Synthesis and structure-activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs

被引:7
作者
Garcia-Rodriguez, Jose [1 ]
Mendiratta, Saurabh [2 ]
White, Michael A. [2 ]
Xie, Xiao-Song [3 ]
De Brabander, Jef K. [1 ]
机构
[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA
[2] Univ Texas SW Med Ctr Dallas, Dept Cell Biol, Dallas, TX 75390 USA
[3] Univ Texas SW Med Ctr Dallas, Eugene McDermott Ctr Human Growth & Dev, Dallas, TX 75390 USA
关键词
V-ATPase; Antiviral; Anticancer; Benzolactone; Salicylihalamide; FORMAL TOTAL-SYNTHESIS; VACUOLAR H+-ATPASE; SALICYLIHALAMIDE-A; POTENT SALICYLIHALAMIDE; 1,3-DIOL ACETONIDES; CANCER; (-)-SALICYLIHALAMIDE-A; IDENTIFICATION; MECHANISM; INFECTION;
D O I
10.1016/j.bmcl.2015.09.021
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An efficient total synthesis of the potent V-ATPase inhibitor saliphenylhalamide (SaliPhe), a synthetic variant of the natural product salicylihalamide A (SaliA), has been accomplished aimed at facilitating the development of SaliPhe as an anticancer and antiviral agent. This new approach enabled facile access to derivatives for structure-activity relationship studies, leading to simplified analogs that maintain SaliPhe's biological properties. These studies will provide a solid foundation for the continued evaluation of SaliPhe and analogs as potential anticancer and antiviral agents. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4393 / 4398
页数:6
相关论文
共 57 条
[1]   Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue [J].
Balan, Dan ;
Burns, Christopher J. ;
Fisk, Nicholas G. ;
Huegel, Helmut ;
Huang, David C. S. ;
Segal, David ;
White, Charlotte ;
Wagler, Joerg ;
Rizzacasa, Mark A. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (40) :8147-8153
[2]   Novel marine and microbial natural product inhibitors of vacuolar ATPase [J].
Beutler, JA ;
McKee, TC .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (09) :787-796
[3]   Inhibition of Influenza A Virus Infection in Vitro by Saliphenylhalamide-Loaded Porous Silicon Nanoparticles [J].
Bimbo, Luis M. ;
Denisova, Oxana V. ;
Makila, Ermei ;
Kaasalainen, Martti ;
De Brabander, Jef K. ;
Hirvonen, Jouni ;
Salonen, Jarno ;
Kakkola, Laura ;
Kainov, Denis ;
Santos, Helder A. .
ACS NANO, 2013, 7 (08) :6884-6893
[4]   V-ATPases as drug targets [J].
Bowman, EJ ;
Bowman, BJ .
JOURNAL OF BIOENERGETICS AND BIOMEMBRANES, 2005, 37 (06) :431-435
[5]  
Boyd MR, 2001, J PHARMACOL EXP THER, V297, P114
[6]   Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (-)-Salicylihalamides A and B [J].
Chegondi, Rambabu ;
Tan, Mary M. L. ;
Hanson, Paul R. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) :3909-3916
[7]   Inhibitory and combinatorial effect of diphyllin, a v-ATPase blocker, on influenza viruses [J].
Chen, Hui-Wen ;
Cheng, Jenna Xiao ;
Liu, Ming-Tsan ;
King, Kevin ;
Peng, Ju-Yi ;
Zhang, Xin-Quan ;
Wang, Ching-Ho ;
Shresta, Sujan ;
Schooley, Robert T. ;
Liu, Yu-Tsueng .
ANTIVIRAL RESEARCH, 2013, 99 (03) :371-382
[8]   Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones [J].
Crimmins, MT ;
King, BW ;
Tabet, EA ;
Chaudhary, K .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :894-902
[9]   Obatoclax, Saliphenylhalamide, and Gemcitabine Inhibit Influenza A Virus Infection [J].
Denisova, Oxana V. ;
Kakkola, Laura ;
Feng, Lin ;
Stenman, Jakob ;
Nagaraj, Ashwini ;
Lampe, Johanna ;
Yadav, Bhagwan ;
Aittokallio, Tero ;
Kaukinen, Pasi ;
Ahola, Tero ;
Kuivanen, Suvi ;
Vapalahti, Olli ;
Kantele, Anu ;
Tynell, Janne ;
Julkunen, Ilkka ;
Kallio-Kokko, Hannimari ;
Paavilainen, Henrik ;
Hukkanen, Veijo ;
Elliott, Richard M. ;
De Brabander, Jef K. ;
Saelens, Xavier ;
Kainov, Denis E. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2012, 287 (42) :35324-35332
[10]   Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].
Erickson, KL ;
Beutler, JA ;
Cardellina, JH ;
Boyd, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192