Measuring propargyl-linked drug populations inside bacterial cells, and their interaction with a dihydrofolate reductase target, by Raman microscopy

Biochemistry

Volumn 54, Issue 17, 2015, Pages 2719-2726

  Heidari Torkabadi, Hossein ^a   Che, Tao ^b   Lombardo, Michael N ^c   Wright, Dennis L ^c   Anderson, Amy C ^c   Carey, Paul R ^a,b  

^a Department of Chemistry ^*  (United States)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

^c UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CELLS; ENZYME ACTIVITY; ESCHERICHIA COLI; FERMENTATION; MOLECULES; PROTONATION; SINGLE CRYSTALS; SPECTROSCOPIC ANALYSIS;

DIHYDROFOLATE REDUCTASE; EXTRACELLULAR COMPOUNDS; FERMENTATION MEDIUM; GRAM POSITIVE BACTERIAL CELLS; KLEBSIELLA PNEUMONIAE; RAMAN SPECTROSCOPIC STUDY; SPECTROSCOPIC SIGNATURES; STAPHYLOCOCCUS AUREUS;

CYTOLOGY;

DIHYDROFOLATE REDUCTASE; NITROGEN; FOLIC ACID ANTAGONIST;

ARTICLE; BACTERIAL CELL; ESCHERICHIA COLI; FERMENTATION MEDIUM; FREEZE DRYING; KLEBSIELLA PNEUMONIAE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTON TRANSPORT; RAMAN SPECTROMETRY; STAPHYLOCOCCUS AUREUS; CHEMISTRY; METABOLISM; MICROSCOPY; PROCEDURES; X RAY CRYSTALLOGRAPHY;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; NEGIBACTERIA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

CRYSTALLOGRAPHY, X-RAY; ESCHERICHIA COLI; FOLIC ACID ANTAGONISTS; KLEBSIELLA PNEUMONIAE; MICROSCOPY; SPECTRUM ANALYSIS, RAMAN; STAPHYLOCOCCUS AUREUS; TETRAHYDROFOLATE DEHYDROGENASE;

EID: 84928974565     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/acs.biochem.5b00202     Document Type: Article

References (30)

1. Lewis, K. (2013) Platforms for antibiotic discovery Nat. Rev. Drug Discovery 12, 371-387
2. Kascakova, S., Maigre, L., Chevalier, J., Refregiers, M., and Pages, J. M. (2012) Antibiotic transport in resistant bacteria: synchrotron UV fluorescence microscopy to determine antibiotic accumulation with single cell resolution PLoS One 7, e38624
3. Zimmermann, W. (1980) Penetration of beta-lactam antibiotics into their target enzymes in pseudomonas-aeruginosa-comparison of a highly sensitive mutant with its parent strain Antimicrob. Agents Chemother. 18, 94-100
4. Farmer, T. H., Degnan, B. A., and Payne, D. J. (1999) Penetration of beta-lactamase inhibitors into the periplasm of Gram-negative bacteria FEMS Microbiol. Lett. 176, 11-15
5. Lakaye, B., Dubus, A., Joris, B., and Frere, J. M. (2002) Method for estimation of low outer membrane permeability to beta-lactam antibiotics Antimicrob. Agents Chemother. 46, 2901-2907
6. Yoshimura, F. and Nikaido, H. (1985) Diffusion of beta-lactam antibiotics through the porin channels of Escherichia coli K-12 Antimicrob. Agents Chemother. 27, 84-92
7. Carey, P. R. (2006) Spectroscopic characterization of distortion in enzyme complexes Chem. Rev. 106, 3043-3054
8. Carey, P. R. (1999) Raman spectroscopy, the sleeping giant in structural biology, awakes J. Biol. Chem. 274, 26625-26628
9. Smith, E. and Dent, G. (2005) Modern Raman spectroscopy: a practical approach, John Wiley and Sons, West Sussex, U.K.
10. Carey, P. R. (1982) Biochemical applications of Raman and resonance Raman spectroscopies, Academic Press, New York.
11. Huang, W. E., Li, M. Q., Jarvis, R. M., Goodacre, R., and Banwart, S. A. (2010) Shining light on the microbial world: the application of raman microspectroscopy Adv. Appl. Microbiol. 70, 153-186
12. Jarvis, R. M. and Goodacre, R. (2008) Characterisation and identification of bacteria using SERS Chem. Soc. Rev. 37, 931-936
13. Fu, D., Yu, Y., Folick, A., Currie, E., Farese, R. V., Jr., Tsai, T. H., Xie, X. S., and Wang, M. C. (2014) In vivo metabolic fingerprinting of neutral lipids with hyperspectral stimulated Raman scattering microscopy J. Am. Chem. Soc. 136, 8820-8828
14. Zhang, X., Roeffaers, M. B., Basu, S., Daniele, J. R., Fu, D., Freudiger, C. W., Holtom, G. R., and Xie, X. S. (2012) Label-free live-cell imaging of nucleic acids using stimulated Raman scattering microscopy ChemPhysChem 13, 1054-1059
15. Fu, D., Zhou, J., Zhu, W. S., Manley, P. W., Wang, Y. K., Hood, T., Wylie, A., and Xie, X. S. (2014) Imaging the intracellular distribution of tyrosine kinase inhibitors in living cells with quantitative hyperspectral stimulated Raman scattering Nat. Chem. 6, 614-622
16. Salehi, H., Derely, L., Vegh, A. G., Durand, J. C., Gergely, C., Larroque, C., Fauroux, M. A., and Cuisinier, F. J. G. (2013) Label-free detection of anticancer drug paclitaxel in living cells by confocal Raman microscopy, Appl. Phys. Lett. 102.
17. Ling, J., Weitman, S. D., Miller, M. A., Moore, R. V., and Bovik, A. C. (2002) Direct Raman imaging techniques for study of the subcellular distribution of a drug Appl. Opt. 41, 6006-6017
18. Baik, J. and Rosania, G. R. (2011) Molecular imaging of intracellular drug-membrane aggregate formation Mol. Pharmaceutics 8, 1742-1749
19. Carey, P. R. (2006) Raman crystallography and other biochemical applications of Raman microscopy Annu. Rev. Phys. Chem. 57, 527-554
20. Carey, P. R., Chen, Y. Y., Gong, B., and Kalp, M. (2011) Kinetic crystallography by Raman microscopy Biochim. Biophys. Acta, Proteins Proteomics 1814, 742-749
21. Torkabadi, H. H., Bethel, C. R., Papp-Wallace, K. M., de Boer, P. A. J., Bonomo, R. A., and Carey, P. R. (2014) Following drug uptake and reactions inside escherichia coil cells by raman microspectroscopy Biochemistry 53, 4113-4121
22. Baba, T., Ara, T., Hasegawa, M., Takai, Y., Okumura, Y., Baba, M., Datsenko, K. A., Tomita, M., Wanner, B. L., and Mori, H. (2006) Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection, Mol. Syst. Biol. 2.
23. Frey, K. M., Liu, J., Lombardo, M. N., Bolstad, D. B., Wright, D. L., and Anderson, A. C. (2009) Crystal structures of wild-type and mutant methicillin-resistant Staphylococcus aureus dihydrofolate reductase reveal an alternate conformation of NADPH that may be linked to trimethoprim resistance J. Mol. Biol. 387, 1298-1308
24. Stephens, P. J., Devlin, F. J., Chabalowski, C. F., and Frisch, M. J. (1994) Ab-initio calculation of vibrational absorption and circular-dichroism spectra using density-functional force-fields J. Phys. Chem. 98, 11623-11627
25. Kim, K. and Jordan, K. D. (1994) Comparison of density-functional and MP2 calculations on the water monomer and dimer J. Phys. Chem. 98, 10089-10094
26. Leopold, N., Cinta-Pinzaru, S., Baia, M., Antonescu, E., Cozar, O., Kiefer, W., and Popp, J. (2005) Raman and surface-enhanced Raman study of thiamine at different pH values Vibr. Spectrosc. 39, 169-176
27. Wunder, S. L., Bell, M. I., and Zerbi, G. (1986) Band broadening of CH2 vibrations in the Raman-spectra of polymethylene chains J. Chem. Phys. 85, 3827-3839
28. Liu, J. Y., Bolstad, D. B., Smith, A. E., Priestley, N. D., Wright, D. L., and Anderson, A. C. (2008) Structure-guided development of efficacious antifungal agents targeting Candida glabrata dihydrofolate reductase Chem. Biol. 15, 990-996
29. Vandecasteele, S. J., Peetermans, W. E., Merckx, R., and Van Eldere, J. (2001) Quantification of expression of Staphylococcus epidermidis housekeeping genes with Taqman quantitative PCR during in vitro growth and under different conditions J. Bacteriol. 183, 7094-7101
30. Kiefer, W. and Bernstei, Hj. (1971) Rotating Raman sample technique for colored crystal powders-resonance Raman effect in solid KMn04 Appl. Spectrosc. 25, 609-613