Synthesis and characterization of heteroarotinoids demonstrate structure specificity relationships

Journal of Medicinal Chemistry

Volumn 41, Issue 19, 1998, Pages 3753-3757

  Benbrook, Doris M ^a   Subramanian, Shankar ^b   Gale, Jonathan B ^b   Liu, Shengquan ^b   Brown, Chad W ^b   Boehm, Marcus F ^c   Berlin, K Darrell ^b  

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

^b OKLAHOMA STATE UNIVERSITY   (United States)

^c LIGAND PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 (2,3 DIHYDRO 3,3 DIMETHYL 5 BENZOFURANYL) 3 METHYL 2,4,6 OCTATRIENOIC ACID; [4 (4,4 DIMETHYLTHIOCHROMAN 6 YL)PROPENYL]BENZOIC ACID METHYL ESTER; ANTINEOPLASTIC AGENT; HETEROAROTINOID; RETINOIC ACID RECEPTOR; RETINOID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN;

ANIMALS; CELL LINE; CERCOPITHECUS AETHIOPS; RECEPTORS, RETINOIC ACID; RETINOIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032505176     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980308p     Document Type: Article

References (28)

1. Dawson, M. I.; Hobbs, P. D.; Derdzinski, K.; Chan, R. L.-S.; Gruber, J.; Chao, W.-r.; Smith, S.; Thies, R. W.; Schiff, L. J. Conformationally Restricted Retinoids. J. Med. Chem. 1984, 27, 1516-1531.
2. 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.
3. Auvinen, M.; Paasinen, A.; Andersson, L. C.; Holtta, E. Ornithine decarboxylase activity is critical for cell transformation. Nature 1992, 360, 355-358.
4. Benbrook, D. M.; Madler, M. M.; Spruce, L. W.; Birckbichler, P. J.; Nelson, E. C.; Subramanian, S.; Weerasekare, G. M.; Gale, J. B.; Patterson, J., M. K.; Wang, B.; Wang, W.; Lu, S.; Rowland, T. C.; DiSilvestro, 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.
5. 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.
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 1-(1-1-dioxa-3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyra-6-yl)ethanone and ethyl (E)-4-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)-1-propenyl] benzoate. J. Med. Chem. 1985, 27, 116-124.
7. Benbrook, D. M.; Lu, S.; Flanagan, 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.
8. Lehmann, J. M.; Dawson, M. I.; Hobbs, P. D.; Husmann, M.; Pfahl, M. Identification of retinoids with nuclear receptor subtype-selective activities. Cancer Res. 1991, 51, 4804-4809.
9. 3H)-9-cis-retinoic acid and its application for identifying retinoids with unusual binding properties. J. Med. Chem. 1994, 37, 408-414.
10. de The, H.; Chomienne, C.; Lanotte, M.; Degos, L.; Dejean, A. The t(15:17) translocation of acute promyelocytic leukemia fuses the retinoic acid receptor a gene to a novel transcribed locus. Nature 1990, 343, 177-180.
11. Borrow, J.; Goddard, A. D.; Sheer, D.; Solomon, E. Molecular analysis of acute promyelocytic leukemia breakpoint cluster region on chromosome 17. Science 1990, 249, 1577-1580.
12. Alcalay, M.; Zangrilli, D.; Pandolfi, P. P.; Longo, L. K.; Mencarelli, A.; Giacommucci, A.; Rocchi, M.; Giondi, A.; Rambaldi, A.; LoCoco, G.; Diverio, D.; Donti, E.; Grignani, G.; Pelicci, P. G. Translocation breakpoint of acute promyelocytic leukemia lies within the retinoic acid receptor a locus. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1977-1981.
13. Dawson, M. I.; Chao, W.-r.; Pine, P.; Jong, L.; Hobbs, P. D.; Rudd, C. K; Quick, T. C.; Niles, R. M.; Zhang, X.-k.; Lomardo, A.; Ely, K. R.; Shroot, B.; Fontana, J. A. Correlation of retinoid binding affinity to retinoic acid receptor alpha with retinoid inhibition of growth of estrogen receptor-positive MCF-7 mammary carcinoma cells. Cancer Res. 1995, 55, 4446-4451.
14. Hu, L.; Crowe, D. L.; Rheinwald, J. G.; Chambon, P.; Gudas, L. J. Abnormal expression of retinoic acid receptors and keratin 19 by human oral and epidermal squamous cell carcinoma cell lines. Cancer Res. 1991, 51, 3972-3981.
15. Gebert, J. F.; Moghal, N.; Frangioni, J. V.; Sugarbaker, D. J.; Neel, B. G. High frequency of retinoic acid receptor β abnormalities in human lung cancer. Oncogene 1991, 6, 1859-1868.
16. Swisshelm, K.; Ryan, K.; Lee, X.; Tsou, H. C.; Peacocke, M.; Sager, R. Down-regulation of retinoic acid receptor beta in mammary carcinoma cell lines and its up-regulation in senescing normal mammary epithelial cells. Cell Growth Diff. 1994, 5, 133-141.
17. Crowe, D. L. Retinoic acid receptor β induces terminal differentiation of squamous cell carcinoma lines in the absence of cyclin-dependent kinase inhibitor expression. Cancer Res. 1998, 58, 142-148.
18. Li, C.; Wan, Y. J. Differentiation and antiproliferation effects of retinoic acid receptor beta in hepatoma cells. Cancer Lett. 1998, 124, 205-211.
19. Lotan, R. Suppression of squamous cell carcinoma growth and differentiation by retinoids. Cancer Res. 1994, 54, 1987s-1990s.
20. Look, J.; Landwehr, J.; Bauer, F.; Hoffman, A. S.; Bluethmann, H.; Lemotte, P. Marked resistance of RARγ-deficient mice to the toxic effects of retinoic acid. Am. J. Physiol. 1995, 269, E91-E98.
21. 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-independent cell proliferation. EMBO J. 1995, 14, 1187-1197.
22. Fanjul, A. N.; Bouterfa, H.; Dawson, M.; Pfahl, M. Potential role for retinoic acid receptor α in the inhibition of breast cancer cells by selective retinoids and interferons. Cancer Res. 1996, 56, 1571-1577.
23. 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.
24. Beard, R. L.; Chandraratna, R. A. S.; Colon, D. F.; Gillett, S. J.; Henry, E.; Marler, D. K.; Song, T.; Denys, L.; Garst, M. E.; Arefieg, T.; Klein, E.; Gil, D. W.; Wheeler, L.; Kochhar, D. M.; Davies, P. J. A. Synthesis and structure-activity relationships of stilbene retinoid analogs substituted with heteroaromatic carboxylic acids. J. Med. Chem, 1995, 38, 2820-2829.
25. Elmazar, M. M. A.; Reichert, U.; Shroot, B.; Nau, H. Pattern of retinoid-induced teratogenic effects: Possible relationship with relative selectivity for nuclear retinoid receptors RARα, RARβ, and RARγ. Teratology 1996, 53, 158-167.
26. Standeven, A. M.; Beard, R. L.; Johnson, A. T.; Boehm, M. F.; Excobar, M.; Heyman, R. A.; Chandraratna, R. A. Retinoid-induced hypertriglyceridemia in rats is mediated by retinoic acid receptors. Fundam. Applied Tox. 1996, 33, 264-271.
27. Welsh, W. J.; Cody, V.; Suwinska, K.; Berlin, K. D.; Rajadhyaksha, S. N.; Subramanian, S.; Verma, A. K. Heteroarotinoids: crystal and molecular structure analysis of the methyl (Z)- and methyl (E)-4-[2-(4,4-dimethylchroman-6-yl)-1-propenyl]benzoate. Struct. Chem. 1991, 2, 515-522.
28. Berger, T. S.; Parandoosh, Z.; Perry, B. W.; Stein, R. B. Interaction of glucocorticoid analogues with the human glucocorticoid receptor. J. Steroid Biochem. 1992, 41, 733-738.