Sesquiterpene lactones inhibit luciferase but not β-galactosidase activity in vitro and ex vivo

Analytical Biochemistry

Volumn 328, Issue 2, 2004, Pages 147-154

  Lindenmeyer, Maja T ^a   García Piñeres, Alfonso J ^a   Castro, Victor ^b   Merfort, Irmgard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

^b UNIVERSIDAD DE COSTA RICA   (Costa Rica)

Author keywords

Luciferase; Parthenolide; Reporter gene assay; Sesquiterpene lactones; Galactosidase

Indexed keywords

BIOACTIVITY; BIOLUMINESCENCE; ENZYME ACTIVITY; ESCHERICHIA COLI; ESTERS;

GALACTOSIDASES; LUCIFERASE; PARTHENOLIDE; REPORTER GENE ASSAYS; SESQUITERPENE LACTONES;

TRANSCRIPTION;

BACTERIAL ENZYME; BETA GALACTOSIDASE; ENZYME INHIBITOR; MILLERIA QUINQUEFLORA EXTRACT; PARTHENOLIDE; PLANT EXTRACT; SESQUITERPENE LACTONE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG TARGETING; ENZYME ACTIVITY; ENZYME CONFORMATION; ENZYME INHIBITION; ESCHERICHIA COLI; IN VITRO STUDY; IN VIVO STUDY; MEDICINAL PLANT; MILLERIA QUINQUEFLORA; NONHUMAN; PRIORITY JOURNAL;

ESCHERICHIA COLI;

EID: 2142824175     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ab.2004.01.021     Document Type: Article

References (36)

1. Lee J.I., Burckart G.J. Nuclear factor kappa B: important transcription factor and therapeutic target. J. Clin. Pharmacol. 38:1998;981-993
2. Zhong H., Voll R.E., Ghosh S. Phosphorylation of NF-kappaB p65 by PKA stimulates transcriptional activity by promoting a novel bivalent interaction with the coactivator CBP/p300. Mol. Cell. 1:1998;661-671
3. Karin M., Ben Neriah Y. Phosphorylation meets ubiquitination: the control of NF-kappaB activity. Annu. Rev. Immunol. 18:2000;621-663
4. Chen L.F., Greene W.C. Regulation of distinct biological activities of the NF-kappaB transcription factor complex by acetylation. J. Mol. Med. 81:2003;549-557
5. Bremner P., Heinrich M. Natural products as targeted modulators of the nuclear factor-kappaB pathway. J. Pharm. Pharmacol. 54:2002;453-472
6. D'Acquisto F., May M.J., Ghosh S. Inhibition of nuclear factor kappa B (NF-κB): an emerging theme in anti-inflammatory therapies. Mol. Interv. 2:2002;22-35
7. Bronstein I., Fortin J., Stanley P.E., Stewart G.S., Kricka L.J. Chemiluminescent and bioluminescent reporter gene assays. Anal. Biochem. 219:1994;169-181
8. Conti E., Franks N.P., Brick P. Crystal structure of firefly luciferase throws light on a superfamily of adenylate-forming enzymes. Structure. 4:1996;287-298
9. Huber R.E., Gupta M.N., Khare S.K. The active site and mechanism of the beta-galactosidase from Escherichia coli. Int. J. Biochem. 26:1994;309-318
10. Jacobson R.H., Zhang X.J., DuBose R.F., Matthews B.W. Three-dimensional structure of beta-galactosidase from E. coli. Nature. 369:1994;761-766
11. Nichtl A., Buchner J., Jaenicke R., Rudolph R., Scheibel T. Folding and association of beta-galactosidase. J. Mol. Biol. 282:1998;1083-1091
12. Nguyen V.T., Morange M., Bensaude O. Protein denaturation during heat shock and related stress. Escherichia coli beta-galactosidase and Photinus pyralis luciferase inactivation in mouse cells. J. Biol. Chem. 264:1989;10487-10492
13. Deroo B.J., Archer T.K. Proteasome inhibitors reduce luciferase and beta-galactosidase activity in tissue culture cells. J. Biol. Chem. 277:2002;20120-20123
14. Lee R., McElroy W.D. Role and reactivity of sulfhydryl groups in firefly luciferase. Biochemistry. 8:1969;130-136
15. Ohmiya Y., Tsuji F.I. Mutagenesis of firefly luciferase shows that cysteine residues are not required for bioluminescence activity. FEBS Lett. 404:1997;115-117
16. Roth N.J., Rob B., Huber R.E. His-357 of beta-galactosidase (Escherichia coli) interacts with the C3 hydroxyl in the transition state and helps to mediate catalysis. Biochemistry. 37:1998;10099-10107
17. Franks N.P., Jenkins A., Conti E., Lieb W.R., Brick P. Structural basis for the inhibition of firefly luciferase by a general anesthetic. Biophys. J. 75:1998;2205-2211
18. Rocha S., Campbell K.J., Roche K.C., Perkins N.D. The p53-inhibitor pifithrin-alpha inhibits firefly luciferase activity in vivo and in vitro. BMC Mol. Biol. 4:2003;9
19. Schmidt T.J. Toxic activities of sesquiterpene lactones: structural and biochemical aspects. Curr. Org. Chem. 3:1999;577-608
20. Garcia-Pineres A.J., Castro V., Mora G., Schmidt T.J., Strunck E., Pahl H.L., Merfort I. Cysteine 38 in p65/NF-kappaB plays a crucial role in DNA binding inhibition by sesquiterpene lactones. J. Biol. Chem. 276:2001;39713-39720
21. Lyss G., Schmidt T.J., Merfort I., Pahl H.L. Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB. Biol. Chem. 378:1997;951-961
22. Bork P.M., Schmitz M.L., Kuhnt M., Escher C., Heinrich M. Sesquiterpene lactone containing Mexican Indian medicinal plants and pure sesquiterpene lactones as potent inhibitors of transcription factor NF-kappaB. FEBS Lett. 402:1997;85-90
23. Kwok B.H., Koh B., Ndubuisi M.I., Elofsson M., Crews C.M. The anti-inflammatory natural product parthenolide from the medicinal herb feverfew directly binds to and inhibits IkappaB kinase. Chem. Biol. 8:2001;759-766
24. Li-Weber M., Giaisi M., Treiber M.K., Krammer P.H. The anti-inflammatory sesquiterpene lactone parthenolide suppresses IL-4 gene expression in peripheral blood T. Eur. J. Immunol. 32:2002;3587-3597
25. Mazor R.L., Menendez I.Y., Ryan M.A., Fiedler M.A., Wong H.R. Sesquiterpene lactones are potent inhibitors of interleukin 8 gene expression in cultured human respiratory epithelium. Cytokine. 12:2000;239-245
26. Castro V., Rungeler P., Murillo R., Hernandez E., Mora G., Pahl H.L., Merfort I. Study of sesquiterpene lactones from Milleria quinqueflora on their anti-inflammatory activity using the transcription factor NF-kappa B as molecular target. Phytochemistry. 53:2000;257-263
27. Hehner S.P., Hofmann T.G., Droge W., Schmitz M.L. The antiinflammatory sesquiterpene lactone parthenolide inhibits NF-kappa B by targeting the I kappa B kinase complex. J. Immunol. 163:1999;5617-5623
28. Altschmied J., Duschl J. Set of optimized luciferase reporter gene plasmids compatible with widely used CAT vectors. Biotechniques. 23:1997;436-438
29. Baldari C.T., Di Somma M.M., Majolini M.B., Ulivieri C., Milia E., Telford J.L. NF-AT-luciferase reporter T cell lines as tools to screen immunosuppressive drugs. Biologicals. 26:1998;1-5
30. Fukuda K., Hibiya Y., Mutoh M., Ohno Y., Yamashita K., Akao S., Fujiwara H. Inhibition by parthenolide of phorbol ester-induced transcriptional activation of inducible nitric oxide synthase gene in a human monocyte cell line THP-1. Biochem. Pharmacol. 60:2000;595-600
31. Leclerc G.M., Boockfor F.R., Faught W.J., Frawley L.S. Development of a destabilized firefly luciferase enzyme for measurement of gene expression. Biotechniques. 29:2000;590-596. 598
32. Naider F., Bohak Z., Yariv J. Reversible alkylation of a methionyl residue near the active site of -galactosidase. Biochemistry. 11:1972;3202-3208
33. Meier J.L., Pruessner J.A. The human cytomegalovirus major immediate-early distal enhancer region is required for efficient viral replication and immediate-early gene expression. J. Virol. 74:2000;1602-1613
34. Stinski M.F. Cytomegalovirus promotor for expression in mammalian cells. Fernandez J.M., Fernandez J., Hoeffler J.P. Gene Expression Systems: Using Nature for the Art of Expression. 1999;211-233 Academic Press, San Diego, USA
35. Rüngeler P., Castro V., Mora G., Goren N., Vichnewski W., Pahl H.L., Merfort I., Schmidt T.J. Inhibition of transcription factor NF-kappaB by sesquiterpene lactones: a proposed molecular mechanism of action. Bioorg. Med. Chem. 7:1999;2343-2352
36. Hilmi F., Gertsch J., Bremner P., Valovic S., Heinrich M., Sticher O., Heilmann J. Cytotoxic versus anti-inflammatory effects in HeLa, Jurkat T and human peripheral blood cells caused by guaianolide-type sesquiterpene lactones. Bioorg. Med. Chem. 11:2003;3659-3663