Biomaterial Database

Synthesis, physicochemical properties, and cytotoxicity of a series of 5'-ester prodrugs of 5-iodo-2'-deoxyuridine. 1988

M M Narurkar, and A K Mitra

Department of Industrial and Physical Pharmacy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.

Five aliphatic 5'-esters of 5-iodo-2'deoxyuridine (IDU) were synthesized via an acid chloride alcoholysis reaction. The solubility in pH 7.4 phosphate buffer, lipophilicity as determined by partition experiments in octanol/pH 7.4 buffer, and cytotoxicity of these potential prodrugs were evaluated. The esters showed a 43- to 250-fold increase in lipophilicity and a 1.6- to 14-fold decrease in aqueous solubility relative to IDU. At a concentration of 50 microM, all esters showed reduced cytotoxicity toward uninfected Vero cells relative to IDU.

UI	MeSH Term	Description	Entries
D007065	Idoxuridine	An analog of DEOXYURIDINE that inhibits viral DNA synthesis. The drug is used as an antiviral agent.	5-Iodo-2'-deoxyuridine,IUdR,Iododeoxyuridine,5-Iododeoxyuridine,Allergan 211,Herplex Liquifilm,Idoxuridine, 123I-Labeled,Idoxuridine, 125I-Labeled,Idoxuridine, 131I-Labeled,Idoxuridine, 3H-Labeled,Idoxuridine, Radical Ion (+1),Idoxuridine, Radical Ion (1-),Kerecide,NSC-39661,Oftan-IDU,SK&F-14287,Stoxil,123I-Labeled Idoxuridine,125I-Labeled Idoxuridine,131I-Labeled Idoxuridine,3H-Labeled Idoxuridine,5 Iodo 2' deoxyuridine,5 Iododeoxyuridine,Idoxuridine, 123I Labeled,Idoxuridine, 125I Labeled,Idoxuridine, 131I Labeled,Idoxuridine, 3H Labeled,Liquifilm, Herplex,NSC 39661,NSC39661,Oftan IDU,OftanIDU
D010766	Phosphorylation	The introduction of a phosphoryl group into a compound through the formation of an ester bond between the compound and a phosphorus moiety.	Phosphorylations
D011355	Prodrugs	A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.	Drug Precursor,Drug Precursors,Pro-Drug,Prodrug,Pro-Drugs,Precursor, Drug,Precursors, Drug,Pro Drug,Pro Drugs
D002627	Chemistry, Physical	The study of CHEMICAL PHENOMENA and processes in terms of the underlying PHYSICAL PHENOMENA and processes.	Physical Chemistry,Chemistries, Physical,Physical Chemistries
D002851	Chromatography, High Pressure Liquid	Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed.	Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012995	Solubility	The ability of a substance to be dissolved, i.e. to form a solution with another substance. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed)	Solubilities
D014709	Vero Cells	A CELL LINE derived from the kidney of the African green (vervet) monkey, (CHLOROCEBUS AETHIOPS) used primarily in virus replication studies and plaque assays.	Cell, Vero,Cells, Vero,Vero Cell
D055598	Chemical Phenomena	The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes.	Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical