Retinoid related molecules an emerging class of apoptotic agents with promising therapeutic potential in oncology: Pharmacological activity and mechanisms of action

Current Pharmaceutical Design

Volumn 10, Issue 4, 2004, Pages 433-448

  Garattini, Enrico ^a   Gianni', Maurizio ^a   Terao, Mineko ^a  

^a Laboratory of Molecular Biology   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 [3' (1 ADAMANTYL) 4' HYDROXYBIPHENYL 4 YL]ACRYLIC ACID; 4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; 4 (4 FLUOROPHENYL) 2 (4 NITROPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; 4 [2 [5,6 DIHYDRO 5,5 DIMETHYL 8 (4 METHYLPHENYL) 2 NAPHTHYL]ETHYNYL]BENZOIC ACID; 6 [3 (1 ADAMANTYL) 4 HYDROXYPHENYL] 2 NAPHTHOIC ACID; ANTHRA[1,9 CD]PYRAZOL 6(2H) ONE; ANTINEOPLASTIC AGENT; APOPTOSIS INDUCING FACTOR; CARBOPLATIN; CD 2325; CISPLATIN; CYTARABINE; CYTOTOXIC AGENT; DOXORUBICIN; FENRETINIDE; MM 002; MM 11253; MM 11453; MX 2870 1; MX 3350 1; MX 84; MX 90 1; OLOMOUCINE; PACLITAXEL; RETINOIC ACID; RETINOIC ACID RECEPTOR GAMMA; RETINOID DERIVATIVE; ROSCOVITINE; ST 2065; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; CANCER CELL; CANCER GROWTH; CELL DIFFERENTIATION; CROSS RESISTANCE; CYTOTOXICITY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENTIATION; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ACTIVATION; GROWTH INHIBITION; HUMAN; LEUKEMIA; MEDICAL LITERATURE; MITOCHONDRION; MULTIDRUG RESISTANCE; NONHUMAN; ONCOLOGY; PRIORITY JOURNAL; REVIEW; SOLID TUMOR; TUMOR CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; MOLECULAR STRUCTURE; NEOPLASMS; RETINOIDS;

EID: 0742271644     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/1381612043453351     Document Type: Review

References (143)

1. Tallman MS, Andersen JW, Schiffer CA, Appelbaum FR, Feusner JH, Woods WG, et al. All-trans retinoic acid in acute promyelocytic leukemia: long-term outcome and prognostic factor analysis from the North American Intergroup protocol. Blood 2002; 100: 4298-302.
2. Avvisati G, Petti MC, Lo-Coco F, Vegna ML, Amadori S, Baccarani M, et al. GIMEMA (Gruppo Italiano Malattie Ematologische dell'Adulto) Italian Cooperative Group. Induction therapy with idarubicin alone significantly influences event-free survival duration in patients with newly diagnosed hypergranular acute promyelocytic leukemia: final results of the GIMEMA randomized study LAP 0389 with 7 years of minimal follow-up. Blood 2002; 100: 3141-6,
3. Villablanca JG, Khan AA, Avramis VI, Seeger RC, Matthay KK, Ramsay NK, et al. Phase I trial of 13-cis-retinoic acid in children with neuroblastoma following bone marrow transplantation. J Clin Oncol 1995; 13: 894-901.
4. Sun SY, Lotan R. Retinoids and their receptors in cancer development and chemoprevention. Crit Rev Oncol Hematol 2002, 41: 41-55. Review.
5. Garattini E, Terao M. Cytodifferentiation: a novel approach to cancer treatment and prevention. Curr Opin Pharmacol 2001; 1: 358-63. Review.
6. Warrell RP Jr. Pathogenesis and management of acute promyelocytic leukemia. Annu Rev Med 1996; 47: 555-65. Review.
7. Warrel RP Jr, de The H, Wang ZY, Degos L. Acute promyelocytic leukemia. N Engl J Med 1993; 329: 177-89. Review.
8. Chambon P, A decade of molecular biology of retinoic acid receptors. FASEB J 1996; 10: 940-54. Review.
9. Mangelsdorf DJ, Thummel C, Beato M, Herrlich P, Schutz G, Umesono K, et al. The nuclear receptor superfamily: the second decade. Cell 1995; 83: 835-9. Review.
10. Xu XC, Wong WY, Goldberg L, Baer SC, Wolf JE, Ramsdell WM, et al. Progressive decreases in nuclear retinoid receptors during skin squamous carcinogenesis. Cancer Res 2001; 61: 4306-10.
11. Klaassen I, Brakenhoff RH, Smeets SJ, Snow GB, Braakhuis BJ. Expression of retinoic acid receptor gamma correlates with retinoic acid sensitivity and metabolism in head and neck squamous cell carcinoma cell lines. Int J Cancer 2001; 92: 661-5.
12. Xu XC, Sneige N, Liu X, Nandagiri R, Lee JJ, Lukmanji F, et al. Progressive decrease in nuclear retinoic acid receptor beta messenger RNA level during breast carcinogenesis. Cancer Res 1997; 57: 4992-6.
13. Sun SY, Wan H, Yoe P, Hong WK, Lotan R. Evidence that retinoic acid receptor beta induction by retinoids is important for tumor cell growth inhibition. J Biol Chem 2000; 275: 17149-53.
14. Gianni M, Ponzanelli I, Mologni L, Reichert U, Rambaldi A, Terao M, et al. Retinoid-dependent growth inhibition, differentiation and apoptosis in acute promyelocytic leukemia cells. Expression and activation of caspases. Cell Death Differ 2000; 7: 447-60.
15. Bissonnette RP, Brunner T, Lazarchik SB, Yoo NJ, Boehm MF, Green DR, et al. 9-cis retinoic acid inhibition of activation-induced apoptosis is mediated via regulation of fas ligand and requires retinoic acid receptor and retinoid X receptor activation. Mol Cell Biol 1995; 15: 5576-85.
16. Mistry AR, Pedersen EW, Solomon E, Grimwade D. The molecular pathogenesis of acute promyelocytic leukaemia: implications for the clinical management of the disease. Blood Rev 2003; 17: 71-97
17. Bernard BA, Bernardon JM, Delescluse C, Martin B, Lenoir MC, Maignan J, et al. Identification of synthetic retinoids with selectivity for human nuclear retinoic acid receptor gamma. Biochem Biophys Res Commun 1992; 186: 977-83.
18. Charpentier B, Bernardon JM, Eustache J, Millois C, Martin B, Michel S, et al. Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes. J Med Chem 1995; 38: 4993-5006.
19. Delescluse C, Cavey MT, Martin B, Bernard BA, Reichert U, Maignan J, et al. Selective high affinity retinoic acid receptor alpha or beta-gamma ligands. Mol Pharmacol 1991; 40: 556-62.
20. Gianni M, Zanotta S, Terao M, Garattini S, Garattini E. Effects of synthetic retinoids and retinoic acid isomers on the expression of alkaline phosphatase in F9 teratocarcinoma cells. Biochem Biophys Res Commun 1993; 196: 252-9.
21. Costa SL, Paillaud E, Fages C, Rochette-Egly C, Plassat JL, Jouault H, et al. Effects of a novel synthetic retinoid on malignant glioma in vitro: inhibition of cell proliferation, induction of apoptosis and differentiation. Eur J Cancer 2001; 37: 520-30.
22. Arafa HM, Elmazar MM, Hamada FM, Reichert U, Shroot B, Nau H. Selective agonists of retinoic acid receptors: comparative toxicokinetics and embryonic exposure. Arch Toxicol 2000; 73: 547-56.
23. Shao ZM, Dawson MI, Li XS, Rishi AK, Sheikh MS, Han QX, et al. p53 independent G0/G1 arrest and apoptosis induced by a novel retinoid in human breast cancer cells. Oncogene 1995; 11: 493-504.
24. Hsu CK, Rishi AK, Li XS, Dawson MI, Reichert U, Shroot B, et al. Bcl-X(L) expression and its downregulation by a novel retinoid in breast carcinoma cells. Exp Cell Res 1997; 232: 17-24.
25. Oridate N, Higuchi M, Suzuki S, Shroot B, Hong WK, Lotan R. Rapid induction of apoptosis in human C33A cervical carcinoma cells by the synthetic retinoid 6-[3-(1 adamantyl)liydroxyphenyl]-2-naphtalene carboxylic acid (CD437). Int J Cancer 1997: 70: 484-7.
26. Jiang SY, Lin DY, Shyu RY, Reichert U, Yeh MY. The RARgamma selective agonist CD437 inhibits gastric cell growth through the mechanism of apoptosis, Cancer Lett 1999; 137: 217-25.
27. Gianni M, de The H. In acute promyelocytic leukemia NB4 cells, the synthetic retinoid CD437 induces contemporaneously apoptosis, a caspase-3-mediated degradation of PML/RARalpha protein and the PML retargeting on PML-nuclear bodies. Leukemia 1999; 13: 739-49.
28. Sun SY, Yue P, Lotan R. Implication of multiple mechanisms in apoptosis induced by the synthetic retinoid CD437 in human prostate carcinoma cells. Oncogene 2000; 19: 4513-22.
29. Schadendorf D, Kern MA, Artuc M, Pahl HL, Rosenbach T, Fichtner I, et al. Treatment of melanoma cells with the synthetic retinoid CD437 induces apoptosis via activation of AP-1 in vitro, and causes growth inhibition in xenografts in vivo. J Cell Biol 1996; 135: 1889-98.
30. Sun SY, Yue P, Shroot B, Hong WK, Lotan R. Induction of apoptosis in human non-small cell lung carcinoma cells by the novel synthetic retinoid CD437. J Cell Physiol 1997; 173: 279-84.
31. Mologni L, Ponzanelli I, Bresciani F, Sardiello G, Bergamaschi D, Gianni M, et al. The novel synthetic retinoid 6-[3-adamantyl-4-hydroxyphenyl]-2-naphtalene carboxylic acid (CD437) causes apoptosis in acute promyelocytic leukemia cells through rapid activation of caspases. Blood 1999; 93: 1045-61.
32. Garattini E, Parrella E, Diomede L, Gianni M, Kalac Y, Merlini L, et al. ST1926 a novel and orally active retinoid related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis. Blood 2003; Sep 4 [Epub ahead of print]
33. Cincinelli R, Dallavalle S, Merlini L, Penco S, Pisano C, Carminati P, et al. A novel atypical retinoid endowed with proapoptotic and antitumor activity. J Med Chem 2003; 46: 909-12.
34. Zuco V, Zanchi C, Cassinelli G, Lanzi C, Supino R, Pisano C, et al. Induction of apoptosis and stress response in ovarian carcinoma cell lines treated with ST1926, an atypical retinoid Cell Death Diff, in press.
35. Dawson MI, Hobbs PD, Peterson VJ, Leid M, Lange CW, Feng KC, et al. Apoptosis induction in cancer cells by a novel analogue of 6-[3-(1 -adamantyl)-4-hydroxyplienyl]-2-naphthalenecarboxylic acid lacking retinoid receptor transcriptional activation activity. Cancer Res 2001; 61: 4723-30.
36. Bayon Y, Ortiz MA, Lopez-Hernandez FJ, Gao F, Karin M, Pfahl M, et al. Inhibition of IkappaB kinase by a new class of retinoid-related anticancer agents that induce apoptosis. Mol Cell Biol 2003; 23: 1061-74.
37. Ortiz MA, Lopez-Hernandez FJ, Bayon Y, Pfahl M, Piedrafita FJ. Retinoid-related molecules induce cytochrome c release and apoptosis through activation of c-Jun NH(2)-terminal kinase/p38 mitogen-activated protein kinases. Cancer Res 2001; 61: 8504-12.
38. Zhang Y, Dawson MI, Mohammad R, Rishi AK, Farhana L, Feng KC, et al. Induction of apoptosis of human B-CLL and ALL cells by a novel retinoid and its nonretinoidal analog. Blood 2002; 100: 2917-25.
39. Lu XP, Fanjul A, Picard N, Pfahl M, Rungta D, Nared-Hood K, et al. Novel retinoid-related molecules as apoptosis inducers and effective inhibitors of human lung cancer cells in vivo. Nat Med 1997; 3: 686-90.
40. Yarovoi SV, Lu XP, Picard N, Rungta D, Rideout D, Pfahl M. Selective activation of an apoptotic retinoid precursor in macrophage cell lines. J Biol Chem 1998; 273: 20852-9.
41. Hsu CA, Rishi AK, Su-Li X, Gerald TM, Dawson MI, Schiffer C, et al. Retinoid induced apoptosis in leukemia cells through a retinoic acid nuclear receptor-independent pathway. Blood 1997; 89: 4470-9.
42. Zang Y, Beard RL, Chandraratna RA, Kang JX. Evidence of a lysosomal pathway for apoptosis induced by the synthetic retinoid CD437 in human leukemia HL-60 cells. Cell Death Differ 2001, 8: 477-85.
43. Schadendorf D, Worm M, Jurgovsky K, Dippel E, Reichert U, Czarnetzki BM. Effects of various synthetic retinoids on proliferation and immunophenotype of human melanoma cells in vitro. Recent Results Cancer Res 1995; 139: 183-93.
44. Joseph B, Marchetti P, Lefebvre O, Schraen-Maschke S, Mereau-Richard C, Formstecher P. The novel retinoid AHPN/CD437 induces a rapid but incomplete apoptotic response in human myeloma cells. Biochim Biophys Acta 2003; 1593: 277-82.
45. Holmes WF, Soprano DR, Soprano KJ. Elucidation of molecular events mediating induction of apoptosis by synthetic retinoids using a CD437-resistant ovarian carcinoma cell line. J Biol Chem 2002; 277: 45408-19.
46. Sun SY, Yue P, Chen X, Hong WK, Lotan R. The synthetic retinoid CD437 selectively induces apoptosis in human lung cancer cells while sparing normal human lung epithelial cells. Cancer Res 2002; 62: 2430-6.
47. Schneider SM, Offterdinger M, Huber H, Grunt TW. Activation of retinoic acid receptor alpha is sufficient for full induction of retinoid responses in SK-BR-3 and T47D human breast cancer cells. Cancer Res 2000; 60: 5479-87.
48. Wan X, Duncan MD, Nass P, Harmon JW. Synthetic retinoid CD437 induces apoptosis of esophageal squamous HET-1A cells through the caspase-3-dependent pathway. Anticancer Res. 2001; 21: 2657-63.
49. Hail N Jr, Lotan R. Synthetic retinoid CD437 promotes rapid apoptosis in malignant human epidermal keratinocytes and G1 arrest in their normal counterparts. J Cell Physiol 2001; 186: 24-34.
50. Sun SY, Yue P, Chandraratna RA, Tesfaigzi Y, Hong WK, Lotan R. Dual mechanisms of action of the retinoid CD437: nuclear retinoic acid receptor-mediated suppression of squamous differentiation and receptor-independent induction of apoptosis in UMSCC22B human head and neck squamous cell carcinoma cells. Mol Pharmacol 2000; 58: 508-14.
51. Liang JY, Fontana JA, Rao JN, Ordonez JV, Dawson MI, Shroot B, et al. Synthetic retinoid CD437 induces S-phase arrest and apoptosis in human prostate cancer cells LNCaP and PC-3. Prostate 1999; 38: 228-36.
52. Zhang XK. Vitamin A and apoptosis in prostate cancer. Endocr Relat Cancer 2002; 9:87-102. Review.
53. Lovat PE, Ranalli M, Bernassola F, Tilby M, Malcolm AJ, Pearson AD, et al. Synergistic induction of apoptosis of neuroblastoma by fenretinide or CD437 in combination with chemotherapeutic drugs. Int J Cancer 2000; 88: 977-85.
54. Meister B, Fink FM, Hittmair A, Marth C, Widschwendter M. Antiproliferative activity and apoptosis induced by retinoic acid receptor-gamma selectively binding retinoids in neuroblastoma. Anticancer Res 1998; 18: 1777-86.
55. Zhao X, Demary K, Wong L, Vaziri C, McKenzie AB, Eberlein TJ, et al. Retinoic acid receptor-independent mechanism of apoptosis of melanoma cells by the retinoid CD437 (AHPN). Cell Death Differ 2001; 8: 878-86.
56. Culig Z, Klocker H, Bartsch G, Steiner H, Hobisch A. Androgen receptors in prostate cancer. J Urol 2003; 170: 1363-9.
57. Cooper LS, Gillett CE, Patel NK, Barnes DM, Fentiman IS. Survival of premenopausal breast carcinoma patients in relation to menstrual cycle timing of surgery and estrogen receptor/ progesterone receptor status of the primary tumor. Cancer 1999: 86: 2053-8.
58. Mauri FA, Caffo O, Veronese S, Verderio P, Boracchi P, Bonzanini M, et al. Tissue carcinoembryonic antigen and oestrogen receptor status in breast carcinoma: an immunohistochemical study of clinical outcome in a series of 252 patients with long-term follow-up. Br J Cancer 1998; 77: 1661-8.
59. Kumar A, Soprano DR, Parekh HK. Cross-resistance to the synthetic retinoid CD437 in a paclitaxel-resistant human ovarian carcinoma cell line is independent of the overexpression of retinoic acid receptor-gamma, Cancer Res 2001; 61: 7552-5.
60. Zhao X, Spanjaard RA. The Apoptotic Action of the Retinoid CD437/AHPN: Diverse Effects, Common Basis. J Biomed Sci. 2003; 10: 44-9.
61. Wanner R. Henseleit-Walter U, Wittig B, Kolde G. Proliferation-dependent induction of apoptosis by the retinoid CD437 in p53-mutated keratinocytes. J Mol Med 2002; 80: 61-7.
62. Sun SY, Yue P, Wu GS, El-Deiry WS, Shroot B, Hong WK, et al. Implication of p53 in growth arrest and apoptosis induced by the synthetic retinoid CD437 in human lung cancer cells. Cancer Res 1999; 59: 2829-33.
63. Hollstein M, Sidransky D, Vogelstein B, Harris CC. p53 mutations in human cancers. Science 1991; 253: 49-53. Review.
64. Bush JA, Li G. Cancer chemoresistance: the relationship between p53 and multidrug transporters. Int J Cancer 2002; 98: 323-30. Review.
65. Zhang Y, Dawson MI, Ning Y, Polin L, Parchment RE, Corbett T, et al. Induction of apoptosis in retinoid refractory acute myelogenous leukemia by a novel AHPN analog. Blood 2003; Jul 3 [Epub ahead of print]
66. Boisvieux-Ulrich E, Le Pechon-Vallee C, Million K, Baeza-Squiban A, Houcine O, Guennou C, et al. Differential effects of several retinoid receptor-selective ligands on squamous differentiation and apoptosis in airway epithelial cells. Cell Tissue Res 2000; 300: 67-81.
67. Kaufmann SH, Earnshaw WC. Induction of apoptosis by cancer chemotherapy. Exp Cell Res. 2000, 256: 42-9. Review.
68. Kroemer G. Mitochondrial control of apoptosis: an introduction. Biochem Biophys Res Commun 2003; 304: 433-5. Review.
69. Srinivasula SM, Ahmad M, Fernandes-Alnemri T, Alnemri ES. Autoactivation of procaspase-9 by Apaf-1-mediated oligomerization. Mol Cell 1998; 1: 949-57.
70. Datta SR, Dudek H, Tao X, Masters S, Fu H, Gotoh Y, et al. Akt phosphorylation of BAD couples survival signals to the cell-intrinsic death machinery. Cell 1997; 91: 231-41.
71. Wajant H. The Fas signaling pathway: more than a paradigm. Science 2002; 296: 1635-6. Review.
72. Sidoti-de Fraisse C, Rincheval V, Risler Y, Mignotte B, Vayssiere JL. TNF-alpha activates at least two apoptotic signaling cascades. Oncogene 1998; 17: 1639-51.
73. van Gurp M, Festjens N, van Loo G, Saelens X, Vandenabeele P. Mitochondrial intermembrane proteins in cell death. Biochem Biophys Res Commun 2003; 304: 487-97. Review.
74. Scorrano L, Korsmeyer SJ. Mechanisms of cytochrome c release by proapoptotic BCL-2 family members. Biochem Biophys Res Commun 2003; 304: 437-44. Review.
75. Deng Y, Ren X, Yang L, Lin Y, Wu X. A JNK-Dependent Pathway Is Required for TNFalpha-Induced Apoptosis. Cell 2003; 115: 61-70.
76. Adams JM, Cory S. Apoptosomes: engines for caspase activation. Curr Opin Cell Biol 2002; 14: 715-20. Review.
77. Chen M, Wang J. Initiator caspases in apoptosis signaling pathways. Apoptosis 2002; 7: 313-9. Review.
78. Shi Y. Apoptosome: the cellular engine for the activation of caspase-9. Structure 2002; 10: 285-8. Review.
79. Shi Y. Mechanisms of caspase activation and inhibition during apoptosis. Mol Cell 2002; 9: 459-70. Review.
80. Muzio M, Stockwell BR, Stennicke HR, Salvesen GS, Dixit VM. An induced proximity model for caspase-8 activation. J Biol Chem 1998; 273: 2926-30.
81. Muzio M, Salvesen GS, Dixit VM. FLICE induced apoptosis in a cell-free system. Cleavage of caspase zymogens. J Biol Chem 1997; 272: 2952-6.
82. Muzio M, Chinnaiyan AM, Kischkel FC, O'Rourke K, Shevchenko A, Ni J, et al. FLICE, a novel FADD-homologous ICE/CED-3-like protease, is recruited to the CD95 (Fas/APO-1) death - inducing signaling complex. Cell 1996; 85: 817-27.
83. Kuwana T, Smith JJ, Muzio M, Dixit V, Newmeyer DD, Kornbluth S. Apoptosis induction by caspase-8 is amplified through the mitochondrial release of cytochrome c. J Biol Chem 1998; 273: 16589-94.
84. Ponzanelli I, Gianni M, Giavazzi R, Garofalo A, Nicoletti I, Reichert U, et al. Isolation and characterization of an acute promyelocytic leukemia cell line selectively resistant to the novel antileukemic and apoptogenic retinoid 6-[3-adamantyl-4-liydroxyphenyl]-2-naphtthaline carboxylic acid. Blood 2000; 95: 2672-82.
85. Marchetti P, Zamzami N, Joseph B, Schraen-Maschke S, Mereau-Richard C, Costantini P, et al. The novel retinoid 6-[3-(1-adamantyl)-4-hydroxyplienyl]-2-naphtalene carboxylic acid can trigger apoptosis through a mitochondrial pathway independent of the nucleus. Cancer Res 1999; 59: 6257-66.
86. Sun SY, Yue P, Wu GS, El-Deiry WS, Shroot B, Hong WK, et al. Mechanisms of apoptosis induced by the synthetic retinoid CD437 in human non-small cell lung carcinoma cells. Oncogene 1999; 18: 2357-65.
87. Fontana JA, Rishi AK. Classical and novel retinoids: their targets in cancer therapy. Leukemia 2002; 16: 463-72. Review.
88. Sun SY, Yue P, Shroot B, Hong WK, Lotan R. Implication of c-Myc in apoptosis induced by the retinoid CD437 in human lung carcinoma cells. Oncogene 1999; 18: 3894-901.
89. Sun SY, Yue P, Hong WK, Lotan R. Augmentation of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis by the synthetic retinoid 6-[3-(1-adamantyl)-4-hydroxyplienyl]-2-naphthaline carboxylic acid (CD437) through up-regulation of TRAIL receptors in human lung cancer cells. Cancer Res 2000; 60: 7149-55.
90. Sun SY, Yue P, Hong WK, Lotan R. Induction of Fas expression and augmentation of Fas/Fas figand-mediated apoptosis by the synthetic retinoid CD437 in human lung cancer cells. Cancer Res 2000; 60: 6537-43.
91. Fontana JA, Dawson MI, Leid M, Rishi AK, Zhang Y, Hsu CA, et al. Identification of a unique binding protein specific for a novel retinoid inducing cellular apoptosis. Int J Cancer 2000; 86: 474-9.
92. Solary E, Bettaieb A, Dubrez-Daloz L, Corcos L. Mitochondria as a target for inducing death of malignant hematopoietic cells. Leuk Lymphoma 2003; 44: 563-74.
93. Garattini E, Donelli MG, Catalani P, Pantarotto C. Intact rat liver nuclei catalyze adriamycin irreversible interactions with DNA and nuclear proteins. Toxicol Lett 1983; 17: 343-8.
94. Garattini E, Colombo T, Donelli MG, Catalani P, Bianchi M, D'Incalci M, et al. Distribution, metabolism, and irreversible binding of hexamethylmelamine in mice bearing ovarian carcinoma. Cancer Chemother Pharmacol 1983; 11: 51-5.
95. Garattini E, Donelli MG, Colombo T, Paesani R, Pantarotto C. In vivo and in vitro irreversible binding of hexamethylmelamine to liver and ovarian tumor macromolecules of mice. Biochem Pharmacol 1981; 30: 1151-4.
96. Rishi AK, Sun RJ, Gao Y, Hsu CK, Gerald TM, Saeed Sheikh M, et al. Post-transcriptional regulation of the DNA damage-inducible gadd45 gene in human breast carcinoma cells exposed to a novel retinoid CD437. Nucleic Acids Res 1999; 27: 3111-9.
97. Li CQ, Trudel LJ, Wogan GN. Nitric oxide-induced genotoxicity, mitochondrial damage, and apoptosis in human lymphoblastoid cells expressing wild-type and mutant p53. Proc Natl Acad Sci USA 2002; 99: 10364-9.
98. Marrot L, Belaidi JP, Jones C, Perez P, Rion L, Sarasin A, Meunier JR. Molecular responses to photogenotoxic stress induced by the antibiotic lomefloxacin in human skin cells: from DNA damage to apoptosis. J Invest Dermatol 2003; 121: 596-606.
99. Aubrecht J, Narla RK, Ghosh P, Stanek J, Uckun FM. Molecular genotoxicity profiles of apoptosis-inducing vanadocene complexes. Toxicol Appl Pharmacol 1999; 154: 228-35.
100. Patton GW, Paciga JE, Shelley SA. NR8383 alveolar macrophage toxic growth arrest by hydrogen peroxide is associated with induction of growth-arrest and DNA damage-inducible genes GADD45 and GADD153. Toxicol Appl Pharmacol 1997; 147: 126-34.
101. Hail N Jr, Youssef EM, Lotan R. Evidence supporting a role for mitochondrial respiration in apoptosis induction by the synthetic retinoid CD437. Cancer Res 2001; 61: 6698-702.
102. Costantini P, Jacotot E, Decaudin D, Kroemer G. Mitochondrion as a novel target of anticancer chemotherapy. J Natl Cancer Inst 2000; 92: 1042-53. Review.
103. Belzacq AS, El Hamel C, Vieira HL, Cohen I, Haouzi D, Metivier D, et al. Adenine nucleotide translocator mediates the mitochondrial membrane permeabilization induced by Ionidamine, arsenite and CD437. Oncogene 2001; 20: 7579-87.
104. Hsu SL, Yin SC, Liu MC, Reichert U, Ho WL. Involvement of cyclin-dependent kinase activities in CD437-induced apoptosis. Exp Cell Res 1999; 252: 332-41.
105. Fontana JA, Sun RJ, Rishi AK, Dawson MI, Ordonez JV, Zhang Y, et al. Overexpression of bcl-2 or bcl-XL fails to inhibit apoptosis mediated by a novel retinoid. Oncol Res 1998; 10: 313-24.
106. Sakaue M, Adachi H, Dawson M, Jetten AM. Induction of Egr-1 expression by the retinoid AHPN in human lung carcinoma cells is dependent on activated ERK1/2. Cell Death Differ 2001; 8: 411-24.
107. Zhang Y, Rishi AK, Dawson MI, Tschang R, Farhana L, Boyanapalli M, et al. S-phase arrest and apoptosis induced in normal mammary epithelia cells by a novel retinoid. Cancer Res 2000; 60: 2025-32.
108. Piedrafita FJ, Pfahl M. Retinoid-induced apoptosis and Sp1 cleavage occur independently of transcription and require caspase activation. Mol Cell Biol 1997; 17: 6348-58.
109. Holmes WF, Dawson MI, Soprano RD, Soprano KJ. Induction of apoptosis in ovarian carcinoma cells by AHPN/CD437 is mediated by retinoic acid receptors. J Cell Physiol 2000; 185: 61-7.
110. Zhang D, Holmes WF, Wu S, Soprano DR, Soprano K.J. Retinoids and ovarian cancer. J Cell Physiol 2000; 185: 1-20. Review.
111. Shyu RY, Lin DY, Reichert U, Jiang SY. Synthetic retinoid CD437 induces cell-dependent cycle arrest by differential regulation of cell cycle associated proteins. Anticancer Res 2002; 22: 2757-64.
112. Zhang Y, Rishi AK, Dawson MI, Tschang R, Farhana L, Boyanapalli M, et al. S-phase arrest and apoptosis induced in normal mammary epithelia cells by a novel retinoid. Cancer Res 2000; 289: 1159-64
113. Li H, Kolluri SK, Gu J, Dawson MI, Cao X, Hobbs PD, et al. Cytochrome c release and apoptosis induced by mitochondrial targeting of nuclear orphan receptor TR3. Science 2000; 289: 1159-64.
114. Shyu RY, Lin DY, Reichert U, Jiang SY. Synthetic retinoid CD437 induces cell-dependent cycle arrest by differential regulation of cell cycle associated proteins. Anticancer Res 2002; 22: 2757-64.
115. Holmes WF, Soprano DR, Soprano KJ. Early events in the induction of apoptosis in ovarian carcinoma cells by CD437: activation of the p38 MAP kinase signal pathway. Oncogene. 2003; 22: 6377-86.
116. Lopez-Hernandez FJ, Ortiz MA, Bayon Y, Piedrafita FJ. Reduced concentrations of serum enhance the antiproliferative activity of retinoid-related molecules and accelerate the onset of apoptosis. Biochem Pharmacol 2003; 65: 2021-30.
117. Tournier C, Hess P, Yang DD, Xu J, Turner TK, Nimnual A, et al. Requirement of JNK for stress-induced activation of the cytochrome c-mediated death pathway. Science 2000; 288: 870-4.
118. Rishi AK, Zhang L, Boyanapalli M, Wali A, Mohammad RM, Yu Y, et al. Identification and characterization of a cell cycle and apoptosis regulatory protein-1 as a novel mediator of apoptosis signaling by retinoid CD437. J Biol Chem 2003; 278: 33422-35.
119. Li XS, Rishi AK, Shao ZM, Dawson MI, Jong L, Shroot B, et al. Posttranscriptional regulation of p21WAF1/CIP1 expression in human breast carcinoma cells. Cancer Res 1996; 56: 5055-62.
120. Adachi H, Preston G, Harvat B, Dawson MI, Jetten AM. Inhibition of cell proliferation and induction of apoptosis by the retinoid AHPN in human lung carcinoma cells. Am J Respir Cell Mol Biol 1998; 18: 323-33.
121. Farhana L, Dawson M, Rishi AK, Zhang Y, Van Buren E, Trivedi C, et al. Cyclin B and E2F-1 expression in prostate carcinoma cells treated with the novel retinoid CD437 are regulated by the ubiquitin-mediated pathway. Cancer Res 2002; 62: 3842-9.
122. Li Y, Lin B, Agadir A, Lin R, Dawson MI, Reed JC, et al. Molecular determinants of AHPN (CD437)-induced growth arrest and apoptosis in human lung cancer cell lines. Mol Cell Biol 1998; 18: 4719-31.
123. Lehar SM, Nacht M, Jacks T, Vater CA, Chittenden T, Guild BC. Identification and cloning of EI24, a gene induced by p53 in etoposide-treated cells. Oncogene 1996; 12: 1181-7.
124. Gu Z, Flemington C, Chittenden T, Zambetti GP. ei24, a p53 response gene involved in growth suppression and apoptosis. Mol Cell Biol 2000; 20: 233-41.
125. Garattini E, Gianni M, Terao M. Correspondence re: A. Kumar et al. cross-resistance to the synthetic retinoid CD437 in a paclitaxel-resistant human ovarian carcinoma cell line is independent of the overexpression of retinoic acid receptor-gamma. Cancer Res. 2001; 61: 7552-7555. Cancer Res. 2000; 62: 2192-3.
126. Ashkenazi A, Dixit VM. Death receptors: signaling and modulation. Science 1998; 281: 1305-08.
127. Ashkenazi A, Dixit VM. Apoptosis control by death and decoy receptors. Curr Opin Cell Biol 1999; 11: 255-260.
128. Lotan R. Receptor-independent induction of apoptosis by synthetic retinoids. J Biol Regul Homeost Agents 2003; 17: 13-28. Review.
129. Widschwendter M, Daxenbichler G, Culig Z, Michel S, Zeimet AG, Mortl MG, et al. Activity of retinoic acid receptor-gamma selectively binding retinoids alone and in combination with interferon-gamma in breast cancer cell lines. Int J Cancer 1997; 71: 497-504.
130. Lovat PE, Ranalli M, Bernassola F, Tilby M, Malcolm AJ, Pearson AD, et al. Distinct properties of fenretinide and CD437 lead to synergistic responses with chemotherapeutic reagents. Med Pediatr Oncol 2000; 35: 663-8
131. Danielsson C, Torma H, Vahlquist A, Carlberg C. Positive and negative interaction of 1 25-dihydroxyvitamin D3 and the retinoid CD437 in the induction of human melanoma cell apoptosis. Int J Cancer 1999; 81: 467-70.
132. Jinno H, Steiner MG, Mehta RG, Osborne MP, Telang NT. Inhibition of aberrant proliferation and induction of apoptosis in HER-2/neu oncogene transformed human mammary epithelial cells by N-(4-hydroxyphenyl)retinamide. Carcinogenesis 1999; 20: 229-36.
133. Green A, Shilkaitis A, Christov K. 4-(hydroxyphenyl)retinamide selectively inhibits the development and progression of ductal hyperplastic lesions and carcinoma in situ in mammary gland. Carcinogenesis 1999; 20: 1535-40.
134. Kurie JM, Lee JS, Khuri FR, Mao L, Morice RC, Lee JJ, et al. N-(4-hydroxyphenyl)retinamide in the chemoprevention of squamous metaplasia and dysplasia of the bronchial epithelium. Clin Cancer Res 2000; 6: 2973-9.
135. Veronesi U, De Palo G, Marubini E, Costa A, Formelli F, Mariani L, et al. Randomized trial of fenretinide to prevent second breast malignancy in women with early breast cancer. J Natl Cancer Inst 1999; 91: 1847-56.
136. Fanjul AN, Delia D, Pierotti MA, Rideout D, Yu JQ, Pfahl M, et al. 4-Hydroxyphenyl retinamide is a highly selective activator of retinoid receptors. J Biol Chem 1996; 271: 22441-6.
137. Boya P, Morales MC, Gonzalez-Polo RA, Andreau K, Gourdier I, Perfettini JL, et al. The chemopreventive agent N-(4-hydroxyphenyl)retinamide induces apoptosis through a mitochondrial pathway regulated by proteins from the Bcl-2 family. Oncogene 2003; 22: 6220-30.
138. Delia D, Aiello A, Formelli F, Fontanella E, Costa A, Miyashita T, et al. Regulation of apoptosis induced by the retinoid N-(4-hydroxyphenyl) retinamide and effect of deregulated bcl-2. Blood 1995; 85: 359-67.
139. Hail N Jr, Lotan R. Mitochondrial respiration is uniquely associated with the prooxidant and apoptolic effects of N-(4-hydroxyphenyl)retinamide. J Biol Chem 2001; 276: 45614-21.
140. Tosetti F, Vene R, Arena G, Morini M, Minghelli S, Noonan DM, et al. N-(4-hydroxyphenyl)retinamide inhibits retinoblastoma growth through reactive oxygen species-mediated cell death. Mol Pharmacol 2003; 63: 565-73.
141. Simoni D, Tolomeo M. Retinoids, apoptosis and cancer. Curr Pharm Design 2001; 7(17): 1823-37.
142. Tzimas G, Nan H. The role of metabolism and toxicokinetics in retinoid teratogenesis. Curr Pharm Design 2001; 7(9): 803-31.
143. Uckun FM. Rationally designed anti-mitotic agents with proapoptotic activity. Curr Pharm Design 2001; 7(16): 1627-39.