Petroff John T, Isor Ankita, Chintala Satyanarayana M, Albert Carolyn J, Franke Jacob D, Weinstein David, Omlid Sara M, Arnatt Christopher K, Ford David A, McCulla Ryan D
Department of Chemistry, Saint Louis University St. Louis MO USA
Department of Biochemistry and Molecular Biology, Saint Louis University School of Medicine St. Louis MO USA.
RSC Adv. 2020 Jul 15;10(44):26553-26565. doi: 10.1039/d0ra01517b. eCollection 2020 Jul 9.
A beneficial property of photogenerated reactive oxygen species (ROS) is the capability of oxidant generation within a specific location or organelle inside a cell. Dibenzothiophene -oxide (DBTO), which is known to undergo a photodeoxygenation reaction to generate ground state atomic oxygen [O(P)] upon irradiation, was functionalized to afford localization within the plasma membrane of cells. The photochemistry, as it relates to oxidant generation, was studied and demonstrated that the functionalized DBTO derivatives generated O(P). Irradiation of these lipophilic O(P)-precursors in the presence of LDL and within RAW 264.7 cells afforded several oxidized lipid products (oxLP) in the form of aldehydes. The generation of a 2-hexadecenal (2-HDEA) was markedly increased in irradiations where O(P) was putatively produced. The substantial generation of 2-HDEA is not known to accompany the production of other ROS. These cellular irradiation experiments demonstrate the potential of inducing oxidation with O(P) in cells.
光生活性氧物种（ROS）的一个有益特性是能够在细胞内的特定位置或细胞器内产生氧化剂。二苯并噻吩 - 氧化物（DBTO）已知在照射时会发生光脱氧反应生成基态原子氧[O(P)]，对其进行功能化处理以使其定位于细胞膜内。研究了与氧化剂生成相关的光化学过程，并证明功能化的DBTO衍生物会生成O(P)。在低密度脂蛋白（LDL）存在的情况下以及在RAW 264.7细胞内照射这些亲脂性的O(P)前体，会产生几种醛形式的氧化脂质产物（oxLP）。在推测产生O(P)的照射中，2-十六碳烯醛（2-HDEA）的生成显著增加。目前尚不清楚其他ROS的产生是否会伴随大量2-HDEA的生成。这些细胞照射实验证明了在细胞中用O(P)诱导氧化的潜力。
