1,4-Anthraquinone: An anticancer drug that blocks nucleoside transport, inhibits macromolecule synthesis, induces DNA fragmentation, and decreases the growth and viability of L1210 leukemic cells in the same nanomolar range as daunorubicin in vitro

Anti-Cancer Drugs

Volumn 11, Issue 5, 2000, Pages 339-352

  Perchellet, Elisabeth M ^a   Magill, Molly J ^a   Huang, Xiaodong ^b   Dalke, Dawn M ^b   Hua, Duy H ^b   Perchellet, Jean Pierre ^a,b  

^a Anti Cancer Drug Laboratory   (United States)

^b KANSAS STATE UNIVERSITY   (United States)

Author keywords

1,4 Anthraquinone; DNA cleavage; L1210 cells; Macromolecule synthesis; Mitotic index; Nucleoside transport; Tumor cell growth and viability

Indexed keywords

ANTHRACENE DERIVATIVE; ANTHRACYCLINE ANTIBIOTIC AGENT; ANTHRAQUINONE DERIVATIVE; ANTINEOPLASTIC AGENT; AURINTRICARBOXYLIC ACID; CYCLOHEXIMIDE; DACTINOMYCIN; DAUNORUBICIN; DNA; DNA FRAGMENT; PROTEIN; PURINE NUCLEOSIDE; PYRIMIDINE NUCLEOSIDE; QUINIZARIN; RNA;

ARTICLE; CELL VIABILITY; CYTOSTASIS; DNA CLEAVAGE; DNA SYNTHESIS INHIBITION; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; LEUKEMIA L 1210; MACROMOLECULE; MITOSIS INDEX; NUCLEOSIDE TRANSPORT; PRIORITY JOURNAL; PROTEIN SYNTHESIS INHIBITION; RNA SYNTHESIS;

ANIMALS; ANTHRAQUINONES; ANTIBIOTICS, ANTINEOPLASTIC; BIOLOGICAL TRANSPORT; CELL SURVIVAL; DAUNORUBICIN; DNA FRAGMENTATION; DNA, NEOPLASM; DOSE-RESPONSE RELATIONSHIP, DRUG; LEUKEMIA L1210; MITOSIS; MITOTIC INDEX; NEOPLASM PROTEINS; NUCLEOSIDES; RNA, NEOPLASM; TUMOR CELLS, CULTURED;

EID: 0033910817     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/00001813-200006000-00004     Document Type: Article

References (45)

1. 1. Thomson RH. Naturally occuring quinones III: recent advances. New York: Chapman & Hall 1987.
2. 2. Moore HW. Bioactivation as a model for drug design bioreductive alkylation. Science 1977; 197: 527-32.
3. 3. Lin AJ, Cosby LA, Shansky CW, Sartorelli AC. Potential bioreductive alkylating agents. 1. Benzoquinone derivatives. J Med Chem 1972; 15: 1247-52.
4. 4. Lin AJ, Pardini RS, Cosby LA, Lillis BJ, Shansky CW, Sartorelli AC. Potential bioreductive alkylating agents. 2. Antitumor effect and biochemical studies of naphthoquinone derivatives. J Med Chem 1973; 16: 1268-71.
5. 5. Lin AJ, Shansky CW, Sartorelli AC. Potential bioreductive alkylating agents. 3. Synthesis and antineoplastic activity of acetoxymethyl and corresponding ethyl carbamate derivatives of benzoquinones. J Med Chem 1974; 17: 558-61.
6. 6. Lin AJ, Lillis BJ, Sartorelli AC. Potential bioreductive alkylating agents. 5. Antineoplastic activity of quinoline-5,8-diones, naphthazarins, and naphthoquinones. J Med Chem 1975; 18: 917-21.
7. 7. Brunmark A, Cadenas E. Redox and addition chemistry of quinoid compounds and its biological implications. Free Radical Biol Med 1989; 7: 435-77.
8. 8. O'Brien PJ. Molecular mechanisms of quinone cytotoxicity. Chem-Biol Interact 1991; 80: 1-41.
9. 9. Monks TJ, Hanzlik RP, Cohen GM, Ross D, Graham DG. Quinone chemistry and toxicity. Toxicol Appl Pharmacol 1992; 112: 2-16.
10. 10. Myers CE, Chabner BA. Anthracyclines. In: Chabner BA, Collins JM, eds. Cancer chemotherapy: principles and practice. Philadelphia, PA: Lippincott 1990: 356-81.
11. 11. Rossi L, Moore GA, Orrenius S, O'Brien PJ. Quinone toxicity in hepatocytes without oxidative stress. Arch Biochem Biophys 1986; 251: 25-35.
12. 12. Begleiter A, Leith MK, McClarty G, Beenken S, Goldenberg GJ, Wright JA. Characterization of L5178Y murine lymphoblasts resistant to quinone antitumor agents. Cancer Res 1988; 48: 1727-35.
13. 2/M cell cycle arrest and apoptosis. Free Rad Biol Med 1998; 24: 848-54.
14. 14. Liu LF. DNA topoisomerase poisons as antitumor drugs. Annu Rev Biochem 1989; 58: 351-75.
15. 15. Mimnaugh EG, Kennedy KA, Trush MA, Sinha BK. Adriamycin-enhanced membrane lipid peroxidation in isolated rat nuclei. Cancer Res 1985; 45: 3296-304.
16. 16. Ganapathi R, Grabowski D, Hoeltge G, Neelon R. Modulation of doxorubicin-induced chromosomal damage by calmodulin inhibitors and its relationship to cytotoxicity in progressively doxorubicin-resistant tumor cells. Biochem Pharmacol 1990; 40: 1657-62.
17. 17. Ling Y-H, Priebe W, Perez-Soler R. Apoptosis induced by anthracycline antibiotics in P388 parent and multidrug-resistant cells. Cancer Res 1993; 53: 1845-52.
18. 18. Ramachandran C, You W, Krishan A. Bcl-2 and mdr-1 gene expression during doxorubicin-induced apoptosis in murine leukemic P388 and P388/R84 cells. Anticancer Res 1997; 17: 3369-76.
19. 19. Motoyama N, Kulkarni AP, Hodgson E, Dauterman WC. Endogenous inhibitors of glutathione S-transferases in house flies. Pestic Biochem Physiol 1978; 9: 255-62.
20. 20. Giddings JM. Acute toxicity to Selenastmm capricornutum of aromatic compounds from coal conversion. Bull Environ Contain Toxicol 1979; 23: 360-4.
21. 2 1. Dobias L, Fiala B, Janca L. Production of anthraquinones and their effect on the life of the environment. Chem Prum 1980; 30: 183-7.
22. 22. Karukstis KK, Gruber SM, Fruetel JA, Boegeman SC. Quenching of chlorophyll fluorescence by substituted anthraquinones. Biochim Biophys Acta 1988; 932: 84-90.
23. 23. Bodian DL, Yamasaki RB, Buswell RL, Stearns JF, White JM, Kuntz ID. Inhibition of the fusion-inducing conformational change of influenza hemagglutinin by benzoquinones and hydroquinones. Biochemistry 1993; 32: 2967-78.
24. 24. Schultz TW, Sinks GD, Cronin MTD. Quinone-induced toxicity to Tetrahymena: structure-activity relationships. Aquat Toxicol 1997; 39: 267-78.
25. 25. Perchellet JP, Newell SW, Ladesich JB, et al. Antitumor activity of novel tricyclic pyrone analogs in murine leukemia cells in vitro. Anticancer Res 1997; 17: 2427-34.
26. 26. Newell SW, Perchellet EM, Ladesich JB, et al. Tricyclic pyrone analogs: a new class of microtubule-disrupting anticancer drugs effective against murine leukemia cells in vitro. Int J Oncol 1998; 12: 433-42.
27. 27. Perchellet EM, Ladesich JB, Chen Y, et al. Antitumor activity of tricyclic pyrone analogs, a new synthetic class of microtubule de-stabilizing agents, in the murine EMT-6 mammary tumor cell line in vitro. Anti-Cancer Drugs 1998; 9: 565-76.
28. 28. Perchellet EM, Ladesich JB, Magill MJ, Chen Y, Hua DH, Perchellet JP. Tricyclic pyrone analogs: a new synthetic class of bifunctional anticancer drugs that inhibit nucleoside transport, microtubule assembly, the viability of leukemic cells in vitro and the growth of solid tumors in vivo. Anti-Cancer Drugs 1999; 10: 489-504.
29. 29. Perchellet EM, Magill MJ, Huang X, Brantis CE, Hua DH, Perchellet JP. Triptycenes: a novel synthetic class of bifunctional anticancer drugs that inhibit nucleoside transport, induce DNA cleavage and decrease the viability of leukemic cells in the nanomolar range in vitro. Anti-Cancer Drugs 1999; 10: 749-66.
30. 30. Cory AH, Owen TC, Barltrop JA, Cory JG. Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture. Cancer Commun 1991; 3: 207-12.
31. 31. Chen H-X, Bamberger U, Heckel A, Guo X, Cheng Y-C. BIBW 22, a dipyridamole analogue, acts as a bifunctional modulator on tumor cells by influencing both P-glycoprotein and nucleoside transport. Cancer Res 1993; 53: 1974-7.
32. 32. Kolber MA, Broschat KO, Landa-Gonzalez B. Cytochalasin B induces cellular DNA fragmentation. FASEB J 1990; 4: 3021-7.
33. 33. Etienne A, Lepage Y, Dufraisse MC. Dihydroxy-1,4-anthracene et derives alcoyles correspondants. Leur photooxydation et leur photodimerisation. C R Seances Acad Sci D 1955; 1233-5.
34. 34. Barranco E, Martin N, Segura JL, et al. Syntheses, electrochemistry and molecular modeling of N,N'-dicyanoquinonediimine (DCNQI) derivatives of substituted 1,4-anthracenediones: precursors for organic metals. Tetrahedron 1993; 49: 4881-92.
35. 35. Martin N, Segura JL, Seoane C, et al. Synthesis and characterization of 11,11,12,12-tetracyano-1,4-anthraquinodimethanes (1,4-TCAQs): novel electron acceptors with photoinduced charge-transfer properties. J Org Chem 1995; 60: 4077-84.
36. 36. Bedworth PV, Perry JW, Marder SR. The synthesis of a symmetrically substituted α-octa(isopentoxy)anthralocyanine. J Chem Soc Chem Commun 1997; 1353-4.
37. 37. Brown JM. NCI's anticancer drug screening program may not be selecting for clinically active compounds. Oncol Res 1997; 9: 213-5.
38. 38. Morgan PF, Fine RL, Montgomery P, Marangos PJ. Multidrug resistance in MCF-7 human breast cancer cells is associated with increased expression of nucleoside transporters and altered uptake of adenosine. Cancer Chemother Pharmacol 1991; 29: 127-32.
39. 39. Marina NM, Belt JA. Effect of nucleoside transport inhibitors on thymidine salvage and the toxicity of nucleoside analogs in mouse bone marrow granulocyte-macrophage progenitor cells. Cancer Commun 1991; 3: 367-72.
40. 40. Cao SS, Zhen YS. Potentiation of antimetabolite antitumor activity in vivo by dipyridamole and amphotericin B. Cancer Chemother Pharmacol 1989; 24: 181-6.
41. 41. Hughes JM, Tattersall MHN. Potentiation of methotrexate lymphocytotoxicity in vitro by inhibitors of nucleoside transport. Br J Cancer 1989; 59: 381-4.
42. 42. Muggia FM, Slowiaczek P, Tattersall MHN. Characterization of conditions in which dipyridamole enhances methotrexate toxicity in L1210 cells. Anticancer Res 1987; 7: 161-6.
43. 43. Grem JL, Fischer PH. Augmentation of 5-fluorouracil cytotoxicity in human colon cancer cells by dipyridamole. Cancer res 1985; 45: 2967-72.
44. 44. Kusumoto H, Maehara Y, Anai H, Kusumoto T, Sugimachi K. Potentiation of adriamycin cytotoxicity by dipyridamole against HeLa cells in vitro and sarcoma 180 cells in vivo. Cancer Res 1988; 48: 1208-12.
45. 45. Ramu N, Ramu A. Circumvention of adriamycin resistance by dipyridamole analogues: a structure-activity relationship study. Int Cancer 1989; 43: 487-91.