Photoactivatable HNO-releasing compounds using the retro-Diels-Alder reaction

被引：40
作者：
Adachi, Yusuke [1 ]
Nakagawa, Hidehiko [1 ]
Matsuo, Kazuya [1 ]
Suzuki, Takayoshi [1 ]
Miyata, Naoki [1 ]
机构：
[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Aichi 4678673, Japan
来源：
CHEMICAL COMMUNICATIONS | 2008年 / 41期
关键词：
D O I：
10.1039/b811985f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We synthesized hetero-Diels-Alder cycloadducts from acyl nitroso derivatives and 9,10-dimethylanthracene, to be photo-inducible HNO-releasing agents and found that introduction of conjugated nitroaromatic groups effectively enhanced the responsiveness of HNO release to UV-A irradiation; we confirmed photoinduced HNO formation by EPR and GCMS analysis.
引用
收藏
页码：5149 / 5151
页数：3
相关论文
共 13 条
  • [1] Angeli A., 1896, GAZZ CHIM ITAL, V26, P17
  • [2] Reactions of acyl nitroso compounds with amines: Production of nitroxyl (HNO) with the preparation of amides
    Atkinson, RN
    Storey, BM
    King, SB
    [J]. TETRAHEDRON LETTERS, 1996, 37 (52) : 9287 - 9290
  • [3] EVIDENCE FROM THE REACTION BETWEEN TRIOXODINITRATE(II) AND (NO)-N-15 THAT TRIOXODINITRATE(II) DECOMPOSES INTO NITROSYL HYDRIDE AND NITRITE IN NEUTRAL AQUEOUS-SOLUTION
    BAZYLINSKI, DA
    HOLLOCHER, TC
    [J]. INORGANIC CHEMISTRY, 1985, 24 (25) : 4285 - 4288
  • [4] HUGHES MN, 1976, J CHEM SOC DALTON, P703
  • [5] EVIDENCE FOR NITROXYL IN THE CATALASE-MEDIATED BIOACTIVATION OF THE ALCOHOL DETERRENT AGENT CYANAMIDE
    NAGASAWA, HT
    DEMASTER, EG
    REDFERN, B
    SHIROTA, FN
    GOON, JW
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (12) : 3120 - 3122
  • [6] Nitroxyl inhibits breast tumor growth and angiogenesis
    Norris, Andrew J.
    Sartippour, Maryam R.
    Lu, Ming
    Park, Taylor
    Rao, Jian Yu
    Jackson, Matthew I.
    Fukuto, Jon M.
    Brooks, Mai N.
    [J]. INTERNATIONAL JOURNAL OF CANCER, 2008, 122 (08) : 1905 - 1910
  • [7] Nitroxyl affords thiol-sensitive myocardial protective effects akin to early preconditioning
    Pagliaro, P
    Mancardi, D
    Rastaldo, R
    Penna, C
    Gattullo, D
    Miranda, KM
    Feelisch, M
    Wink, DA
    Kass, DA
    Paolocci, N
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 2003, 34 (01) : 33 - 43
  • [8] Nitroxyl anion exerts redox-sensitive positive cardiac inotropy in vivo by calcitonin gene-related peptide signaling
    Paolocci, N
    Saavedra, WF
    Miranda, KM
    Martignani, C
    Isoda, T
    Hare, JM
    Espey, MG
    Fukuto, JM
    Feelisch, M
    Wink, DA
    Kass, DA
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (18) : 10463 - 10468
  • [9] Piloty O., 1896, BER DTSCH CHEM GES, V29, P1559
  • [10] Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO)
    Sha, Xin
    Isbell, T. Scott
    Patel, Rakesh P.
    Day, Cynthia S.
    King, S. Bruce
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) : 9687 - 9692
12