[Synthesis and properties of 5-fluorouracil derivatives].
| Title: | [Synthesis and properties of 5-fluorouracil derivatives]. |
|---|---|
| Authors: | Semakov AV; Blinkov AA; Gaenko GP; Vostrova AG; Molotkovskiĭ IuG |
| Source: | Bioorganicheskaia khimiia [Bioorg Khim] 2013 May-Jun; Vol. 39 (3), pp. 338-45. |
| Publication Type: | English Abstract; Journal Article |
| Language: | Russian |
| Journal Info: | Publisher: Nauka Country of Publication: Russia (Federation) NLM ID: 7804941 Publication Model: Print Cited Medium: Print ISSN: 0132-3423 (Print) Linking ISSN: 01323423 NLM ISO Abbreviation: Bioorg Khim Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Moskva, Nauka |
| MeSH Terms: | Fluorouracil/*administration & dosage ; Fluorouracil/*chemical synthesis ; Fluorouracil/*chemistry; 4-Aminobenzoic Acid/chemical synthesis ; 4-Aminobenzoic Acid/chemistry ; Adamantane/analogs & derivatives ; Adamantane/chemical synthesis ; Adamantane/chemistry ; Breast Neoplasms/drug therapy ; Breast Neoplasms/pathology ; Cell Line, Tumor/drug effects ; Fluorouracil/analogs & derivatives ; Liposomes/administration & dosage ; Liposomes/chemistry ; Palmitic Acid/chemical synthesis ; Palmitic Acid/chemistry ; Humans ; Hydrolysis ; Kinetics |
| Abstract: | A series of N-acyl derivatives of 5-fluorouracil (5-FU) bearing residues of palmitic, p-myristoylaminobenzoic, p-oleoylaminobenzoic, and 1-adamantanecarbonic acids was synthesized. Relative rates of hydrolysis of derivatives mentioned under physiological conditions, at pH 7.2 and 37 degrees C, have shown that stability of these compounds increases with reducing of spatial accessibility of amide group at N1 in 5-FU. These substances incorporate easily into lipid bilayer; their liposomal preparations showed substantial cytostatic activity on HBL (human breast lymphoma) cells and are of interest as potential antitumor preparations. Also, a fluorescent analog, 1-[8-(3-perylenyl)octanoyl]-5-fluorouracil, destined for studies of the 5-FU derivatives behavior in cells and tissues was prepared. |
| Substance Nomenclature: | 0 (Liposomes); 2V16EO95H1 (Palmitic Acid); 828-51-3 (adamantanecarboxylic acid); PJY633525U (Adamantane); TL2TJE8QTX (4-Aminobenzoic Acid); U3P01618RT (Fluorouracil) |
| Entry Date(s): | Date Created: 20140109 Date Completed: 20140221 Latest Revision: 20191027 |
| Update Code: | 20260130 |
| DOI: | 10.1134/s1068162013030138 |
| PMID: | 24397032 |
| Database: | MEDLINE |
English Abstract; Journal Article