Synthesis and photochemical properties of photoactivated antitumor prodrugs releasing 5-fluorouracil.
A new family of antitumor prodrugs (1-3) of 5-fluorouracil (5-FU) possessing photolabile 2-nitrobenzyl chromophores have been designed and synthesized to investigate the efficiency and mechanism of photoactivated 5-FU release upon UV-irradiation at lambda(ex)= 365 nm. The photoactivated prodrug 3 derived from conjugation of 2 with a tumor-homing cyclic peptide Cys-Asn-Gly-Arg-Cys (CNGRC) was so designed as to manifest a tumor-targeting function.
Zhang
Zhouen
Z
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan.
Hatta
Hiroshi
H
Ito
Takeo
T
Nishimoto
Sei-ichi
S
D000840:Anisoles / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D016503:Drug Delivery Systems; D005021:Ethylamines / Q000737:chemistry; D005472:Fluorouracil / Q000031:analogs & derivatives / Q000737:chemistry*; D006801:Humans; D007834:Lasers; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry; D010777:Photochemistry; D010782:Photolysis; D011355:Prodrugs / Q000138:chemical synthesis*; D014230:Triazoles / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D014466:Ultraviolet Rays
D000840:Anisoles; D000970:Antineoplastic Agents; D005021:Ethylamines; D010456:Peptides, Cyclic; D011355:Prodrugs; D014230:Triazoles; D014297:Trimethylsilyl Compounds; C027070:N,N-diisopropylethylamine; C060998:anisole; D005472:Fluorouracil