Cytotoxicity and radiosensitising activity of synthesized dinitrophenyl derivatives of 5-fluorouracil View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2012-12

AUTHORS

Khosrou Abdi, Ali Khalaj, Syeed-Naser Ostad, Mohammad Reza Khoshayand

ABSTRACT

BACKGROUND AND THE PURPOSE OF THE STUDY: Dual functional agents in which nitroaromatic or nitroheterocyclic compounds are attached through a linker unit to mustards and aziridines have shown higher cytotoxicities than the corresponding counterparts to both aerobic and hypoxic cells and enhanced radiosensitizing activity. In the present investigation cytotoxicity and radiosensitizing activity of 2,4-dinitrobenzyl, 2,4-dinitrobenzoyl, and 2,4-dinitrophenacetyl derivatives of 5-fluorouracil which was assumed to release cytotoxic active quinone methidide and 5-fluorouracil under hypoxic conditions on HT-29 cell line under both aerobic and hypoxic conditions was investigated. METHODS: 5-fluorouracil derivative X-XIII were prepared by the reaction of the corresponding di-nitro substituted benzyl, benzoyl and phenacetyl halides with 5-fluorouracil protected at N-1 with di-t-butoxydicarbonate (BOC) in dimethyl formamide (DMF) in the presence of the potassium carbonate followed by hydrolysis of the blocking group by potassium carbonate in methanol. Cytotoxicity of fluorouracil VIII and tested compounds X-XIII against HT-29 cell line under both aerobic and hypoxic conditions after 48 hrs incubation were measured by determination of the percent of the survival cells using 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and percent of the dead cells using propidium iodide(PI)-digitonine assay and results were used to calculate the corresponding IC(50) values. Radiosensitization experiments were carried out by irradiation of the incubations with a (60)Co source and clonogenic assay was performed to determine the cell viabilities following treatment with the tested compounds and/or radiation. Sensitization Enhancement Ratio (SER) of each tested compound was obtained from the radiation survival curves in the absence and presence of each sensitizer for 37% survival respectively. RESULTS AND MAJOR CONCLUSION: Findings of the present study showed that alkylation or acylation of 5-fluorouracil result in compounds which have little or no cytotoxicity and radiosensitizing activity under aerobic conditions, but have high cytotoxicity and radiosensitizing effects under hypoxic conditions. Furthermore radiosensitizing activities of compounds under hypoxic conditions increased by increase in their concentrations and SER of the tested 5-FU derivatives at concentrations higher than 50 μmol were equal or higher than 1.6 which is the minimum effective SER of a radiosensitizer in an in vitro assay. More... »

PAGES

3

References to SciGraph publications

  • 2006-12. Clonogenic assay of cells in vitro in NATURE PROTOCOLS
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1186/1560-8115-20-3

    DOI

    http://dx.doi.org/10.1186/1560-8115-20-3

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1015668255

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/23226112


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