Our interest in the study of bioconjugate functional compounds for biosensoring and pharmacological applications1 prompted us to scout new molecules integrating a photocaged NO radical with 2'-deoxyadenosine and bile acid derivatives in the same molecular skeleton. This was motivated by the already assessed cytotoxic activity of 2'-deoxyadenosine and bile acid based compounds. Moreover, 2'-deossiadenosine-bile acid conjugates were recently found to exhibit a selective antiproliferative activity towards both leukemic T Jurkat and K562 cells.2 In this contribution we report the conjugation of the 4-nitro-2-(trifluoromethyl)aniline derivative, a suitable NO photodonor, with 2'-deoxyadenosine and urso- and cheno-deoxycholic acid derivatives. Photochemical experiments demonstrated the effective release of NO from the bioconjugates under the exclusive control of visible light inputs. Studies for the in vitro anti-proliferative activity against leukemic K562 and colon carcinoma HCT116 cell lines, are reported for all the compounds as well as a case study of photo-cytotoxicity against HCT116.3
NO photoreleaser-deoxyadenosine and -bile acid derivatives bioconjugates as novel potential photo-chemotherapeutics
Maria Luisa Navacchia;
2017
Abstract
Our interest in the study of bioconjugate functional compounds for biosensoring and pharmacological applications1 prompted us to scout new molecules integrating a photocaged NO radical with 2'-deoxyadenosine and bile acid derivatives in the same molecular skeleton. This was motivated by the already assessed cytotoxic activity of 2'-deoxyadenosine and bile acid based compounds. Moreover, 2'-deossiadenosine-bile acid conjugates were recently found to exhibit a selective antiproliferative activity towards both leukemic T Jurkat and K562 cells.2 In this contribution we report the conjugation of the 4-nitro-2-(trifluoromethyl)aniline derivative, a suitable NO photodonor, with 2'-deoxyadenosine and urso- and cheno-deoxycholic acid derivatives. Photochemical experiments demonstrated the effective release of NO from the bioconjugates under the exclusive control of visible light inputs. Studies for the in vitro anti-proliferative activity against leukemic K562 and colon carcinoma HCT116 cell lines, are reported for all the compounds as well as a case study of photo-cytotoxicity against HCT116.3I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
