Photoinduced nitric oxide release from nitrobenzene derivatives.
A new type of photoinduced nitric oxide (NO) donors was designed from nitrobenzene derivatives. Visible-light irradiation of 2,6-dimethylnitrobenzenes bearing extended pi-electron systems at the 4-position revealed efficient NO release using ESR analysis and the Griess assay. Computational study and ultraviolet spectrum analysis suggested that the NO-releasing activity was closely related to the conformation of the nitro group, the absorption intensity, and the length of the conjugated pi-electron system. Employing the photodependent cytotoxicity of compound 14 against HCT116 human colon cancer cells, it was demonstrated that 4-substituted-2,6-dimethylnitrobenzene analogues are useful NO donors for the time- and site-controlled NO treatment.
Suzuki
Takayoshi
T
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya, Aichi 467-8603, Japan.
Nagae
Osamu
O
Kato
Yuka
Y
Nakagawa
Hidehiko
H
Fukuhara
Kiyoshi
K
Miyata
Naoki
N
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects / Q000528:radiation effects; D005609:Free Radicals / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D009569:Nitric Oxide / Q000138:chemical synthesis* / Q000494:pharmacology / Q000528:radiation effects*; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D010777:Photochemistry
D005609:Free Radicals; D009578:Nitrobenzenes; D009569:Nitric Oxide