Optimization of biguanide derivatives as selective antitumor agents blocking adaptive stress responses in the tumor microenvironment

References

• Philip B Ito K Moreno-Sánchez R Ralph SJ HIF expression and the role of hypoxic microenvironments within primary tumours as protective sites driving cancer stem cell renewal and metastatic progression Carcinogenesis 2013 34 8 1699 1707 23740838
   PubMed Web of Science ®Google Scholar
• Borovski T De Sousa E Melo F Vermeulen L Medema JP Cancer stem cell niche: the place to be Cancer Res 2011 71 3 634 639 21266356
   PubMed Web of Science ®Google Scholar
• Fang H Declerck YA Targeting the tumor microenvironment: from understanding pathways to effective clinical trials Cancer Res 2013 73 16 4965 4977 23913938
   PubMed Web of Science ®Google Scholar
• Nagasawa H Pathophysiological response to hypoxia – from the molecular mechanisms of malady to drug discovery: drug discovery for targeting the tumor microenvironment J Pharmacol Sci 2011 115 4 446 452 21422725
   PubMed Web of Science ®Google Scholar
• Semenza GL HIF-1 inhibitors for cancer therapy: from gene expression to drug discovery Curr Pharm Des 2009 15 33 3839 3843 19671047
   PubMed Web of Science ®Google Scholar
• Hattori H Okuda K Murase T Isolation, identification, and biological evaluation of HIF-1-modulating compounds from Brazilian green propolis Bioorg Med Chem 2011 19 18 5392 5401 21865046
   PubMed Web of Science ®Google Scholar
• Semenza GL Hypoxia-inducible factors in physiology and medicine Cell 2012 148 3 399 408 22304911
   PubMed Web of Science ®Google Scholar
• Semenza GL HIF-1: upstream and downstream of cancer metabolism Curr Opin Genet Dev 2010 20 1 51 56 19942427
   PubMed Web of Science ®Google Scholar
• Kaufman RJ Scheuner D Schröder M The unfolded protein response in nutrient sensing and differentiation Nat Rev Mol Cell Biol 2002 3 6 411 421 12042763
   PubMed Web of Science ®Google Scholar
• Wouters BG Koritzinsky M Hypoxia signalling through mTOR and the unfolded protein response in cancer Nat Rev Cancer 2008 8 11 851 864 18846101
   PubMed Web of Science ®Google Scholar
• Suh DH Kim MK Kim HS Chung HH Song YS Unfolded protein response to autophagy as a promising druggable target for anticancer therapy Ann N Y Acad Sci 2012 1271 20 32 23050960
   PubMed Web of Science ®Google Scholar
• Feldman DE Chauhan V Koong AC The unfolded protein response: a novel component of the hypoxic stress response in tumors Mol Cancer Res 2005 3 11 597 605 16317085
   PubMed Web of Science ®Google Scholar
• Ueda JY Athikomkulchai S Miyatake R Saiki I Esumi H Awale S (+)-Grandifloracin, an antiausterity agent, induces autophagic PANC-1 pancreatic cancer cell death Drug Des Devel Ther 2014 8 39 47
   Web of Science ®Google Scholar
• Awale S Lu J Kalauni SK Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation Cancer Res 2006 66 3 1751 1757 16452235
   PubMed Web of Science ®Google Scholar
• Saito S Furuno A Sakurai J Chemical genomics identifies the unfolded protein response as a target for selective cancer cell killing during glucose deprivation Cancer Res 2009 69 10 4225 4234 19435925
   PubMed Web of Science ®Google Scholar
• Kourelis TV Siegel RD Metformin and cancer: new applications for an old drug Med Oncol 2012 29 2 1314 1327 21301998
   PubMed Web of Science ®Google Scholar
• Luo Z Zang M Guo W AMPK as a metabolic tumor suppressor: control of metabolism and cell growth Future Oncol 2010 6 3 457 470 20222801
   PubMed Web of Science ®Google Scholar
• Matsuo J Tsukumo Y Saito S Hyperactivation of 4E-binding protein 1 as a mediator of biguanide-induced cytotoxicity during glucose deprivation Mol Cancer Ther 2012 11 5 1082 1091 22402126
   PubMed Web of Science ®Google Scholar
• Mayer S Daigle DM Brown ED Khatri J Organ MG An expedient and facile one-step synthesis of a biguanide library by microwave irradiation coupled with simple product filtration. Inhibitors of dihydrofolate reductase J Comb Chem 2004 6 5 776 782 15360213
   PubMedGoogle Scholar
• Wick AN Murphy PJinventors San Diego State College Foundation, assignee N1-[2-(p-Hydroxyphenyl)ethyl]biguanide United States patent US3456059 A 7 15 1969
   Google Scholar
• Alkalay D Volk J Bartlett MF Conversion of biguanides into substituted s-triazines assayable by GC or mass fragmentography J Pharm Sci 1976 65 4 525 529 1271251
   PubMed Web of Science ®Google Scholar
• Shapiro SL Parrino VA Freedman L Hypoglycemic agents. III.1–3 N1-alkyl- and aralkylbiguanides J Am Chem Soc 1959 81 14 3728 3736
   Web of Science ®Google Scholar
• Park HR Tomida A Sato S Effect on tumor cells of blocking survival response to glucose deprivation J Natl Cancer Inst 2004 96 17 1300 1310 15339968
   PubMedGoogle Scholar
• Kasai S Nagasawa H Shimamura M Uto Y Hori H Design and synthesis of antiangiogenic/heparin-binding arginine dendrimer mimicking the surface of endostatin Bioorg Med Chem Lett 2002 12 6 951 954 11959001
   PubMed Web of Science ®Google Scholar
• Semenza GL Jiang BH Leung SW Hypoxia response elements in the aldolase A, enolase 1, and lactate dehydrogenase A gene promoters contain essential binding sites for hypoxia-inducible factor 1 J Biol Chem 1996 271 51 32529 32537 8955077
   PubMed Web of Science ®Google Scholar
• Viollet B Guigas B Sanz Garcia N Leclerc J Foretz M Andreelli F Cellular and molecular mechanisms of metformin: an overview Clin Sci (Lond) 2012 122 6 253 270 22117616
   PubMed Web of Science ®Google Scholar
• Sogame Y Kitamura A Yabuki M Komuro S A comparison of uptake of metformin and phenformin mediated by hOCT1 in human hepatocytes Biopharm Drug Dispos 2009 30 8 476 484 19768675
   PubMed Web of Science ®Google Scholar
• Segal ED Yasmeen A Beauchamp MC Rosenblatt J Pollak M Gotlieb WH Relevance of the OCT1 transporter to the antineoplastic effect of biguanides Biochem Biophys Res Commun 2011 414 4 694 699 21986525
   PubMed Web of Science ®Google Scholar
• Yuan P Ito K Perez-Lorenzo R Phenformin enhances the therapeutic benefit of BRAF(V600E) inhibition in melanoma Proc Natl Acad Sci U S A 2013 110 45 18226 18231 24145418
   PubMed Web of Science ®Google Scholar
• Shitara Y Nakamichi N Norioka M Shima H Kato Y Horie T Role of organic cation/carnitine transporter 1 in uptake of phenformin and inhibitory effect on complex I respiration in mitochondria Toxicol Sci 2013 132 1 32 42 23221006
   PubMed Web of Science ®Google Scholar
• Charton M Steric effects. I. Esterification and acid-catalyzed hydrolysis of esters J Am Chem Soc 1975 97 6 1552 1556
   Web of Science ®Google Scholar
• Soraya H Esfahanian N Shakiba Y Anti-angiogenic Effects of Metformin, an AMPK Activator, on Human Umbilical Vein Endothelial Cells and on Granulation Tissue in Rat Iran J Basic Med Sci 2012 15 6 1202 1209 23653852
   PubMed Web of Science ®Google Scholar