Novel a-ketoamide based diazeniumdiolates as hydrogen peroxide responsive nitric oxide donors with anti-lung cancer activity

被引:24
作者
Fu, Junjie [1 ]
Han, Jing [2 ]
Meng, Tingting [1 ]
Hu, Jing [1 ,3 ]
Yin, Jian [1 ]
机构
[1] Jiangnan Univ, Sch Biotechnol, Minist Educ, Key Lab Carbohydrate Chem & Biotechnol, Wuxi 214122, Jiangsu, Peoples R China
[2] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
[3] Jiangnan Univ, Wuxi Sch Med, Wuxi 214122, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
OLEANOLIC ACID; PRODRUG; APOPTOSIS; MOLECULE; DELIVERY; DESIGN; PI;
D O I
10.1039/c9cc05266f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel type of hydrogen peroxide (Hy(2)O(2))-activated diazeniumdiolate based on an a-ketoamide moietey was developed as a nitric oxide (NO) donor. KA-NO-4 inhibited lung cancer cells with submicromolar activity. The H2O2-responsive behaviour of KA-NO-4 was thoroughly investigated. The NO-centered mechanism of action of KA-NO-4 was intracellularly studied.
引用
收藏
页码:12904 / 12907
页数:4
相关论文
共 29 条
[1]   Self-Immolative Spacers: Kinetic Aspects, Structure-Property Relationships, and Applications [J].
Alouane, Ahmed ;
Labruere, Raphael ;
Le Saux, Thomas ;
Schmidt, Frederic ;
Jullien, Ludovic .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) :7492-7509
[2]   O2-( 6-Oxocyclohex-1-en-1-yl) methyl diazen-1-ium1,2-diolates: a new class of nitric oxide donors activatable by GSH/GSTπ with both anti-proliferative and anti-metastatic activities against melanoma [J].
Bai, Chengfeng ;
Xue, Rongfang ;
Wu, Jianbing ;
Lv, Tian ;
Luo, Xiaojun ;
Huang, Yun ;
Gong, Yan ;
Zhang, Honghua ;
Zhang, Yihua ;
Huang, Zhangjian .
CHEMICAL COMMUNICATIONS, 2017, 53 (36) :5059-5062
[3]   Cascade photocaging of diazeniumdiolate: a novel strategy for one and two photon triggered uncaging with real time reporting [J].
Behara, Krishna Kalyani ;
Rajesh, Y. ;
Venkatesh, Yarra ;
Pinninti, Bhaskar Rao ;
Mandal, Mahitosh ;
Singh, N. D. Pradeep .
CHEMICAL COMMUNICATIONS, 2017, 53 (68) :9470-9473
[4]   A Nonmetal-Containing Nitric Oxide Donor Activated with Single-Photon Green Light [J].
Blangetti, Marco ;
Fraix, Aurore ;
Lazzarato, Loretta ;
Marini, Elisabetta ;
Rolando, Barbara ;
Sodano, Federica ;
Fruttero, Roberta ;
Gasco, Alberto ;
Sortino, Salvatore .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (38) :9026-9029
[5]   Anti-metastatic effects of isolinderalactone via the inhibition of MMP-2 and up regulation of NM23-H1 expression in human lung cancer A549 cells [J].
Chuang, Cheng-Hung ;
Wang, Li-Yu ;
Wong, Yuen Man ;
Lin, En-Shyh .
ONCOLOGY LETTERS, 2018, 15 (04) :4690-4696
[6]   ROS as signalling molecules:: mechanisms that generate specificity in ROS homeostasis [J].
D'Autreaux, Benoit ;
Toledano, Michel B. .
NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2007, 8 (10) :813-824
[7]   Arylboronate Ester Based Diazeniumdiolates (BORO/NO), a Class of Hydrogen Peroxide Inducible Nitric Oxide (NO) Donors [J].
Dharmaraja, Allimuthu T. ;
Ravikumar, Govindan ;
Chakrapani, Harinath .
ORGANIC LETTERS, 2014, 16 (10) :2610-2613
[8]   Identification of nitric oxide-releasing derivatives of oleanolic acid as potential anti-colon cancer agents [J].
Fu, Junjie ;
Zou, Yu ;
Huang, Zhangjian ;
Yan, Chang ;
Zhou, Qimeng ;
Zhang, Huibin ;
Lai, Yisheng ;
Peng, Sixun ;
Zhang, Yihua .
RSC ADVANCES, 2015, 5 (25) :19445-19454
[9]   Hybrid Molecule from O2-(2,4-Dinitrophenyl)diazeniumdiolate and Oleanolic Acid: A Glutathione S-Transferase π-Activated Nitric Oxide Prodrug with Selective Anti-Human Hepatocellular Carcinoma Activity and Improved Stability [J].
Fu, Junjie ;
Liu, Ling ;
Huang, Zhangjian ;
Lai, Yisheng ;
Ji, Hui ;
Peng, Sixun ;
Tian, Jide ;
Zhang, Yihua .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (11) :4641-4655
[10]   Aminoferrocene-Based Prodrugs Activated by Reactive Oxygen Species [J].
Hagen, Helen ;
Marzenell, Paul ;
Jentzsch, Elmar ;
Wenz, Frederik ;
Veldwijk, Marlon R. ;
Mokhir, Andriy .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (02) :924-934