Dimeric naphthoquinones, a novel class of compounds with prostate cancer cytotoxicity

BJU International

Volumn 108, Issue 3, 2011, Pages 447-454

  Ross, Ashley E ^a   Emadi, Ashkan ^a   Marchionni, Luigi ^a   Hurley, Paula J ^a   Simons, Brian W ^a   Schaeffer, Edward M ^a   Vuica Ross, Milena ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

cytotoxicity; dimeric naphthoquinones; oxidative stress; prostate cancer; radiation synergy

Indexed keywords

ADENOSINE TRIPHOSPHATE; ANTINEOPLASTIC AGENT; DIMERIC NAPHTHOQUINONE; DOCETAXEL; NAPHTHOQUINONE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER CELL DESTRUCTION; CELL DEATH; CELL SURVIVAL; CELL VIABILITY; CLONOGENIC ASSAY; COLONY FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENTIATION; DRUG SCREENING; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; IONIZING RADIATION; LD 50; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN EXPRESSION; RADIATION EXPOSURE;

ADENOSINE TRIPHOSPHATE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SYNERGISM; HUMANS; MALE; NAPHTHOQUINONES; PROSTATIC NEOPLASMS; RADIATION, IONIZING; REACTIVE OXYGEN SPECIES;

EID: 79960570066     PISSN: 14644096     EISSN: 1464410X     Source Type: Journal    
DOI: 10.1111/j.1464-410X.2010.09907.x     Document Type: Article

References (34)

1. ACS. Cancer Facts and Figures. Atlanta, GA: Atlanta American Cancer Society, 2009
2. Horner MJRL, Krapcho M, Neyman N, et al,. SEER Cancer Statistics Review, 1975-2006. Available at:. Accessed 2009
3. O'Brien PJ,. Molecular mechanisms of quinone cytotoxicity. Chem Biol Interact 1991; 80: 1-41
4. Stagliano KW, Emadi A, Lu Z, et al,. Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone. Bioorg Med Chem 2006; 14: 5651-65 (Pubitemid 43994473)
5. Dai JR, Decosterd LA, Gustafson KR, Cardellina J,. H, 2nd, Gray GN, Boyd MR. Novel naphthoquinones from Conospermum incurvum. J Nat Prod 1994; 57: 1511-6
6. Kayser O, Kiderlen AF, Laatsch H, Croft SL,. In vitro leishmanicidal activity of monomeric and dimeric naphthoquinones. Acta Trop 2000; 76: 131-8 (Pubitemid 30628859)
7. Lim ES, Rhee YH, Park MK, et al,. DMNQ S-64 induces apoptosis via caspase activation and cyclooxygenase-2 inhibition in human nonsmall lung cancer cells. Ann N Y Acad Sci 2007; 1095: 7-18
8. Emadi A, Ross AE, Cowan KM, Fortenberry YM, Vuica-Ross M,. A chemical genetic screen for modulators of asymmetrical 2,2′-dimeric naphthoquinones cytotoxicity in yeast. PLoS One 2010; 5: e10846
9. Stagliano KW, Lu Z, Emadi A, Harwood JS, Harwood CA,. Effect of methoxyl group position on the regioselectivity of ammonia substitution reactions involving 3,3′-dichloro-2,2′-binaphthoquinones. J Org Chem 2004; 69: 5128-31 (Pubitemid 39014077)
10. Emadi A, Harwood JS, Kohanim S, Stagliano KW,. Regiocontrolled synthesis of the trimeric quinone framework of conocurvone. Org Lett 2002; 4: 521-4
11. Emadi A,. Regiocontrolled Synthesis and HIV Inhibitory Properties of Binapthoquinone and Trimeric Naphthoqinone Derivates of Conocurvone. Chicago, IL: Illinois institute of Technology, 2004
12. Mosmann T,. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63 (Pubitemid 14203433)
13. Ezekwudo D, Shashidharamurthy R, Devineni D, Bozeman E, Palaniappan R, Selvaraj P,. Inhibition of expression of anti-apoptotic protein Bcl-2 and induction of cell death in radioresistant human prostate adenocarcinoma cell line (PC-3) by methyl jasmonate. Cancer Lett 2008; 270: 277-85
14. Berenbaum MC,. Criteria for analyzing interactions between biologically active agents. Adv Cancer Res 1981; 35: 269-335
15. Dong Y, Chin SF, Blanco E, et al,. Intratumoral delivery of beta-lapachone via polymer implants for prostate cancer therapy. Clin Cancer Res 2009; 15: 131-9
16. Fernandez Villamil S, Stoppani AO, Dubin M,. Redox cycling of beta-lapachone and structural analogues in microsomal and cytosol liver preparations. Methods Enzymol 2004; 378: 67-87
17. Pink JJ, Planchon SM, Tagliarino C, Varnes ME, Siegel D, Boothman DA,. NAD(P)H: Quinone oxidoreductase activity is the principal determinant of beta-lapachone cytotoxicity. J Biol Chem 2000; 275: 5416-24 (Pubitemid 30115173)
18. Planchon SM, Pink JJ, Tagliarino C, Bornmann WG, Varnes ME, Boothman DA,. beta-Lapachone-induced apoptosis in human prostate cancer cells: involvement of NQO1/xip3. Exp Cell Res 2001; 267: 95-106 (Pubitemid 32579145)
19. Kanaan YM, Das JR, Bakare O, et al,. Biological evaluation of 2,3-dichloro-5,8-dimethoxy-1,4-naphthoquinone as an anti-breast cancer agent. Anticancer Res 2009; 29: 191-9
20. Rockwell S, Sartorelli AC, Tomasz M, Kennedy KA,. Cellular pharmacology of quinone bioreductive alkylating agents. Cancer Metastasis Rev 1993; 12: 165-76 (Pubitemid 23220679)
21. Wang X, Thomas B, Sachdeva R, et al,. Mechanism of arylating quinone toxicity involving Michael adduct formation and induction of endoplasmic reticulum stress. Proc Natl Acad Sci U S A 2006; 103: 3604-9 (Pubitemid 43376602)
22. Suzuki M, Amano M, Choi J, et al,. Synergistic effects of radiation and beta-lapachone in DU-145 human prostate cancer cells in vitro. Radiat Res 2006; 165: 525-31
23. Sedelnikova OA, Redon CE, Dickey JS, Nakamura AJ, Georgakilas AG, Bonner WM,. Role of oxidatively induced DNA lesions in human pathogenesis. Mutat Res 2010; 704: 152-9
24. Dayal D, Martin SM, Owens KM, et al,. Mitochondrial complex II dysfunction can contribute significantly to genomic instability after exposure to ionizing radiation. Radiat Res 2009; 172: 737-45
25. Cook JA, Gius D, Wink DA, Krishna MC, Russo A, Mitchell JB,. Oxidative stress, redox, and the tumor microenvironment. Semin Radiat Oncol 2004; 14: 259-66 (Pubitemid 38903230)
26. Boothman DA, Trask DK, Pardee AB,. Inhibition of potentially lethal DNA damage repair in human tumor cells by beta-lapachone, an activator of topoisomerase I. Cancer Res 1989; 49: 605-12 (Pubitemid 19050323)
27. Boothman DA, Meyers M, Fukunaga N, Lee SW,. Isolation of x-ray-inducible transcripts from radioresistant human melanoma cells. Proc Natl Acad Sci U S A 1993; 90: 7200-4 (Pubitemid 23222417)
28. Simic M, Hayon E,. A model of radiation sensitization by quinones. Int J Radiat Biol Relat Stud Phys Chem Med 1972; 22: 507-11
29. Werbin H, Strom ET,. Photochemistry of electron-transport quinones. I. Model studies with 2-methyl-1,4-naphthoquinone (vitamin K3). J Am Chem Soc 1968; 90: 7296-301
30. Wu CT, Chen WC, Liao SK, Hsu CL, Lee KD, Chen MF,. The radiation response of hormone-resistant prostate cancer induced by long-term hormone therapy. Endocr Relat Cancer 2007; 14: 633-43
31. Cronauer MV, Schulz WA, Burchardt T, Ackermann R, Burchardt M,. Inhibition of p53 function diminishes androgen receptor-mediated signaling in prostate cancer cell lines. Oncogene 2004; 23: 3541-9 (Pubitemid 38658420)
32. Tagliarino C, Pink JJ, Reinicke KE, Simmers SM, Wuerzberger-Davis SM, Boothman DA,. Mu-calpain activation in beta-lapachone-mediated apoptosis. Cancer Biol Ther 2003; 2: 141-52
33. Jeong SY, Park SJ, Yoon SM, et al,. Systemic delivery and preclinical evaluation of Au nanoparticle containing beta-lapachone for radiosensitization. J Control Release 2009; 139: 239-45
34. Blanco E, Bey EA, Khemtong C, et al,. Beta-lapachone micellar nanotherapeutics for non-small cell lung cancer therapy. Cancer Res 2010; 70: 3896-904