Transformation kinetics of the 5'-chloro-5'-deoxy analogue of arabinosylcytosine.
5'-Chloro-5'-deoxy arabinosylcytosine (Cl-araC) is a more lipophilic analog of the clinically used drug--arabinosylcytosine (araC). The resistance toward the enzyme cytidine-deaminase action was described as an characteristic feature of this synthetic nucleoside. The kinetics of the Cl-araC transformation in acid and alkaline solutions was studied at various temperatures. When compared with parent compound araC, the chlorine atom at the 5' position of the nucleoside sugar moiety increases the Cl-araC stability. The chlorine atom stabilizing effect is higher in acidic conditions. Cl-araC increased stability, antileukemic activity accompanied by higher lipophilicity confirm the fact that Cl-araC belong among interesting compounds from the point of view of cancer chemotherapy.
Stankovicová
M
M
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Bratislava, Slovak Republic.
Novotný
L
L
Bachratá
M
M
Bílková
J
J
Rauko
P
P
D000970:Antineoplastic Agents / Q000737:chemistry*; D003561:Cytarabine / Q000031:analogs & derivatives* / Q000737:chemistry; D003562:Cytidine / Q000737:chemistry; D003596:Cytosine / Q000737:chemistry; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D000970:Antineoplastic Agents; D003561:Cytarabine; C073835:5'-chloro-5'-deoxyarabinosylcytosine; D003562:Cytidine; D003596:Cytosine