimethyl sulfide ; elevated plus-maze test ; ethnobotany ; gas chromatography-mass spectrometry ; headspace analysis ; histology ; inflammation ; leaves ; locomotion ; lungs ; macrophages ; morphometry ; nerolidol ; Petiveria alliacea ; Phytolaccaceae ; rats ; respiratory tract diseases ; smoke ; surveys ; toxicity ; tranquilizers ; volatile compounds
Language	English
Dates of publication	2019-09
Size	p. 656-664.
Publishing place	Elsevier Editora Ltda.
Document type	Article
ISSN	0102-695X
DOI	10.1016/j.bjp.2019.06.005
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Predictive metabolomic signatures of end-stage renal disease: A multivariate analysis of population-based data.

Silva, Robson E / Baldim, João L / Chagas-Paula, Daniela A / Soares, Marisi G / Lago, João H G / Gonçalves, Reggiani V / Novaes, Rômulo D

Biochimie

2018 Volume 152, Page(s) 14–30

Abstract: The variability of molecular signatures and predictive low molecular weight markers of chronic kidney disease (CKD) in different populations are poorly understood. Thus, in a large sample with 4763 people we compare the molecular signatures and ... ...

Abstract	The variability of molecular signatures and predictive low molecular weight markers of chronic kidney disease (CKD) in different populations are poorly understood. Thus, in a large sample with 4763 people we compare the molecular signatures and metabolites with diagnostic relevance in plasma and urine of CKD patients of different geographical origins. From an integrated model based on dynamic networks and multivariate statistics, metabolites with predictive value obtained from targeted and untargeted molecular analysis, interactions between metabolic pathways affected by CKD, and the methodological quality of metabolomic studies were analyzed. The metabolites 3-methylhistidine, citrulline, kynurenine, p-cresol sulfate, urea, and citrate presented consistent expression in all population groups. Only increased kynurenine and p-cresol sulfate in plasma samples obtained acceptable scores as CKD biomarkers, independent of geographic origin. Metabolites such as leucine, alanine, isoleucine, serine, histidine, and citrate were nodal points, indicating that protein metabolism pathways are similarly impaired in Asian, European and North American patients. Based on our integrated model, we show that the metabolome of CKD patients exhibits a strong geographic influence, leading to unique metabolic signatures. Contrary to the likelihood of molecular similarities between geographically distinct populations, metabolic convergences in protein metabolism pathways and the molecules kynurenine and p-cresol sulfate were relevant as general predictors of CKD. In general, the quality assessment indicated that the current evidence is based on research models with variable methodological quality, whose limitations described in this study should be considered in the refinement of molecular approaches.
MeSH term(s)	Biomarkers/blood ; Biomarkers/urine ; Case-Control Studies ; Cresols/metabolism ; Female ; Humans ; Kidney Failure, Chronic/blood ; Kidney Failure, Chronic/metabolism ; Kidney Failure, Chronic/pathology ; Kidney Failure, Chronic/urine ; Kynurenine/metabolism ; Male ; Metabolomics ; Multivariate Analysis ; Oxidative Stress ; Population Surveillance ; Sulfuric Acid Esters/metabolism
Chemical Substances	Biomarkers ; Cresols ; Sulfuric Acid Esters ; Kynurenine (343-65-7) ; 4-cresol sulfate (56M34ZQY1S)
Language	English
Publishing date	2018-06-15
Publishing country	France
Document type	Journal Article
ZDB-ID	120345-9
ISSN	1638-6183 ; 0300-9084
ISSN (online)	1638-6183
ISSN	0300-9084
DOI	10.1016/j.biochi.2018.06.009
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Article ; Online: Synthesis and Structure-Activity Relationship of Dehydrodieugenol B Neolignans against

Sear, Claire E / Pieper, Pauline / Amaral, Maiara / Romanelli, Maiara M / Costa-Silva, Thais A / Haugland, Marius M / Tate, Joseph A / Lago, João H G / Tempone, Andre G / Anderson, Edward A

ACS infectious diseases

2020 Volume 6, Issue 11, Page(s) 2872–2878

Abstract: Trypanosoma ... ...

Abstract	Trypanosoma cruzi
MeSH term(s)	Anisoles ; Lignans/pharmacology ; Structure-Activity Relationship ; Trypanosoma cruzi
Chemical Substances	Anisoles ; Lignans ; dehydrodieugenol B
Language	English
Publishing date	2020-10-13
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	2373-8227
ISSN (online)	2373-8227
DOI	10.1021/acsinfecdis.0c00523
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Article ; Online: Sesquiterpene Lactones from

Caldas, Lhaís Araújo / Rodrigues, Mariana T / Batista, Andrea N L / Batista, João M / Lago, João H G / Ferreira, Marcelo J P / Rubio, Ileana G S / Sartorelli, Patricia

Molecules (Basel, Switzerland)

2020 Volume 25, Issue 13

Abstract: This work describes the chromatographic fractionation of the aerial parts ... ...

Abstract	This work describes the chromatographic fractionation of the aerial parts of
MeSH term(s)	Antineoplastic Agents, Phytogenic/chemistry ; Antineoplastic Agents, Phytogenic/pharmacology ; Asteraceae/chemistry ; Carcinoma/drug therapy ; Carcinoma/pathology ; Carcinoma, Papillary/drug therapy ; Carcinoma, Papillary/pathology ; Cell Proliferation ; Humans ; Lactones/pharmacology ; Molecular Structure ; Phytochemicals/chemistry ; Phytochemicals/pharmacology ; Plant Leaves/chemistry ; Sesquiterpenes/chemistry ; Sesquiterpenes/pharmacology ; Thyroid Neoplasms/drug therapy ; Thyroid Neoplasms/pathology ; Tumor Cells, Cultured
Chemical Substances	Antineoplastic Agents, Phytogenic ; Lactones ; Phytochemicals ; Sesquiterpenes ; calealactone B
Language	English
Publishing date	2020-06-30
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules25133005
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Article ; Online: Effects of Eugenol and Dehydrodieugenol B from

Bittencourt-Mernak, Márcia I / Pinheiro, Nathalia M / da Silva, Rafael C / Ponci, Vitor / Banzato, Rosana / Pinheiro, Aruanã J M C R / Olivo, Clarice R / Tibério, Iolanda F L C / Lima Neto, Lídio G / Santana, Fernanda P R / Lago, João H G / Prado, Carla M

Journal of natural products

2021 Volume 84, Issue 8, Page(s) 2282–2294

Abstract: Acute lung injury (ALI) is an important public health problem. The present work investigated whether dehydrodieugenol B treatment, a compound isolated from Brazilian ... ...

Abstract	Acute lung injury (ALI) is an important public health problem. The present work investigated whether dehydrodieugenol B treatment, a compound isolated from Brazilian plant
MeSH term(s)	Acute Lung Injury/chemically induced ; Acute Lung Injury/drug therapy ; Animals ; Anisoles/pharmacology ; Brazil ; Eugenol/pharmacology ; Lauraceae/chemistry ; Lipopolysaccharides ; Male ; Mice ; Mice, Inbred BALB C ; Phytochemicals/pharmacology ; Plant Leaves/chemistry ; Pneumonia/chemically induced ; Pneumonia/drug therapy ; RAW 264.7 Cells
Chemical Substances	Anisoles ; Lipopolysaccharides ; Phytochemicals ; dehydrodieugenol B ; Eugenol (3T8H1794QW)
Language	English
Publishing date	2021-07-15
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.1c00386
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