Targeting cancer using cholesterol conjugates

Saudi Pharmaceutical Journal

Volumn 22, Issue 1, 2014, Pages 3-16

  Radwan, Awwad A ^a,b   Alanazi, Fares K ^a  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b Assiut University   (Egypt)

Author keywords

Anticancer; Cholesterol; Drug delivery systems

Indexed keywords

ANTINEOPLASTIC AGENT; CHOLESTEROL; CHOLESTEROL CONJUGATE; CHOLESTEROL DERIVATIVE; DNA TOPOISOMERASE; LIPOPROTEIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CANCER CELL; CANCER DIAGNOSIS; CANCER INHIBITION; CANCER RISK; CANCER THERAPY; CHOLESTEROL BLOOD LEVEL; DRUG DELIVERY SYSTEM; HUMAN; MOLECULARLY TARGETED THERAPY; PROSTATE CANCER; REVIEW;

EID: 84892987007     PISSN: 13190164     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsps.2013.01.003     Document Type: Review

References (85)

1. Abul-Hajj Y.J. Stereospecificity of hydrogen transfer from NADPH by steroid δ4-5α-and δ4-5β-reductase. Steroids 1972, 20:215-222.
2. Ahmad F., Leri S.F., Takashi N., Takahito Y., Mami K., Hiroyuki S., Toyo N., Nurhayat U., Hiroyuki K., Takayuki A., Hiroyuki K., Shin Y. Chemically synthesized sugar-cholestanols possess a preferential anticancer activity involving promising therapeutic potential against human esophageal cancer. Cancer Sci. 2007, 98:1358-1367.
3. Alanazi F., Halpern D.S., Lu D.R. Development of cholesterol-based conjugates for targeted drug delivery. S.T.P. Pharma Sci. 2003, 13:27-35.
4. Alanazi F., Halpern D.S., Lu D.R. Intracerebral diffusion of new cholesterol-based anticancer conjugate in tumor-bearing rat model. J. Appl. Res. 2004, 4:127-134.
5. Amagata T., Doi M., Tohgo M., Minoura K., Numata A. Dankasterone, a new class of cytotoxic steroid produced by a Gymnascella species from a marine sponge. Chem. Commun. 1999, 14:1321-1322.
6. Cancer facts and figures: 2012 2012, American Cancer Society, American Cancer Society, Atlanta.
7. Andersson S., Russell D.W. Structural and biochemical properties of cloned expressed human and rat steroid 5α-reductase. Proc. Natl. Acad. Sci. USA 1990, 87:3544-3640.
8. Andersson S.R., Bishop R.W., Russell D.W. Expression cloning and regulation of steroid 5α-reductase, an enzyme essential for male sexual differentiation. J. Biol. Chem. 1989, 264:16249-16255.
9. Asao T., Yazawa S., Kudo S., Takenoshita S., Nagamachi Y. A novel ex vivo method for assaying adhesion of cancer cells to the peritoneum. Cancer Lett. 1994, 78:57-62.
10. Asao T., Nagamachi Y., Morinaga N., Shitara Y., Takenoshita S., Yazawa S. Fucosyltransferases of the peritoneum contributed to the adhesion of cancer cells to the mesothelium. Cancer 1995, 75:1539-1544.
11. Audia J.E., Lawhorn D.E., Deeter J.B. Synthesis of the individual enantiomers of the benzoquinolinone human type 1 steroid 5α-reductase inhibitors LY191704 and LY266111. Tetrahedron Lett. 1993, 34:7001-7004.
12. Awad A.B., Fink C.S. Phytosterols as anticancer dietary components: evidence and mechanism of action. J. Nutr. 2000, 130:2127-2130.
13. Baier C.J., Barrantes F.J. Sphingolipids are necessary for nicotinic acetylcholine receptor export in the early secretory pathway. J. Neurochem. 2007, 101:1072-1084.
14. Barrantes F.J. Cholesterol effects on nicotinic acetylcholine receptor: cellular aspects. Subcell Biochem. 2010, 51:467-487.
15. Barres B.A., Smith S.J. Cholesterol-making or breaking the synapse. Science 2001, 294:1296-1297.
16. Barth R.F. A critical assessment of boron neutron capture therapy: an overview. J. Neurooncol. 2003, 62:1-210.
17. Barth R.F., Yang W., Adams D.M., Rotaru J.H., Shukla S., Sekido M., Tjarks W., Fenstermaker R.A., Ciesielski M., Nawrocky M.M., Coderre J.A. Molecular targeting of the epidermal growth factor receptor for neutron capture therapy of gliomas. Cancer 2002, 62:3159-3166.
18. Barth R.F., Coderre J.A., Vicente M.G., Blue T.E. Boron neutron capture therapy of cancer: current status and future prospects. Clin. Canc. Res. 2005, 11:3987-4002.
19. Bouillon R., Okamura W.H., Norman A.W. Structure-function relationships in the vitamin D endocrine system. Endocr. Rev. 1995, 16:200-257.
20. Brassart B., Gomez D., De Cian A., Paterski R., Montagnac A., Qui K.-H., Temime-Smaali N., Trentesaux C., Mergny J.-L., Gueritte F. A new steroid derivative stabilizes G-quadruplexes and induces telomere uncapping in human tumor cells. Mol. Pharmacol. 2007, 72:631-640.
21. Bruchovsky N., Wilson J.D. The conversion of testosterone to 5-androstan-17-ol-3-one by rat prostate in vivo and in vitro. J. Biol. Chem. 1968, 242:2012-2021.
22. Cabeza M., Flores E., Heuze I., Sanchez M., Bratoeff E., Ramirez E., Francolugo V.A. Novel 17-substituted pregnadiene derivatives as 5α-reductase inhibitors and their binding affinity for the androgen receptor. Chem. Pharm. Bull. 2004, 52:535-539.
23. Chen Y., Wang S., Lu X., Zhang H., Fu Y., Luo Y. Cholesterol sequestration by nystatin enhances the uptake and activity of endostatin in endothelium via regulating distinct endocytic pathways. Blood 2011, 117:6392-6403.
24. Chida K., Murakami A., Tagawa T., Ikuta T., Kuroki T. Cholesterol sulfate, a second messenger for the g isoform of protein kinase C, inhibits promotional phase in mouse skin carcinogenesis. Cancer Res. 1995, 55:4865-4869.
25. Chytil P., Etrych T., Kostka L., Ulbrich K. Hydrolytically degradable polymer micelles for anticancer drug delivery to solid tumors. Macromol. Chem. Phys. 2012, 213:858-867.
26. Cichewicz R.H., Kouzi S.A. Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection. Med. Res. Rev. 2004, 24:90-114.
27. de Bree E., Theodoropoulos P.A., Rosing H., Michalakis J., Romanos J., Beijnen J.H., Tsiftsis D.D. Treatment of ovarian cancer using intraperitoneal chemotherapy with taxanes: from laboratory bench to bedside. Cancer Treat. Rev. 2006, 32:471-482.
28. Denniston, K., Topping, J., Caret, R., 2007. General Organic and Biochemistry: 6th Edition. McGraw Hill, New York, pp. 602-603.
29. Dietschy J.M., Turley S.D. Thematic review series: brain lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J. Lipid. Res. 2004, 45:1375-1397.
30. Fantini J., Barrantes F.J. Sphingolipid/cholesterol regulation of neurotransmitter receptor conformation and function. Biochim. Biophys. Acta 2009, 1788:2345-2361.
31. Fars K. A., 2003. Application of lipoprotein as drug delivery system for anticancer drug and DNA-based vaccine. Thesis pp. 11-14.
32. Favre G. Targeting of tumor cells by low-density lipoproteins: principle and use of ellipticin derivatives. C. R. Seances Soc. Biol. Fil. 1992, 186:73-87.
33. Flores E., Bratoeff E., Cabeza M., Ramirez E., Quiroz A., Heuze I. Steroid 5-reductase inhibitors. Mini Rev. Med. Chem. 2003, 3:225-237.
34. Gross M.D., Shapiro B., Francis I.R., Glazer G.M., Bree R.L., Arcomano M.A., Schteingart D.E., McLeod M.K., Sanfield J.A., Thompson N.W. Scintigraphy evaluation of clinically silent adrenal masses. J. Nucl. Med. 1994, 35:1145-1152.
35. Gums J.G., Wilt V.M. Disorders of the adrenal gland. Pharmacotherapy, A pathophysiologic approach 1997, 1547-1583. Appleton and Lange, Connecticut. J.T. Dipiro (Ed.).
36. Guo W.J., Lee T., Sudimack J., Lee R.J. Receptor-specific delivery of liposomes via folate-PEG-Chol. J. Liposome Res. 2000, 10:179-195.
37. Hartmann R.W., Hector M., Haidar S., Ehmer P.B., Reichert W., Jose J. Synthesis and evaluation of novel steroidal oxime inhibitors of P450 17 (17α-hydroxylase/C17,20-lyase) and 5α-reductase types 1 and 2. J. Med. Chem. 2000, 43:4266-4277.
38. Hawkins L.A., Brritton K.E., Shairo B. Selenium-75 selenomethyl cholesterol: a new agent for quantitative functional scintigraphy of the adrenals: physical aspects. Br. J. Radiol. 1980, 53:883-889.
39. Hume R., Boyd G.S. Cholesterol metabolism and steroid-hormone production. Biochem. Soc. Trans. 1978, 6:893-898.
40. Ishimaru C., Yonezawa Y., Kuriyama I., Nishida M., Yoshida H., Mizushina Y. Inhibitory effects of cholesterol derivatives on DNA polymerase and topoisomerase activities, and human cancer cell growth. Lipids 2008, 43:373-382.
41. Itoh H., Ito H., Hibasami H. Blazein of a new steroid isolated from Agaricus blazei Murrill (himematsutake) induces cell death and morphological change indicative of apoptotic chromatin condensation in human lung cancer LU99 and stomach cancer KATO III cells. Oncol. Rep. 2008, 20:1359-1361.
42. Johnson S.D., Welch M.J. Synthesis, biological and baboon PET imaging of the potential adrenal imaging agent cholesteryl-p-[18F]fluorobenzoate. Nucl. Med. Biol. 1999, 26:131-138.
43. Jones C.D., Audia J.E., Lawhorn D.E., McQuaid L.A., Neubauer B.L., Pike A.J., Pennington P.A., Stamm N., Toomey R.E., Hirsch K.S. Nonsteroidal inhibitors of human type I steroid 5α-reductase. J. Med. Chem. 1993, 36:421-423.
44. Kim S., Ma E. Synthesis of pregnane derivatives, their cytotoxicity on LNCap and PC-3 cells, and screening on 5α-reductase inhibitory activity. Molecules 2009, 14:4655-4668.
45. Klimov A.N., Korovkin B.F., Kuznetsov A.S., Popov I.N. Apolipoprotein B of plasma lipoproteins incorporated in liposomes: immunological properties and organ distribution when administered to rabbits. Bull. Eksp. Biol. Med. 1983, 96:47-50.
46. Koppe M.J., Boerman O.C., Oyen W.J., Bleichrodt R.P. Peritoneal carcinomatosis of colorectal origin: incidence and current treatment strategies. Ann. Surg. 2006, 243:212-222.
47. Kritchevsky S.B. Serum cholesterol and cancer risk: an epidemiologic perspective. Annu. Rev. Nutr. 1992, 12:391-416.
48. Kurup A., Garg R., Hansch C. Comparative QSAR analysis of 5α-reductase inhibitors. Chem. Rev. 2000, 100:909-924.
49. Lazier C.B., Thomas L.N., Douglas R.C., Vessey J.P., Rittmaster R.S. Dutasteride, the dual 5α-reductase inhibitor, inhibits androgen action and promotes cell death in the LNCaP prostate cancer cell line. Prostate 2004, 58:130-144.
50. Lee R.J., Low P.S. Delivery of liposomes into cultured KB cells via folate receptor-mediated endocytosis. J. Biol. Chem. 1994, 269:3198-3204.
51. 131I-19-iodocholesterol. N. Engl. J. Med. 1971, 285:1387-1393.
52. Longino M.A., Glazer G.M., Weichert J.P., Groziak M.P., Schwendner S.W., Counsell R.E. Esters of iopanoic acid as liver-specific CT contrast agents: biodistribution and CT evaluation. J. Comput. Assist. Tomogr. 1984, 8:1099-1104.
53. Lu D.R., Mehta S.C., Chen W. Selective boron drug delivery to brain tumors for boron neutron capture therapy. Adv. Drug Deliv. Rev. 1997, 26:231-247.
54. Ma C.-M., Cai S.-Q., Cui J.-R., Wang R.-Q., Tu P.-F., Hattori M., Daneshtalab M. The cytotoxic activity of ursolic acid derivatives. Eur. J. Med. Chem. 2005, 40:582-589.
55. Maletinska L., Blakely E.A., Bjornstad K.A., Deen D.F., Knoff L.J., Forte T.M. Human glioblastoma cell lines: levels of low-density lipoprotein receptor and low-density lipoprotein receptor-related protein. Cancer Res. 2000, 60:2300-2303.
56. Mihai V.P., Marius L., Louis P.S. Quantitative structure inter-activity relationship (QSInAR). Cytotoxicity study of some hemisynthetic and isolated natural steroids and precursors on human fibrosarcoma cells HT1080. Molecules 2011, 16:6603-6620.
57. Mullauer F.B., Kessler J.H., Medema J.P. Betulin Is a potent anti-tumor agent that is enhanced by cholesterol. PLoS One 2009, 4:e5361.
58. Okamura A., Yazawa S., Nishimura T., Tanaka S., Takai I., Kudo S., Asao T., Kuwano H., Matta K.L., Akamatsu S., Kochibe N. A new method for assaying adhesion of cancer cells to the greater omentum and its application for evaluating antiadhesion activities of chemically synthesized oligosaccharides. Clin. Exp. Metastasis 2000, 18:37-43.
59. Pan X., Wu G., Yang W., Barth R.F., Tjarks W., Lee R.J. Synthesis of cetuximab-immunoliposomes via a cholesterol-based membrane anchor for targeted delivery of a neutron capture therapy (NCT) agent to glioma cells. Bioconjug. Chem. 2007, 18:101-108.
60. Peacock G., Sidwell R., Pan G., Oie S., Lu D.R. In vitro uptake of a new cholesteryl carborane ester compound in human glioma cell lines. J. Pharm. Sci. 2004, 93:13-19.
61. Peto R., Borenham J., Chen J., Li J., Campbell T.C., Brun T. Plasma cholesterol, coronary heart disease, and cancer. Br. Med. J. 1989, 298:1249.
62. Proksch E. The epidermis as metabolically active tissue: regulation of lipid synthesis by the barrier function. Z. Hautkr. 1990, 65:296-300.
63. Ramírez E., Cabeza M., Heuze I., Gutierrez E., Bratoeff E., Membrillo M., Lira A. Synthesis and pharmacological evaluation of new 16-methyl pregnenolone derivatives. Chem. Pharm. Bull. 2002, 50:15-20.
64. Rudling M.J., Angelin B., Peterson C.O., Collins V.P. Low density lipoprotein receptor activity in human intracranial tumors and its relation to the cholesterol requirement. Cancer Res. 1990, 50:483-487.
65. Russell D.W., Wilson J.D. Steroid 5 alpha-reductase: two genes/two enzymes. Ann. Rev. Biochem. 1994, 63:25-61.
66. Samadi A.K., Tong X., Mukerji R., Zhang H., Timmermann B.N., Cohen M.S. Withaferin A, a cytotoxic steroid from Vassobia breviflora, induces apoptosis in human head and neck squamous cell carcinoma. J. Nat. Prod. 2010, 73:1476-1481.
67. Shang X.-Y., Li J.-J., Liu M.-T., Li S., Liu Y., Wang Y.-F., Huang X., Jin Z.-L. Cytotoxic steroids from Monascus purpureus-fermented rice. Steroids 2011, 76:1185-1189.
68. Shawer M., Greenspan P., Øie S., Lu D.R. VLDL-resembling phospholipid-submicron emulsion for cholesterol-based drug targeting. J. Pharm. Sci. 2002, 91:1405-1413.
69. Shinji H., Shin Y., Takayuki A., Ahmad F., Toyo N., Kaori T., Takashi N., Takahito Y., Noriyuki K., Ken U., Abbi R.S., Hiroyuki K. Novel sugar-cholestanols as anticancer agents against peritoneal dissemination of tumor cells. Glycoconj J. 2008, 25:531-544.
70. Strott C.A., Higashi Y. Cholesterol sulfate in human physiology: what's it all aboutα. J. Lipid Res. 2003, 44:1268-1278.
71. Sudduth S.L., Koronkowski M.J. Finasteride, the first 5 alpha-reductase inhibitor. Pharmacotherapy 1993, 309-325.
72. Sugarbaker P.H. Strategies for the prevention and treatment of peritoneal carcinomatosis from gastrointestinal cancer. Cancer Invest. 2005, 23:155-172.
73. Sujeong K., Yong-ung K., Eunsook M. Synthesis and 5α-reductase inhibitory activity of C21 steroids having 1,4-diene or 4,6-diene 20-ones and 4-azasteroid 20-oximes. Molecules 2012, 17:355-368.
74. Thigpen A.E., Silver R.I., Guileyardo J.M., Casey M., McConnel J.D., Russell D.W. Tissue distribution and ontogeny of steroid 5alpha-reductase isozyme expression. J. Clin. Invest. 1993, 92:903-910.
75. Vicente M.G.H. Boron in medicinal chemistry. Anticancer Agents Med. Chem. 2006, 6:73-181.
76. Vitols S. Uptake of low-density lipoprotein by malignant cells-possible therapeutic applications. Cancer Cells 1991, 3:488-495.
77. Vogel I., Kalthoff H. Disseminated tumour cells. Their detection and significance for prognosis of gastrointestinal and pancreatic carcinomas. Virchows Arch. 2001, 439:109-117.
78. Wang Y.-S., Yang J.-H., Luo S.-D., Zhang H.-B., Li L. New cytotoxic steroid from Stachyurus himalaicus var. himalaicus. Molecules 2006, 11:536-542.
79. Wu G., Barth R.F., Yang W., Lee R.J., Tjarks W., Backer M.V., Backer J.M. Boron containing macromolecules and nanovehicles as delivery agents for neutron capture therapy. Anticancer Agents Med. Chem. 2006, 6:167-184.
80. Yan T.D., Stuart O.A., Yoo D., Sugarbaker P.H. Preoperative intraperitoneal chemotherapy for peritoneal surface malignancy. J. Transl. Med. 2006, 4:1-7.
81. Yat-Ching T. The role of cholesterol in prostatic diseases. Urol. Sci. 2011, 22:97-102.
82. Yeagle P.L. Cholesterol and cell membrane. Biology of Cholesterol 1988, 121-146. CRC Press, Boca Raton, Florida. P.L. Yeagle (Ed.).
83. Zamenhof R.G., Coderre J.A., Rivard M.J., Patel H. Topics in neutron capture therapy. Proceedings of the eleventh world congress on neutron capture therapy. Appl. Radiat. Isot. 2004, 61:731-1130.
84. Zee-Cheng R.K., Cheng C.C. Delivery of anticancer drugs. Methods Find. Exp. Clin. Pharmacol. 1989, 11:439-529.
85. Zhang H.-J., Sun J.-B., Lin H.-W., Wang Z.-L., Tang H., Cheng P., Chen W.-S., Yi Y.-H. A new cytotoxic cholesterol sulfate from marine sponge Halichondria rugosa. Nat. Prod. Res. 2007, 21:953-958.