Novel Anticancer Prodrugs of Butyric Acid. 2

Journal of Medicinal Chemistry

Volumn 35, Issue 4, 1992, Pages 687-694

  Nudelman, Abraham ^a   Ruse, Margaretta ^a   Aviram, Adina ^b   Rabizadeh, Ester ^b   Shaklai, Matityahu ^b   Zimrah, Yael ^b   Rephaeli, Ada ^b  

^a BAR ILAN UNIVERSITY   (Israel)

^b RABIN MEDICAL CENTER   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; 4 AMINOBUTYRIC ACID DERIVATIVE; ANTINEOPLASTIC AGENT; BUTYRIC ACID; BUTYRIC ACID (PIVALOYLOXY)METHYL ESTER; BUTYRIC ACID DERIVATIVE; CYCLOPHOSPHAMIDE; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL DIFFERENTIATION; CELL GROWTH; CELL STRAIN HL 60; INTRAPERITONEAL DRUG ADMINISTRATION; LUNG CANCER; MALE; MELANOMA; METASTASIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMAL; ANTINEOPLASTIC AGENTS; BUTYRATES; CELL DIFFERENTIATION; CELL DIVISION; COMPARATIVE STUDY; FEMALE; HUMAN; LEUKEMIA, PROMYELOCYTIC, ACUTE; MALE; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED BALB C; MICE, INBRED C57BL; MOLECULAR STRUCTURE; NEOPLASM METASTASIS; PRODRUGS; TUMOR CELLS, CULTURED;

EID: 0026507070     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00082a009     Document Type: Article

References (33)

1. Rephaeli, A.; Rabizadeh, E.; Aviram, A.; Shaklai, M.; Ruse, M.; Nudelman, A. Derivatives of Butyric Acid as Potential Anti-Neoplastic Agents. Int. J. Cancer 1991, 49, 66-72
2. Bloch, A. Induced Cell Differentiation in Cancer Therapy. Cancer Treat. Rep. 1984, 68, 199-205
3. Prasad, K. N. Butyric Acid: A Small Fatty Acid with Diverse Biological Functions. Life Sci. 1980, 27,1351-1358
4. Januszewicz, E.; Rabizadeh, E.; Novogradsky, A.; Shaklai, M. Inhibition of Non-Leukemic and Chronic Myeloid Leukemia, Granulocyte Macrophage Clonal Growth. Med. Oncol. Tumor Pharmacother. 1988, 5, 259-263
5. Novogradsky, A.; Dvir, A.; Ravid, A.; Shkolnik, T.; Stenzel, K. H.; Rubin, A. L.; Zaizov, R. Effect of Polar Organic Compounds on Leukemic Cells. Cancer 1983, 51, 9-14
6. Rephaeli, A.; Rabizadeh, E.; Nordenberg, J.; Kluska, A.; Prokocimer, M.; Rosenberg, I.; Novogradsky, A.; Shaklai, M. Effect of the Ceil Differentiation Inducers, Butyrate, Retinoic Acid and Low Dose Cytosine Arabinoside on Leukemic Cells of Patients with Acute Nonlymphatic Leukemia. Blood 1986, 68, 192
7. Miller, A. A.; Kurschel, E.; Osieka, R.; Schmidt, C. Clinical Pharmacology of Sodium Butyrate in Patients with Acute Leukemia. Eur. J. Cancer Clin. Oncol. 1987, 23, 1283-1287
8. Rephaeli, A.; Rabizadeh, E.; Aviram, A.; Shaklai, M.; Ruse, M.; Nudelman, A. Antineoplastic Activity of Butyric Acid Prodrugs. J. Cancer Bes., Clin. Oncol. 15th International Cancer Congress, Hamburg, 1990,119, 315
9. Rabizadeh, E.; Rephaeli, A.; Aviram, A.; Nudelman, A.; Ruse, M.; Shaklai, M. Effects of Pivaloyloxymethyl Butyrate on Leukemic Cells Differentiation and Proliferation and on Mononuclear Cells Lymphokine(s) Secretion. Blood 1990, 76 suppl. 1:113a/444
10. Ferres, H. Prodrugs of β-Lactam Antibiotics. Chem. Ind. 1980, 435-440
11. Daehne, W. v.; Fredriksen, E.; Gundersen, E.; Lund, F.; Morch, P.; Petersen, H. J.; Roholt, K.; Tybring, L.; Godtfredsen, W. O. Acyloxymethyl Esters of Ampicillin. J. Med. Chem. 1970,13, 607-611
12. Ehrnebo, M.; Nilsson, S. O.; Boreus, L. P. Pharmacokinetics of Ampicillin and Its Prodrugs Bacampicillin and Pivampicillin in Man. J. Pharmacokinet. Biopharm. 1979, 7, 429-451
13. Shiobara, Y.; Tachibana, A.; Sasaki, H.; Watanabe, T.; Sado, T. Phthalydyl-D-α-aminobenzylpenicillinate Hydrochloride (PC-183). A new Orally Active Ampicillin Ester I. Absorption, Excretion and Metabolism of PC-183 and Ampicillin. J. Antibiot. 1974, 27, 665-673
14. Wheeler, W. J.; Wright, W. E.; Line, V. D.; Frogge, J. A. Orally Active Esters of Cephalosporin Antibiotics. Synthesis and Biological Properties of Acyloxymethyl Esters of 7-(D-2-Amino-2-phenylacetamido)-3-[5-methyl-(1,3,4-thiadiazol-2-yl)thiomethyl]-3-cephem-4-carboxylic Acid. J. Med. Chem. 1977, 20, 1159-1167
15. Ozaki, S.; Watanabe, Y.; Hoshiko, T.; Mizuno, H.; Ishikawa, K.; Mori, H. 5-Fluorouracil Derivatives IV. Synthesis of Antitumor Active Acyloxyalkyl-5-fluorouracils. Chem. Pharm. Bull. 1984, 32, 733-738
16. Coffin, C. C.; Breazly, B. Homogeneous First-Order Gas Reactions (VI). Decomposition of Methylene Diacetate, Methylene Dipropionate and Methylene Dibutyrate. Can. J. Res. B, 1937, 15, 229-236
17. Coffin, C. C.; Deacey, Y. R.; Parlee, N. A. D. Homogeneous First-Order Gas Reactions (VII). Decomposition of Ethylidene Dibutyrate and Heptylidene Diacetate. Can. J. Res. B 1937,15, 247-258
18. Mann, E. H.; Sanderson, J. J.; Hauser, C. R. Boron Fluoride Catalyzed Addition of Aliphatic Anhydrides to Aldehydes. J. Am. Chem. Soc. 1950, 72, 847-848
19. Weatherby, L. S.; livable, L. M.; Maltin, D. Butyrin. J. Am. Chem. Soc. 1925, 47, 2249-2252
20. U.S. Department of Health and Human Services: In Vivo Cancer Models, NIH publication No. 84-2635, 1984
21. Chomienne, C.; Ballerini, P.; Balitrand, N.; Amar, M.; Bernard, J. F.; Boivin, I.; Daniel, T.; Berger, R.; Castaigne, S.; Degos, L. Retinoic Acid - An Alternative Therapy of Promyelocytic Leukemia. Lancet 1989, 2, 746
22. Flandrin, G.; Sigaux, F.; Castaigne, S.; Billard, C.; Aguet, M.; Boiron, M.; Falcoff, E.; Degos, J. Treatment of Hairy Cell Leukemia With Recombinant Alpha Interferon I. Quantitative Study of Bone Marrow Changes During the First Months of Treatment. Blood 1986, 67, 817.
23. Gavosto, F.; Maiolo, A. T.; Aglietta, M.; Alimenza, G.; Bemasconi, C.; Castoldi, G.; Cazzola, M.; Cortelezzi, A.; Mandelli, F.; Resegott, L.; Polli, E. Treatment with Interferon Gama in Myelodysplastic Syndromes; A Pilot Study. In The Status of Differentiation Therapy in Cancer, Waxman, S., Rossi, G. B.; Takaku, F., Eds.; Raven Press: New York, 1987; p 375
24. Ganser, A.; Vokers, B.; Greher, H.; Walther, F.; Hoelzer, D. Recombinant Human Granulocyte-Macrophage Colony Stimulating Factor in Patients with Myelodysplastic Syndromes - A Phase 1/11 Trial. Onkologie 1988, 1, 53
25. Binderup, E.; Hansen, E. T. Chlorosulfates as Reagents in the Synthesis of Carboxylic Acid Esters Under Phase-Transfer Conditions. Synth. Commun. 1984, 14, 857-864
26. Bodor, N.; Kaminski, J. J.; Selk, S. Soft Drugs 1. Labile Quaternary Ammonium Salts as Soft Antimicrobials. J. Med. Chem. 1980, 23, 469-474
27. Rassmusen, M.; Leonard, N. J. The Synthesis of 3-(2′-Deoxy-D-ribofuranosyl)adenine. Application of a New Protecting Group, Pivaloyloxymethyl (POM). J. Am. Chem. Soc. 1967,89, 5439-5445
28. Bedford, C. D.; Harris, R. N.; Howd, R. A.; Gof, D. A.; Koolpe, G. A.; Petesch, M.; Miller, A.; Nolen, H. W.; Musallam, A.; Pick, R. O.; Jones, D. E.; Koplovitz, I. ; Sultan, W. E. Quaternary Salts of 2-[(Hydroxyimino)-methyl]imidazole. 2. Preparation and In Vitro and In Vivo Evaluation of 1-(Alkoxymethyl)-2-[(hydroxyimino)methyl]-3-methylimidazolium Halides for Reactivation of Organophosphorus-Inhibited Acetylcholinesterases. J. Med. Chem. 1989, 32, 493-503
29. Sakamoto, F.; Ikeda, S.; Kondo, H.; Tsukamoto, J. Studies on Prodrugs II. Preparation and Characterization of (5-Substituted-2-oxo-1,3-dioxolen-4-yl)methyl Esters of Ampicillin. Chem. Pharm. Bull. 1984, 32, 2241-2248
30. Iyer, R. P.; Phillips, L. R.; Biddle, J. A.; Thakker, D. R.; Egan, W.; Aoki, S.; Mitsuya, H. Synthesis of Acyloxyalkyl Acylphosphonates as Potential Prodrugs of the Antiviral Trisodium Phosphonoformate (Foscarnet Sodium). Tetrahedron Lett. 1989, 30, 7141-7144
31. Schnabel, E. Improved Synthesis of tert-Butoxycarbonyl Amino Acids by a Constant pH Reaction. Justus Liebigs Ann. Chem. 1967, 702, 188-196
32. Koeffler, H. P. Induction of Differentiation of Human Acute Myelogenous Leukemia Cells: Therapeutic Implications. Blood 1983, 62, 709-721
33. Hamburger, A. W.; Salmon, S. E. Primary Bioassay of Human Tumor Stem Cells. Science 1977, 197, 461-463