Synthesis of gonadotropin-releasing hormone III analogs. Structure- antitumor activity relationships

Journal of Medicinal Chemistry

Volumn 40, Issue 21, 1997, Pages 3353-3358

  Mezo, Imre ^a  

^a SEMMELWEIS UNIVERSITY OF MEDICINE   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

GONADORELIN DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION; CELL STRAIN MCF 7; DRUG SYNTHESIS; ENDOMETRIUM CANCER; HUMAN; HUMAN CELL; PROSTATE CANCER; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL DIVISION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; GONADOTROPIN-RELEASING HORMONE; HUMANS; OLIGOPEPTIDES; PROTEIN CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 9844252335     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9700981     Document Type: Article

References (28)

1. Vickery, B. H. Comparison of the potential for therapeutic utilities with gonadotropin-releasing hormone agonists and antagonists. Endocr. Rev. 1986, 7, 115-124.
2. Höffken, K. LH-RH agonists in the treatment of premenopausal patients with advanced breast cancer. Peptides in oncology. I. LH-RH agonists and antagonists. Recent Results Cancer Res. 1992,124, 91-104.
3. Santen, R. J.; Manni, A.; Harvey, H. Gonadotropin releasing hormone (GnRH) analogs for the treatment of breast and prostatic carcinoma. Breast Cancer Res. Treat. 1986, 7, 129-145.
4. Miller, W. R. Endocrine treatment for breast cancers: Biological rationale and current progress J. Steroid Biochem. Mol. Biol. 1990, 37, 467-480.
5. Auclair, C.; Kelly, P. A.; Labrie, F.; Coy, D. H.; Schally, A. V. Inhibition of testicular luteinizing hormone receptor level by treatment with a potent luteinizing hormone-releasing hormone agonist or human chorionic gonadotropin. Biochem. Biophys. Res. Commun. 1977, 76, 855-861.
6. Conn, P. M.; Huckle, W. R.; Andrews, W. V.; McArdle, C. A., The molecular mechanism of action of gonadotropin releasing hormone (GnRH) in the pituitary. Recent Prog. Harm. Res. 1987, 43, 29-68.
7. Belchetz, P. E.; Plant, T. M.; Nakai, Y.; Keogh, E. J.; Knobil, E. Hypophysial responses to continous and intermittent delivery of hypothalamic gonadotropin-releasing hormone. Science 1978, 202, 631-632.
8. Hazun, E.; Conn, P. M. Molecular mechanism of Gonadotropin Releasing Hormone (GnRH) action. I. The GnRH receptor. Endocr. Rev. 1988, 9, 379-386.
9. Eidene, K. A.; Flanagan, C. A.; Harris, N. S.; Millar, R. P. Gonadotropin-releasing hormone (GnRH)-binding sites in human breast cancer lines and inhibitory effects of GnRH antagonists. J. Clin. Endocrinol. Metab. 1987, 64, 425-432.
10. Baumann, K. H.; Kiesel, L.; Kaufmann, M.; Basiert, G.; Runnebaum, B. Characterization of binding sites for a GnRH-agonist (Buserelin) in human breast cancer biopsies and their distribution in relation to tumor parameters. Breast Cancer Res. Treat. 1993, 25, 37-56.
11. Kleinman, D.; Roberts, C. T., Jr.; LeRoith, D.; Schally, A. V.; Levy, J.; Sharoni, Y. Regulation of endometrial cancer cell growth by insulin-like growth factors and the luteinizing hormonereleasing hormone antagonist SB-75. Regul. Pept. 1993,48,9198.
12. Limonta, P.; Dondi, D.; Roberta, M.; Moretti, R. M.; Fermo, D.; Garattini, E.; Motta, M. Expression of luteinizing hormonerelelasing hormone mRNA in the human prostatic cancer cell line LNCaP. J. Clin. Endocrinol. Metab. 1993, 76, 797-800.
13. Hierowski, M. T.; Altamirano, P.; Redding, T. W.; Schally, A. V. The presence of LHRH- like receptors in dunning R3327H prostate tumors. FEES Lett. 1983, 154, 92-96.
14. Sower, S. A.; Chiang, Y-C.; Lovas, S.; Conlon, J. M. Primary srtucture and biological activity of a third gonadotropin-releasing hormone from lamprey brain. Endocrinology 1993, 732, 11251131.
15. Mezö, L; Seprödi, J.; Vadâsz, Zs.; Teplân, I.; Vincze, B.; Pâlyi, I.; Kâlnay, A.; Turi, G.; M6ra, M.; Patô, J.; Tôth, G.; Lovas, S.; Murphy, R. F. Antitumor activity of GnRH analogs and their conjugates with poly-(N-vinylpyrrolidone-co-maleic acid). In Peptides Chemistry, Structure and Biology; Kaumaya, P. T. P.; Hodges, R. S. Eds.; Mayflower Scientific Ltd.: Kingswinford, England, 1996; pp 239-240.
16. Sharoni, Y.; Bosin, E.; Münster, A.; Levy, J.; Schally, A. V. Inhibition of growth of human mammary tumor cells by potent antagonists of luteinizing hormone-releasing hormone. Proc. Nat. Acad. Sei. U.SA. 1989, 86, 1648-1651.
17. Koväcs, M.; Mezö, I.; Seprödi, J.; Csernus, V.; Teplân, L; Flerkö, B. Effects of long-term administration of a superactive agonistic and an antagonistic GnRH analog on the pituitary-gonad system. Peptides 1989, 10, 925-931.
18. Mezö, L; Seprödi, J.; Vadâsz, Zs. Teplan; I. Vincze, B.; Palyi, L; Gaäl, D.; Kälnay, A.; Patö, J.; Mora, M. GnRH analogs and their conjugates with enhanced antitumor activity. In Peptides 1994; Maia, H. L. S., Ed.; Escom: Leiden, 1995; pp 763-764.
19. Lovas, S.; Pâlyi, I.; Vincze, B.; Mezö, L; Teplân, L; Töth, G.; Koväcs, AI.; Murphy, R. F. Antitumor activity of lamprey-GnRH-III. (in preparation).
20. Redding, T. W.; Kastin, A. J.; Gonzalez-Barcena, P.; Coy, D. H.; Coy, E. J.; Schalen, D. S.; Schally, A. V. The half-life, metabolism and excretion of tritiated LH-RH in man. J. Clin. Endocrinol. Metab. 1973, 37, 626-631.
21. 2. Neurosci. Lett. 1979, 14, 275-279.
22. Bauer, K.; Horsthemke, B.; Knisatschek, H.; Nowak, P.; Kleinkauf, H. Degradation of luliberin by brain and pituitary tissue enzymes. Z. Physiol. Chem. 1979, 360, 229.
23. Mezö, L; Seprödi, J.; Vincze, B.; Pâlyi I.; Kéri, Gy.; Vadâsz, Zs.; Töth, G.; Koväcs, M.; Koppân, AI.; Horvâth, E. J.; Kälnay, A.; Teplân, I. Synthesis of GnRH analogs having direct antitumor and low LH-releasing activity. Biomed. Pept. Proteins Nucleic Acids 1996, 2, 33-40.
24. Palyi, I.; Vincze, B.; Kälnay, A.; Turi, G.; Alezö, I.; Teplân, I.; Seprödi, J.; Patö, J.; Alöra, AI. Effect of GnRH analogs and their ._ conjugates on GnRH receptor-positive human cancer cell lines. Cancer Detect. Preu. 1996, 20, 145-152.
25. 6-Angiotensin II via halogen-derivatives of Angiotensin II J. Label. Compound Radiopharm. 1978, 14, 557-567.
26. Wang, S. S.; Gisin, B. F.; Winter, D. P.; Makafske, T.; Kulesha, J. D.; Tzougraki, C.; Meienhofer, J. Facile synthesis of amino acid and peptide esters under mild conditions via cesium salts. J. Org. Chetn. 1977, 42, 1286-1290.
27. Vadasz, Zs.; Seprödi, J.; Teplân, I. Studies on epimerizationfree methods for the preparation of aminosuccinyl peptides. Lett. Pept. Sei. 1995, 2, 339-344.
28. Abbreviations: These are in accordance with the recommendations of the IUPAC-IUB Commission of Biochemical Nomenclature (Eur. J. Biochem. 1984, 138, 9-37 and J. Biol. Chem. 1989,264, 633-673. Other abbreviations: Asu, aminosuccinyl; DCM, dichloromethane; DMF, AW-dimethylformamide; TEA, triethylamine; DIEA, N-ethyldiisopropylamine; EA, ethylamine; TFA, trifluoroacetic acid; DIG, diisopropylcarbodiimide; HOBt, 1-hydroxybenzotriazole; BOP, benzotriazol-l-yloxy trisfdimethylaminojphosphonium hexafluorophosphate; HF, hydrogen fluoride; TBTU reagent, 2-(lH-benzotriazol-l-yl)-l,l,3,3-tetramethyluronium tetrafluoroborate; EtOAc, ethyl acetate; DMSO, methyl sulfoxide.