Indoleamine 2,3-Dioxygenase Inhibitors Isolated from the Sponge Xestospongia vansoesti: Structure Elucidation, Analogue Synthesis, and Biological Activity

被引:24
作者
Centko, Ryan M. [1 ,2 ]
Steino, Anne [3 ]
Rosell, Federico I. [3 ]
Patrick, Brian O. [1 ]
de Voogd, Nicole [4 ]
Mauk, A. Grant [3 ]
Andersen, Raymond J. [1 ,2 ]
机构
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
[2] Univ British Columbia, Dept Earth Ocean & Atmospher Sci, Vancouver, BC V6T 1Z1, Canada
[3] Univ British Columbia, Dept Biochem & Mol Biol, Vancouver, BC V6T 1Z3, Canada
[4] Netherlands Ctr Biodivers Nat, NL-2300 RA Leiden, Netherlands
关键词
HALENAQUINONE DERIVATIVES; IDO; CANCER; XESTOQUINONE; INFLAMMATION;
D O I
10.1021/ol503337f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two new IDO inhibitory meroterpenoids, xestolactone A (1) and xestosaprol O (2), have been isolated from the sponge Xestospongia vansoesti. Xestolactone A (1) has an unprecedented degraded meroterpenoid carbon skeleton. A short synthesis of the xestosaprol O (2) analogues 3 and 4 features the application of a rarely used photochemical coupling reaction. Synthetic analogue 3 is similar to 40 times more potent than the inspirational natural product 2.
引用
收藏
页码:6480 / 6483
页数:4
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共 24 条
  • [1] An expedient synthesis of 1,2-dihydrobenzo[g]quinoline-5,10-diones via copper(II) triflate-catalyzed intramolecular cyclization of N-propargylaminonaphthoquinones
    Bala, Balasubramanian Devi
    Muthusaravanan, Sivasubramanian
    Perumal, Subbu
    [J]. TETRAHEDRON LETTERS, 2013, 54 (29) : 3735 - 3739
  • [2] Exiguamine A, an indoleamine-2,3-dioxygenase (IDO) inhibitor isolated from the marine sponge Neopetrosia exigua
    Brastianos, Harry C.
    Vottero, Eduardo
    Patrick, Brian O.
    Van Soest, Rob
    Matainaho, Teatulohi
    Mauk, A. Grant
    Andersen, Raymond J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) : 16046 - 16047
  • [3] Plectosphaeroic Acids A, B, and C, Indoleamine 2,3-Dioxygenase Inhibitors Produced in Culture by a Marine Isolate of the Fungus Plectosphaerella cucumerina
    Carr, Gavin
    Tay, Wendy
    Bottriell, Helen
    Andersen, Sarah K.
    Mauk, A. Grant
    Andersen, Raymond J.
    [J]. ORGANIC LETTERS, 2009, 11 (14) : 2996 - 2999
  • [4] Indoleamine 2,3-dioxygenase inhibitors: a patent review (2008-2012)
    Dolusic, Eduard
    Frederick, Raphael
    [J]. EXPERT OPINION ON THERAPEUTIC PATENTS, 2013, 23 (10) : 1367 - 1381
  • [5] Structures and Mechanisms of Antitumor Agents: Xestoquinones Uncouple Cellular Respiration and Disrupt HIF Signaling in Human Breast Tumor Cells
    Du, Lin
    Mahdi, Fakhri
    Datta, Sandipan
    Jekabsons, Mika B.
    Zhou, Yu-Dong
    Nagle, Dale G.
    [J]. JOURNAL OF NATURAL PRODUCTS, 2012, 75 (09): : 1553 - 1559
  • [6] Indoleamine 2,3-dioxygenase 1 (IDO1) activity in leukemia blasts correlates with poor outcome in childhood acute myeloid leukemia
    Folgiero, Valentina
    Goffredo, Bianca M.
    Filippini, Perla
    Masetti, Riccardo
    Bonanno, Giuseppina
    Caruso, Roberta
    Bertaina, Valentina
    Mastronuzzi, Angela
    Gaspari, Stefania
    Zecca, Marco
    Torelli, Giovanni F.
    Testi, Anna M.
    Pession, Andrea
    Locatelli, Franco
    Rutella, Sergio
    [J]. ONCOTARGET, 2014, 5 (08) : 2052 - 2064
  • [7] SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF (+)-ADOCIAQUINONE-A (+)ADOCIAQUINONE-B
    HARADA, N
    SUGIOKA, T
    SOUTOME, T
    HIYOSHI, N
    UDA, H
    KURIKI, T
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 375 - 376
  • [8] TOTAL SYNTHESIS, ABSOLUTE-CONFIGURATION, AND LATER ISOLATION OF (-)-PREHALENAQUINONE, A PUTATIVE BIOSYNTHETIC PRECURSOR TO THE MARINE NATURAL-PRODUCTS HALENAQUINONE AND XESTOQUINONE
    HARADA, N
    SUGIOKA, T
    UDA, H
    KURIKI, T
    KOBAYASHI, M
    KITAGAWA, I
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) : 6606 - 6613
  • [9] Host Indoleamine 2,3-Dioxygenase: Contribution to Systemic Acquired Tumor Tolerance
    Johnson, Theodore S.
    Munn, David H.
    [J]. IMMUNOLOGICAL INVESTIGATIONS, 2012, 41 (6-7) : 765 - 797
  • [10] Vinyl quinones as Diels-Alder dienes: Concise synthesis of (-)-halenaquinone
    Kienzler, Michael A.
    Suseno, Sandy
    Trauner, Dirk
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8604 - +