2-[(E)-3-(6-chloroimidazo[2,1-b]thiazol-5-yl)prop-2-enyl]-5, 6-dimethoxy-3-methyl-1,4-benzoquinone: A new inhibitor of NADH dehydrogenase with antitumor activity

Arkivoc

Volumn 2004, Issue 5, 2004, Pages 76-84

  Andreani, Aldo ^a   Granaiola, Massimiliano ^a   Leoni, Alberto ^a   Locatelli, Alessandra ^a   Morigi, Rita ^a   Rambaldi, Mirella ^a   Lenaz, Giorgio ^b   Fato, Romana ^b   Bergamini, Christian ^b  

^a Dipto di Scienze Farmaceutiche   (Italy)

^b Dipto di Biochim Giovanni Moruzzi   (Italy)

Author keywords

Antitumor activity; Coenzyme Q; Imidazothiazole; Quinone

Indexed keywords

2 [3 (6 CHLOROIMIDAZO[2,1 B]THIAZOL 5 YL)PROP 2 ENYL] 5,6 DIMETHOXY 3 METHYL 1,4 BENZOQUINONE; BENZOQUINONE DERIVATIVE; ENZYME INHIBITOR; MITOCHONDRIAL ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); THIAZOLE DERIVATIVE; UBIQUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BEEF CATTLE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; GROWTH INHIBITION; HEART; IC 50; IN VITRO STUDY; MITOCHONDRIAL MEMBRANE; NONHUMAN;

EID: 2942679549     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. Potential antitumor agents 36. For part 35 see Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Garaliene, V.; Farruggia, G.; Masotti, L. Bioorg. Med. Chem. in press.
2. Wallace, D.C. Science 1992, 256, 628-632.
3. Erecinska, M.; Bryla, J.; Michalik, M.; Meglasson, M.D.; Nelson, D. Biochim. Biophys. Acta 1992, 1101, 273-295.
4. Ahammadsahib, K.I.; Hollingworth, R.M.; McGovern, J.P.; Hui, Y.H.; McLaughlin, J.L. Life Sci. 1993, 53, 1113-1120.
5. Uslu, R.; Bonavida, B. Cancer 1996, 77, 725-732.
6. Degli Esposti M. Biochem. Biophys. Acta 1998, 1364, 222-235.
7. Fato, R.; Estornell, E.; Di Bernardo, S.; Pallotti, F.; Parenti Castelli, G.; Lenaz, G. Biochemistry 1996, 35, 2705-2716.
8. Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Ghelli, A.; Ratta, M.; Benelli, B.; Degli Esposti, M. J. Med. Chem. 1995, 38, 1090-1097.
9. Andreani, A.; Rambaldi, M.; Leoni, A.; Morigi, R.; Locatelli, A.; Giorgi, G.; Lenaz, G.; Ghelli, A.; Degli Esposti, M. Eur. J. Med. Chem. 1999, 34, 883-889.
10. Merck & Co. Brit. 927531, May 29, 1963. Chem. Abstr. 1963, 59, 12710f.
11. Gu, L.Q.; Yu, L.; Yu, C. A. Biochim. Biophys. Acta 1990, 1015, 482-492.
12. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A. J. Natl. Cancer Inst. 1991, 83, 757-766.
13. Paolini, J.P.; Lendvay, L.J. J. Med. Chem. 1969, 12, 1031-1034.
14. Beyer R. E. Methods Enzymol. 1967, 10, 519-522.
15. Fato, R.; Cavazzoni, M.; Castelluccio, C.; Parenti Castelli, G.; Palmer, G.; Degli Esposti, M.; Lenaz, G. Biochem. J. 1993, 290, 225-236.
16. Gornall, A.G.; Bardawill, C. J.; David, M.M. J. Biol. Chem. 1949, 177, 751-766.
17. Yagi, T. Arch. Biochem. Biophys. 1990, 281, 305-311.
18. Degli Esposti, M.; Ghelli, A.; Crimi, M.; Estornell, E.; Fato, R; Lenaz, G. Biochem. Biophys. Res. Commun. 1993, 190, 1090-1096.