Quantum-chemical investigation on 5-fluorouracil anticancer drug

Mohamed, Hala Sh.; Dahy, AbdelRahman A.; Hassan, G. S.; Eid, Samir; Mahfouz, R. M.

doi:10.1007/s11224-017-0913-3

Cited by 13 publications

(3 citation statements)

References 66 publications

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“…Different research groups have used density functional theory (DFT) studies , and X-ray crystal data ,− to analyze the driving force behind the self-assembly of 5-FU and 5-FDMU. Recently, Mohamed et al have shown the interactions behind the dimer formation of 5-FU in aqueous solution by DFT studies . All of these reports support our microscopic and spectroscopic observations of different kind of aggregates formed by 5-FU and 5-FDMU.…”

Section: Resultssupporting

confidence: 86%

“…Recently, Mohamed et al have shown the interactions behind the dimer formation of 5-FU in aqueous solution by DFT studies. 49 All of these reports support our microscopic and spectroscopic observations of different kind of aggregates formed by 5-FU and 5-FDMU. As previously mentioned, 5-FDMU does not have any −NH group and hence cannot form strong hydrogen-bond network as 5-FU to form fibril.…”

Section: Methodsmentioning

confidence: 99%

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Unveiling the Self-Assembling Behavior of 5-Fluorouracil and its N,N′-Dimethyl Derivative: A Spectroscopic and Microscopic Approach

et al. 2017

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Under physiological conditions, 5-fluorouracil (5-FU), an anticancer drug, self-assembles into fibrils by strong hydrogen-bonding network, whereas its N,N'-dimethyl derivative, 5-fluoro-1,3-dimethyluracil (5-FDMU), does not make fibrils due to lack of strong hydrogen-bonding motif. In vitro, 5-FU self-assembly is sensitive to physicochemical conditions like the pH and ionic strength of the solution, which tune the strength of the noncovalent driving forces. Here we report a surprising finding that the buffer, which is necessary to control the pH and is typically considered to be inert, also significantly influences 5-FU self-assembly, which indicates an important role of counterions in the fibril formation. We have also monitored concentration- and time-dependent fibrillar growth of 5-FU. Again, fibril growth process is probed under dynamic conditions using microfluidic platform. The self-assembly of 5-FU compared with its N,N'-dimethyl derivative shows lower cytotoxicity to the cultured human erythroleukemic cells (K562 cells), which plausibly states the reason behind the greater effectiveness of 5-FU derivative drugs than 5-FU itself.

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Section: Resultssupporting

confidence: 86%

Section: Methodsmentioning

confidence: 99%

Unveiling the Self-Assembling Behavior of 5-Fluorouracil and its N,N′-Dimethyl Derivative: A Spectroscopic and Microscopic Approach

et al. 2017

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“…Implementing natural bond orbital (NBO) analysis 110 can explore the hyperconjugation interactions within a molecule. These interactions stabilize the system by transferring electron density from a donor to an acceptor orbital.…”

Section: Resultsmentioning

confidence: 99%