Heteroarotinoids inhibit head and neck cancer cell lines in vitro and in vivo through both RAR and RXR retinoic acid receptors

Journal of Medicinal Chemistry

Volumn 42, Issue 21, 1999, Pages 4434-4445

  Zacheis, David ^a   Dhar, Arindam ^b   Lu, Shennan ^b   Madler, Matora M ^c   Klucik, Jozef ^c   Brown, Chad W ^c   Liu, Shengquan ^c   Clement, Francis ^c   Subramanian, Shankar ^c   Mahika Weerasekare, G ^c   Darrell Berlin, K ^c   Gold, Michael A ^b   Houck Jr , John R ^a   Fountain, Kenneth R ^d   Benbrook, Doris M ^b  

^a UNIVERSITY OF OKLAHOMA HEALTH SCIENCES CENTER   (United States)

^b UNIVERSITY OF OKLAHOMA COLLEGE OF MEDICINE   (United States)

^c OKLAHOMA STATE UNIVERSITY   (United States)

^d TRUMAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RETINOIC ACID RECEPTOR; RETINOID DERIVATIVE; RETINOID X RECEPTOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL LINE; HEAD CANCER; MODEL; MOUSE; NECK CANCER; NONHUMAN; SQUAMOUS CELL CARCINOMA; TUMOR REGRESSION; TUMOR VOLUME; XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZAMIDES; BICYCLO COMPOUNDS, HETEROCYCLIC; CARCINOMA, SQUAMOUS CELL; CELL DIVISION; DRUG SCREENING ASSAYS, ANTITUMOR; HEAD AND NECK NEOPLASMS; HUMANS; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; RECEPTORS, RETINOIC ACID; RETINOID X RECEPTORS; RETINOIDS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION FACTOR AP-1; TRANSCRIPTION FACTORS; TRANSCRIPTION, GENETIC; TUMOR CELLS, CULTURED;

EID: 0032718908     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990292i     Document Type: Article

References (44)

1. (a) Moon, R. C.; Mehta, R. G.; Rao, K. V. N. Retinoids and Cancer In Experimental Animals. In The Retinoids-Biology, Chemistry, and Medicine; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Raven Press: New York, 1994.
2. (b) Hong, W. K.; Iti, L. M. Retinoids in Human Cancer. In The Retinoids-Biology, Chemistry, and Medicine; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Raven Press: New York, 1994.
3. (a) Armstrong, R. B.; Ashenfelter, K. O.; Eckhoff, C.; Levin, A. A.; Shapiro, S. S. General and Reproductive Toxicology of Retinoids. In The Retinoids-Biology, Chemistry, and Medicine; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Raven Press: New York, 1994.
4. (b) Kamm, J. J.; Ashenfleter, K. O.; Ehmann, C. W. Preclinical and Clinical Toxicology of Selected Retinoids. In The Retinoids; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Academic Press: Orlando, 1984.
5. Gross, E. G.; Helfgott, M. A. Retinoids and the Eye. Dermatol. Clin. 1992, 10, 521-531.
6. Waugh, K. M.; Berlin, K. D.; Ford, W. T.; Holt, E. M.; Carroll, J. P.; Schomber, P. R.; Schiff, L. J. Synthesis and Characterization of Selected Heteroarotinoids. Pharmacological Activity as Assessed in Vitamin A Deficient Hamster Tracheal Organ Cultures. Single-Crystal X-ray Diffraction Analysis of 4,4-Dimethylthiochroman-6-yl Methyl Ketone 1,1-Dioxide and Ethyl (E)-4-[2-(4,4-Dimethylthiochroman-6-yl)-1-propenyl]benzoate. J. Med. Chem. 1985, 27, 116-124.
7. Spruce, L. W.; Gale, J. B.; Berlin, K. D.;Verma, A. K.; Breitman, T. R.; Ji, X.; van der Helm, D. Novel Heteroarotinoids: Synthesis and Biological Activity. J. Med. Chem. 1991, 34, 430-439.
8. Spruce, L. W.; Rajadhyaksha, S. N.; Berlin, K. D.; Gale, J. B.; Miranda, E. T.; Ford, W. T.; Blossey, E. C.; Verma, A. K.; Hossain, M. B; van der Helm, D.; Breitman, T. R. Heteroarotinoids. Synthesis, Characterization, and Biological Activity in Terms of an Assessment of These Systems to Inhibit Induction of Ornithine Decarboxylase Activity and to Induce Terminal Differentiation of HL-60 Cells. J. Med. Chem. 1987, 30, 1474-1482.
9. Benbrook, D. M.; Madler, M. M.; Spruce, L. W.; Birckbichler, P. J.; Nelson, E. C.; Subramanian, S.; Weerasekare, G. M.; Gale, J. B.; Patterson, Jr., M. K.; Wang, B.; Wang, W.; Lu, S.; Rowland, T. C.; DiSivestro, P.; Lindamood, C.; Hill, D. L.; Berlin, K. D. Biologically Active Heteroarotinoids Exhibit Anticancer Activity and Decreased Toxicity. J. Med. Chem. 1997, 40, 3567-3583.
10. Benbrook, D. M.; Subramanian, S.; Gale, J. B.; Liu, S.; Brown, C. W.; Boehm, M. F.; Berlin, K. D. Synthesis and Characterization of Heteroarotinoids Demonstrates Structure-Activity Relationships. J. Med. Chem. 1998, 41, 3753-3757.
11. (a) Mangelsdorf, D. J.; Umesono, K.; Evans, R. M. The Retinoid Receptors. In The Retinoids-Biology, Chemistry, and Medicine; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Raven Press: New York, 1994.
12. (b) Dawson, M. I. Retinoids. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; Wiley: New York, 1996.
13. Cooper, J. S.; Pajak, T. F.; Rubin, P.; Tupchong, L.; Brady, L. W.; Leibel, S. A.; Laramore, G. E.; Marcial, V. A.; Davis, L. W.; Cox, J. D. Second Malignancies in Patients Who Have Head and Neck Cancers: Incidence, Effect on Survival and Implications for Chemoprevention Based on the RTOG Experience. Int. J. Radiat. Oncol. Biol. Phys. 1988, 19, 449-456.
14. Slaughter, D. P.; Southwick, H. W.; Smejkal, W. Field Cancerization in Oral Stratified Squamous Epithelium: Clinical Implications of Multicentric Origin. Cancer 1953, 6, 963-968.
15. Lotan, R. Squamous Cell Differentiation Markers in Normal, Premalignant, and Malignant Epithelium: Effects of Retinoids. J. Cell. Biochem. 1993, 17, 167-174.
16. Wolbach, S. B.; Howe, P. R. Tissue Changes Following Deprivation of Fat Soluble A Vitamin. J. Exp. Med. 1926, 42, 753-777.
17. Lippman, S. M.; Batsakis, J. G.; Toth, B. B.; Weber, R. S.; Lee, J. J.; Martin, J. W.; Hays, G. L.; Goepfert, H.; Hong, W. K. Comparison of Low-Dose Isotretinoin Therapy with β-Carotene for Prevention of Oral Carcinogenesis. N. Engl. J. Med. 1993, 325, 15-20.
18. Chiesa, F.; Tradati, N.; Marazzara, M.; Rossi, N.; Boraccchi, p.; Mariani, L.; Formelli, F.; Giardini, R.; Costa, A.; DePalo, G.; Veronesi, U. Fenretinide (4HPR) in Chemoprevention of Oral Leukoplakia. J. Cell. Biochem. 1993, 17 (Suppl), 255-261.
19. Kurie, J. M.; Lippman, S. M.; Hong, W. K. Potential of Retinoids in Cancer Prevention. Cancer Treat. Rev. 1994, 20, 1-10.
20. Benner, S. E.; Pajak, T. F.; Lippman, S. M.; Early, C.; Hong, W. K. Prevention of Second Primary Tumors with Isotretinoin in Patients with Squamous Cell Carcinoma of the Head and Neck: Long Term Followup. J. Natl. Cancer Inst. 1994, 86, 140-141.
21. Dimery, I. W.; Hong, W. K.; Lee, J. J.; Guillory-Perez, C.; Pham. F.; Fritsche, Jr., H. A.; Lippman, S. M. Phase I Trial of Alpha-Tocopherol Effects on 13-cis-Retinoic Acid Toxicity. Ann. Oncol. 1997, 8, 85-89.
22. Shalinsky, D. R.; Bischoff, E. D.; Gregory, M. L.; Gottaris, M. M.; Hayes, J. S.; Lamph, W. W.; Heyman, R. A.; Shirley, M. A.; Cooke, T. A.; Davies, P. J.; Thomazy, V. Retinoid-Induced Suppression of Squamous Cell Differentiation in Human Oral Squamous Cell Carcinoma Xenographs (line 1483) in Athymic Nude Mice. Cancer Res. 1995, 55, 3183-3191.
23. Scher, R. L.; Saito, W.; Dodge, R. K.; Richtsmeier, W. J.; Fine, R. L. Fenretinide-Induced Apoptosis of Human Head and Neck Squamous Carcinoma Cell Lines. Otol. Head Neck Surg. 1998, 118, 464-471.
24. Cooper, M. P.; Klassen, I.; Brakenhoff, R. H., Cloos, J.; Snow, G. B.; Braakhuis, B. J. All-trans-Retinoic Acid Induced Gene Expression and Growth Inhibition in Head and Neck Cancer Cell Lines. Oral Oncol. 1997, 33, 270-274.
25. Eicher, S.A.; Lotan, R. Differential Effects of Retinoic Acid and N-(4-Hydroxyphenyl)retinamide on Head and Neck Squamous Cell Carcinoma Cells. Laryngoscope 1996, 106, 1471-1475.
26. Lotan, R. Retinoids and Their Receptors in Modulation of Differentiation, Development, and Prevention of Head and Neck Cancers. Anticancer Res. 1996, 16, 2415-2419.
27. Mourad, W. A.; Bruner, J. M.; Vallieres, E.; McName, C.; Alabdulwahed, S.; Scott, K.; Oldring, D. J. The Effect of High Dose Vitamin A on the Morphology and Proliferative Ability of Xenograph Lung and Neck Cancer. In Vivo 1996, 10, 329-33.
28. Kagechika, H.; Kawachi, E.; Hashimoto, I.; Himi, T.; Shudo, K. Retinobenzoic Acids. 1. Structure-Activity Relationships of Aromatic Acids With Retinoidal Activity. J. Med. Chem. 1988, 31, 2182-2192.
29. Apfel, C.; Bauer, F.; Crettaz, M.; Forni, L.; Kamber, M.; Kaufmann, F.; LeMotte, P.; Pirson, W.; Klaus, M. A Retinoic Acid Receptor α Antagonist Selectivity Counteracts Retinoic Acid Effects. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 7129-7133.
30. Wang, B.; Liu, S.; Borchardt, R. T. Development of a Novel Redox-Sensitive Protecting Group for Amines Which Utilize a Facilitated Lactonization Reaction. J. Org. Chem. 1995, 60, 539-543.
31. Nakatani, K.; Numata, S.; Inoue, T.; Fujisawa, K. K.; Kawasaki, T. I.; Toyama, T.; Tachibana, H.; Udagave, T.; Gohbara, M. UP 254135, U.S. Patent 4397864; Chem. Abstr. 1982, 97, 5964e.
32. Boehm, M. F.; Zhang, L.; Zhi, L.; Badea, B. A.; White, S. K.; Mais, D. E.; Berger, E.; Suto, M. C.; Goldman, M. E.; Heyman, R. A. Synthesis and Structure-Activity Relationships of Novel Retinoid X Receptor-Selective Retinoids. J. Med. Chem. 1994, 37, 2930-2941.
33. Mangelsdorf, D. J.; Umesono, K.; Evans, R. M. In The Retinoids-Biology, Chemistry, and Medicine; Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds.; Raven Press: New York, 1994; pp 319-349.
34. Pfahl, M. Nuclear Receptor/AP-1 Interaction. Endocrinol. Rev. 1993, 14, 651-658.
35. Chen, J. Y.; Penco, S.; Ostrowski, J.; Balaguer, P.; Pons, M.; Starrett, J. E.; Preczek, P.; Chambon, P.; Gronemeyer, H. RAR-Specific Agonist/Antagonists Which Dissociate Transactivation and AP1 Tranrepression Inhibit Anchorage-Dependent Cell proliferation. EMBO J. 1995, 14, 1187-1197.
36. Fanjul, A.; Dawson, M. I.; Hobbs, P. D.; Jong, L.; Cameron, J. F.; Harlev, E.; Graupner, G.; Lu, C.-P.; Pfahl, M. A Novel Class of Retinoids with Selective Inhibition of AP-1 Exhibit Anti-Proliferative Activity. Nature 1994, 372, 107-111.
37. Grandis, J. R.; Zeng, Q.; Tweardy, D. J. Retinoic Acid Normalizes the Increased Gene Transcription Rate of TGF-Alpha and EGFR in Head and Neck Cancer Cell Lines. Nature Med. 1996, 2, 237-240.
38. Issing, W. J.; Wustrow, T. P. Expression of Retinoic Acid Receptors in Squamous Cell Carcinomas and Their Possible Implication in Chemoprevention. Anticancer Res. 1996, 16, 2373-2377.
39. Oridate, N.; Esumi, N.; Lotan, D.; Hing, W. K.; Rochette-Egly, C.; Chambon, P.; Lotan, R. Implication of Retinoic Acid Receptor Gamma in Squamous Differentiation and Response to Retinoic Acid in Head and Neck SqSCC/Y1 Squamous Carcinoma Cells. Oncogene 1996, 12, 2019-2028.
40. Lotan, R.; Dawson, M. I.; Zou, C.-C.; Jong, L.; Lotan, D.; Zou, C.-P. Enhanced Efficacy of Combinations of Retinoic Acid- and Retinoid X Receptor-Selective Retinoids and α-Interferon in Inhibition of Cervical Carcinoma Cell proliferation. Cancer Res. 1995, 55, 232-236.
41. Shalinsky, D. R.; Bischoff, E. D., Lamph, W. W.; Zhang, L.; Boehm, M. F.; Davies, P. J. A.; Nadzan, A. M.; Heyman, R. A. A Novel Retinoic Acid Receptor-Selective Retinoid, ALRT1550, Has Potent Antitumor Activity Against Human Oral Squamous Carcinoma Xenograph in Nude Mice. Cancer Res. 1997, 57, 162-168.
42. Dhar, A.; Liu, S.; Klucik, J.; Berlin, K. D.; Madler, M. M.; Lu, S.; Ivey, R. T.; Zacheis, D.; Brown, C. W.; Nelson, E. C.; Birckbichler, P. J.; Benbrook, D. M. Synthesis, Structure-Activity Relationships, and RARγ-Ligand Interactions of Nitrogen Heteroarotinoids. J. Med. Chem. 1999, 42, 3602-3614.
43. Madler, M. M.; Klucik, J.; Soell, P. S.; Brown, C. W.; Lui, S.; Berlin, K. D.; Benbrook, D. M.; Birckbichler, P. J.; Nelson, E. C. LiOCl/NaOCl as a Novel Oxidative Mixture for Methyl Ketones and Methyl Carbinols. Org. Prep. Proc. Int. 1998, 30, 230-234.
44. Benbrook, D. M.; Lu, S.; Flangan, C.; Shen-Gunther, J.; Angros, L. H.; Lightfoot, S. A. Biological Assay for Activity and Molecular Mechanism of Retinoids in Cervical Tumor Cells. Gyn. Oncol. 1997, 66, 114-121.