Antioxidant and UV-radiation absorption activity of aaptamine derivatives - potential application for natural organic sunscreens

• Published in: RSC advances 2021-06, Vol.11 (35), p.21433-21446
• Main Authors: Nguyen, Thi Le Anh, Doan, Thi Hoai Nam, Truong, Dinh Hieu, Ai Nhung, Nguyen Thi, Quang, Duong Tuan, Khiri, Dorra, Taamalli, Sonia, Louis, Florent, El Bakali, Abderrahman, Dao, Duy Quang
• Format: Article
• Language: English
• Subjects: Antioxidants; Chelation; Chemical Sciences; Chemistry; Cosmetics; Density functional theory; Electron transfer; or physical chemistry; Piperidine; Radiation absorption; Scavenging; Single electrons; Sun screens; Theoretical and; Thermochemical properties; Ultraviolet radiation
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d1ra04146k

Antioxidant and UV absorption activities of three aaptamine derivatives including piperidine[3,2- b ]demethyl(oxy)aaptamine ( C1 ), 9-amino-2-ethoxy-8-methoxy-3 H -benzo[de][1,6]naphthyridine-3-one ( C2 ), and 2-( sec -butyl)-7,8-dimethoxybenzo[de]imidazo[4,5,1- ij ][1,6]-naphthyridin-10(9 H )-one ( C3 ) were theoretically studied by density functional theory (DFT). Direct antioxidant activities of C1-C3 were firstly evaluated via their intrinsic thermochemical properties and the radical scavenging activity of the potential antioxidants with the HOO&z.rad;/HO&z.rad; radicals via four mechanisms, including: hydrogen atom transfer (HAT), single electron transfer (SET), proton loss (PL) and radical adduct formation (RAF). Kinetic calculation reveals that HOO&z.rad; scavenging in water occurs via HAT mechanism with C1 ( k app , 7.13 × 10 6 M −1 s −1 ) while RAF is more dominant with C2 ( k app , 1.40 × 10 5 M −1 s −1 ) and C3 ( k app , 2.90 × 10 5 M −1 s −1 ). Antioxidant activity of aaptamine derivatives can be classified as C1 > C3 > C2 . Indirect antioxidant properties based on Cu( i ) and Cu( ii ) ions chelating activity were also investigated in aqueous phase. All three studied compounds show spontaneous and favorable Cu( i ) ion chelating activity with Δ G 0 being −15.4, −13.7, and −15.7 kcal mol −1 , whereas Δ G 0 for Cu( ii ) chelation are −10.4, −10.8, and −2.2 kcal mol −1 for C1 , C2 and C3 , respectively. In addition, all compounds show UVA and UVB absorption; in which the excitations are determined mostly as π-π* transition. Overall, the results suggest the potential applications of the aaptamines in pharmaceutics and cosmetics, i.e. as a sunscreen and antioxidant ingredient. Antioxidant and UV absorption activities of three aaptamine derivatives were theoretically studied by density functional theory (DFT) and time-dependent density functional theory (TD-DFT).