Anthracenedione Analogues-Synthesis and Biological Activity

Dzierzbicka, K.; Kołodziejczyk, A.

Artykuł - szczegóły

Tytuł artykułu

Anthracenedione Analogues-Synthesis and Biological Activity

Autorzy

Dzierzbicka K. , Kołodziejczyk A.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

This article concerns synthesis and biological activity of anthracenedione analogues which are considered as prodrugs.

Słowa kluczowe

anthracyclines anthracenedione anthraquinone analogues synthesis biological activity antineoplastic agent

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2005

Tom

Vol. 79 / nr 1

Strony

1--29

Opis fizyczny

Bibliogr. 106 poz., rys.

Twórcy

autor

Dzierzbicka K.

Department of Organic Chemistry, Gdansk University of Technology, 11/12 G. Narutowicza Street, 80-952 Gdansk, Poland

autor

Kołodziejczyk A.

Department of Organic Chemistry, Gdansk University of Technology, 11/12 G. Narutowicza Street, 80-952 Gdansk, Poland

Bibliografia

1. Wiese M. and Pajeva I.K., Curı: Med. Chem., 8, 685 (2001).
2. Avendano C. and Menendez I.C., Cum Med. Chem., 9, 159 (2002).
3. Robert J. and Jarry Ch., J. Med. Chem., 46, 4805 (2003).
4. a) Arcamone F. in Daxorubicin Antícancer Antibiatics, Academic, New York, 1981; b) Young R.C., Ozols R.F. and Myers C.E., N. Engl. J Med., 305, 139 (1981).
5. Zee-Cheng R.K.Y. and Cheng C.C., .I. Med. Chem., 21, 291 (1978).
6. Cheng C.C. and Zee-Cheng R.K.Y., Pmg. Med. Chem., 20, 83 (1983).
7. Zee-Cheng R.K.Y. and Cheng C.C., Drugs Future, 8, 229 (1983).
8. Cheng R.K.Y., Podrebaıac E.G., Menon C.S. and Cheng C.C., J. Med. Chem., 22, 501 (1979).
9. Murdock K.C., Child KG., Fabio P.F., Angier R.B., Wallace R.E., Durr F.E. and Citarella R.V., J. Med. Chem., 22, 1024 (1979).
10. Murdock K.C., U.S. Patent 4,428,882, 1981; Chem. Abstı: 1981, 94, 156626; U.S. Patent 4, 278, 605, 1981; Chem. Abstr 1981, 95, 168867.
11. Faulds D., Balfour J.A., Chrisp P. and Langtry H.D., Drugs, 41, 400 (1991).
12. Reszka K., Hartley J.A., Kolodziejczyk P. and Lown J.W., Bíachem. Pharmacal., 38, 4253 (1989).
13. Kolodziejczyk P., Reszka K. and Lown J.W., Free Radical Biol. Med., 5, 13 (1988).
14. Blanz J., Mewes K., Ehninger G., Proksch B., Waidelich D., Greger B. and Zeller K.P., Drug Metab. Dispas., 19, 371 (1991).
15. Mewes K., Blanz J., Ehninger G., Gebhardt R. and Zeller K.P., Cancer Res., 53, 5135 (1993).
16. a) Fisher G.R., Gutierrez P.L., Oldcome M.A. and Patterson L.H., Biochem. Pharmacol. , 43, 575 (1992);b) Tumminello F.M., Leto G., Gebbia N., Gebbia V., Russo A. and Rausa L., Cancer Treat. Rep., 71, 529(l987); c) Perkins W.E., Schroeder R.L., Carrano R.A. and Imondi A.R., Cancer Dear. Rep., 68, 841(1984).
17. a) Fabio P.F., Fields T.L., Yang-I Lin E., Burden E.J., Carvajal S., Murdock K C. and Lang Jr. S.A.,J Med. Chem., 21, 273 (l978); b) Rutia M. and Shubik P., J Nail. Cancer Inst., 48, 721 (1972).
18. Elson-Dew R., Adu Parasitol., 1-62 (1968); WHO Tech Rep. Sen, 421, 5-52 (1969).
19. Showalter 1-1.D.H., Johnson J .L., Hoftiezer J .M., Turner W.R., Werbel L.M., Leopold W.R., Shillis J .L.,Jackson R.C. and Elslager E.F., J. Med. Chem., 30, 121 (1987).
20. Klohs W.D., Steinkampf R.W., Havlick M.J. and Jackson R.C., Cancer Res., 46, 4352 (1986).
21. a) Dzieduszycka M., Stefańska B., Kołodziejczyk P., Borowski E. and Martelli S., II Farmaco, 42, 219 (1987); b) Stefanska B., Dzieduszycka M., Martelli S. and Borowski E.,J Med. Chem., 32, 1724 (1989).
22. Dzieduszycka M., Martelli S., Tarasiuk J ., Paradziej-Lukowicz J. and Borowski E., J. Med. Chem. , 34, 541 (1991).
23. Stefańska B., Dzieduszycka M., Martelli S., Tarasiuk J., Bontemps-Gracz M.M. and Borowski E., J. Med. Chem., 36, 38 (1993).
24. Dzieduszycka M., Stefańska B. and Borowski E., Polish J Chem., 68, 1669 ( 1994).
25. a) Pawlowska J ., Tarasiuk J., Wolf C.R., Paine M.J.I. and Borowski E., Oncol. Res., l3(5), 245 (2003);b) Tarasiuk J., Tkaczyk-Gobis K., Stefańska B., Dzieduszycka M., Priebe W., Martelli S. and Borowski E., Anti-Cancer Drug Des., 13, 923 (1998).
26. Stefańska B., Dzieduszycka M., Bontemps-Graez M.M., Borowski E., Martelli S., Supino R., Pratesi G., De Cesare M.A., Zunino F., Kuśnierczyk H. and Radzikowski Cz., J. Med Chem., 42, 3494 (1999).
27. Tkaczyk-Gobis K., Tarasiuk J., Seksek O., Stefańska B., Borowski E. and Gamier-Suillerot A., Eur J Pharmacol., 413, 131 (2001).
28.Dzieduszycka M., Martelli S., Arciemiuk M., Bontemps-Gracz M.M., Kupiec A. and Borowski E.,Bioorg. Med Chem., 10, 1025 (2002).
29. Tarasiuk J., Stefańska B., Plodzich J., Tkaczyk-Gobis K., Seksek O., Martelli S., Garnier-Suillerot A. and Borowskí E., Brit. J Pharmacol., 135, 1513 (2002).
30. Stefańska B., Arciemiuk M., Bontemps-Gracz M.M., Dzíeduszycka M., Kupiec A., Martelli S. and Borowski E., Bioorg. Med. Chem., 11, 561 (2003).
31. a) Tempczyk A., Tarasiuk J., Ossowski T. and Borowski E., Anti-Cancer DrugDes., 2, 371 (1988); b) Tarasíuk J., Garnier-Suillerot A., Stefanska B. and Borowski E., Anti-Cancer Drug Des., 7, 329 (1992).
32. Bontemps-Gracz M.M., Stefańska B., Dzieduıszycka M., Borowski E., Antonini I., Martelli S., Supino R. and Zunino F., Mnltidisciplinary Conference of Medieinal Science, March 3-5, 1999, Muszyna, Poland; Abstract Book, Abstract P-80.
33. Mazerski J., Martellí S. and Borowski E., Polish J Chem., 71, 338 (1997).
34. Krapcho A.P., Menta E., Oliva A., Di Domenico R., Fiocchi L., Maresch M.E., Gallagher C.E., Hacker M.P., Beggiolin G., Giuliani F.C., Penoni G. and Spinelli S., J Med. Chem., 41, 5429 (1998).
35. Antonini I., Polucci P., Kelland L.R., Menta E., PescalliI N.and Martelli S., J Med. Chem., 42, 2535 ( 1999).
36. Gandolﬁ C.A., Beggiolin G., Menta E., Palumbo M., Sissi C., Spinelli S. and Johnson F., J Med. Chem. ,as, 526 (1995).
37. Krapcho A.P., Getahun Z. and Avery K.L., .Synth. Commun., 20, 2139 (1990).
38. Krapcho A.P., Getahun Z., Avery K.L., Vargas K.J., Hacker M.P., Spinelli S., Pezzoni G. and Manzotti c., J Med. Chem., 34, 2373 (1991).
39.Krapcho A.P., Petry M.E., Getahun Z., Landi J.J. Jr., Stallman J., Polsenberg J.F., Gallagher C.E., Maresch M.J., Hacker M.P., Giuliani F.C., Beggolin G., Pezzoni G., Menta E., Manzotti C., Oliva A.,Spinelli S. and Tognella S., J Med. Chem., 37, 828 (1994).
40. Krapcho A.P., Landi Jr. J.J., Hacker M.P. and McCormack J .J., J. Med. Chem., 28,1l24 (1985).
41. Gandolﬁ C.A., Johnson F., Menta E., Spinelli S. and Tognella S., U.S. Pat. 5, 162, 320,Nov. 10, 1992.
42. Krapcho A.R, PCT Int. Appl. Wo 92/15300, sepı 17, 1992.
43. Gandolﬁ C.A., Menta E., Oliva A., Spinelli S. and Tognella S., PC'1`Int. Appl. W0 92/ 15566, Sept 17,1992.
44. Krapcho A.P., Maresch M.J., Hacker M.P., Hazelhurst L., Menta E., Oliva A., Spinelli S., Giuliani F.C.,"Beggiolin G., Pezzoní G., and Tognella S., Curr Med. Chem., 2, 803 (1995).
45. Krapcho A.P. and Menta E., Drugs Future, 22, 641 (1997).
46. Menta E., Di Domenico R., Oliva A., Spinelli S., Beggiolin G., Penoni G., Giuliani F.C. and Krapcho A.P., Proc. Am. Assoc. Cancer Res., 37, Absix 2015 (1996).
47. Beggiolin G., Pezzoni G., Torriani D., Ruggeri F., Randisi E., De Giorgi M., Krapcho A.P. and Giuliani F.C., Proc. Am. Assoc. Cancer Res., 37, Abstr 2663 (1996).
48. Krapcho A.P., Gallagher C.E., Hammach A., Ellis M., Menta E. and Oliva A., .I. Heterocycl. Chem., 27, 27 (1997).
49. Talbot D.C., Smith I.E., Mansi J.L., Hudson 1., Calvert A.H. and Ashley S.E., J. Clin 0ncaI., 9, 2141 (1991).
50. Walsh S.M., WalleyV.M., C11andraL., Huan S.D., Veinot J.P. and Higginson L.A.J., Can. J." CardioI., 11, 419 (1995).
51. Zalupski M.M., Benedetti J., Balcermk S.P., Hutchins L.F., Belt R.J., Hantel A. and Goodwin J .W., Invest. New Drugs, 11, 337 (1993).
52. Ingle J.N., Kuross S.A., Mailliard J.A., Loprinzi C.L., Jung S.H., Nelimark R.A., Krook J.E. and Long H.J., Cancer; 74, 1733 (1994).
53. Sosman J.A., F laherty L.E., Liu P.Y., Fletcher W., Thompson J .A., Hantel A. and Sondak V., Invest. New Drugs, 13, 83 (1995).
54. Hazlehurst L.A., Krapcho A.P. and Hacker M.P., Biochem. Pharmacal., 50, 1087 (1995).
55. Hazlehurst L.A., Krapcho A.P. and Hacker M.P., Cancer Lem, 91, 115 (1995).
56. Pezzoni G., Beggiolini G., Manzotti C., Spinelli S., Tognella S. and Guiliani F.C., Proc. Am. Assoc. Cancer Res., 34, 373 (1993).
57. Chou 1(.M., Krapcho A.P., Hom D. and Hacker M., Biochem. PharmacoI., 63, 1143 (2002).
58. Larsen A.K., Escargueil A.E. and Składanowski A., Pharmaeol. Then, 85, 217 (2000).
59. Nielsen D. and Skovsgaard T., Biachim. Biophys. Acta, 1139, 169 (1992).
60. Robert J ., Ann. Biol. Clin (Paris), 54, 3 (1996).
61. Chou K.-M., Krapcho A.P. and Hacker M., Biochem. Pharmacol., 62, 1337 (2001).
62. a) Morier-Teissier E., Bernier J .L., Lohez M., Catteau J .P. and Henichart J .P., Anti-Cancer Drug Design, 5, 291 (1990); b) Morier-Teissier E., Boitte N., Helbecque N., Bemier J .L., Pommery N., Duvalet J .L., Fournier Ch., Hecquet B., Catteau J .J. and Henichart J.P., .7. Med. Chem., 36, 2084 (1993).
63. Gatto B., Zagotto G., Sissi C., Cera C., Uriarte E., Palu G., Capranico G. and Palumbo M., .I. Med. Chem. , 39, 3114 (1996).
64. Teijeira M., Santana L., Uriarte E., Jorge M.L. and Seoane R., Farmaco, 51, 447 (1996).
65. Johnson M.G., Kiyokawa H., Tani S., Koyama J., Morris-Natsehke S.L. Mauger A., Bowers-Daines ' M.M., Lange B.C. and Lee K.H., Bioorg. Med. Chem., 5, 1469 (1997).
66. Collins K. and Mitchell J.R., Oncogene, 21, 564 (2002).
67.Perry P.J., Gowan S.M., Reszka A.P., Polucci P., Jenkins T.C., Kelland L.R. and Neidle S., .J. Med. Chem., 41, 3253 (1998).
68. Huang H.S., Hwang J.M., Jen Y.M., Lin J J., Lee K.Y., Shi C.H. and Hsu H.C., Chem. Pharm. BuII., 49, 969 (2001).
69. Huang H.S., Chiu H.F., Hwang J.M., Jen Y.M. and Tao C.W., Chem. Pharm. BuII., 49, 1346 (2001).
70. Huang H.S., Lin P.Y., Hwang J .M., Tao C.W. and Hsu H.C., Chem. Pharm. Bull., 49, 1288 (2001).
71 . Huang H.S., Chiu H.F., Chiou J.F., YehP.F., Tao C.W. and Jeng W.R.,Arch Pharm., 335, 481 (2002).
72. Huang H.S., Chiou J.F., Chiu H.F., Hwang J.M., Lin P.Y., Tao C.W., Yeh P.F. and Jeng W.R., Chem. Pharm. BuII., 50, 1491 (2002).
73. Huang H.S., Chiou J.F., Fong Y., Hou Ch.Ch., Lu Y.Ch., Wang J .Y., Shih J .W., Pan Y.R. and Lin J.J., J. Med. Chem., 46, 3300 (2003).
74. Lee H., Lee C.W. and Yang S.I., Arch Pharm. Res., 22, 380 (1999).
75.Nam N.H., Jin G.Z., Tam M.N. and Alm B.Z., Arch. Pharm. Res., 22, 592 (1999).
76. Tam M.N., Nam N.H., Jin G.Z., Song G.Y. and Ahn B.Z., Arch. Pharm., 333, 189 (2000).
77. Wei B.L., Wu S.H., Chung M.I., Won S.J. and Lin C.N., Eur: .I. Med. Chem., 35, 1089 (2000).
78. Kuo D.H., Kuo S.C. and Cheng J .T., .1. Pharm. PharmacoI., 52, 839 (2000).
79. Zagotto G., Supino R., Favini E., Moro S. and Palumbo M., Farmaco, 55, 1 (2000).
80. a) Gibson V., Anderson R.J., Brown J .R., Haﬂley S.A., Cassidy S.A., Fox K.R. and Cairns D., Pharm. Sci., 2, 49 (1996); b) Gibson V., Anderson R.J., Hartley J .A., McAdam S.R. and Cairns D., J. Pharm. Pharmac0I., 52, 599 (2000).
81. Cardia M.C., Begala M., DeLogu A. and Maccioni E., Farmaca, 56, 549 (2001).
82. Bu X., Deady L.W., Finlay G.J., Baguley B.C. and Denny W.A., .1. Med. Chem., 44, 2004 (2001).
83. Pors K., Paniwnyk Z., Ruparelia K.C., Teasdale-Spittle P.H., Hartley J .A., Kelland L.R. and Patterson L.H., .1. Med. Chem, 47, 1856 (2004).
84. Booser D.J. and Hortobagyi G.N., Drugs, 47, 223 (1994).
85. Frichc E., Skovsgaard T. and Nissan N.I., Acta 0ncoI., 28, 877 (1989).
86. Selassie C.D., Hansch C. and Khwaja T.A., .1. Med Chem., 33, 1914 (1990).
87. Bradley G., Juranka P.F. and Ling V., Biochim. Biophys. Acta, 948, 87 (1988).
88.Endicott J.A. and Ling V.,Annu. Rev Biochem., 58, 137 (1989).
89. Cholody W.M., Martelli S., Paladziej-Lukowicz J. and Konopa J., .1 Med. Chem., 33, 49 (1990).
90. Berger B., Maxquandt H. and Westendorfl, Cancer Res., 56, 2094 (1996).
91. Cholody W.M., Martelli S. and Konopa J., .1 Med. Chem., 33, 2852 (1990).
92. Sugaya T., Mimura Y., Shida Y., Osawa Y., Matsukuma I., Ikeda S., Akinaga S., Morimoto M., Ashimwa T., Okabe M., Ohno H., Gomi K. and Kasai M., .1. Med. Chem., 37,1028 (1994).
93. Antonini I., Cola D., Polucci P., Bontemps-Gracz M.M., Borowski E. and Martelli S., J. Med. Chem., 38, 3282 (1995).
94.Chołody, W. M., Martelli S. and Konopa J., .J.. Med. Chem., 35, 378 (1992).
95.Mazerski J., J. and Muchniewicz K., Acta Biachim. PoI., 47, 65 (2000).
96.Thierry A.R., Vige D., Cougblin S.S., Belli A., Drit A. and Rahman A., FASEB .1, 7, 572 (1993).
97. Cuvier C., Robles-Troupel L., Millot J.M., Lizard G., Manfait M., and et aI., Biochem. Pharm., 44, 509 (1992).
98.Cashman D. and Kellogg G.E., .J. Med Chem., 47, 1360 (2004). 6
99. Dzirzbicka K., Kolodziejczyk A.M., Wysocka-Skrzela B., Myśliwski A. and Sosnowska D., .J. Med. Chem., 44, 3606 (2001).
100. Dzierzbicka K. and Kolodziejczyk A.M., .1 Med. Chem., 46, 183 (2003).
101.Dzierzbicka K., Trzonkowski P., Sewerynek P. and Myśliwski A., .J. Med. Chem., 46, 978 (2003).
102. Dzierzbicka K., PoIish.J. Chem, 78, 409 (2004).
103. Dzierzbicka K. and Kołodziejczyk A.M., 4th Multidisciplinary Conference on Drug Research, Gdańsk-Sobieszewo 2004, Book of Abstracts P-19.
104. Najjar V.A. and Nishioka K., Nature, 228, 672 (1970).
105. Siemion Z. and Kluczyk A., Peptides, 20, 647 (1999).
106. Dzierzbicka K., Rakowski T. and Kolodziejczyk A.M., Post. Biochem., 46(4), 327 (2000).

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Bibliografia

Identyfikator YADDA

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