Potent effect of 5-HPBR, a butanoate derivative of 4-HPR, on cell growth and apoptosis in cancer cells

International Journal of Cancer

Volumn 109, Issue 1, 2004, Pages 58-64

  Han, Hye Sook ^a   Kwon, Youn Ja ^a   Park, Si Ho ^a   Kim, Eun Joo ^b   Rho, Young Soy ^c   Sin, Hong Sig ^a   Um, Soo Jong ^a  

^a Sejong University   (South Korea)

^b The Catholic University of Korea   (South Korea)

^c Chonbuk National University   (South Korea)

Author keywords

2 butanoate 4 HPR (5 HPBR); 4 (N hydroxyphenyl)retinamide (4 HPR); Antitumor activity; Apoptosis; Cytotoxicity; RAR

Indexed keywords

5 HYDROXYPHENYLBUTANOATE RETINAMIDE; 5 HYDROXYPHENYLBUTANOATERETINAMIDE; 5-HYDROXYPHENYLBUTANOATERETINAMIDE; ALITRETINOIN; ANTINEOPLASTIC AGENT; BUTYRIC ACID; BUTYRIC ACID DERIVATIVE; CASPASE; CASPASE 3; CASPASE 8; DIMETHYL SULFOXIDE; DNA FRAGMENT; DRUG DERIVATIVE; FENRETINIDE; LIGAND; RETINOIC ACID; RETINOIC ACID DERIVATIVE; RETINOIC ACID RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BRONCHUS; CANCER CELL; CELL SEPARATION; CELL STRAIN COS1; CELL STRAIN HL 60; CELL STRAIN K 562; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONTROLLED STUDY; CYTOLOGY; CYTOTOXICITY; DOSE RESPONSE; DRUG CYTOTOXICITY; ENZYME ACTIVATION; ENZYME ASSAY; FLOW CYTOMETRY; GENETIC TRANSCRIPTION; HUMAN; HUMAN CELL; IC 50; METABOLISM; PRIORITY JOURNAL; TIME; TUMOR CELL LINE; WESTERN BLOTTING;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BLOTTING, WESTERN; BRONCHI; BUTYRATES; BUTYRIC ACID; CASPASE 3; CASPASE 8; CASPASES; CELL LINE, TUMOR; CELL SEPARATION; COS CELLS; DIMETHYL SULFOXIDE; DNA FRAGMENTATION; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME ACTIVATION; FENRETINIDE; FLOW CYTOMETRY; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; K562 CELLS; LIGANDS; MODELS, CHEMICAL; TIME FACTORS; TRANSCRIPTION, GENETIC; TRETINOIN;

EID: 0742322816     PISSN: 00207136     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijc.11643     Document Type: Article

References (38)

1. Ulukaya E, Wood EJ. Fenretinide and its relation to cancer. Cancer Treat Rev 1999;25:229-35.
2. Formelli F, Barua AB, Olson JA. Bioactivities of N-(4-hydroxyphenyl) retinamide and retinoyl beta-glucuronide. FASEB J 1996;10:1014-24.
3. Moon RC, Pritchard JF, Mehta RG, Nomides CT, Thomas CF, Dinger NM. Suppressions of rat mammary cancer development by 4-HPR following surgical removal of first palpable tumor. Carcinogenesis 1989;10:1645-9.
4. Pollard M, Luckert PH, Sporn MB. Prevention of primary prostate cancer in Lobund-Wistar rats by N-(4-hydroxyphenyl)retinamide. Cancer Res 1991;51:3610-1.
5. Pienta KJ, Nguyen NM, Lehr JE. Treatment of prostate cancer in the rat with the synthetic retinoid fenretinide. Cancer Res 1993;53:224-6.
6. Formelli F, Cleris L. Synthetic retinoid fenretinide is effective against a human ovarian carcinoma xenograft and potentiates cisplatin activity. Cancer Res 1993;53:5374-6.
7. Swisshelm K, Ryan K, Lee X, Tsou HC, Peacocke M, Sager R. Down-regulation of retinoic acid receptor β in mammary carcinoma cell lines and its up-regulation in senescing normal mammary epithelial cells. Cell Growth Different 1994;5:133-41.
8. Sabichi AL, Hendricks DT, Bober MA, Birrer MJ. Retinoic acid receptor β expression and growth inhibition of gynecologic cancer cells by the synthetic retinoid N-(4-hydroxyphenyl)retinamide. J Natl Cancer Inst 1998;90:597-605.
9. Pergolizzi R, Appierto V, Crosti M, Cavadini E, Cleris L, Guffanti A, Formelli F. Role of retinoic acid receptor overexpression in sensitivity to fenretinide and tumorigenicity of human ovarian carcinoma cells. Int J Cancer 1999;81:829-34.
10. Delia D, Aiello A, Meroni L, Nicolini M, Reed JC, Pierotti MA. Role of antioxidants and intracellular free radicals in retinamide-induced cell death. Carcinogenesis 1997;18:943-8.
11. Oridate N, Suzuki S, Higuchi M, Mitchell MF, Hong WK, Lotan R. Involvement of reactive oxygen species in N-(4-hydroxyphenyl)retinamide-induced apoptosis in cervical carcinoma cells. J Natl Cancer Inst 1997;89:1191-8.
12. Wang H, Maurer BJ, Reynolds CP, Cabot MC. N-(4-hydroxyphenyl)retinamide elevates ceramide in neuroblastoma cell lines by coordinate activation of serine palmitoyltransferase and ceramide synthase. Cancer Res 2001;61:5102-5.
13. Erdreich-Epstein A, Tran LB, Bowman NN, Wang H, Cabot MC, Durden DL, Vlckova J, Reynolds CP, Stins MF, Groshen S, Millard M. Ceramide signaling in fenretinide-induced endothelial cell apoptosis. J Biol Chem 2002;277:49531-7.
14. Chen YR, Zhou G, Tan TH. c-Jun N-terminal kinase mediates apoptotic signaling induced by N-(4-hydroxyphenyl)retinamide. Mol Pharmacol 1999;56:1271-9.
15. Puduvalli VK, Saito Y, Xu R, Kouraklis GP, Levin VA, Kyritsis AP. Fenretinide activates caspases and induces apoptosis in gliomas. Clin Cancer Res 1999;5:2230-5.
16. DiPietrantonio AM, Hsieh TC, Juan G, Traganos F, Darzynkiewicz Z, Wu JM. Fenretinide-induced caspase 3 activity involves increased protein stability in a mechanism distinct from reactive oxygen species elevation. Cancer Res 2000;60:4331-5.
17. You KR, Shin MN, Park RK, Lee SO, Kim DG. Activation of caspase-8 during N-(4-hydroxyphenyl)retinamide-induced apoptosis in Fas-defective hepatoma cells. Hepatology 2001;34:1119-27.
18. Veronesi U, De Palo G, Costa A, Formelli F, Decensi A. Chemoprevention of breast cancer with fenretinide. IARC Sci Publ 1996;136:87-94.
19. Pienta KJ, Esper PS, Zwas F, Krzeminski R, Flaherty LE. Phase II chemoprevention trial of oral fenretinide in patients at risk for adenocarcinoma of the prostate. Am J Clin Oncol 1997;20:36-9.
20. Reynolds CP. Differentiating agents in pediatric malignancies: retinoids in neuroblastoma. Curr Oncol Rep 2000;2:511-8.
21. Kurie JM, Lee JS, Khuri FR, Mao L, Morice RC, Lee JJ, Walsh GL, Broxson A, Lippman SM, Ro JY, Kemp BL, Liu D, Fritsche HA, Xu X, Lotan R, Hong WK. N-(4-hydroxyphenyl)retinamide in the chemoprevention of squamous metaplasia and dysplasia of the bronchial epithelium. Clin Cancer Res 2000;6:2973-9.
22. Formelli F, Clerici M, Campa T, Di Mauro MG, Magni A, Mascotti G, Moglia D, De Palo G, Costa A, Veronesi U. Five-year administration of fenretinide: pharmacokinetics and effects on plasma retinol concentrations. J Clin Oncol 1993;11:2036-42.
23. Clifford JL, Sabichi AL, Zou C, Yang X, Steele VE, Kelloff GJ, Lotan R, Lippman SM. Effects of novel phenylretinamides on cell growth and apoptosis in bladder cancer. Cancer Epidemiol Biomarkers Prev 2001;10:391-5.
24. Sun SY, Yue P, Kelloff GJ, Steele VE, Lippman SM, Hong WK, Lotan R. Identification of retinamides that are more potent than N-(4-hydroxyphenyl)retinamide in inhibiting growth and inducing apoptosis of human head and neck and lung cancer cells. Cancer Epidemiol Biomarkers Prev 2001;10:595-601.
25. Hague A, Elder DJ, Hicks DJ, Paraskeva C. Apoptosis in colorectal tumour cells: induction by the short chain fatty acids butyrate, propionate and acetate and by the bile salt deoxycholate. Int J Cancer 1995;60:400-6.
26. Um SJ, Lee SY, Kim EJ, Han HS, Koh YM, Hong KJ, Sin HS, Park JS. Antiproliferative mechanism of retinoid derivatives in ovarian cancer cells. Cancer Lett 2001;174:127-34.
27. Um SJ, Kim EJ, Hwang ES, Kim SJ, Namkoong SE, Park JS. Antiproliferative effects of retinoic acid/interferon in cervical carcinoma cell lines: cooperative growth suppression of IRF-1 and p53. Int J Cancer 2000;85:416-23.
28. Fanjul AN, Delia D, Pierotti MA, Rideout D, Yu JQ, Pfahl M. 4-Hydroxyphenyl retinamide is a highly selective activator of retinoid receptors. J Biol Chem 1996;271:22441-6.
29. Altucci L, Gronemeyer H. The promise of retinoids to fight against cancer. Nat Rev Cancer 2001;1:181-93.
30. IARC. IARC Handbooks of Cancer Prevention, Vol. 3, Vitamin A. Lyon: International Agency for Research on Cancer. 1998.
31. Vigushin DM. Coombes RC. Histone deacetylase inhibitors in cancer treatment. Anticancer Drugs 2002;13:1-13.
32. Buommino E, Pasquali D, Sinisi AA, Bellastella A, Morelli F, Metafora S. Sodium butyrate/retinoic acid costimulation induces apoptosis-independent growth arrest and cell differentiation in normal and ras-transformed seminal vesicle epithelial cells unresponsive to retinoic acid. J Mol Endocrinol 2000;24:83-94.
33. Demary K, Wong L, Spanjaard RA. Effects of retinoic acid and sodium butyrate on gene expression, histone acetylation and inhibition of proliferation of melanoma cells. Cancer Lett 2001;163:103-7.
34. Boatright JH, Stodulkova E, Do VT, Padove SA, Nguyen HT, Borst DE, Nickerson JM. The effect of retinoids and butyrate on the expression of CRX and IRBP in retinoblastoma cells. Vision Res 2002; 42:933-8.
35. Nudelman A, Rephaeli A. Novel mutual prodrug of retinoic and butyric acids with enhanced anticancer activity. J Med Chem 2000; 43:2962-6.
36. Hail N Jr, Lotan R. Mitochondrial permeability transition is a central coordinating event in N-(4-hydroxyphenyl)retinamide-induced apoptosis. Cancer Epidemiol Biomarkers Prev 2000;9:1293-301.
37. Hoyos B, Imam A, Chua R, Swenson C, Tong GX, Levi E, Noy N, Hammerling U. The cysteine-rich regions of the regulatory domains of Raf and protein kinase C as retinoid receptors. J Exp Med 2000; 192:835-45.
38. Costa A, Malone W, Perloff M, Buranelli F, Campa T, Dossena G, Magni A, Pizzichetta M, Andreoli C, Vecchio MD, Formelli F, Barbieri A. Tolerability of the synthetic retinoid fenretinide (HPR). Eur J Cancer Clin Oncol 1989;25:805-8.