loading...
Our research is centered in solid state chemistry of organic compounds, aiming at the design, search, and selective preparation of solid forms. Active pharmaceutical ingredients, APIs, are the main targets of research owing to the potential impact of dissimilarities in physico-chemical properties of the different solid forms on API stability and effectiveness.
Engineering multicomponent pharmaceutical solid samples - co-crystals, salts, solvates, solid solutions, binary eutectics - aiming at biopharmaceutical performance improvement or dual-drug therapy, is one the targets of research. A special emphasis is placed on co-crystals investigation, namely on the effect of co-former structural changes and synthon competition on co-crystal formation capability, and on the potential use of co-crystals for chiral resolution.
Polymorphism of organic APIs and other organic compounds (with emphasis on chiral ones, both enantiomers and racemates) is also being addressed. Solvent effects on polymorph crystallization and rationalization of the ability of molecular compounds to give rise to plastic crystal mesophases are topics being investigated.
Polymorphism
of organic APIs and other organic compounds (with emphasis on chiral
ones, both enantiomers and racemates) is also being addressed.
Solvent effects on polymorph crystallization and rationalization of
the ability of molecular compounds to give rise to plastic crystal
mesophases are topics being investigated.
M. Ermelinda S. Eusébio, Department of Chemistry, FCTUC | João
Canotilho, Faculty of Pharmacy, UC | Mário
T. S. Rosado, Department of Chemistry, FCTUC |
| | | |
| | ||
Ricardo
A. E. Castro, Faculty of Pharmacy, UC | Teresa
M. R. Maria, Department of Chemistry, FCTUC | |
Manuela
Ramos Silva, Department of Physics, FCTUC | Ewa
Dryzek, Henryk Niewodniczański Institute of Nuclear Physics Polish Academy of Sciences, Krakow, Poland |
Gilbert
Bannach, UNESP, Universidade Estadual Paulista, Brazil | Glauco
Lini Perpétuo, UNESP, Universidade Estadual Paulista, Brazil |
| ||
Mariani
Armagni Ciciliati, PhD student - sandwich, (Universidade de São Paulo, Brazil) | Bruno
Barreto da Cunha Holanda, PhD student – sandwich, (Universidade Estadual Paulista, Brazil) | Joana
Silva, MSc Student |
| | | |
João
Agria Baptista, MSc researcher | | |
|
|
| |
| Machado, S.M.T., Castro, R.A.E., Maria, T.M.R., Canotilho, J., Eusébio, M.E.S., Levetiracetam + nonsteroidal anti-inflammatory drug binary systems: a contribution to the development of new solid dosage forms, Int. J. Pharm., 533, pp. 1-13, 2017. DOI:10.1016/j.ijpharm.2017.09.012 |
Maria, T.M.R., Marins, F.A., Costa, J.B.S., Ramos Silva, M. Carrilho, R.M.B., Monteiro, C.J.P., Pereira, M.M., Eusébio, M.E.S., Solid state investigation of BINOL and BINOL derivatives: A contribution to enantioselective symmetry breaking by crystallization, Thermochim. Acta, 648, pp. 32-43, 2017. DOI: 10.1016/j.tca.2016.12.008 |
Cortesão, A.M., Henriques, J.G., Castro, R.A.E., Maria, T.M.R., Canotilho, J., Eusébio, M. E.S., Binary phase diagrams of pyridinecarboxamide isomers, J. Therm. Anal. Calorim., 130, pp. 1727–1733, 2017. DOI: 10.1007/s10973-017-6474-2 |
Nogueira, B.A., Ildiz, G.O., Canotilho, J., Eusébio, M.E.S., Henriques, M.S.C., Paixão, J.A., Fausto, R., 5-Methylhydantoin: From Isolated Molecules in a Low-Temperature Argon Matrix to Solid State Polymorphs Characterization, J. Phys. Chem. A, 121, pp. 5267-5279, 2017. DOI: 10.1021/acs.jpca.7b05030 |
Viel, Q., Brandel, C., Cartigny, Y., Eusébio, M.E.S., Canotilho, J., Dupray, V., Dargent, E., Coquerel, G., Petit, S., Crystallization from the Amorphous State of a Pharmaceutical Compound: Impact of Chirality and Chemical Purity, Cryst. Growth Des., 17, pp. 337-346, 2017. DOI: 10.1021/acs.cgd.6b01566 |
Susano, M.T., Martín-Ramos, P., Maria, T.M.R., Folkersma, S., Pereira, L.C.J., Ramos Silva, M., Co-crystal of suberic acid and 1,2-bis(4-pyridyl)ethane: A new case of packing polymorphism, J. Mol. Struct., 1147, pp, 76-83, 2017. DOI: 10.1016/j.molstruc.2017.06.043 |
Martín-Ramos, P., Maria, T.M.R., Guimaraes, A.C., Carrión-Prieto, P., Hernández-Navarro, S., Martín-Gil, J., Crude and refined oils from Elaeis guineensis: Facile characterization by FTIR and thermal analysis techniques, Int. J. Food Prop., 20S3, pp. S2739-S2749, 2017. DOI: 10.1080/10942912.2017.1372470 |
Perpétuo, G.L., Chierice, G.O., Ferreira, L.T., Fraga-Silva, T.F.C., Venturini, J., Arruda, M.S.P., Bannach, G., Castro, R.A.E., A combined approach using differential scanning calorimetry with polarized light thermomicroscopy in the investigation of ketoprofen and nicotinamide cocrystal, J. Therm. Anal. Calorim., 651, pp. 1-10, 2017. DOI: 10.1016/j.tca.2017.02.014 |
Évora, A.O.L., Castro, R.A.E., Maria, T.M.R., Ramos Silva, M., ter Horst, J.H., Canotilho J., Eusébio, M.E.S., Co-crystals of diflunisal and isomeric pyridinecarboxamides - a thermodynamics and crystal engineering contribution, Cryst. Eng.Comm., 18, pp. 4749-4759, 2016. DOI: 10.1039/c6ce00380j |
Miranda, M.D., Chávez, F.V., Maria, T.M.R., Eusébio, M.E.S., Sebastião, P.J., Martín-Ramos, P., Figueirinhas, J.L., Ramos Silva, M., Synthesis of liquid crystals based on hydrogen-bonding of 4-(Octyloxy)benzoic acid with 4-alkylbenzoic acids, Mol. Cryst. Liq. Cryst., 630, pp. 87-101, 2016. DOI: 10.1080/15421406.2016.1146881 |
Gallo, R.C., Ferreira, A.P.G., Castro, R.A.E., Cavalheiro, E.T.G., Studying the thermal decomposition of carvedilol by coupled TG-FTIR, J. Therm. Anal. Calorim., 123, pp. 2307-2312, 2016. DOI:10.1007/s10973-015-4931-3 |
Sousa, A.F., Gandini, A., Caetano, A., Maria, T.M.R., Freire, C.S.R., Neto, C. P.l, Silvestre, A.J.D., Unravelling the distinct crystallinity and thermal properties of suberin compounds from Quercus suber and Betula pendula outer barks, Int. J. Biol. Macromol. 93, pp. 686-694, 2016. DOI: 10.1016/j.ijbiomac.2016.09.031 |
Brandel, C., Cartigny, Y., Couvrat, N., Eusébio, M.E.S., Canotilho, J., Petit, S., Coquerel, G., Mechanisms of Reversible Phase Transitions in Molecular Crystals: Case of Ciclopirox, Chem. Mater., 27, pp. 6360-6373, 2015. DOI: 10.1021/acs.chemmater.5b02389 |
Silva, P.S.P., Castro, R.A.E., Melro, E., Ramos Silva, M., Maria, T.M.R., Canotilho, J., Eusébio, M.E.S., Structural evidence of polymorphism and conformational isomorphism of a somewhat flexible molecule: m-anisic acid, J. Therm. Anal. Calorim., 120, pp. 667-677, 2015. DOI: 10.1007/s10973-014-4289-y |
Évora, A.O.L., Castro, R.A.E., Maria, T.M.R., Ramos Silva, M., ter Horst, J.H., Canotilho J., Eusébio, M.E.S., A thermodynamic based approach on the investigation of a diflunisal pharmaceutical co-crystal with improved intrinsic dissolution rate. Int. J. Pharm., 466, pp.67–74, 2014. DOI: 10.1016/j.ijpharm.2014.02.048 |
Bebiano, S.V.S., Rosado, M.T.S., Castro, R.A.E., Ramos Silva, M., Canotilho, J., Maria, T.M.R., Eusébio, M.E.S., Polymorphism of cis-1,4-cyclohexanediol, a new plastic crystal former. Considerations on isomeric cyclohexanediols plastic crystal forming abilities, J. Mol. Struct., Polymorphism and Disorder issue, 1078, pp. 10-19, 2014. DOI: 10.1016/j.molstruc.2014.02.008 |
Rosado, M.T.S., Maria, T.M.R., Castro, R.A.E., Canotilho, J., Ramos Silva, M., Eusébio, M.E.S., Molecular structure and polymorphism of a cyclohexanediol: trans-1,4-cyclohexanedimethanol, Cryst. Eng. Comm., 16, pp. 10977-10986, 2014. DOI:10.1039/c4ce01211a |
Nogueira, B., Ildiz, G., Canotilho, J., Eusébio, M.E.S., Fausto, R., Molecular Structure, Infrared Spectra, Photochemistry and Thermal Properties of 1-Methylhydantoin, J. Phys. Chem. A, 118, pp. 5994-6008, 2014. DOI: 10.1021/jp505335c |
Arranja, C.T., Marcos, M., Ramos Silva, M., Eusébio, M.E.S., Castro, R.A.E., Sobral, A.J.F.N., Synthesis and polymorphism evaluation of the 3,5-bis(decyloxy)benzaldehyde, J. Therm. Anal. Calorim., 117, pp. 1375-1383, 2014. DOI 10.1007/s10973-014-3904-2 |
Miranda, M.D., Chávez, F.V., Maria, T.M.R., Eusébio, M.E.S., Sebastião, P.J., Ramos Silva, M., Self-assembled liquid crystals by hydrogen bonding between bipyridyl and alkylbenzoic acids: solvent free synthesis by mechanochemistry, Liq. Cryst., 41, pp. 1743-1751, 2014. DOI: 10.1080/02678292.2014.950048 |
Maria, T.M.R., Castro, R.A.E., Ramos Silva, M., Ramos, M.L., Justino, L.L.G., Burrows, H.D., Canotilho, J., Eusébio, M.E.S., Polymorphism and melt crystallisation of racemic betaxolol, a beta-adrenergic antagonist drug, J. Thermal Anal. Calorim., 111, pp. 2171-2178, 2013. DOI: 10.1007/s10973-012-2765-9 |
Cabral, L.I.L., Maria, T.M.R., Martelo, L., Eusébio, M.E.S., Cristiano, M.L.S., Fausto, R., The Thermal sigmatropic isomerization of pseudosaccharyl crotyl ether, Tetrahedron, 69, pp. 810-815, 2013. DOI: 10.1016/j.tet.2012.10.100 |
| Polarized-light thermomicroscope | |
| One of our DSC systems |
Variable temperature FTIR with interchangeable ATR accessory | |