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Application of Thermoresponsive PNIPAAM‑b‑PAMPTMA Diblock Copolymers in siRNA D...
Cardoso, Ana M.; Calejo, M. Teresa; Morais, Catarina M.; Cardoso, Ana L.; Cruz, Rita; Zhu, Kaizheng; de Lima, M. C. P.; Jurado, A. S.; Nyström, BoGene knockdown has emerged as an important tool for cancer gene therapy as well as for viral infections and dominantly inherited genetic disorders. The generation of suitable siRNA delivery systems poses some challenges, namely, to avoid nuclease degradation, to surpass the cytoplasmic membrane, and to release the nucleic acids into the cytosol. Aiming at evaluating the ability of thermoresponsive block copolym...
Tumor-targeted Chlorotoxin-coupled Nanoparticles for Nucleic Acid Delivery to G...
Costa, Pedro M.; Cardoso, Ana L.; Mendonça, Liliana S.; Serani, Angelo; Custódia, Carlos; Conceição, Mariana; Simões, Sérgio; Moreira, João N.The present work aimed at the development and application of a lipid-based nanocarrier for targeted delivery of nucleic acids to glioblastoma (GBM). For this purpose, chlorotoxin (CTX), a peptide reported to bind selectively to glioma cells while showing no affinity for non-neoplastic cells, was covalently coupled to liposomes encapsulating antisense oligonucleotides (asOs) or small interfering RNAs (siRNAs). T...
S4(13)-PV cell-penetrating peptide induces physical and morphological changes i...
Cardoso, Ana M. S.; Trabulo, Sara; Cardoso, Ana L.; Lorents, Annely; Morais, Catarina M.; Gomes, Paula; Nunes, Cláudia; Lúcio, Marlene; Reis, SaletteThe present work aims to gain insights into the role of peptide–lipid interactions in the mechanisms of cellular internalization and endosomal escape of the S4(13)-PV cell-penetrating peptide, which has been successfully used in our laboratory as a nucleic acid delivery system. A S4(13)-PV analogue, S4(13)-PVscr, displaying a scrambled amino acid sequence, deficient cell internalization and drug delivery inabil...
Substituent effects on the photolysis of methyl 2-carboxylate substituted aliph...
Gómez-Zavaglia, Andrea; Kaczor, Agnieszka; Cardoso, Ana L.; Melo, Teresa M. V. D. Pinho e; Fausto, RuiIn this study, the UV induced photochemical reactions of two 2H-azirines - methyl 2-chloro-3-methyl-2H-azirine-2-carboxylate (MCMAC) and methyl 3-methyl-2H-azirine-2-carboxylate (MMAC) - isolated in argon matrices are compared. For both compounds, irradiation with [lambda] > 235 nm led to observation of two primary photoprocesses: (a) CC bond cleavage, with production of nitrile ylides (P1-type products), and (...
Unusual Photochemical C−N Bond Cleavage in the Novel Methyl 2-Chloro-3-methyl-2...
Gómez-Zavaglia, Andrea; Kaczor, Agnieszka; Cardoso, Ana L.; Melo, Teresa M. V. D. Pinho e; Fausto, RuiThe structure, preferred conformers, vibrational spectrum, and photochemical behavior of the novel azirine, methyl 2-chloro-3-methyl-2H-azirine-2-carboxylate (MCMAC) were investigated in low-temperature matrixes and in the neat solid amorphous state by infrared spectroscopy and quantum-chemical calculations. Two conformers of the compound were observed in argon, krypton, and xenon matrixes, in agreement with th...
Intermolecular cycloaddition of nonstabilized azomethine ylides generated from ...
Cardoso, Ana L.; Kaczor, Agnieszka; Silva, Artur M. S.; Fausto, Rui; Melo, Teresa M. V. D. Pinho e; Gonsalves, António M. d'A. RochaThe 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate with nonstabilized azomethine ylides, generated via the decarboxylative condensation of 1,3-thiazolidine-4-carboxylic acids with aldehydes, afforded 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole derivatives. 2-Substituted-1,3-thiazolidine-4-carboxylic acids led to the stereoselective formation of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles. Quantum-che...
Methyl 3-Methyl-2H-azirine-2-carboxylate Photochemistry Studied by Matrix-isola...
Kaczor, Agnieszka; Gómez-Zavaglia, Andrea; Cardoso, Ana L.; Melo, Teresa M. V. D. Pinho e; Fausto, RuiThe aliphatic 2H-azirine, methyl 3-methyl-2H-azirine-2-carboxylate (MMAC), has been synthesized and its monomeric form investigated by IR spectroscopy in an argon matrix, at 10 K, as well as theoretically (DFT/B3LYP/6-311++G(d,p)). Two low-energy conformers of MMAC (Ct and Cc) were found in the matrix, both exhibiting the cis conformation around the C−O bond but differing in the arrangement around the C−Cα bond...
Intermolecular cycloaddition of nonstabilized azomethine ylides generated from ...
Cardoso, Ana L.; Kaczor, Agnieszka; Silva, Artur M.S.; Fausto, Rui; Melo, Teresa M.V.D. Pinho e; Gonsalves, António M. d'A. RochaThe 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate with nonstabilized azomethine ylides, generated via the decarboxylative condensation of 1,3-thiazolidine-4-carboxylic acids with aldehydes, afforded 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole derivatives. 2-Substituted-1,3-thiazolidine-4-carboxylic acids led to the stereoselective formation of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles. Quantum-che...
Novel Asymmetric Wittig Reaction: Synthesis of Chiral Allenic Esters
Melo, Teresa M. V. D. Pinho e; Cardoso, Ana L.; Gonsalves, António M. d'A. Rocha; Pessoa, João Costa; Paixão, José A.; Beja, Ana M.Wittig reactions between 10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetates (1 and 6) and ketenes resulted in asymmetric induction, with the selective synthesis of allenes with axial chirality. Use of the (1R)-(-)-10-(phenylsulfonyl)isoborneol unit allows the synthesis of allenes with S configuration, whereas use of the (1S)-(+)-10-(phenylsulfonyl)isoborneol unit produces allenes with R configura...
Contribution to the synthesis of chiral allenic esters
Melo, Teresa M. V. D. Pinho e; Cardoso, Ana L.; Gonsalves, António M. D'A. Rocha; Storr, Richard C.; Pessoa, João Costa; Paixão, José A.; Beja, Ana M.A phosphorus ylide bearing a 10-phenylsulfonylisoborneol unit reacted with ketenes, generated in situ from acid chlorides and triethylamine, to give allenic compounds. The reaction with methylketene led to asymmetric induction with the selective synthesis of an allene with axial chirality corresponding to an S configuration. The structure of the chiral allene 10-phenylsulfonylisobornyl penta-2,3-dienoate was de...
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