Receptor-mediated targeting of a photosensitizer by its conjugation to gonadotropin-releasing hormone analogues

Journal of Medicinal Chemistry

Volumn 46, Issue 19, 2003, Pages 3965-3974

  Rahimipour, Shai ^a   Ben Aroya, Nurit ^a   Ziv, Keren ^a   Chen, Alon ^a   Fridkin, Mati ^a   Koch, Yitzhak ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTRIAZOL 1 YLOXYTRIS(PYRROLIDINOPHOSPHONIUM) HEXAFLUOROPHOSPHATE; GONADORELIN ANTAGONIST; GONADORELIN DERIVATIVE; GONADORELIN PROTOPORPHYRIN CONJUGATE; GONADORELIN[1 DEXTRO PYROGLUTAMIC ACID 2 DEXTRO PHENYLALANINE 3 DEXTRO TRYPTOPHAN 6 DEXTRO LYSINE]; GONADORELIN[6 DEXTRO LYSINE]; LUTEINIZING HORMONE; PHOTOSENSITIZING AGENT; REAGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BREAST CANCER; CANCER THERAPY; CELL DAMAGE; CELL STRAIN MCF 7; CONJUGATION; CONTROLLED STUDY; DRUG POTENCY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYPOPHYSIS CELL; IN VITRO STUDY; IN VIVO STUDY; LUTEINIZING HORMONE RELEASE; MOUSE; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; PHOTOTOXICITY; RADIOIMMUNOASSAY; RAT;

AMINO ACID SEQUENCE; ANIMALS; BINDING, COMPETITIVE; BREAST NEOPLASMS; CELL LINE; CELL SURVIVAL; ESTRUS; GONADOTROPIN-RELEASING HORMONE; GROWTH HORMONE; HUMANS; LUTEINIZING HORMONE; PHOTOSENSITIZING AGENTS; PITUITARY GLAND; PROTOPORPHYRINS; RADIOLIGAND ASSAY; RATS; RECEPTORS, LHRH; SPECTROPHOTOMETRY, ULTRAVIOLET; TUMOR CELLS, CULTURED;

EID: 0141455888     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020535y     Document Type: Article

References (48)

1. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. Photodynamic therapy. J. Natl. Cancer Inst. 1998, 90, 889-905.
2. Pass, H. Photodynamic therapy in oncology: mechanisms and clinical use. J. Natl. Cancer Inst. 1993, 85, 443-456.
3. FitzGerald, D.; Pastan, I. Targeted toxin therapy for the treatment of cancer. J. Natl. Cancer Inst. 1989, 81, 1455-1463.
4. Vrouenraets, M. B.; Visser, G. W.; Stigter, M.; Oppelaar, H.; Snow, G. B.; van Dongen, G. A. Targeting of aluminum(III) phthalocyanine tetrasulfonate by use of internalizing monoclonal antibodies: improved efficacy in photodynamic therapy. Cancer Res. 2001, 61, 1970-1975.
5. Allen, C. M.; Sharman, W. M.; La Madeleine, C.; Weber, J. M.; Langlois, R.; Ouellet, R.; van Lier, J. E. Photodynamic therapy: tumor targeting with adenoviral proteins. Photochem. Photobiol. 1999, 70, 512-523.
6. Brokx, R. D.; Bisland, S. K.; Gariepy, J. Designing peptide-based scaffolds as drug delivery vehicles. J. Controlled Release 2002, 78, 115-123.
7. Weiner, L. M. Oxygen radicals generation and DNA scission by anticancer and synthetic quinones. Methods Enzymol. 1994, 233, 92-105.
8. Akhlynina, T. V.; Rosenkranz, A. A.; Jans, D. A.; Sobolev, A. S. Insulin-mediated intracellular targeting enhances the photodynamic activity of chlorin e6. Cancer Res. 1995, 55, 1014-1019.
9. Gijsens, A.; Missiaen, L.; Merlevede, W.; de Witte, P. Epidermal growth factor-mediated targeting of chlorin e6 selectively potentiates its photodynamic activity. Cancer Res. 2000, 60, 2197-2202.
10. Bajusz, S.; Janaky, T.; Csernus, V. J.; Bokser, L.; Fekete, M.; Srkalovic, G.; Redding, T. W.; Schally, A. V. Highly potent analogues of luteinizing hormone-releasing hormone containing D-phenylalanine nitrogen mustard in position 6. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 6318-6322.
11. Janaky, T.; Juhasz, A.; Bajusz, S.; Csernus, V.; Srkalovic, G.; Bokser, L.; Milovanovic, S.; Redding, T. W.; Rekasi, Z.; Nagy, A.; Schally, A. V. Analogues of luteinizing hormone-releasing hormone containing cytotoxic groups. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 972-976.
12. Nagy, A.; Schally, A. V.; Armatis, P.; Szepeshazi, K.; Halmos, G.; Kovacs, M.; Zarandi, M.; Groot, K.; Miyazaki, M.; Jungwirth, A.; Horvath, J. Cytotoxic analogs of luteinizing hormone-releasing hormone containing doxorubicin or 2-pyrrolinodoxorubicin, a derivative 500-1000 times more potent. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 7269-7273.
13. Schally, A. V.; Arimura, A.; Kastin, A. J.; Matsuo, H.; Baba, Y.; Redding, T. W.; Nair, R. M. G.; Debeljuk, L.; White, W. F. Gonadotropin-releasing hormone: one polypeptide regulates secretion of luteinizing hormone and follicle-stimulating hormones. Science 1971, 173, 1036-1038.
14. Burgus, R.; Butcher, M.; Amoss, M.; Ling, N.; Monahan, M.; Rivier, J.; Fellows, R.; Blackwell, R.; Vale, W.; Guillemin, R. Primary structure of the ovine hypothalamic luteinizing hormone-releasing factor (LRF) (LH-hypothalamus-LRF-gas chromatography - mass spectrometry-decapeptide-Edman degradation). Proc. Natl. Acad. Sci. U.S.A. 1972, 69, 278-282.
15. Emons, G.; Schally, A. V. The use of luteinizing hormone releasing hormone agonists and antagonists in gynaecological cancers. Hum. Reprod. 1994, 9, 1364-1379.
16. Foekens, J. A.; Klijn, J. G. Direct antitumor effects of LH-RH analogs. Recent Results Cancer Res. 1992, 124, 7-17.
17. Schally, A. V. Luteinizing hormone-releasing hormone analogs: their impact on the control of tumorigenesis. Peptides 1999, 20, 1247-1262.
18. Eidne, K. A.; Flanagan, C. A.; Millar, R. P. Gonadotropin-releasing hormone binding sites in human breast carcinoma. Science 1985, 229, 989-991.
19. Halmos, G.; Arencibia, J. M.; Schally, A. V.; Davis, R.; Bostwick, D. G. High incidence of receptors for luteinizing hormone-releasing hormone (LHRH) and LHRH receptor gene expression in human prostate cancers. J. Urol. 2000, 163, 623-629.
20. Limonta, P.; Dondi, D.; Moretti, R. M.; Maggi, R.; Motta, M. Antiproliferative effects of luteinizing hormone-releasing hormone agonists on the human prostatic cancer cell line LNCaP. J. Clin. Endocrinol. Metab. 1992, 75, 207-212.
21. Eidne, K. A.; Flanagan, C. A.; Harris, N. S.; Millar, R. P. Gonadotropin-releasing hormone (GnRH)-binding sites in human breast cancer cell lines and inhibitory effects of GnRH antagonists. J. Clin. Endocrinol. Metab. 1987, 64, 425-432.
22. Yano, T.; Pinski, J.; Radulovic, S.; Schally, A. V. Inhibition of human epithelial ovarian cancer cell growth in vitro by agonistic and antagonistic analogues of luteinizing hormone-releasing hormone. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 1701-1705.
23. Hazum, E.; Meidan, R.; Liscovitch, M.; Keinan, D.; Lindner, H. R.; Koch, Y. Receptor-mediated internalization of LHRH antagonists by pituitary cells. Mol. Cell. Endocrinol. 1983, 30, 291-301.
24. Kovacs, M.; Schally, A. V.; Nagy, A.; Koppan, M.; Groot, K. Recovery of pituitary function after treatment with a targeted cytotoxic analog of luteinizing hormone-releasing hormone. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1420-1425.
25. Meidan, R.; Koch, Y. Binding of luteinizing hormone-releasing hormone analogues to dispersed rat pituitary cells. Life Sci. 1981, 28, 1961-1967.
26. Wynn, P. C.; Suarez-Quian, C. A.; Childs, G. V.; Catt, K. J. Pituitary binding and internalization of radioiodinated gonadotropin-releasing hormone agonist and antagonist ligands in vitro and in vivo. Endocrinology 1986, 119, 1852-1863.
27. Loumaye, E.; Wynn, P. C.; Coy, D.; Catt, K. J. Receptor-binding properties of gonadotropin-releasing hormone derivatives. Prolonged receptor occupancy and cell-surface localization of a potent antagonist analog. J. Biol. Chem. 1984, 259, 12663-12671.
28. Horn, F.; Bilezikjian, L. M.; Perrin, M. H.; Bosma, M. M.; Windle, J. J. ; Huber, K. S.; Blount, A. L.; Hille, B.; Vale, W.; Mellon, P. L. Intracellular responses to gonadotropin-releasing hormone in a clonal cell line of the gonadotrope lineage. Mol. Endocrinol. 1991, 5, 347-355.
29. Rahimipour, S.; Ben-Aroya, N.; Fridkin, M.; Koch, Y. Design, synthesis and evaluation of long-acting, potent analog of gonadotropin-releasing hormone. J. Med. Chem. 2001, 44, 3645-3652.
30. Aveline, B. M.; Hasan, T.; Redmond, R. W. The effects of aggregation, protein binding and cellular incorporation on the photophysical properties of benzoporphyrin derivative monoacid ring A (BPDMA). J. Photochem. Photobiol. B 1995, 30, 161-169.
31. Anderson, L.; Milligan, G.; Eidne, K. A. Characterization of the gonadotrophin-releasing hormone receptor in alpha T 3-1 pituitary gonadotroph cells. J. Endocrinol. 1993, 136, 51-58.
32. Belchetz, P. E.; Plant, T. M.; Nakai, Y.; Keogh, E. J.; Knobil, E. Hypophysial responses to continuous and intermittent delivery of hypothalamic gonadotropin-releasing hormone. Science 1978, 202, 631-632.
33. Szoke, B.; Horvath, J.; Halmos, G.; Rekasi, Z.; Groot, K.; Nagy, A.; Schally, A. V. LH-RH analogue carrying a cytotoxic radical is internalized by rat pituitary cells in vitro. Peptides 1994, 15, 359-366.
34. Naor, Z.; Clayton, R. N.; Catt, K. J. Characterization of gonadotropin-releasing hormone receptors in cultured rat pituitary cells. Endocrinology 1980, 107, 1144-1152.
35. Catt, K. J.; Dufau, M. L. Spare gonadotrophin receptors in rat testis. Nat. New Biol. 1973, 244, 219-221.
36. Carter, D. C.; Ho, J. X. Structure of serum albumin. Adv. Protein Chem. 1994, 45, 153-203.
37. Liang, J. W.; Hsiu, S. L.; Wu, P. P.; Chao, P. D. Emodin pharmacokinetics in rabbits. Planta Med. 1995, 61, 406-408.
38. Hasan, T.; Parrish, J. A. Cancer Medicine; Williams and Wilkins: Baltimore, MD, 1996; pp 739-751.
39. Kakar, S. S.; Grizzle, W. E.; Neill, J. D. The nucleotide sequences of human GnRH receptors in breast and ovarian tumors are identical with that found in pituitary. Mol. Cell. Endocrinol. 1994, 106, 145-149.
40. Mullen, P.; Bramley, T.; Menzies, G.; Miller, B. Failure to detect gonadotrophin-releasing hormone receptors in human benign and malignant breast tissue and in MCF-7 and MDA-MB-231 cancer cells. Eur. J. Cancer 1993, 29A, 248-252.
41. Rahimipour, S.; Weiner, L.; Shrestha-Dawadi, P. B.; Bittner, S.; Koch, Y.; Fridkin, M. Cytotoxic peptides: Naphthoquinonyl derivatives of luteinizing hormone-releasing hormone. Lett. Pept. Sci. 1998, 5, 421-427.
42. Windle, J. J.; Weiner, R. I.; Mellon, P. L. Cell lines of the pituitary gonadotrope lineage derived by targeted oncogenesis in transgenic mice. Mol. Endocrinol. 1990, 4, 597-603.
43. Liscovitch, M.; Ben-Aroya, N.; Meidan, R.; Koch, Y. A differential effect of trypsin on pituitary gonadotropin-releasing hormone receptors from intact and ovariectomized rats. Evidence for the existence of two distinct receptor populations. Eur. J. Biochem. 1984, 140, 191-197.
44. Sambrook, J.; Fritsch, E. F.; Maniatis, T. Molecular Cloning: A Laboratory Manual, 2nd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1989.
45. Yahalom, D.; Koch, Y.; Ben-Aroya, N.; Fridkin, M. Synthesis and bioactivity of fatty acid-conjugated GnRH derivatives. Life Sci. 1999, 64, 1543-1552.
46. Yahalom, D.; Rahimipour, S.; Koch, Y.,; Ben-Aroya, N.; Fridkin, M. Structure - activity studies of reduced-size gonadotropin-releasing hormone agonists derived from the sequence of an endothelin antagonist. J. Med. Chem. 2000, 43, 2824-2830.
47. Daane, T. A.; Parlow, A. F. Periovulatory patterns of rat serum follicle stimulating hormone and luteinizing hormone during the normal estrous cycle: effects of pentobarbital. Endocrinology 1971, 88, 653-667.
48. Desbuquois, B.; Aurbach, G. D. Use of polyethylene glycol to separate free and antibody-bound peptide hormones in radioimmunoassays. J. Clin. Endocrinol. Metab. 1971, 33, 732-738.