Supramolecular synthesis and characterization of crystalline solids obtained from the reaction of 5-fluorocytosine with nitro compounds

Dublin Core

Título

Supramolecular synthesis and characterization of crystalline solids obtained from the reaction of 5-fluorocytosine with nitro compounds

Tema

SINTESIS SUPRAMOLECULAR
CANCER
FLUOROCITOSINA
BIBLIOGRAFIA NACIONAL QUIMICA
2019

Abstract

Two novel multicomponent crystal forms of the prodrug 5-fluorocytosine (5-FC), an ionic cocrystal and a monohydrate salt, with 2,4,6-trinitrophenol (picric acid, PA) and 3,5-dinitrosalicylic acid (DNSA), respectively, were rationally designed and synthesized. Nitro compounds are used to treat many diseases, such as cancer, one of the 5-FC targets via gene-directed prodrug therapy. In addition, within the wide range of applications for nitro compounds is the formation of charge-transfer complexes with organic molecules. Among all 5-FC crystalline structures depicted, only two contain nitro compounds: a salt with PA and a dihydrate cocrystal with 5-nitrouracil. Therefore, the two new single translucent pale gold prism crystals of 5FC-PA and 5FC-DNSA were successfully obtained by slow evaporation from aqueous solution and characterized by X-ray diffraction (single crystal and powder), Fourier Transform Infrared (FT-IR), and Raman (FT-Raman) spectroscopies. In both crystal structures, the 5-FC pyrimidine ring is protonated at the N3 atom and the respective packings are mainly stabilized by N–H⋯O H-bonds. For the 5FC-PA ionic cocrystal, the formation of triple H-bonds (two N–H⋯O and one charge assisted N–H+⋯N H-bonds) among the 5-FC molecules was observed. This is consistent with the expected stability of the duplex structure, which is considered the strongest association between two species. In addition to the structural study, Hirshfeld surface analysis was carried out based on the single crystal X-ray diffraction data. Thermal stability was assessed through thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and hot-stage microscopy (HSM), indicating that these compounds are stable up to approximately 200 °C. The results contribute to the diversity of new 5-FC solid forms and introduce two novel compounds, with possible application in fungal/cancer medicine formulations or to better understand the behavior of cytosine in DNA/RNA base pairing.

Autor

Souza, Matheus S.
Diniz, Luan F.
da Silva, Cecília C. P.
Ellena, Javier

Fuente

New Journal Chemistry v. 43, 2019. -- p. 15924-15934

Editor

Royal Society of Chemistry

Fecha

2019

Derechos

Información sobre Derechos de Autor

(Por favor lea este aviso antes de abrir los documentos u objetos)

La legislación uruguaya protege el derecho de autor sobre toda creación literaria, científica o artística, tanto en lo que tiene que ver con sus derechos morales, como en lo referente a los derechos patrimoniales con sujeción a lo establecido por el derecho común y las siguientes leyes

(LEY 9.739 DE 17 DE DICIEMBRE DE 1937 SOBRE PROPIEDAD LITERARIA Y ARTISTICA CON LAS MODIFICACIONES INTRODUCIDAS POR LA LEY DE DERECHO DE AUTOR Y DERECHOS CONEXOS No. 17.616 DE 10 DE ENERO DE 2003, LEY 17.805 DE 26 DE AGOSTO DE 2004, LEY 18.046 DE 24 DE OCTUBRE DE 2006 LEY 18.046 DE 24 DE OCTUBRE DE 2006)

ADVERTENCIA - La consulta de este documento queda condicionada a la aceptación de las siguientes condiciones de uso: Este documento es únicamente para usos privados enmarcados en actividades de investigación y docencia. No se autoriza su reproducción con fines de lucro. Esta reserva de derechos afecta tanto los datos del documento como a sus contenidos. En la utilización o cita de partes debe indicarse el nombre de la persona autora.

Formato

Pdf

Idioma

Inglès

Tipo

Artìculo

Identificador

DOI: 10.1039/C9NJ03329G

Document Item Type Metadata

Original Format

Pdf
Fecha de agregación
January 16, 2020
Colección
Bibliografía Nacional Química
Tipo de Elemento
Document
Citación
Souza, Matheus S., “Supramolecular synthesis and characterization of crystalline solids obtained from the reaction of 5-fluorocytosine with nitro compounds,” RIQUIM - Repositorio Institucional de la Facultad de Química - UdelaR, accessed June 3, 2020, http://riquim.fq.edu.uy/items/show/5956.
Archivos