%0 Journal Article %1 WOS:000386402900059 %A Silva, Camilla V N S %A Barbosa, Jessica A P %A Ferraz, Milena S %A Silva, Nicacio H %A Honda, Neli K %A Rabello, Marcelo M %A Hernandes, Marcelo Z %A Bezerra, Beatriz P %A Cavalcanti, Isabella M F %A Ayala, Alejandro P %A Santos, Noemia P S %A Santos-Magalhaes, Nereide S %C RADARWEG 29, 1043 NX AMSTERDAM, NETHERLANDS %D 2016 %I ELSEVIER %J INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES %K Cyclodextrin; Microspheres} acid; {Diffractaic %P 494-503 %R 10.1016/j.ijbiomac.2016.06.073 %T Molecular modeling and cytotoxicity of diffractaic acid: HP-beta-CD inclusion complex encapsulated in microspheres %V 92 %X In this pioneer study, 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CD) was used to improve the solubility of the diffractaic acid (DA) via inclusion complex (DA:HP-beta-CD). Subsequently, DA:HP-beta-CD was incorporated into poly-epsilon-caprolactone (PCL) microspheres (DA:HP-beta-CD-MS). Microspheres containing DA (DA-MS) or DA:HP-beta-CD (DA:HP-beta-CD-MS) were prepared using the multiple W/O/W emulsion-solvent evaporation technique. The phase-solubility diagram of DA in HP-beta-CD (10-50mM) showed an A(L) type curve with a stability constant K-1:1=821 M-1. H-1 NMR, FTIR, X-ray diffraction and thermal analysis showed changes in the molecular environment of DA in DA:HP-beta-CD. The molecular modeling approach suggests a guest-host complex formation between the carboxylic moiety of both DA and the host (HP-beta-CD). The mean particle size of the microspheres were ODA-MS=5.23 +/- 1.65 mu m and ODA:HP-beta-CD-MS = 4.11 +/- 1.39 mu m, respectively. The zeta potential values of the microspheres were zeta(DA-MS) = -7.85 +/- 0.32 mV and zeta(DA):(HP-beta-CD-MS) = -6.93 +/- 0.46mV. Moreover, the encapsulation of DA:HP-beta-CD into microspheres resulted in a more slower release (k(2)=0.042 +/- 0.001; r(2) = 0.996) when compared with DA-MS (k(2)= 0.183 +/- 0.005; r(2) = 0.996). The encapsulation of DA or DA:HP-beta-CD into microspheres reduced the cytotoxicity of DA (IC50 = 43.29 mu M) against Vero cells (IC50 of DA-MS = 108.48 mu M and IC50 of DA:HP-beta-CD-MS = 142.63 mu M). (C) 2016 Elsevier B.V. All rights reserved.

@article{WOS:000386402900059, abstract = {In this pioneer study, 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CD) was used to improve the solubility of the diffractaic acid (DA) via inclusion complex (DA:HP-beta-CD). Subsequently, DA:HP-beta-CD was incorporated into poly-epsilon-caprolactone (PCL) microspheres (DA:HP-beta-CD-MS). Microspheres containing DA (DA-MS) or DA:HP-beta-CD (DA:HP-beta-CD-MS) were prepared using the multiple W/O/W emulsion-solvent evaporation technique. The phase-solubility diagram of DA in HP-beta-CD (10-50mM) showed an A(L) type curve with a stability constant K-1:1=821 M-1. H-1 NMR, FTIR, X-ray diffraction and thermal analysis showed changes in the molecular environment of DA in DA:HP-beta-CD. The molecular modeling approach suggests a guest-host complex formation between the carboxylic moiety of both DA and the host (HP-beta-CD). The mean particle size of the microspheres were ODA-MS=5.23 +/- 1.65 mu m and ODA:HP-beta-CD-MS = 4.11 +/- 1.39 mu m, respectively. The zeta potential values of the microspheres were zeta(DA-MS) = -7.85 +/- 0.32 mV and zeta(DA):(HP-beta-CD-MS) = -6.93 +/- 0.46mV. Moreover, the encapsulation of DA:HP-beta-CD into microspheres resulted in a more slower release (k(2)=0.042 +/- 0.001; r(2) = 0.996) when compared with DA-MS (k(2)= 0.183 +/- 0.005; r(2) = 0.996). The encapsulation of DA or DA:HP-beta-CD into microspheres reduced the cytotoxicity of DA (IC50 = 43.29 mu M) against Vero cells (IC50 of DA-MS = 108.48 mu M and IC50 of DA:HP-beta-CD-MS = 142.63 mu M). (C) 2016 Elsevier B.V. All rights reserved.}, added-at = {2022-05-23T20:00:14.000+0200}, address = {RADARWEG 29, 1043 NX AMSTERDAM, NETHERLANDS}, author = {Silva, Camilla V N S and Barbosa, Jessica A P and Ferraz, Milena S and Silva, Nicacio H and Honda, Neli K and Rabello, Marcelo M and Hernandes, Marcelo Z and Bezerra, Beatriz P and Cavalcanti, Isabella M F and Ayala, Alejandro P and Santos, Noemia P S and Santos-Magalhaes, Nereide S}, biburl = {https://www.bibsonomy.org/bibtex/285473a6f95d7693b7e8c3e08f3032bc5/ppgfis_ufc_br}, doi = {10.1016/j.ijbiomac.2016.06.073}, interhash = {e1068d60b1311533212842206ff101d0}, intrahash = {85473a6f95d7693b7e8c3e08f3032bc5}, issn = {0141-8130}, journal = {INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES}, keywords = {Cyclodextrin; Microspheres} acid; {Diffractaic}, pages = {494-503}, publisher = {ELSEVIER}, pubstate = {published}, timestamp = {2022-05-23T20:00:14.000+0200}, title = {Molecular modeling and cytotoxicity of diffractaic acid: HP-beta-CD inclusion complex encapsulated in microspheres}, tppubtype = {article}, volume = 92, year = 2016 }