Bioorthogonal Catalytic Activation of Platinum and Ruthenium Anticancer Complexes by FAD and Flavoproteins

被引:55
|
作者
Alonso-de Castro, Silvia [2 ]
Cortajarena, Aitziber L. [2 ,3 ]
Lopez-Gallego, Fernando [2 ,4 ]
Salassa, Luca [1 ,3 ]
机构
[1] Donostia Int Phys Ctr, Paseo Manuel de Lardizabal 4, Donostia San Sebastian 20018, Spain
[2] CIC biomaGUNE, Paseo Miramon 182, Donostia San Sebastian 20014, Spain
[3] Basque Fdn Sci, Ikerbasque, Bilbao 48011, Spain
[4] ARAID Fdn, Zaragoza, Spain
基金
欧洲研究理事会;
关键词
bioorthogonal chemistry; flavoproteins; metal-based prodrugs; photocatalysis; photochemotherapy; DNA-BINDING; OXYGEN; AGENTS; CELLS; GENERATION; REDUCTION; CHEMISTRY; MECHANISM; DELIVERY;
D O I
10.1002/anie.201800288
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Recent advances in bioorthogonal catalysis promise to deliver new chemical tools for performing chemoselective transformations in complex biological environments. Herein, we report how FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), and four flavoproteins act as unconventional photocatalysts capable of converting Pt-IV and Ru-II complexes into potentially toxic Pt-II or Ru-II-OH2 species. In the presence of electron donors and low doses of visible light, the flavoproteins mini singlet oxygen generator (miniSOG) and NADH oxidase (NOX) catalytically activate Pt-IV prodrugs with bioorthogonal selectivity. In the presence of NADH, NOX catalyzes Pt-IV activation in the dark as well, indicating for the first time that flavoenzymes may contribute to initiating the activity of Pt-IV chemotherapeutic agents.
引用
收藏
页码:3143 / 3147
页数:5
相关论文
共 50 条
  • [41] New Trends for Ruthenium Complexes with Anticancer Activity
    Chen Yu
    Du Kejie
    Chao Hui
    Ji Liangnian
    [J]. PROGRESS IN CHEMISTRY, 2009, 21 (05) : 836 - 844
  • [42] Synthesis and electrochemistry of heterobimetallic ruthenium/platinum and molybdenum/platinum complexes
    Orth, SD
    Terry, MR
    Abboud, KA
    Dodson, B
    McElweeWhite, L
    [J]. INORGANIC CHEMISTRY, 1996, 35 (04) : 916 - 922
  • [43] Multinuclear ruthenium(II) complexes as anticancer agents
    Gorle, Anil K.
    Ammit, Alaina J.
    Wallace, Lynne
    Keene, F. Richard
    Collins, J. Grant
    [J]. NEW JOURNAL OF CHEMISTRY, 2014, 38 (09) : 4049 - 4059
  • [44] ACTIVATION OF ALKYNES WITH RUTHENIUM COMPLEXES
    DIXNEUF, PH
    [J]. PURE AND APPLIED CHEMISTRY, 1989, 61 (10) : 1763 - 1770
  • [45] CATALYTIC PROPERTIES OF BLUE RUTHENIUM COMPLEXES
    FREIDLIN, LK
    LITVIN, EF
    KARIMOV, KG
    [J]. IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1974, (04): : 821 - 824
  • [46] Ruthenium (II) complexes in catalytic oxidation
    Aguirre, P
    Sariego, R
    Moya, SA
    [J]. JOURNAL OF COORDINATION CHEMISTRY, 2001, 54 (3-4) : 401 - 413
  • [47] CATALYTIC DISPROPORTIONATION OF ALDEHYDES WITH RUTHENIUM COMPLEXES
    MENASHE, N
    SHVO, Y
    [J]. ORGANOMETALLICS, 1991, 10 (11) : 3885 - 3891
  • [48] CATALYTIC DEHYDROGENATION OF METHANOL WITH RUTHENIUM COMPLEXES
    FUJII, T
    SAITO, Y
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1991, 67 (02): : 185 - 190
  • [49] Anticancer Activity and Catalytic Potential of Ruthenium(11)-Arene Complexes with N,O-Donor Ligands
    Haghdoost, Mohammad Mehdi
    Guard, Juliette
    Golbaghi, Golara
    Castonguay, Annie
    [J]. INORGANIC CHEMISTRY, 2018, 57 (13) : 7558 - 7567
  • [50] Platinum-ruthenium Carbonyl Cluster Complexes
    Adams, RD
    Barnard, TS
    Cortopassi, JE
    Wu, W
    Li, Z
    Shapley, JR
    Lee, K
    [J]. INORGANIC SYNTHESES, VOL 32, 1998, 32 : 280 - 284