Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Mini-Review Article

A Review on the Synthetic Approach of Marinopyrroles: A Natural Antitumor Agent from the Ocean

Author(s): Ashish Patel*, Hirak Shah, Umang Shah, Tushar Bambharoliya, Mehul Patel, Ishan Panchal, Vruti Parikh, Afzal Nagani, Harnisha Patel, Jitendra Vaghasiya, Nilay Solanki, Swayamprakash Patel, Ashish Shah and Ghanshyam Parmar

Volume 18, Issue 4, 2021

Published on: 17 July, 2020

Page: [251 - 264] Pages: 14

DOI: 10.2174/1570178617999200718004012

Price: $65

Abstract

Natural products play an important role in various drug discovery and development approaches. They are known to be the rich resources for the identification of new chemical entities (NCEs) intended to treat various diseases. Many drugs have been discovered and developed from natural sources. Indeed, collaborative efforts involving biologists as well as organic, medicinal, and phytochemists usually facilitate the identification of potent NCEs derived from natural sources. Over the past 20 years, more than 50% of NCEs have been derived either from marine sources or synthetic/ semisynthetic derivatives of natural products. Indeed, many drug molecules have been designed by considering natural products as the starting scaffold. The first bis-pyrrole alkaloid derivative of marinopyrroles was obtained from the marine-derived streptomycete species. In the laboratory, it can be synthesized via Clauson-Kaas and Friedel-Crafts arylation as well as copper-mediated N-arylation process under microwave irradiation. The marinopyrrole A (±)-28 was discovered to overcome resistance against human cancer cells by antagonizing B-cell lymphoma extra-large (Bcl-xL) and induced myeloid leukaemia cell (Mcl-1). In this review, we elaborated on various synthetic pathways of marinopyrroles possessing anti-cancer potential, which could encourage researchers to discover promising anti-tumor agents.

Keywords: Marinopyrroles, bis-pyrrole, anti-tumor agents, new chemical entities, natural products, streptomycete.

Next »
Graphical Abstract
[1]
Li, R. Med. Res. Rev., 2016, 36(1), 169-189.
[http://dx.doi.org/10.1002/med.21359] [PMID: 26332654]
[2]
Li, J.W.; Vederas, J.C. Science, 2009, 325(5937), 161-165.
[http://dx.doi.org/10.1126/science.1168243] [PMID: 19589993]
[3]
Koehn, F.E.; Carter, G.T. Nat. Rev. Drug Discov., 2005, 4(3), 206-220.
[http://dx.doi.org/10.1038/nrd1657] [PMID: 15729362]
[4]
Martins, A.; Vieira, H.; Gaspar, H.; Santos, S. Mar. Drugs, 2014, 12(2), 1066-1101.
[http://dx.doi.org/10.3390/md12021066] [PMID: 24549205]
[5]
Harvey, A.L.; Edrada-Ebel, R.; Quinn, R.J. Nat. Rev. Drug Discov., 2015, 14(2), 111-129.
[http://dx.doi.org/10.1038/nrd4510] [PMID: 25614221]
[6]
Newman, D.J.; Cragg, G.M. J. Nat. Prod., 2012, 75(3), 311-335.
[http://dx.doi.org/10.1021/np200906s] [PMID: 22316239]
[7]
Clardy, J.; Walsh, C. Nature, 2004, 432(7019), 829-837.
[http://dx.doi.org/10.1038/nature03194] [PMID: 15602548]
[8]
Wani, M.C.; Taylor, H.L.; Wall, M.E.; Coggon, P.; McPhail, A.T.; Plantantitumoragents, V.I. J. Am. Chem. Soc., 1971, 93, 2325-2327.
[http://dx.doi.org/10.1021/ja00738a045] [PMID: 5553076]
[9]
Sehgal, S.N.; Baker, H.; Vézina, C. J. Antibiot. (Tokyo), 1975, 28(10), 727-732.
[http://dx.doi.org/10.7164/antibiotics.28.727] [PMID: 1102509]
[10]
Noble, R.L.; Beer, C.T.; Cutts, J.H. Ann. N. Y. Acad. Sci., 1958, 76(3), 882-894.
[http://dx.doi.org/10.1111/j.1749-6632.1958.tb54906.x] [PMID: 13627916]
[11]
US Department of Commerce. NOAA: National Oceanic and Atmospheric Administration., http://www.noaa.gov/ocean.html (Accessed September 29, 2019)
[12]
Molinski, T.F.; Dalisay, D.S.; Lievens, S.L.; Saludes, J.P. Nat. Rev. Drug Discov., 2009, 8(1), 69-85.
[http://dx.doi.org/10.1038/nrd2487] [PMID: 19096380]
[13]
Sudek, S.; Lopanik, N.B.; Waggoner, L.E.; Hildebrand, M.; Anderson, C.; Liu, H.; Patel, A.; Sherman, D.H.; Haygood, M.G. J. Nat. Prod., 2007, 70(1), 67-74.
[http://dx.doi.org/10.1021/np060361d] [PMID: 17253852]
[14]
Schumacher, M.; Kelkel, M.; Dicato, M.; Diederich, M. Biotechnol. Adv., 2011, 29(5), 531-547.
[http://dx.doi.org/10.1016/j.biotechadv.2011.02.002] [PMID: 21371549]
[15]
Mishra, B.B.; Tiwari, V.K. Eur. J. Med. Chem., 2011, 46(10), 4769-4807.
[http://dx.doi.org/10.1016/j.ejmech.2011.07.057] [PMID: 21889825]
[16]
Ivan, B.A. FASEB J., 2018, 33, 872-878.
[17]
Kijjoa, A.; Sawangwong, P. Mar. Drugs, 2004, 2, 73-82.
[http://dx.doi.org/10.3390/md202073]
[18]
Wang, W.S.; Tzeng, C.H.; Chiou, T.J.; Liu, J.H.; Hsieh, R.K.; Yen, C.C.; Chen, P.M. Jpn. J. Clin. Oncol., 1997, 27(3), 154-157.
[http://dx.doi.org/10.1093/jjco/27.3.154] [PMID: 9255269]
[19]
Towle, M.J.; Salvato, K.A.; Budrow, J.; Wels, B.F.; Kuznetsov, G.; Aalfs, K.K.; Welsh, S.; Zheng, W.; Seletsky, B.M.; Palme, M.H.; Habgood, G.J.; Singer, L.A.; Dipietro, L.V.; Wang, Y.; Chen, J.J.; Quincy, D.A.; Davis, A.; Yoshimatsu, K.; Kishi, Y.; Yu, M.J.; Littlefield, B.A. Cancer Res., 2001, 61(3), 1013-1021.
[PMID: 11221827]
[20]
Aicher, T.D.; Buszek, K.R.; Fang, F.G.; Forsyth, C.J.; Jung, S.H.; Kishi, Y.; Matelich, M.C.; Scola, P.M.; Spero, D.M.; Yoon, S.K. J. Am. Chem. Soc., 1992, 114, 3162-3164.
[http://dx.doi.org/10.1021/ja00034a086]
[21]
FDA News Release: FDA approves new treatment option for late-stage breast cancer., http://www.fda.gov/?NewsEvents/Newsroom/PressAnnouncements/ucm233863.html(Accessed May 28, 2019)
[22]
Skov, M.J.; Beck, J.C.; de Kater, A.W.; Shopp, G.M. Int. J. Toxicol., 2007, 26(5), 411-421.
[http://dx.doi.org/10.1080/10915810701582970] [PMID: 17963128]
[23]
Miljanich, G.P. Curr. Med. Chem., 2004, 11(23), 3029-3040.
[http://dx.doi.org/10.2174/0929867043363884] [PMID: 15578997]
[24]
McGivern, J.G. Neuropsychiatr. Dis. Treat., 2007, 3(1), 69-85.
[http://dx.doi.org/10.2147/nedt.2007.3.1.69] [PMID: 19300539]
[25]
Olivera, B.M.; Cruz, L.J.; de Santos, V.; LeCheminant, G.W.; Griffin, D.; Zeikus, R.; McIntosh, J.M.; Galyean, R.; Varga, J.; Gray, W.R. Biochemistry, 1987, 26(8), 2086-2090.
[http://dx.doi.org/10.1021/bi00382a004] [PMID: 2441741]
[26]
Wright, A.E.; Forleo, D.A.; Gunawardana, G.P.; Gunasekera, S.P.; Koehn, F.E.; McConnell, O.J. J. Org. Chem., 1990, 55, 4508-4512.
[http://dx.doi.org/10.1021/jo00302a006]
[27]
Rinehart, K.L.; Holt, T.G.; Fregeau, N.L.; Stroh, J.G.; Keifer, P.A.; Sun, F.; Li, L.H.; Martin, D.G. J. Org. Chem., 1990, 55, 4512-4515.
[http://dx.doi.org/10.1021/jo00302a007]
[28]
Corey, E.J.; Gin, D.Y.; Kania, R.S. J. Am. Chem. Soc., 1996, 118, 9202-9203.
[http://dx.doi.org/10.1021/ja962480t]
[29]
Cuevas, C.; Pérez, M.; Martín, M.J.; Chicharro, J.L.; Fernández-Rivas, C.; Flores, M.; Francesch, A.; Gallego, P.; Zarzuelo, M.; de La Calle, F.; García, J.; Polanco, C.; Rodríguez, I.; Manzanares, I. Org. Lett., 2000, 2(16), 2545-2548.
[http://dx.doi.org/10.1021/ol0062502] [PMID: 10956543]
[30]
Roberts, J.N.; Buck, C.B.; Thompson, C.D.; Kines, R.; Bernardo, M.; Choyke, P.L.; Lowy, D.R.; Schiller, J.T. Nat. Med., 2007, 13(7), 857-861.
[http://dx.doi.org/10.1038/nm1598] [PMID: 17603495]
[31]
Buck, C.B.; Thompson, C.D.; Roberts, J.N.; Müller, M.; Lowy, D.R.; Schiller, J.T. PLoS Pathog., 2006, 2(7)e69
[http://dx.doi.org/10.1371/journal.ppat.0020069] [PMID: 16839203]
[32]
González, M.E.; Alarcón, B.; Carrasco, L. Antimicrob. Agents Chemother., 1987, 31(9), 1388-1393.
[http://dx.doi.org/10.1128/AAC.31.9.1388] [PMID: 2823697]
[33]
Rupp, H. Adv. Ther., 2009, 26(7), 675-690.
[http://dx.doi.org/10.1007/s12325-009-0045-2] [PMID: 19629408]
[34]
Glueck, C.J.; Khan, N.; Riaz, M.; Padda, J.; Khan, Z.; Wang, P. Lipids Health Dis., 2012, 11, 143.
[http://dx.doi.org/10.1186/1476-511X-11-143] [PMID: 23110706]
[36]
Science Medicines Health. European Medicines Agency: EPAR summary for the public, https://www.ema.europa.eu/en/medicines/human/EPAR/epidyolex.html(Accessed October 12, 2019)
[37]
Francisco, J.A.; Cerveny, C.G.; Meyer, D.L.; Mixan, B.J.; Klussman, K.; Chace, D.F.; Rejniak, S.X.; Gordon, K.A.; DeBlanc, R.; Toki, B.E.; Law, C.L.; Doronina, S.O.; Siegall, C.B.; Senter, P.D.; Wahl, A.F. Blood, 2003, 102(4), 1458-1465.
[http://dx.doi.org/10.1182/blood-2003-01-0039] [PMID: 12714494]
[38]
Eccles, R.; Meier, C.; Jawad, M.; Weinmüllner, R.; Grassauer, A.; Prieschl-Grassauer, E. Respir. Res., 2010, 11, 108.
[http://dx.doi.org/10.1186/1465-9921-11-108] [PMID: 20696083]
[39]
Hale, K.J.; Hummersone, M.G.; Manaviazar, S.; Frigerio, M. Nat. Prod. Rep., 2002, 19(4), 413-453.
[http://dx.doi.org/10.1039/b009211h] [PMID: 12195811]
[40]
Hale, K.J.; Manaviazar, S. Chem. Asian J., 2010, 5(4), 704-754.
[http://dx.doi.org/10.1002/asia.200900634] [PMID: 20354984]
[41]
Pettit, G.R.; Herald, C.L.; Doubek, D.L.; Herald, D.L. J. Am. Chem. Soc., 1982, 104, 6846-6848.
[http://dx.doi.org/10.1021/ja00388a092]
[42]
Keck, G.E.; Poudel, Y.B.; Cummins, T.J.; Rudra, A.; Covel, J.A. J. Am. Chem. Soc., 2011, 133(4), 744-747.
[http://dx.doi.org/10.1021/ja110198y] [PMID: 21175177]
[43]
Wang, S.; Wang, Z.; Dent, P.; Grant, S. Blood, 2003, 101(9), 3648-3657.
[http://dx.doi.org/10.1182/blood-2002-09-2739] [PMID: 12522001]
[44]
Schwartz, G.K.; Shah, M.A. J. Clin. Oncol., 2005, 23(36), 9408-9421.
[http://dx.doi.org/10.1200/JCO.2005.01.5594] [PMID: 16361640]
[45]
Way, K.J.; Katai, N.; King, G.L. Diabet. Med., 2001, 18(12), 945-959.
[http://dx.doi.org/10.1046/j.0742-3071.2001.00638.x] [PMID: 11903393]
[46]
Sun, M.K.; Hongpaisan, J.; Nelson, T.J.; Alkon, D.L. Proc. Natl. Acad. Sci. USA, 2008, 105(36), 13620-13625.
[http://dx.doi.org/10.1073/pnas.0805952105] [PMID: 18768786]
[47]
Alkon, D.L.; Sun, M.K.; Nelson, T.J. Trends Pharmacol. Sci., 2007, 28(2), 51-60.
[http://dx.doi.org/10.1016/j.tips.2006.12.002] [PMID: 17218018]
[48]
Newman, D.J.; Cragg, G.M. J. Nat. Prod., 2004, 67(8), 1216-1238.
[http://dx.doi.org/10.1021/np040031y] [PMID: 15332835]
[49]
Rinehart, K.L. Med. Res. Rev., 2000, 20(1), 1-27.
[http://dx.doi.org/10.1002/(SICI)1098-1128(200001)20:1<1:AID-MED1>3.0.CO;2-A] [PMID: 10608919]
[50]
Schwartsmann, G.; Da Rocha, A.B.; Mattei, J.; Lopes, R. Expert Opin. Investig. Drugs, 2003, 12(8), 1367-1383.
[http://dx.doi.org/10.1517/13543784.12.8.1367] [PMID: 12882622]
[51]
Adrio, J.; Cuevas, C.; Manzanares, I.; Joullié, M.M. J. Org. Chem., 2007, 72(14), 5129-5138.
[http://dx.doi.org/10.1021/jo070412r] [PMID: 17555353]
[52]
Fontana, A.; Cavaliere, P.; Wahidulla, S.; Naik, C.G.; Cimino, G.A. Tetrahedron, 2000, 56, 7305-7308.
[http://dx.doi.org/10.1016/S0040-4020(00)00629-3]
[53]
Oku, N.; Matsunaga, S.; van Soest, R.W.; Fusetani, N.; Renieramycin, J. J. Nat. Prod., 2003, 66(8), 1136-1139.
[http://dx.doi.org/10.1021/np030092g] [PMID: 12932144]
[54]
Martin, L.P.; Krasner, C. Med. Oncol., 2013, 30, 627.
[http://dx.doi.org/10.1007/s12032-013-0627-3] [PMID: 23771800]
[55]
Leal, J.F.; Martínez-Díez, M.; García-Hernández, V.; Moneo, V.; Domingo, A.; Bueren-Calabuig, J.A.; Negri, A.; Gago, F.; Guillén-Navarro, M.J.; Avilés, P.; Cuevas, C.; García-Fernández, L.F.; Galmarini, C.M. Br. J. Pharmacol., 2010, 161(5), 1099-1110.,
[http://dx.doi.org/10.1111/j.1476-5381.2010.00945.x] [PMID: 20977459]
[56]
A phase II clinical trial of PM01183 in BRCA 1/2-associated or unselected metastatic breast cancer., http://www.ClinicalTrials.gov/show/NCT01525589.html (Accessed October 16, 2019)
[57]
Elez, M.E.; Tabernero, J.; Geary, D.; Macarulla, T.; Kang, S.P.; Kahatt, C.; Pita, A.S.; Teruel, C.F.; Siguero, M.; Cullell-Young, M.; Szyldergemajn, S.; Ratain, M.J. Clin. Cancer Res., 2014, 20(8), 2205-2214.,
[http://dx.doi.org/10.1158/1078-0432.CCR-13-1880] [PMID: 24563480]
[58]
Briggs, C.A.; Anderson, D.J.; Brioni, J.D.; Buccafusco, J.J.; Buckley, M.J.; Campbell, J.E.; Decker, M.W.; Donnelly-Roberts, D.; Elliott, R.L.; Gopalakrishnan, M.; Holladay, M.W.; Hui, Y.H.; Jackson, W.J.; Kim, D.J.; Marsh, K.C.; O’Neill, A.; Prendergast, M.A.; Ryther, K.B.; Sullivan, J.P.; Arneric, S.P. Pharmacol. Biochem. Behav., 1997, 57(1-2), 231-241.
[http://dx.doi.org/10.1016/S0091-3057(96)00354-1] [PMID: 9164577]
[59]
Meyer, E.M.; Tay, E.T.; Papke, R.L.; Meyers, C.; Huang, G.L.; de Fiebre, C.M. Brain Res., 1997, 768(1-2), 49-56.
[http://dx.doi.org/10.1016/S0006-8993(97)00536-2] [PMID: 9369300]
[61]
Martín, M.J.; Coello, L.; Fernández, R.; Reyes, F.; Rodríguez, A.; Murcia, C.; Garranzo, M.; Mateo, C.; Sánchez-Sancho, F.; Bueno, S.; de Eguilior, C.; Francesch, A.; Munt, S.; Cuevas, C. J. Am. Chem. Soc., 2013, 135(27), 10164-10171.
[http://dx.doi.org/10.1021/ja404578u] [PMID: 23750450]
[62]
Pera, B.; Barasoain, I.; Pantazopoulou, A.; Canales, A.; Matesanz, R.; Rodriguez-Salarichs, J.; García-Fernandez, L.F.; Moneo, V.; Jiménez-Barbero, J.; Galmarini, C.M.; Cuevas, C.; Peñalva, M.A.; Díaz, J.F.; Andreu, J.M. ACS Chem. Biol., 2013, 8(9), 2084-2094.
[http://dx.doi.org/10.1021/cb400461j] [PMID: 23859655]
[63]
Martínez-Díez, M.; Guillén-Navarro, M.J.; Pera, B.; Bouchet, B.P.; Martínez-Leal, J.F.; Barasoain, I.; Cuevas, C.; Andreu, J.M.; García-Fernández, L.F.; Díaz, J.F.; Avilés, P.; Galmarini, C.M. Biochem. Pharmacol., 2014, 88(3), 291-302.
[http://dx.doi.org/10.1016/j.bcp.2014.01.026] [PMID: 24486569]
[64]
Feling, R.H.; Buchanan, G.O.; Mincer, T.J.; Kauffman, C.A.; Jensen, P.R.; Fenical, W.; Salinosporamide, A. Angew. Chem. Int. Ed. Engl., 2003, 42(3), 355-357.
[http://dx.doi.org/10.1002/anie.200390115] [PMID: 12548698]
[65]
Reddy, L.R.; Saravanan, P.; Corey, E.J. J. Am. Chem. Soc., 2004, 126(20), 6230-6231.
[http://dx.doi.org/10.1021/ja048613p] [PMID: 15149210]
[66]
Endo, A.; Danishefsky, S.J. J. Am. Chem. Soc., 2005, 127(23), 8298-8299.
[http://dx.doi.org/10.1021/ja0522783] [PMID: 15941259]
[67]
Ling, T.; Macherla, V.R.; Manam, R.R.; McArthur, K.A.; Potts, B.C. Org. Lett., 2007, 9(12), 2289-2292.
[http://dx.doi.org/10.1021/ol0706051] [PMID: 17497868]
[68]
Ma, G.; Nguyen, H.; Romo, D. Org. Lett., 2007, 9(11), 2143-2146.
[http://dx.doi.org/10.1021/ol070616u] [PMID: 17477539]
[69]
Beer, L.L.; Moore, B.S. Org. Lett., 2007, 9(5), 845-848.
[http://dx.doi.org/10.1021/ol063102o] [PMID: 17274624]
[70]
Tsueng, G.; McArthur, K.A.; Potts, B.C.; Lam, K.S. Appl. Microbiol. Biotechnol., 2007, 75(5), 999-1005.
[http://dx.doi.org/10.1007/s00253-007-0899-7] [PMID: 17340108]
[71]
U.S National library of medicine: Glembatumumab vedotin (CDX- 011) - antibody-drug conjugate targeting GPNMB in metastatic breast cancer and metastatic melanoma. , https://clinicaltrials.gov/ct2/show/NCT01997333.html(Accessed November 9, 2019)(Accessed November 9, 2019)
[72]
U.S National library of medicine: A study of CDX-011 (CR011-vcMMAE) in patients with advanced GPNMB-expressing Breast Cancer., https://clinicaltrials.gov/ct2/show/NCT01156753.html(Accessed November 9, 2019) Accessed November 9, 2019)
[73]
Agensys and Seattle Genetics announce interim phase I data from ASG-5ME clinical trial for prostate cancer., https://www.astellas.us/docs/us/ASG-5ME_Release_FINAL_04June12.pdf.html(Accessed November 12, 2019)(Accessed November 12 2019)
[74]
Gudas, J.M.; An, Z.; Miorrison, R.K.; Morrison, K.J.; Jia, X.; Raitano, A.B.; Duniho, S.; Smith, L.; Hayes, D.; Senter, P.D.; Benjamin, D.; Jackobovits, A. Cancer Res., 2010, 70, 4393.
[75]
Coveler, A.L.; Ko, A.H.; Catenacci, D.V.; Von Hoff, D.; Becerra, C.; Whiting, N.C.; Yang, J.; Wolpin, B. Invest. New Drugs, 2016, 34(3), 319-328.
[http://dx.doi.org/10.1007/s10637-016-0343-x] [PMID: 26994014]
[77]
Mayer, A.M.; Glaser, K.B.; Cuevas, C.; Jacobs, R.S.; Kem, W.; Little, R.D.; McIntosh, J.M.; Newman, D.J.; Potts, B.C.; Shuster, D.E. Trends Pharmacol. Sci., 2010, 31(6), 255-265.
[http://dx.doi.org/10.1016/j.tips.2010.02.005] [PMID: 20363514]
[78]
Hughes, C.C.; Prieto-Davo, A.; Jensen, P.R.; Fenical, W. Org. Lett., 2008, 10(4), 629-631.
[http://dx.doi.org/10.1021/ol702952n] [PMID: 18205372]
[79]
Hughes, C.C.; Kauffman, C.A.; Jensen, P.R.; Fenical, W. J. Org. Chem., 2010, 75(10), 3240-3250.
[http://dx.doi.org/10.1021/jo1002054] [PMID: 20405892]
[80]
Pan, L.; Cheng, C.; Song, H. Chem. J. Chin. Univ., 2012, 33, 1476-1480.
[81]
Yamanaka, K.; Ryan, K.S.; Gulder, T.A.; Hughes, C.C.; Moore, B.S. J. Am. Chem. Soc., 2012, 134(30), 12434-12437.
[http://dx.doi.org/10.1021/ja305670f] [PMID: 22800473]
[82]
Hughes, C.C.; Yang, Y.L.; Liu, W.T.; Dorrestein, P.C.; La Clair, J.J.; Fenical, W. J. Am. Chem. Soc., 2009, 131(34), 12094-12096.
[http://dx.doi.org/10.1021/ja903149u] [PMID: 19673475]
[83]
Cheng, C.; Pan, L.; Chen, Y.; Song, H.; Qin, Y.; Li, R. J. Comb. Chem., 2010, 12(4), 541-547.
[http://dx.doi.org/10.1021/cc100052j] [PMID: 20429575]
[84]
Kanakis, A.A.; Sarli, V. Org. Lett., 2010, 12(21), 4872-4875.
[http://dx.doi.org/10.1021/ol102035s] [PMID: 20886840]
[85]
Nicolaou, K.C.; Simmons, N.L.; Chen, J.S.; Haste, N.M.; Nizet, V. Tetrahedron Lett., 2011, 52(17), 2041-2043.
[http://dx.doi.org/10.1016/j.tetlet.2010.09.059] [PMID: 21499535]
[86]
Cheng, P.; Clive, D.L.; Fernandopulle, S. Chen. Z. Chem. Commun. (Camb.), 2013, 49(6), 558-560.
[http://dx.doi.org/10.1039/C2CC37110C] [PMID: 23128288]
[87]
Cheng, C.; Liu, Y.; Song, H.; Pan, L.; Li, J.; Qin, Y.; Li, R. Mar. Drugs, 2013, 11(8), 2927-2948.
[http://dx.doi.org/10.3390/md11082927] [PMID: 23955285]
[88]
Cheng, C.; Liu, Y.; Balasis, M.E.; Simmons, N.L.; Li, J.; Song, H.; Pan, L.; Qin, Y.; Nicolaou, K.C.; Sebti, S.M.; Li, R. Mar. Drugs, 2014, 12(3), 1335-1348.
[http://dx.doi.org/10.3390/md12031335] [PMID: 24608970]
[89]
Liptak, M.D.; Gross, K.C.; Seybold, P.G.; Feldgus, S.; Shields, G.C. J. Am. Chem. Soc., 2002, 124(22), 6421-6427.
[http://dx.doi.org/10.1021/ja012474j] [PMID: 12033873]
[90]
Li, R.; Cheng, C.; Balasis, M.E.; Liu, Y.; Garner, T.P.; Daniel, K.G.; Li, J.; Qin, Y.; Gavathiotis, E.; Sebti, S.M. Eur. J. Med. Chem., 2015, 90, 315-331.
[http://dx.doi.org/10.1016/j.ejmech.2014.11.035] [PMID: 25437618]
[91]
Chen, T.S.; Palacios, H.; Keating, A.E. J. Mol. Biol., 2013, 425(1), 171-185.
[http://dx.doi.org/10.1016/j.jmb.2012.11.009] [PMID: 23154169]
[92]
Doi, K.; Li, R.; Sung, S.S.; Wu, H.; Liu, Y.; Manieri, W.; Krishnegowda, G.; Awwad, A.; Dewey, A.; Liu, X.; Amin, S.; Cheng, C.; Qin, Y.; Schonbrunn, E.; Daughdrill, G.; Loughran, T.P., Jr; Sebti, S.; Wang, H.G. J. Biol. Chem., 2012, 287(13), 10224-10235.
[http://dx.doi.org/10.1074/jbc.M111.334532] [PMID: 22311987]
[93]
Cheng, C.; Liu, Y.; Balasis, M.E.; Garner, T.P.; Li, J.; Simmonos, N.L.; Berndt, N.; Song, H.; Pan, L.; Qin, Y.; Nicolaou, K.C.; Gavathiotis, E.; Sebti, S.M.; Li, R. Mar. Drugs, 2014, 12, 4311-4325.
[http://dx.doi.org/10.3390/md12084311] [PMID: 25076060]
[94]
Pandey, M.K.; Gowda, K.; Doi, K.; Sharma, A.K.; Wang, H-G.; Amin, S. PLoS One, 2013, 8(11)e78570
[http://dx.doi.org/10.1371/journal.pone.0078570] [PMID: 24223823]
[95]
Jackson, R.S., II; Placzek, W.; Fernandez, A.; Ziaee, S.; Chu, C-Y.; Wei, J.; Stebbins, J.; Kitada, S.; Fritz, G.; Reed, J.C.; Chung, L.W.; Pellecchia, M.; Bhowmick, N.A. Neoplasia, 2012, 14(7), 656-665.
[http://dx.doi.org/10.1593/neo.12640] [PMID: 22904682]
[96]
Bharadwaj, U.; Marin-Muller, C.; Li, M.; Chen, C.; Yao, Q. Mol. Cancer, 2011, 10, 106.
[http://dx.doi.org/10.1186/1476-4598-10-106] [PMID: 21880146]
[97]
Baggstrom, M.Q.; Qi, Y.; Koczywas, M.; Argiris, A.; Johnson, E.A.; Millward, M.J.; Murphy, S.C.; Erlichman, C.; Rudin, C.M.; Govindan, R. Mayo Phase 2 Consortium; California Consortium. J. Thorac. Oncol., 2011, 6(10), 1757-1760.,
[http://dx.doi.org/10.1097/JTO.0b013e31822e2941] [PMID: 21918390]
[98]
Kinross, K.M.; Brown, D.V.; Kleinschmidt, M.; Jackson, S.; Christensen, J.; Cullinane, C.; Hicks, R.J.; Johnstone, R.W.; McArthur, G.A. Mol. Cancer Ther., 2011, 10(8), 1440-1449.,
[http://dx.doi.org/10.1158/1535-7163.MCT-11-0240] [PMID: 21632463]
[99]
Visone, R.; Veronese, A.; Rassenti, L.Z.; Balatti, V.; Pearl, D.K.; Acunzo, M.; Volinia, S.; Taccioli, C.; Kipps, T.J.; Croce, C.M. Blood, 2011, 118(11), 3072-3079.
[http://dx.doi.org/10.1182/blood-2011-01-333484] [PMID: 21636858]
[100]
Hikita, H.; Takehara, T.; Shimizu, S.; Kodama, T.; Shigekawa, M.; Iwase, K.; Hosui, A.; Miyagi, T.; Tatsumi, T.; Ishida, H.; Li, W.; Kanto, T.; Hiramatsu, N.; Hayashi, N. Hepatology, 2010, 52(4), 1310-1321.
[http://dx.doi.org/10.1002/hep.23836] [PMID: 20799354]
[101]
Awan, F.T.; Kay, N.E.; Davis, M.E.; Wu, W.; Geyer, S.M.; Leung, N.; Jelinek, D.F.; Tschumper, R.C.; Secreto, C.R.; Lin, T.S.; Grever, M.R.; Shanafelt, T.D.; Zent, C.S.; Call, T.G.; Heerema, N.A.; Lozanski, G.; Byrd, J.C.; Lucas, D.M. Blood, 2009, 113(3), 535-537.
[http://dx.doi.org/10.1182/blood-2008-08-173450] [PMID: 19008456]
[102]
Ding, Q.; Huo, L.; Yang, J-Y.; Xia, W.; Wei, Y.; Liao, Y.; Chang, C-J.; Yang, Y.; Lai, C-C.; Lee, D-F.; Yen, C-J.; Chen, Y-J.R.; Hsu, J-M.; Kuo, H-P.; Lin, C-Y.; Tsai, F-J.; Li, L-Y.; Tsai, C-H.; Hung, M-C. Cancer Res., 2008, 68(15), 6109-6117.,
[http://dx.doi.org/10.1158/0008-5472.CAN-08-0579] [PMID: 18676833]
[103]
Liu, L.; Nam, S.; Tian, Y.; Yang, F.; Wu, J.; Wang, Y.; Scuto, A.; Polychronopoulos, P.; Magiatis, P.; Skaltsounis, L.; Jove, R. Cancer Res., 2011, 71(11), 3972-3979.,
[http://dx.doi.org/10.1158/0008-5472.CAN-10-3852] [PMID: 21610112]
[104]
Lucas, K.M.; Mohana-Kumaran, N.; Lau, D.; Zhang, X.D.; Hersey, P.; Huang, D.C.; Weninger, W.; Haass, N.K.; Allen, J.D. Clin. Cancer Res., 2012, 18(3), 783-795..
[http://dx.doi.org/10.1158/1078-0432.CCR-11-1166] [PMID: 22173547]
[105]
Weber, A.; Kirejczyk, Z.; Potthoff, S.; Ploner, C.; Häcker, G. Transl. Oncol., 2009, 2(2), 73-83.
[http://dx.doi.org/10.1593/tlo.08223] [PMID: 19412422]
[106]
Thallinger, C.; Wolschek, M.F.; Wacheck, V.; Maierhofer, H.; Günsberg, P.; Polterauer, P.; Pehamberger, H.; Monia, B.P.; Selzer, E.; Wolff, K.; Jansen, B. J. Invest. Dermatol., 2003, 120(6), 1081-1086.,
[http://dx.doi.org/10.1046/j.1523-1747.2003.12252.x] [PMID: 12787138]
[107]
Qin, J-Z.; Xin, H.; Sitailo, L.A.; Denning, M.F.; Nickoloff, B. J.Cancer Res., 2006, 66(19), 9636-9645.,
[http://dx.doi.org/10.1158/0008-5472.CAN-06-0747] [PMID: 17018621]
[108]
Hanahan, D.; Weinberg, R.A. Cell, 2011, 144(5), 646-674.
[http://dx.doi.org/10.1016/j.cell.2011.02.013] [PMID: 21376230]
[109]
Kelly, P.N.; Strasser, A. Cell Death Differ., 2011, 18(9), 1414-1424.,
[http://dx.doi.org/10.1038/cdd.2011.17] [PMID: 21415859]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy