Bisphosphonamidate clodronate prodrug exhibits potent anticancer activity in non-small-cell lung cancer cells

Journal of Medicinal Chemistry

Volumn 54, Issue 19, 2011, Pages 6647-6656

  Webster, Marie R ^a   Zhao, Ming ^b   Rudek, Michelle A ^b   Hann, Christine L ^a   Freel Meyers, Caren L ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROBENZYL DICHLOROMETHYLENE BIS(N 4 CHLOROBUTYL N METHYLPHOSPHONAMIDATE); 4 NITROBENZYL METHYLENE BIS(N 4 CHLOROBUTYL N METHYLPHOSPHONAMIDATE); ANTINEOPLASTIC AGENT; BISPHOSPHONAMIDATE CLODRONATE; BISPHOSPHONIC ACID DERIVATIVE; CLODRONIC ACID; PRODRUG; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL CYCLE ARREST; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVATION; IN VITRO STUDY; LUNG NON SMALL CELL CANCER;

ANTINEOPLASTIC AGENTS; CARCINOMA, NON-SMALL-CELL LUNG; CELL CYCLE; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; CELL SURVIVAL; CLODRONIC ACID; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LUNG NEOPLASMS; ORGANOPHOSPHORUS COMPOUNDS; PRODRUGS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80053898529     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200521a     Document Type: Article

References (35)

1. Morgan, G.; Lipton, A. Antitumor Effects and Anticancer Applications of Bisphosphonates Semin. Oncol. 2010, 37 (5) S30-S40
2. Gnant, M. Bisphosphonates in the Prevention of Disease Rcurrence: Current Results and Ongoing Trials Curr. Cancer Drug Targets 2009, 9, 824-833
3. Boissier, S.; Magnetto, S.; Frappart, L.; Cuzin, B.; Ebetino, F. H.; Delmas, P. D.; Clezardin, P. Bisphosphonates Inhibit Prostate and Breast Carcinoma Cell Adhesion to Unmineralized and Mineralized Bone Extracellular Matrices Cancer Res. 1997, 57 (18) 3890-3894 (Pubitemid 27427670)
4. Boissier, S.; Ferreras, M.; Peyruchaud, O.; Magnetto, S.; Ebetino, F. H.; Colombel, M.; Delmas, P.; Delaissé, J. M.; Clézardin, P. Bisphosphonates Inhibit Breast and Prostate Carcinoma Cell Invasion, an Early Event in the Formation of Bone Metastases Cancer Res. 2000, 60 (11) 2949-2954 (Pubitemid 30395820)
5. Räikkönen, J.; Taskinen, M.; Dunford, J. E.; Mönkkönen, H.; Auriola, S.; Mönkkönen, J. Correlation between Time-Dependent Inhibition of Human Farnesyl Pyrophosphate Synthase and Blockade of Mevalonate Pathway by Nitrogen-Containing Bisphosphonates in Cultured Cells Biochem. Biophys. Res. Commun. 2011, 407, 663-667
6. Rogers, M. J.; Ji, X. H.; Russell, R. G. G.; Blackburn, G. M.; Williamson, M. P.; Bayless, A. V.; Ebetino, F. H.; Watts, D. J. Incorporation of Bisphosphonates into Adenine-Nucleotides by Amebas of the Cellular Slime-Mold Dictyostelium discoideum Biochem. J. 1994, 303, 303-311 (Pubitemid 24302934)
7. Frith, J. C.; Monkkonen, J.; Blackburn, G. M.; Russell, R. G. G.; Rogers, M. J. Clodronate and Liposome-Encapsulated Clodronate Are Metabolized to a Toxic ATP Analog, Adenosine 5′-(beta,gamma-dichloromethylene)Triphosphate, by Mammalian Cells in Vitro J. Bone Miner. Res. 1997, 12 (9) 1358-1367 (Pubitemid 27375378)
8. Lehenkari, P. P.; Kellinsalmi, M.; Napankangas, J. P.; Ylitalo, K. V.; Monkkonen, J.; Rogers, M. J.; Azhayev, A.; Väänänen, K. Further Insight into Mechanism of Action of Clodronate: Inhibition of Mitochondrial ADP/ATP Translocase by a Nonhydrolyzable, Adenine-Containing Metabolite Mol. Pharmacol. 2002, 62, 1255-1262 (Pubitemid 34441791)
9. Domcheck, S. M.; Younger, J.; Finkelstein, D. M.; Seiden, M. V. Predictors of Skeletal Complications in Patients with Metastic Breast Carcinoma Cancer 2000, 89, 363-368 (Pubitemid 30489885)
10. Knight, L. A.; Conroy, M; Fernando, A.; Polak, M.; Kurbacher, C. M.; Cree, I. A. Pilot Studies of the Effect of Zoledronic Acid (Zometa) on Tumor-Derived Cells ex Vivo in the ATP-Based Tumor Chemosensitivity Assay Anti-Cancer Drugs 2005, 16 (9) 969-976 (Pubitemid 41416087)
11. Matsumoto, S.; Kimura, S.; Segawa, H.; Kuroda, J.; Yuasa, T.; Sato, K.; Nogawa, M.; Tanaka, F.; Maekawa, T.; Wada, H. Efficacy of the Third-Generation Bisphosphonate Zoledronic Acid Alone and Combined with Anti-Cancer Agents against Small Cell Lung Cancer Cell Lines Lung Cancer 2005, 47 (1) 31-39 (Pubitemid 39643239)
12. Li, Y.; Chang, J. W.; Chou, W. C.; Liaw, C. C.; Wang, H. M.; Huang, J. S.; Wang, C. H.; Yeh, K. Y. Zoledronic Acid Is Unable to Induce Apoptosis, but Slows Tumor Growth and Prolongs Survival for Non-Small-Cell Lung Cancers Lung Cancer 2008, 59 (2) 180-191 (Pubitemid 351181343)
13. Wood, J.; Bonjean, K.; Ruetz, S.; Bellahcene, A.; Devy, L.; Foidart, J. M.; Castronovo, V.; Gree, J. R. Novel Antiangiogenic Effects of the Bisphosphonate Compound Zoledronic Acid J. Pharmacol. Exp. Ther. 2002, 302 (3) 1055-1061 (Pubitemid 34920226)
14. Croucher, P. I.; De Raeve, H.; Perry, M. J.; Hijzen, A.; Shipman, C. M.; Lippitt, J.; Green, J.; Van Marck, E.; Van Camp, B.; Venderkerken, K. Zoledronic Acid Treatment of 5T2MM-Bearing Mice Inhibits the Development of Myeloma Bone Disease: Evidence for Decreased Osteolysis, Tumor Burden and Angiogenesis, and Increased Survival J. Bone Miner. Res. 2003, 18 (3) 482-492 (Pubitemid 36241065)
15. Santini, D.; Vincenzi, B.; Galluzzo, S.; Battistoni, F.; Rocci, L.; Venditti, O.; Schiavon, G.; Angeletti, S.; Uzzalli, F.; Caraglia, M.; Dicuonzo, G.; Tonini, G. Repeated Intermittent Low-Dose Therapy with Zoledronic Acid Induces an Early, Sustained, and Long-Lasting Decrease of Peripheral Vascular Endothelial Growth Factor Levels in Cancer Patients Clin. Cancer Res. 2007, 13 (15) 4482-4486 (Pubitemid 47219717)
16. Hamma-Kourbali, Y.; Di Benedetto, M.; Ledoux, D.; Oudar, O.; Leroux, Y.; Lecouvey, M.; Kraemer, M. A Novel Non-Containing-Nitrogen Bisphosphonate Inhibits Both in Vitro and in Vivo Angiogenesis Biochem. Biophys. Res. Commun. 2003, 310 (3) 816-823 (Pubitemid 37188695)
17. Lipton, A. Emerging Role of Bisphosphonates in the Clinic-Antitumor Activity and Prevention of Metatasis to Bone Cancer Treat. Rev. 2008, 34, 525-530
18. Mönkkönen, H.; Kuokkanen, J.; Holen, I.; Evans, A.; Lefley, D. V.; Jauhiainen, M.; Auriola, S.; Mönkkönen, J. Bisphosphonate-Induced ATP Analog Formation and Its Effect on Inhibition of Cancer Cell Growth Anti-Cancer Drugs 2008, 19 (4) 391-399
19. Russell, R. G. G.; Watts, N. B.; Ebetino, F. H.; Rogers, M. J. Mechanisms of Action of Bisphosphonates: Similarities and Differences and Their Potential Influence on Clinical Efficacy Osteoporosis Int. 2008, 19 (6) 733-759
20. Ahlmark, M.; Vepsalainen, J.; Taipale, H.; Niemi, R.; Jarvinen, T. Bisphosphonate Prodrugs: Synthesis and in Vitro Evaluation of Novel Clodronic Acid Dianhydrides as Bioreversible Prodrugs of Clodronate J. Med. Chem. 1999, 42 (8) 1473-1476 (Pubitemid 29200884)
21. Vepsalainen, J. Bisphosphonate Prodrugs Curr. Med. Chem. 2002, 9, 1201-1208 (Pubitemid 34568193)
22. Zhang, Y.; Leon, A.; Song, Y.; Studer, D.; Haase, C.; Koscielski, L. A.; Oldfield, E. Activity of Nitrogen-Containing and Non-Nitrogen Containing Bisphosphonates on Tumor Cell Lines J. Med. Chem. 2006, 49 (9) 5804-5814 (Pubitemid 44423717)
23. Neimi, R.; Turhanen, P.; Vepsalainen, J.; Taipale, H.; Jarvinen, T. Bisphosphonate Prodrugs: Synthesis and in Vitro Evaluation of Alkyl and Acyloxymethyl Esters of Etidronic Acid as Bioreversible Prodrugs of Etidronate Eur. J. Pharm. Sci. 2000, 11 (2) 173-180 (Pubitemid 30479859)
24. Szabo, C. M.; Matsumura, Y.; Fukura, S.; Martin, M. B.; Sanders, J. M.; Sengupta, S.; Cieslak, J. A.; Loftus, T. C.; Lea, C. R.; Lee, H. J.; Koohang, A.; Coates, R. M.; Sagami, H.; Oldfield, E. Inhibition of Geranylgeranyl Diphosphate Synthase by Bisphosphonates and Diphosphates: A Potential Route to New Bone Antiresorption and Antiparasitic Agents J. Med. Chem. 2002, 45 (11) 2185-2196 (Pubitemid 34525798)
25. Shull, L. W.; Wiemer, A. J.; Hohl, R. J.; Wiemer, D. F. Synthesis and Biological Activity of Isoprenoid Bisphosphonates Bioorg. Med. Chem. 2006, 14 (12) 4130-4136
26. Barney, R. J.; Wasko, B. M.; Dudakovic, A.; Hohl, R. J.; Wiemer, D. F. Synthesis and Biological Evaluation of a Series of Aromatic Bisphosphopnates Bioorg. Med. Chem. 2010, 18 (20) 7212-7220
27. Wiemer, A. J.; Yu, J. S.; Shull, W. L.; Barney, R. J.; Wasko, B. M.; Lamb, K. M.; Hohl, R. J.; Wiemer, D. F. Pivaloyloxymethyl-Modified Isoprenoid Bisphosphonates Display Enhanced Inhibition of Cellular Geranylgeranylation Bioorg. Med. Chem. 2008, 16 (7) 3652-3660 (Pubitemid 351484050)
28. Tobais, S. C.; Borch, R. F. Synthesis and Biological Studies of Novel Nucleoside Phosphoramidate Prodrugs J. Med. Chem. 2001, 44 (25) 4475-4480 (Pubitemid 33131672)
29. Tobias, S. C.; Borch, R. F. Synthesis and Biological Evaluation of a Cytarabine Phosphoramidate Prodrug Mol. Pharmaceutics 2004, 1 (2) 112-116
30. Cox, J. R.; Ramsay, O. B. Mechanisms of Nucleophilic Substitution in Phosphate Esters Chem. Rev. 1964, 64 (4) 317-352
31. Meyers, C. L.; Borch, R. F. A Novel Method for the Preparation of Nucleoside Diphosphates Org. Lett. 2001, 3 (23) 3765-3768 (Pubitemid 33625461)
32. Prieto, J. A.; Andrade, F.; Martin, S.; Sanjuro, P.; Elorz, J.; Aldámix-Eschevarría, L. Determination of Creatine and Guanidinoacetate by GC-MS study of Their Stability in Urine at Different Temperatures Clin. Biochem. 2009, 42, 125-128
33. Wood, P. L.; Khan, M. A.; Moskai, J. R. Neurochemical Analysis of Amino Acids, Polyamines and Carboxylic Acids: GC-MS Quantitation of t BDMS Derivatives Using Ammonia Positive Chemical Ionization J. Chromatogr., B 2006, 831, 313-319 (Pubitemid 43155810)
34. Yang, W.; Laws, K. A.; Sleczka, B.; S. Burak, E. S. (Guilford Pharmaceuticals, Inc., Baltimore, MD 21224). Development of a LC/MS/MS Method for the Quantitation of 2-(Phosphonomethyl)pentanedioic Acid in Rat Plasma and Brain. Presented at the 1998 American Association of Pharmaceutical Scientists (AAPS) Annual Meeting, 1998; Abstract 2397.
35. Sillero, M. A. G.; Diego, A.; Silles, E.; Perez-Zuniga, F.; Sillero, A. Synthesis of Bisphosphonate Derivatives of ATP by T4 RNA Ligase FEBS Lett. 2006, 580 (24) 5723-5727 (Pubitemid 44498672)