Design, synthesis and structure of novel para-quinones and their antibacterial activity

Chemical Biology and Drug Design

Volumn 78, Issue 5, 2011, Pages 787-799

  Pandurangan, Komala ^a   Murnaghan, Kevin D ^a   Walshe, Aurora ^a   Müller Bunz, Helge ^a   Paradisi, Francesca ^a   Morgan, Grace G ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Antibacterial; Crystal structure; Escherichia coli; Para quinone; Staphylococcus aureus

Indexed keywords

2,5 BIS(1H PYRAZOL 3 YLAMINO) 3,6 DICHLOROCYCLOHEXA 2,5 DIENE 1,4 DIONE; 2,5 DICHLORO 3,6 BIS(2 HYDROXYETHYLAMINO)CYCLOHEXA 2,5 DIENE 1,4 DIONE; 2,5 DICHLORO 3,6 BIS(5 METHYL 1H PYRAZOL 3 YLAMINO)CYCLOHEXA 2,5 DIENE 1,4 DIONE; 2,5 DICHLORO 3,6 BIS(PYRIDIN 2 YLMETHYLAMINO)CYCLOHEXA 2,5 DIENE 1,4 DIONE; 2,5 DICHLORO 3,6 BIS[2 (HYDROXYMETHYL)PHENYLAMINO]CYCLOHEXA 2,5 DIENE 1,4 DIONE; 2,5 DICHLORO 3,6 BIS[2 (PYRIDIN 2 YL)ETHYLAMINO]CYCLOHEXA 2,5 DIENE 1,4 DIONE; 2,5 DICHLORO 3,6 BIS[METHYL[2 (PYRIDIN 2 YL)ETHYL]AMINO]CYCLOHEXA 2,5 DIENE 1,4 DIONE; ANTIBIOTIC AGENT; CHLORANIL; DIETHYL 4,4'(2,5 DICHLORO 3,6 DIOXOCYCLOHEXA 1,4 DIENE 1,4 DIYL)BIS(AZANEDIYL)DIBUTANOATE; DIETHYL 6,6'(2,5 DICHLORO 3,6 DIOXOCYCLOHEXA 1,4 DIENE 1,4 DIYL)BIS(AZANEDIYL)DIHEXANOATE; LIGAND; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC SENSITIVITY; ARTICLE; CONTROLLED STUDY; DIFFRACTION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TEST; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; QUINONES; STAPHYLOCOCCUS AUREUS;

ESCHERICHIA COLI; STAPHYLOCOCCUS AUREUS;

EID: 80054100172     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01187.x     Document Type: Article

References (37)

1. Bernardo P.H., Chai C.L.L., Guen M.L., Smith G.D., Waring P. (2007) Structure-activity delineation of quinones related to the biologically active Calothrixin B. Bioorg Med Chem Lett;17:82-85.
2. Yen G.-C., Duh P.-D., Chuang D.-Y. (2000) Antioxidant activity of anthraquinones and anthrone. Food Chem;70:437-441.
3. Kuo Y.-C., Meng H.-C., Tsai W.-J. (2001) Regulation of cell proliferation, inflammatory cytokine production and calcium mobilization in primary human T lymphocytes by emodin from Polygonum hypoleucum Ohwi. Inflamm Res;50:73-82.
4. Karczewski J.M., Peters J.G.P., Noordhoek J. (1999) Quinone toxicity in DT-diaphorase-efficient and -deficient colon carcinoma cell lines. Biochem Pharmacol;57:27-37.
5. Hazra B., Kumar B., Biswas S., Pandey B.N., Mishra K.P. (2005) Enhancement of the tumour inhibitory activity, in vivo, of diospyrin, a plant-derived quinonoid, through liposomal encapsulation. Toxicol Lett;157:109-117.
6. Lin A.J., Cosby L.A., Sartorelli A.C. (1974) Quinones as anticancer agents: potential bioreductive alkylating agents. Cancer Chemother Rep Part 2;4:23-25.
7. Hoover J.R.E., Day A.R. (1954) Preparation of some imidazole derivatives of 1, 4-naphthoquinone. J Am Chem Soc;76:4148-4152.
8. Curreli N., Sollai F., Massa L., Comandini O., Rufo A., Sanjust E., Rinaldi A., Rinaldi A.C. (2001) Effects of plant-derived naphthoquinones on the growth of Pleurotus sajor-caju and degradation of the compounds by fungal cultures. J Basic Microbiol;41:253-259.
9. Howland J.L. (1963) The reversibility of inhibition by 2-heptyl-4-hydroxyquinoline-n-oxide and 2-hydroxy-3-(3-methylbutyl)-1, 4-naphthoquinone of succinate oxidation. Biochim Biophys Acta;73:665-667.
10. Mukerjee P., Majee S.B., Ghosh S., Hazra B. (2009) Apoptosis-like death in Leishmania donovani promastigotes induced by diospyrin and its ethanolamine derivative. Int J Antimicrobiol;34:596-601.
11. Izumi Y., Sawada H., Sakka N., Yamamoto N., Kume T., Katsuki H., Shimohama S., Akaike A. (2005) p-Quinone mediates 6-hydroxydopamine-induced dopaminergic neuronal death and ferrous iron accelerates the conversion of p-quinone into melanin extracellularly. J Neurosci Res;79:849-860.
12. Furie B., Bouchard B.A., Furie B.C. (1999) Vitamin K-dependent biosynthesis of g-carboxyglutamic acid. Blood;93:1798-1808.
13. Meganathan R. (2001) Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm;61:173-218.
14. Sheldon P.J., Shelman D.H. (2001) Characterization of quinone reductase activity for the mitomycin C binding protein (MRD): functional switching from a drug-activating enzyme to a drug-binding protein. Proc Natl Acad Sci U S A;98:926-931.
15. Frederick C.A., Williams L.D., Ughetto G., van der Marel G.A., van Boom J.H., Rich A., Wang A.H.-J. (1990) Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin. Biochemistry;29:2538-2549.
16. Begleiter A., Leith M.K., Thliveris J.A., Digby T. (2004) Dietary induction of NQO1 increases the antitumour activity of mitomycin C in human colon tumours in vivo. Br J Cancer;91:1624-1631.
17. Linardi M.C.F., de Oliveira M.M., Sampaio M.R.P.A. (1975) Lapachol derivative active against mouse lymphocytic leukemia P-388. J Med Chem;18:1159-1161.
18. Bachur N.R., Gordon S.L., Gee M.V.A. (1978) General mechanism for microsomal activation of quinone anticancer agents to free radicals. Cancer Res;38:1745-1750.
19. Chou F., Khan A.H., Driscoll J.S. (1976) Potential central nervous system antitumour agents. Aziridinylbenzoquinones. J Med Chem;19:1302-1308.
20. Lana E.J.L., Carazza F., Takahashi J.A. (2006) Antibacterial evaluation of 1, 4-benzoquinone derivatives. J Agric Food Chem;54:2053-2056.
21. Ong W., Yang Y., Cruciano A.C., McCarley R.L. (2008) Redox-triggered contents release from liposomes. J Am Chem Soc;130:14739-14744.
22. Nicolaou K.C., Becker J., Lim Y.H., Lemire A., Neubauer T., Montero A. (2009) Total synthesis and biological evaluation of (+)- and (-)-bisanthraquinone antibiotic BE-43472B and related compounds. J Am Chem Soc;131:14812-14826.
23. Mathew A.E., Zee-Cheng R.K.Y., Cheng C.C. (1986) Amino-substituted p-benzoquinones. J Med Chem;29:1792-1795.
24. Batra M., Kriplani P., Batra C., Ojha K.G. (2006) An efficient synthesis and biological activity of substituted p-benzoquinones. Bioorg Med Chem;14:8519-8526.
25. Batra M., Batra C., Ojha K.G. (2008) Non-traditional approaches to the synthesis of some biologically active substituted p-benzoquinones. Med Chem Res;17:604-617.
26. Bondi A., Spaulding H.E., Smith E.D., Dietz C.C. (1947) Routine method for rapid determination of susceptibility to penicillin and other antibiotics. Am J Med Sci;213:221-225.
27. Luria S.E. (1947) Recent advances in bacterial genetics. Bacteriol Rev;11:1-40.
28. Zhang S., Earle J., MacDiarmid J., Bardos T.J. (1988) Synthesis and testing of quinone-based bis(2, 2-dimethyl-l-aziridinyl)phosphinyl carbamates as radiation-potentiating antitumor agents. J Med Chem;31:1240-1244.
29. Pandurangan K., Gallagher S., Morgan G.G., Müller-Bunz H., Paradisi F. (2010) Structure and antibacterial activity of the silver(I) complex of 2-aminophenoxazine-3-one. Metallomics;2:530-534.
30. Jones G., Qian X. (1998) Photochemistry of quinone-bridged amino acids. Intramolecular trapping of an excited charge-transfer state. J Phys Chem A;102:2555-2560.
31. Foster R., Kulevsky N., Wanigasekara D.S. (1974) Reaction of amino-acids with p-benzoquinones. J Chem Soc, Perkin Trans;1:1318-1321.
32. Adams R.D., Miao S. (2004) Metal carbonyl derivatives of 1, 4-quinone and 1, 4-hydroquinone. J Am Chem Soc;126:5056-5057.
33. Nakatsuji S.I., Nobusawa M., Suzuki H., Akutsu H., Yamada J.-I. (2009) Spin-carrying benzoquinone derivatives. J Org Chem;74:9345-9350.
34. Jia W.-G., Han Y.-F., Lin Y.-J., Weng L.-H., Jin G.-X. (2009) Stepwise formation of half-sandwich iridium-based rectangles containing 2, 5-diarylamino-1, 4-benzoquinone derivative linkers. Organometallics;28:3459-3464.
35. Gleeson B., Claffey J., Ertler D., Hogan M., Müller-Bunz H., Paradisi F., Wallis D., Tacke M. (2008) Novel organotin antibacterial and anticancer drugs. Polyhedron;27:3619-3624.
36. Benigni R. (2005) Structure-activity relationship studies of chemical mutagens and carcinogens: mechanistic investigations and prediction approaches. Chem Rev;105:1767-1800.
37. Qabaja G.M., Perchellet E., Perchellet J.-P., Jones G.B. (2000) Regioselective lactonization of naphthoquinones: synthesis and antitumoral activity of the WS-5995 antibiotics. Tetrahedron Lett;41:3007-3010.