1714
Invest New Drugs (2012) 30:1709–1714
10. Acharya BR, Bhattacharyya B, Chakrabarti G (2008) The natural
naphthoquinone plumbagin exhibits antiproliferative activity and
disrupts the microtubule network through tubulin binding.
11. Acharya BR, Choudhury D, Das A, Chakrabarti G (2009) Vitamin
K3 disrupts the microtubule networks by binding to tubulin: a
novel mechanism of its antiproliferative activity. Biochemistry
anticancer drug that exerts its effect via multiple
mechanistic pathways might provide the answer for new
generation of drugs that are able to overcome multidrug
resistant cancer cells. These drugs may be able to inhibit
cross communication among the different pathways that
allow for cancer cell survival.
12. Cai W, Hassani M, Karki R, Walter ED, Koelsch KH, Seradj H,
Lineswala JP, Mirzaei H, York JS, Olang F, Sedighi M, Lucas JS,
Eads TJ, Rose AS, Charkhzarrin S, Hermann NG, Beall HD,
Behforouz M (2010) Synthesis, metabolism and in vitro cytotox-
icity studies on novel lavendamycin antitumore agents. Bioorg &
Acknowledgement This work was supported in part by grant
number 5-U54-CA914-31 (Howard University/Johns Hopkins Cancer
Center Partnership).
13. Tudor G, Gutierrez P, Aguilera_Gutierrez A, Sausville E
(2002) Cytoxocitiy and apoptosis of benzoquinones: redox
cycling, cytochrome c release, and BAD protein expression.
14. Bakare O, Ashendel CL, Peng H, Zalkow LH, Burgess EM (2003)
Synthesis and MEK1 inhibitory activities of imido- substituted 2-
Chloro-1, 4-naphthoquinones. Bioorg Med Chem 11:3165–3170
15. Berhe S, Kanaan Y, Copeland RL, Wright DA, Zalkow LH,
Bakare O (2008) Microwave-assisted synthesis of imido-
substituted 2-chloro-1, 4-naphthoquinone derivatives and their
cytotoxic activities on three human prostate cancer cell lines. Lett
Drug Des Discovery 5(8):485–488
16. Copeland RL Jr, Das JR, Bakare O, Enwerem NM, Berhe S,
Hillaire K, White D, Beyene D, Kassim K, Kanaan Y (2007)
Cytotoxicity of 2, 3-dichloro-5, 8-dimethoxy-1, 4-naphthoquinone
in androgen-dependent and –independent prostate cancer cell
lines. Anticancer Res 27:1537–1546
17. Kanaan Y, Das JR, Bakare O, Enwerem NM, Berhe S, Beyene D,
Williams V, Zhou Y, Copeland RL Jr (2009) Biological evaluation
of 2, 3-dichloro-5, 8-dimethoxy-1, 4-naphthoquinone as an anti-
breast cancer agent. Anticancer Res 29:191–200
References
1. Ashe C (2005) Antitumor quinones. Mini-Rev Med Chem 5:449–467
2. Garuti L, Roberti M, Pizzirani D (2007) Nitrogen-containing
heterocyclic quinones: a class of potential selective antitumor
agents. Med Chem 7:481–489
3. Hadden MK, Hill SA, Davenport J, Matts RL, Blagg BS (2009)
Synthesis and evaluation of Hsp90 inhibitors that contain the 1, 4-
naphthoquinone scaffold. Bioorg Med Chem 17:634–640.
4. Lavergne O, Fernandes A, Brehu L, Sidhu A, Brezak M, Prevost
G, Ducommun B, Contour-Galcera M (2006) Synthesis and
biological evaluation of novel heterocyclic quinines as inhibitors
of the dual specificity protein phosphatase CDC25C. Bioorg Med
5. Brun M, Braud E, Angotti D, Mondesert O, Quaranta M,
Montes M, Miteva M, Gresh N, Ducommun B, Garbay C
(2005) Design, synthesis, and biological evaluation of novel
naphthoquinone derivatives with CDC25 phosphatase inhibito-
ry activity. Bioorg Med Chem 13:4871–4879. doi:10.1016/j.
6. Han Y, Shen H, Carr BI, Wipf P, Lazo JS, Pan S (2004) NAD(P)
H: quinone Oxidoreductase-1-Dependent AND –independent
cytotoxicity of potent quinone Cdc25 phosphatase inhibitors.
7. Kumar S, Malachowski WP, DuHadaway JB, LaLonde JM,
Carroll PJ, Jaller D, Metz R, Prendergast GC, Muller AJ (2008)
Indoleamine 2,3-Dioxygenase is the anticancer target for a novel
series of potent naphthoquinone-based inhibitors. J Med Chem
8. Lee JH, Cheong J, Park Y, Choi YH (2005) Down-regulation of
cyclooxygenase-2 and telomerase activity by β-lapachone in
human prostate carcinoma cells. Pharm Res 51:553–560.
9. Lu Q, Liu W, Ding J, Cai J, Duan W (2002) Shikonin derivatives:
synthesis and inhibition of human telomerase. Bioorg Med Chem
Lett 12:1375–1378
18. Empirical formula, C17H8ClNO3; Temperature, 295(2) K; CuKα,
Space group, P -1; a=8.5956(3) Å, b=12.8824(5) Å, c=13.2479(5)
Å, α=74.485(3)°, β=74.706(3)°, γ=71.518(3)°; Volume, 1314.65
(8) Å3; Z=4; Theta range for data collection, 4.57 to 77.56°;
Reflections collected, 10515; Independent reflections, 5481 [R(int)=
0.0229]; Semi-empirical Absorption correction, Tmax, Tmin,
1.00000 and 0.66678; Full-matrix least-squares refinement on F2;
Data/restraints/parameters, 5481/0/397; Goodness-of-fit on F2,
1.072; Final R indices [I>2sigma(I)], R1=0.0561, wR2=0.1768,
R indices (all data), R1=0.0617, wR2=0.1806; Largest diff. peak
and hole, 0.370 and -0.271 e.Å−3
19. Dzieduszycka M, Bontemps-Gacz MM, Stefanska B, Martell S,
Piwkowska A, Arciemiuk M, Borowski E (2006) Synthesis of 7-
oxo-7H-naphthol[1, 2, 3-de]quinoline derivatives as potential
anticancer agents active on multidrug resistant cell lines Bioorg.
Bioorg Med Chem 14:2880–2886