Chapter 3 Natural substrates and inhibitors of multidrug resistant pumps (MDRs) redefine the plant antimicrobials

Advances in Phytomedicine

Volumn 3, Issue C, 2006, Pages 45-59

  Tegos, George P ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957071948     PISSN: 1572557X     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-557X(06)03003-0     Document Type: Review

References (76)

1. Aeschlimann J.R., Dresser L.D., Kaatz G.W., and Rybak M.J. Effects of NorA inhibitors on in vitro antibacterial activities and postantibiotic effects of levofloxacin, ciprofloxacin, and norfloxacin in genetically related strains of Staphylococcus aureus. Antimicrob Agents Chemother 43 (1999) 335-340
2. Agarwal S.K., Singh S.S., Verma S., and Kumar S. Antifungal activity of anthraquinone derivatives from Rheum emodi. J Ethnopharmacol 72 (2000) 43-46
3. Appendino G., Della Porta C., Conseil G., Sterner O., Mercalli E., Dumontet C., and Di Pietro A. A new P-glycoprotein inhibitor from the caper spurge (Euphorbia lathyris). J Nat Prod 66 (2003) 140-142
4. Barabote R.D., Johnson O.L., Zetina E., San Francisco S.K., Fralick J.A., and San Francisco M.J. Erwinia chrysanthemi tolC is involved in resistance to antimicrobial plant chemicals and is essential for phytopathogenesis. J Bacteriol 185 (2003) 5772-5778
5. Beck W., Cirtain M., Glover C., Felsted R., and Safa A. Effects of indole alkaloids on multidrug resistance and labeling of P-glycoprotein by a photoaffinity analog of vinblastine. Biochem Biophys Res Com 153 (1988) 959-966
6. Belofsky G., Percivil D., Lewis K., Tegos G., and Ekart J. Phenolic metabolites of Dalea versicolor that enhance antibiotic activity against multi-drug resistant bacteria. J Nat Prod 67 (2004) 481-484
7. Chen G., and Waxman D. Complete reversal by thaliblastine of 490-fold adriamycin resistance in multidrug-resistant (MDR) human breast cancer cells. Evidence that multiple biochemical changes in MDR cells need not correspond to multiple functional determinants for drug resistance. J Pharmacol Exp Ther 274 (1995) 1271-1277
8. Chung Y.J., and Saier Jr. M.H. SMR-type multidrug resistance pumps. Curr Opin Drug Discov Devel 4 (2001) 237-245
9. Corea G., Fattorusso E., Lanzotti V., Taglialatela-Scafati O., Appendino G., Ballero M., Simon P.N., Dumontet C., and Di Pietro A. Jatrophane diterpenes as P-glycoprotein inhibitors. First insights of structure-activity relationships and discovery of a new, powerful lead. J Med Chem 46 (2003) 3395-3402
10. Cowan M. Plant products as antimicrobial agents. Clin Microbiol Rev 4 (1999) 564-582
11. Cyong J., Matsumoto T., Arakawa K., Kiyohara H., Yamada H., and Otsuka Y. Anti-bacteroides fragilis substance from rhubarb. J Ethnopharmacol 19 (1987) 279-283
12. Deferme S., Mols R., Van Driessche W., and Augustijns P. Apricot extract inhibits the P-gp-mediated efflux of talinolol. J Pharm Sci 91 (2003) 2539-2548
13. Deferme S., Van Gelder J., and Augustijns P. Inhibitory effect of fruit extracts on P-glycoprotein-related efflux carriers: an in-vitro screening. J Pharm Pharmacol 54 (2002) 1213-1219
14. Didry N., Dubreuil L., and Pinkas M. Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. Pharmazie 49 (1994) 681-683
15. Dixon R. Natural products and plant disease resistance. Nature 411 (2001) 843-847
16. Elkins C.A., and Nikaido H. Substrate specificity of the RND-type multidrug efflux pumps AcrB and AcrD of Escherichia coli is determined predominantly by two large periplasmic loops. J Bacteriol 184 (2002) 6490-6498
17. El-Masry E.M., and Abou-Donia D.M. Reversal of P-glycoprotein expressed in Escherichia coli leaky mutant by ascorbic acid. Life Sci 73 (2003) 981-991
18. Fiamegos Y, Vervoort J, Nanos CG, Tegos G, Lewis K. (2006) Caffeoylquinic acids from Artemisia absinthium inhibit bacterial multidrug resistance pumps. J Agric Food Chem.
19. Foster B.C., Foster M., Vandenhoek S., Krantis A., Budzinski J.W., Arnason J.T., Gallicano K.D., and Choudri S. An in vitro evaluation of human cytochrome P450 3A4 and P-glycoprotein inhibition by garlic. J Pharm Pharm Sci 4 (2001) 176-184
20. Gibbons S., Oluwatuyi M., and Kaatz G.W. A novel inhibitor of multidrug efflux pumps in Staphylococcus aureus. J Antimicrob Chemother 51 (2003) 13-17
21. Gonzalez-Pasayo R., and Martinez-Romero E. Multiresistance genes of Rhizobium etli CFN42. Mol Plant Microbe Interact 13 (2000) 572-577
22. Hatano T., Uebayashi H., Ito H., Shiota S., Tsuchiya T., and Yoshida T. Phenolic constituents of Cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillin-resistant Staphylococcus aureus. Chem Pharm Bull (Tokyo) 47 (1999) 1121-1127
23. Hiraga K., Wanigasekera A., Sugi H., Hamanaka N., and Oda K. A novel screening for inhibitors of a pleiotropic drug resistant pump, Pdr5, in Saccharomyces cerevisiae. Biosci Biotechnol Biochem 65 (2001) 1589-1595
24. Hooper D. Target modification as a mechanism of antimicrobial resistance. In: Lewis K., Salyers A., Taber H., and Wax R. (Eds). Bacterial resistance to antimicrobials. Mechanisms, genetics, medical practice and public health (2001), Marcell Dekker, New York 161-192
25. Hooper D. Fluoroquinolone resistance among Gram-positive cocci. Lancet Infect Dis 2 (2002) 530-538
26. Hsieh P.C., Siegel S., Rogers B., Davis D., and Lewis K. Bacteria lacking a multidrug pump: a sensitive tool for drug discovery. Proc Natl Acad Sci USA 95 (1998) 6602-6606
27. Ikegawa T., Ushigome F., Koyabu N., Morimoto S., Shoyama Y., Naito M., Tsuruo T., Ohtani H., and Sawada Y. Inhibition of P-glycoprotein by orange juice components, polymethoxyflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells. Cancer Lett 160 (2000) 21-28
28. Jennings B.R., and Ridler P. Interaction of chromosomal stains with DNA. An electrofluorescence study. Biophys Struct Mech 10 (1983) 71-79
29. Jodoin J., Demeule M., and Beliveau R. Inhibition of the multidrug resistance P-glycoprotein activity by green tea polyphenols. Biochim Biophys Acta 1542 (2002) 149-159
30. Kaatz G.W., Moudgal V., Seo S.M., and Kristiansen J.E. Phenothiazines and thioxanthenes inhibit multidrug efflux pump activity in Staphylococcus aureus. Antimicrob Agents Chemother 47 (2003) 719-726
31. Kaatz G.W., Seo S.M., O'Brien L., Wahiduzzaman M., and Foster T.J. Evidence for the existence of a multidrug efflux transporter distinct from NorA in Staphylococcus aureus. Antimicrob Agents Chemother 44 (2000) 1404-1406
32. Kean E.A., Gutman M., and Singer T.P. Rhein, a selective inhibitor of the DPNH-flavin step in mitochondrial electron transport. Biochem Biophys Res Commun 40 (1970) 1507-1513
33. Krupka R. Uncoupled active transport mechanisms accounting for low selectivity in multidrug carriers: P-glycoprotein and SMR antiporters. J Membr Biol 172 (1999) 129-143
34. Lage H. ABC-transporters: implications on drug resistance from microorganisms to human cancers. Int J Antimicrob Agents 22 (2003) 188-199
35. Leonard G.D., Fojo T., and Bates S.E. The role of ABC transporters in clinical practice. Oncologist 8 (2003) 411-424
36. Lewis K. Versatile drug sensors of bacterial cells. Curr Biol 9 (1999) 403-407
37. Lewis K. In search of natural substrates and inhibitors of MDR pumps. J Mol Microbiol Biotechnol 2 (2001) 247-254
38. Lewis K, Lomovskaya O. (2001) Drug efflux. In: Lewis K, Salyers A, Taber H, Wax R, editors. Bacterial resistance to antimicrobials: Mechanisms, genetics, medical practice and public health. New York: Marcell Dekker, pp. 61-90.
39. Lomovskaya O., and Lewis K. Emr, an Escherichia coli locus for multidrug resistance. Proc Natl Acad Sci USA 89 (1992) 8938-8942
40. Lomovskaya O., Warren M., Lee A., Galazzo J., Fronko R., Lee M., Blais J., Cho D., Chamberland S., Renau T., Leger R., Hecker S., Watkins W., Hoshino K., Ishida H., and Lee V.J. Identification and characterization of inhibitors of multidrug resistance efflux pumps in Pseudomonas aeruginosa: novel agents for combination therapy. Antimicrob Agents Chemother 45 (2001) 105-116
41. Lomovskaya O., and Watkins W. Inhibition of efflux pumps as a novel approach to combat drug resistance in bacteria. J Mol Microbiol Biotechnol 3 (2001) 225-236
42. Lomovskaya O., Zgurskaya H., and Nikaido H. It takes three to tango. Nat Biotechnol 20 (2003) 1210-1212
43. Mallea M., Mahamoud A., Chevalier J., Alibert-Franco S., Brouant P., Barbe J., and Pages J.M. Alkylaminoquinolines inhibit bacterial antibiotic efflux pump in multidrug resistant clinical isolates. Biochem J 376 (2003) 801-805
44. Mao W., Warren M., Black D.S., Satou T., Murata T., Nishino T., Gotoh N., and Lomovskaya O. On the mechanism of substrate specificity by resistance nodulation division (RND)-type multidrug resistance pumps: the large periplasmic loops of MexD from Pseudomonas aeruginosa are involved in substrate recognition. Mol Microbiol 46 (2002) 889-901
45. Markham P.N., and Neyfakh A.A. Efflux-mediated drug resistance in Gram-positive bacteria. Curr Opin Microbiol 4 (2001) 509-514
46. Markham P.N., Westhaus E., Klyachko K., Johnson M.E., and Neyfakh A.A. Multiple novel inhibitors of the NorA multidrug transporter of Staphylococcus aureus. Antimicrob Agents Chemother 43 (1999) 2404-2408
47. Mitchell B.A., Brown M., and Skurray R.A. QacA multidrug efflux pump from Staphylococcus aureus: comparative analysis of resistance to diamidines, biguanidines, and guanylhydrazones. Antimicrob Agents Chemother 42 (1998) 475-477
48. Morel C., Stermitz F., Tegos G., and Lewis K. Isoflavones as potentiators of antibacterial activity. J Agric Food Chem 51 (2003) 5677-5679
49. Morrissey J.P., and Osbourn A. Fungal resistance to plant antibiotics as a mechanism of pathogenesis. Microbiol Mol Biol Rev 63 (1999) 708-724
50. Motohashi N., Kurihara T., Wakabayashi H., Yaji M., Mucsi I., Molnar J., Maruyama S., Sakagami H., Nakashima H., Tani S., Shirataki Y., and Kawase M. Biological activity of a fruit vegetable, "Anastasia green", a species of sweet pepper. In Vivo 15 (2001) 437-442
51. Murata T., Kuwagaki M., Shin T., Gotoh N., and Nishino T. The substrate specificity of tripartite efflux systems of Pseudomonas aeruginosa is determined by the RND component. Biochem Biophys Res Commun 299 (2002) 247-251
52. Musumeci R., Speciale A., Costanzo R., Annino A., Ragusa S., Rapisarda A., Pappalardo M.S., and Lauk L. Berberis aetnensis C, Presl. extracts: antimicrobial properties and interaction with ciprofloxacin. Int J Antimicrob Agents 22 (2003) 48-53
53. Nikaido H. Microdermatology: cell surface in the interaction of microbes with the external world. J Bacteriol 181 (1999) 4-8
54. Norton S. Useful plants of dermatology. I. Hydnocarpus and chaulmoogra. J Am Acad Dermatol 31 (1994) 683-686
55. Palumbo J.D., Kado C.I., and Phillips D.A. An isoflavonoid-inducible efflux pump in Agrobacterium tumefaciens is involved in competitive colonization of roots. J Bacteriol 180 (1998) 3107-3113
56. Paulsen I.T., Chen J., Nelson K.E., and Saier Jr. M.H. Comparative genomics of microbial drug efflux systems. In: ITPaK L. (Ed). Microbial Multidrug Efflux (2002), Horizon Press, Norfolk 5-21
57. Perloff M.D., von Moltke L., Stormer E., Shader R.I., and Greenblatt D.J. Saint John's wort: an in vitro analysis of P-glycoprotein induction due to extended exposure. Br J Pharmacol 134 (2001) 1601-1608
58. Ranganathan K.R., and Seshadri T. Minor phenolic components of seed hulls of Hydnocarpus-Wightiana - Constitution of methoxyhydnocarpin. Indian J Chem 12 (1974) 993-996
59. Renau T.E., Leger R., Flamme E.M., Sangalang J., She M.W., Yen R., Gannon C.L., Griffith D., Chamberland S., Lomovskaya O., Hecker S.J., Lee V.J., Ohta T., and Nakayama K. Inhibitors of efflux pumps in Pseudomonas aeruginosa potentiate the activity of the fluoroquinolone antibacterial levofloxacin. J Med Chem 42 (1999) 4928-4931
60. Rogers B., Decottignies A., Kolaczkowski M., Carvajal E., Balzi E., and Goffeau A. The pleitropic drug ABC transporters from Saccharomyces cerevisiae. J Mol Microbiol Biotechnol 3 (2001) 207-214
61. Saier Jr. M.H., and Paulsen I.T. Phylogeny of multidrug transporters. Semin Cell Dev Biol 12 (2001) 205-213
62. Schmeller T., Latz-Bruning B., and Wink M. Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores. Phytochemistry 44 (1997) 257-266
63. Spencer CM, Wilde MI. (1997) Diacerein. Drugs 53:98-106; discussion 107-108.
64. Stermitz F.R., Beeson T., Mueller P.J., Hsiang J., and Lewis K. Staphylococcus aureus MDR efflux pump inhibitors from a Berberis and a Mahonia (sensu strictu) species. Biochem Syst Ecol 29 (2001) 793-798
65. Stermitz F.R., Cashman K., Halligan K.M., Morel C., Tegos G.P., and Lewis K. Polyacylated neohesperidosides from Geranium caespitosum: bacterial multidrug resistance pump inhibitors. Bioorg Med Chem Lett 13 (2003) 1915-1918
66. Stermitz F.R., Lorenz P., Tawara J.N., Zenewicz L.A., and Lewis K. Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5′-methoxyhydnocarpin, a multidrug pump inhibitor. Proc Natl Acad Sci USA 97 (2000) 1433-1437
67. Stermitz F.R., Scriven L.N., Tegos G., and Lewis K. Two flavonols from Artemisa annua which potentiate the activity of berberine and norfloxacin against a resistant strain of Staphylococcus aureus. Planta Med 68 (2002) 1140-1141
68. Stermitz F.R., Tawara-Matsuda J., Lorenz P., Mueller P., Zenewicz L., and Lewis K. 5′-Methoxyhydnocarpin-D and pheophorbide A: Berberis species components that potentiate berberine growth inhibition of resistant Staphylococcus aureus. J Nat Prod 63 (2000) 1146-1149
69. Tegos G, Higginbotham A, Ball A, Stermitz FR, Lewis K. (2006) Neohesperidosides from Geranium caespitosum; versatile multidrug pump inhibitors Chemistry & Biology, submitted.
70. Tegos G., Stermitz F.R., Lomovskaya O., and Lewis K. Multidrug pump inhibitors uncover remarkable activity of plant antimicrobials. Antimicrob Agents Chemother 46 (2002) 3133-3141
71. Ulukan H., and Swaan P.S. Camptothecins: a review of their chemotherapeutic potential. Drugs 62 (2002) 2039-2057
72. Van Bambeke F., Balzi E., and Tulkens P.M. Antibiotic efflux pumps. Biochem Pharmacol 60 (2000) 457-470
73. Varma M.V., Ashokraj Y., Dey C.S., and Panchagnula R. P-glycoprotein inhibitors and their screening: a perspective from bioavailability enhancement. Pharmacol Res 48 (2003) 347-359
74. Vazquez-Laslop N., Zheleznova E.E., Markham P.N., Brennan R.G., and Neyfakh A.A. Recognition of multiple drugs by a single protein: a trivial solution of an old paradox. Biochem Soc Trans 28 (2000) 517-520
75. Wang E.J., Casciano C., Clement R.P., and Johnson W.W. Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun 289 (2001) 580-585
76. Zheleznova E.E., Markham P.N., Neyfakh A.A., and Brennan R.G. Structural basis of multidrug recognition by BmrR, a transcription activator of a multidrug transporter. Cell 96 (1999) 353-362