RESUMO
In this study, several derivatives of tetraphenylporphyrin were synthesized, each with unique meso-substituent groups including phenyl, methoxyphenyl, butyloxyphenyl, octyloxyphenyl, and dectyloxyphenyl. Additionally, their corresponding copper complexes were prepared and thoroughly characterized. The structural confirmation of all compounds was established through CHN elemental analysis, mass spectrometry, and FT-IR spectroscopy. As the number of carbon atoms in the alkyl long-chain increased, a slight red shift in the electronic absorption band was observed, which was attributed to the electronic influence of the alkyl group. DFT analysis indicated that electron density predominantly localized on the porphyrin ring of both the metal free porphyrins and copper (II) porphyrin complexes, with relatively low electron density in the p orbital of the meso-aryl long-chain substituent group. EPR spectroscopy of the Copper (II) ion complexes revealed signals, indicating their paramagnetic properties. Additionally, the Copper (II) tetraphenylporphyrin (CuTPP) complexes displayed two reversible oxidation peaks at +0.97 V and +1.35 V, whereas other derivatives exhibited lower oxidation potentials. The cytotoxicity of these compounds against MCF-7 cell lines was assessed using MTT assay, revealing cytotoxic effects in all cases. Among them, Copper (II) tetrakis (4-methyloxyphenyl)porphyrin (CuTOMPP) demonstrated the highest potential, with an IC50 value of 32.07 µg/mL.
Assuntos
Cobre , Porfirinas , Cobre/química , Humanos , Células MCF-7 , Porfirinas/química , Porfirinas/farmacologia , Técnicas Eletroquímicas , Neoplasias da Mama/patologia , FemininoRESUMO
This work presented a simple, rapid, green and efficient approach to the synthesis of gold nanoparticles using pullulan as a reducing/stabilizing/capping agent for drug delivery systems to increase the safety and efficacy of these systems. Monodispersed AuNPs@pullulan with prolonged stability were fully characterized by UV-VIS, FTIR, TEM, EDX, TGA and zeta potential analyses. A mechanism of AuNPs formation was proposed in which pullulan created reducing species for the reduction of Au3+ to AuNPs (Au0) that resulted in the formation of spherical AuNPs@pullulan with an average size of approximately 11±5nm, while the hydroxyl groups of pullulan were oxidized to carboxylate compounds. Novel cassiarin A chloride derivatives (3d and 3i) as candidate anticancer drugs were successfully loaded onto AuNPs@pullulan through electrostatic interactions. AuNPs@pullulan-3d (IC50=6.0±0.1µM) and AuNPs@pullulan-3i (5.2±0.1µM) exhibited a 10.2-fold and 7.1-fold higher cytotoxicity against KATO-III cells than free compounds 3d (60.9±0.6µM), 3i (37.1±0.2µM) and cisplatin (64.5±0.9µM), respectively. AuNPs@pullulan exhibited high cellular uptake, biocompatibility and non-cytotoxicity to normal cells. Therefore, AuNPs@pullulan-3d or AuNPs@pullulan-3i have the potential to be developed for treatment of gastric cancer.
Assuntos
Antineoplásicos/administração & dosagem , Portadores de Fármacos/química , Glucanos/química , Ouro , Nanopartículas Metálicas , Linhagem Celular Tumoral , HumanosRESUMO
Six new chamigrane sesquiterpenes, merulinols AâF (1â6), and four known metabolites (7â10) were isolated from the culture of the basidiomycetous fungus XG8D, a mangrove-derived endophyte. Their structures were elucidated mainly by 1D and 2D NMR, while the structures of 1 and 2 were further confirmed by single-crystal X-ray diffraction analysis. The in vitro cytotoxicity of all compounds was evaluated against three human cancer cell lines, MCF-7, Hep-G2, and KATO-3. Compounds 3 and 4 selectively displayed cytotoxicity against KATO-3 cells with IC50 values of 35.0 and 25.3 µM, respectively.
Assuntos
Basidiomycota/química , Endófitos/química , Fungos/química , Rhizophoraceae/microbiologia , Sesquiterpenos/química , Linhagem Celular Tumoral , Cristalografia por Raios X/métodos , Ensaios de Seleção de Medicamentos Antitumorais/métodos , Células Hep G2 , Humanos , Células MCF-7 , Estrutura Molecular , Sesquiterpenos/farmacologia , Tailândia , Difração de Raios X/métodosRESUMO
Five highly oxygenated chromones, rhytidchromones A-E, were isolated from the culture broth of a mangrove-derived endophytic fungus, Rhytidhysteron rufulum, isolated from Thai Bruguiera gymnorrhiza. Their structures were determined by analysis of 1D and 2D NMR spectroscopic data. The structure of rhytidchromone A was further confirmed by single-crystal X-ray diffraction analysis. These compounds were evaluated for cytotoxicity against four cancer cell lines (MCF-7, Hep-G2, Kato-3 and CaSki). All compounds, except for rhytidchromone D, displayed cytotoxicity against Kato-3 cell lines with IC50 values ranging from 16.0 to 23.3µM, while rhytidchromones A and C were active against MCF-7 cells with IC50 values of 19.3 and 17.7µM, respectively.
Assuntos
Antineoplásicos/isolamento & purificação , Ascomicetos/química , Cromonas/isolamento & purificação , Rhizophoraceae/microbiologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Cromonas/química , Cromonas/farmacologia , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Células Hep G2 , Humanos , Células MCF-7 , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Oxigênio , TailândiaRESUMO
Rhytidenone A (1), a unique spirobisnaphthalene with a 1,7-dioxaspiro[4,4]nonan-2-one motif, and five new spirobisnaphthalenes, rhytidenones B-F (2-6), were isolated from the extract of a cultured fungal endophyte, Rhytidhysteron sp. AS21B. Their structures were elucidated mainly by analysis of NMR spectroscopic data. The structure and configuration of 1 were further confirmed by single-crystal X-ray diffraction analysis. Compounds 3 and 4 exhibited significant inhibitory activity against nitric oxide production from activated macrophages with IC50 values of 0.31 and 3.60 µM, respectively.
Assuntos
Ascomicetos/química , Naftalenos/isolamento & purificação , Compostos de Espiro/isolamento & purificação , Animais , Cristalografia por Raios X , Feminino , Indometacina/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Conformação Molecular , Estrutura Molecular , Naftalenos/química , Naftalenos/farmacologia , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/microbiologia , Salvadoraceae/microbiologia , Compostos de Espiro/química , Compostos de Espiro/farmacologia , TailândiaRESUMO
Seven new limonoids, namely, xylorumphiins E-J (1-2 and 4-7) and 2-hydroxyxylorumphiin F (3), along with three known derivatives (8-10), were isolated from the seeds of Xylocarpus rumphii. 2-Hydroxyxylorumphiin F (3) and xylorumphiin I (6) displayed moderate inhibitory activity against nitric oxide production from lipopolysaccharide-activated macrophages with IC50 values of 24.5 and 31.3 µM, respectively.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Limoninas/isolamento & purificação , Limoninas/farmacologia , Sementes/química , Anti-Inflamatórios/química , Concentração Inibidora 50 , Limoninas/química , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Estrutura Molecular , Óxido Nítrico/biossíntese , Ressonância Magnética Nuclear Biomolecular , TailândiaRESUMO
Three new spirobisnaphthalenes (1-3) were isolated from the mangrove-derived fungus Rhytidhysteron sp., together with five known derivatives (4-8). The structures of the compounds were established on the basis of extensive spectroscopic data, and the relative configurations of their stereogenic carbons were determined by a single-crystal X-ray crystallographic analysis. Compounds 3-5 displayed cytotoxicity against both cancer cell lines, MCF-7 and CaSki, while 2 was active only on CaSKi cells.
Assuntos
Ascomicetos/química , Naftalenos/metabolismo , Naftalenos/farmacologia , Rhizophoraceae/microbiologia , Antibióticos Antineoplásicos/química , Antibióticos Antineoplásicos/isolamento & purificação , Antibióticos Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Fermentação , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Micélio/química , Naftalenos/isolamento & purificação , Espectrofotometria Ultravioleta , Difração de Raios XRESUMO
The title mol-ecule, C(28)H(20)O(8)S(2), has a T-shaped conformation. The central 9,10-anthraquinone moiety is bow-shaped with the two outer aromatic rings being inclined to one another by 13.99â (11)°. The benzenesulfonate rings are inclined to one another by 47.35â (12)°, and by 34.51â (11) and 17.88â (11)° to the bridging aromatic ring of the 9,10-anthraquinone moiety. In the crystal, C-Hâ¯O interactions link the mol-ecules into ribbons in [100].
RESUMO
A new andirobin, thaimoluccensin A (1), and two new phragmalin-type limonoids, thaimoluccensins B (2) and C (3), were isolated from seeds of a Thai mangrove plant, Xylocarpus moluccensis, together with eight known compounds. The structures of these compounds were elucidated on the basis of spectroscopic data. Only 7-deacetylgedunin (7), a gedunin-type limonoid, exhibited significant inhibitory activity against nitric oxide production from activated macrophages with IC(50) value less than 10 µM, suggesting that the compound has anti-inflammatory activity.
Assuntos
Anti-Inflamatórios/química , Cumarínicos/química , Limoninas/química , Meliaceae/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Humanos , Limoninas/isolamento & purificação , Limoninas/farmacologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Espectroscopia de Ressonância Magnética , Conformação Molecular , Óxido Nítrico/metabolismo , Sementes/química , TailândiaRESUMO
A new nor-chamigrane endoperoxide, merulin A (1), and two new chamigrane endoperoxides, merulins B and C (2, 3), were isolated from the culture broth extract of an endophytic fungus of Xylocarpus granatum. Their structures were elucidated on the basis of spectroscopic, mainly NMR and MS, data. X-ray crystallographic analysis confirmed the structure of 1. Compounds 1 and 3 displayed significant cytotoxicity against human breast (BT474) and colon (SW620) cancer cell lines.
Assuntos
Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Basidiomycota/química , Peróxidos/isolamento & purificação , Peróxidos/farmacologia , Antineoplásicos/química , Neoplasias da Mama/tratamento farmacológico , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Peróxidos/químicaRESUMO
Five new 3,4-seco-cycloartanes, sootepins A-E (1-5), along with four known triterpenes (6-9), were isolated from the apical buds of Gardenia sootepensis. Their structures were elucidated on the basis of spectroscopic methods (1D and 2D NMR, HRESIMS, and X-ray crystallography), and the compounds were tested for in vitro cytotoxic activity against human breast (BT474), lung (CHAGO), liver (Hep-G2), gastric (KATO-3), and colon (SW-620) cancer cell lines. Generally, the compounds possessing an exomethylene gamma-lactone ring showed broad cytotoxicity for all cell lines tested.