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dc.contributor.author
Laali, Kenneth K.
dc.contributor.author
Greves, William J.
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Correa-Smits, Sebastian J.
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Zwarycz, Angela T.
dc.contributor.author
Bunge, Scott D.
dc.contributor.author
Borosky, Gabriela Leonor
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dc.contributor.author
Manna, Alak
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Paulus, Aneel
dc.contributor.author
Chanan-Khan, Asher
dc.date.available
2019-10-17T17:54:38Z
dc.date.issued
2018-02
dc.identifier.citation
Laali, Kenneth K.; Greves, William J.; Correa-Smits, Sebastian J.; Zwarycz, Angela T.; Bunge, Scott D.; et al.; Novel fluorinated curcuminoids and their pyrazole and isoxazole derivatives: Synthesis, structural studies, Computational/Docking and in-vitro bioassay; Elsevier Science Sa; Journal of Fluorine Chemistry; 206; 2-2018; 82-98
dc.identifier.issn
0022-1139
dc.identifier.uri
http://hdl.handle.net/11336/86170
dc.description.abstract
In a continuing search for “curcuminoid (CUR) inspired” compounds with potential antitumor activity, a series of 21 new CUR-BF2 adducts and CURs bearing fluorine, trifluoromethylthio, trifluoromethoxy, and trifluoromethyl substitutents were synthesized in an effort to improve physicochemical properties such as lipophilicity and metabolic stability. Bulky activating groups namely methoxy, acetoxy, and benzyloxy groups were introduced as a way to tune steric/electronic effects. Multinuclear NMR, X-ray analysis and DFT optimizations confirmed that despite significant differences in their substitution patterns these curcuminoids all exist as enolic tautomers, and their CUR-BF2 adducts are symmetrical with equal B-O bond distances. To gauge the potential role of the enolic moiety in interaction with proteins, a library consisting of 22 aryl-pyrazole and isoxazole derivatives were synthesized. 19F NMR provided a rapid and convenient assay to monitor these transformations. Computational/docking studies were performed to compare binding efficiency to target proteins involved in specific cancers versus known inhibitor drugs. Several CUR pyrazoles and isoxazoles presented very favorable binding affinities, particularly those bearing CF3 groups. Highly favorable docking affinities were observed for the benzyloxy-substituted CURs. Selected compounds were tested by in-vitro bioassay against a panel of 60 cancer cell lines, and more specifically against leukemia cell lines by cell viability assay.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science Sa
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
COMPUTATIONAL DOCKING
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CURCUMINOID-BF2 ADDUCTS
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FLUORINATED CUR-PYRAZOLES AND ISOXAZOLES
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FLUOROCURCUMINOIDS
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IN-VITRO BIOASSAY
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X-RAY ANALYSIS
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Novel fluorinated curcuminoids and their pyrazole and isoxazole derivatives: Synthesis, structural studies, Computational/Docking and in-vitro bioassay
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2019-09-30T18:50:47Z
dc.journal.volume
206
dc.journal.pagination
82-98
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Laali, Kenneth K.. University Of North Florida; Estados Unidos
dc.description.fil
Fil: Greves, William J.. University Of North Florida; Estados Unidos
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Fil: Correa-Smits, Sebastian J.. University Of North Florida; Estados Unidos
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Fil: Zwarycz, Angela T.. University Of North Florida; Estados Unidos
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Fil: Bunge, Scott D.. Kent State University; Estados Unidos
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Fil: Borosky, Gabriela Leonor. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
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Fil: Manna, Alak. Mayo Clinic. Department of Cancer Biology; Estados Unidos
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Fil: Paulus, Aneel. Mayo Clinic. Department of Cancer Biology; Estados Unidos
dc.description.fil
Fil: Chanan-Khan, Asher. Mayo Clinic. Department of Cancer Biology; Estados Unidos
dc.journal.title
Journal of Fluorine Chemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.jfluchem.2017.11.013
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022113917303871?via%3Dihub
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