Fluorescently labeled macrolides as a tool for monitoring cellular and tissue distribution of azithromycin

Pharmacological Research

Volumn 66, Issue 4, 2012, Pages 332-342

  Matijašić, Mario ^a,b   Munić Kos, Vesna ^a   Nujić, Krunoslav ^a   Čužić, Snježana ^a   Padovan, Jasna ^a   Kragol, Goran ^a   Alihodžić, Sulejman ^a   Mildner, Boris ^a,c   Verbanac, Donatella ^a   Eraković Haber, Vesna ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITY OF ZAGREB   (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Azithromycin; Fluorescent derivate; Macrolide; Subcellular distribution; Tissue distribution

Indexed keywords

9 DEOXO 9A [3 [(7 NITRO 2,1,3 BENZOXADIAZOL 4YL)AMINO]PROPYL]AZITHROMYCIN; AZITHROMYCIN; FLUORESCENT DYE; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; MACROLIDE; MONOCYTE CHEMOTACTIC PROTEIN 1; MONOCYTE CHEMOTACTIC PROTEIN 2; PROSTAGLANDIN E2; RANTES; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIBACTERIAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL TYPE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG KIDNEY LEVEL; DRUG LIVER LEVEL; DRUG RETENTION; DRUG SPLEEN LEVEL; DRUG STRUCTURE; DRUG TISSUE LEVEL; ESCHERICHIA COLI; FLUORESCENCE ANALYSIS; GLOMERULUS; HAEMOPHILUS INFLUENZAE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; KIDNEY PARENCHYMA; KIDNEY TUBULE; LIVER CELL; LIVER PARENCHYMA; LYMPHOCYTE; LYSOSOME; MACROPHAGE; MALE; MINIMUM INHIBITORY CONCENTRATION; MORAXELLA CATARRHALIS; MOUSE; NONHUMAN; PRIORITY JOURNAL; SPLEEN; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; STREPTOCOCCUS PYOGENES;

ANIMALS; ANTI-BACTERIAL AGENTS; AZITHROMYCIN; BACTERIA; BACTERIAL INFECTIONS; CELL LINE; CELL LINE, TUMOR; CELL SURVIVAL; FLUORESCENT DYES; HUMANS; MALE; MICE; MICE, INBRED BALB C; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 84865042069     PISSN: 10436618     EISSN: 10961186     Source Type: Journal    
DOI: 10.1016/j.phrs.2012.06.001     Document Type: Article

References (44)

1. O. Culic, V. Erakovic, and M.J. Parnham Anti-inflammatory effects of macrolide antibiotics European Journal of Pharmacology 429 2001 209 229 (Pubitemid 33043997)
2. N. Marjanovic, M. Bosnar, F. Michielin, D.R. Wille, T. Anic-Milic, and O. Culic Macrolide antibiotics broadly and distinctively inhibit cytokine and chemokine production by COPD sputum cells in vitro Pharmacological Research 63 2011 389 397
3. D.S. Polancec, V. Munic Kos, M. Banjanac, M. Vrancic, S. Cuzic, and D. Belamaric Azithromycin drives in vitro GM-CSF/IL-4-induced differentiation of human blood monocytes toward dendritic-like cells with regulatory properties Journal of Leukocyte Biology 91 2012 229 243
4. M. Shinkai, M.O. Henke, and B.K. Rubin Macrolide antibiotics as immunomodulatory medications: proposed mechanisms of action Pharmacology and Therapeutics 117 2008 393 405
5. M. Vrancic, M. Banjanac, K. Nujic, M. Bosnar, T. Murati, and V. Munic Azithromycin distinctively modulates classical activation of human monocytes in vitro British Journal of Pharmacology 165 2012 1348 1360
6. M.W. Dunne, N. Singh, M. Shukla, N. Valecha, P.C. Bhattacharyya, and V. Dev A multicenter study of azithromycin, alone and in combination with chloroquine, for the treatment of acute uncomplicated Plasmodium falciparum malaria in India Journal of Infectious Diseases 191 2005 1582 1588 (Pubitemid 40656745)
7. H.M. Mattoes, and C.H. Nightingale Pharmacokinetics/pharmacodynamics of macrolides W. Schonfeld, H.A. Kirst, Macrolide antibiotics 2002 Birkhauser Verlag Basel 25 52
8. G.W. Amsden Advanced-generation macrolides: tissue-directed antibiotics International Journal of Antimicrobial Agents 18 Suppl. 1 2001 S11 S15
9. R. Jain, and L.H. Danziger The macrolide antibiotics: a pharmacokinetic and pharmacodynamic overview Current Pharmaceutical Design 10 2004 3045 3053 (Pubitemid 39242900)
10. A. Wildfeuer, I. Reisert, and H. Laufen Uptake and subcellular distribution of azithromycin in human phagocytic cells. Demonstration of the antibiotic in neutrophil polymorphonuclear leucocytes and monocytes by autoradiography and electron microscopy Arzneimittel-Forschung 43 1993 484 486 (Pubitemid 23112991)
11. M.B. Carlier, I. Garcia-Luque, J.P. Montenez, P.M. Tulkens, and J. Piret Accumulation, release and subcellular localization of azithromycin in phagocytic and non-phagocytic cells in culture International Journal of Tissue Reactions 16 1994 211 220
12. C. Miossec-Bartoli, L. Pilatre, P. Peyron, E.N. N'Diaye, V. Collart-Dutilleul, and I. Maridonneau-Parini The new ketolide HMR3647 accumulates in the azurophil granules of human polymorphonuclear cells Antimicrobial Agents and Chemotherapy 43 1999 2457 2462 (Pubitemid 29471227)
13. E.M. Mtairag, H. Abdelghaffar, C. Douhet, and M.T. Labro Role of extracellular calcium in in vitro uptake and intraphagocytic location of macrolides Antimicrobial Agents and Chemotherapy 39 1995 1676 1682
14. C. de Duve, T. de Barsy, B. Poole, A. Trouet, P. Tulkens, and F. Van Hoof Commentary lysosomotropic agents Biochemical Pharmacology 23 1974 2495 2531
15. C.M. Carceles, E. Fernandez-Varon, P. Marin, and E. Escudero Tissue disposition of azithromycin after intravenous and intramuscular administration to rabbits Veterinary Journal 174 2007 154 159 (Pubitemid 46865751)
16. I. Nakayama, E. Yamaji, K. Shimada, S. Yokoyama, K. Miura, and S. Muto Transport of azithromycin into infected tissue observed by macro- and microautoradiography Japanese Journal of Antibiotics 51 1998 139 141
17. S.E. Myrdal, K.C. Johnson, and P.S. Steyger Cytoplasmic and intra-nuclear binding of gentamicin does not require endocytosis Hearing Research 204 2005 156 169 (Pubitemid 40733213)
18. P.S. Steyger, S.L. Peters, J. Rehling, A. Hordichok, and C.F. Dai Uptake of gentamicin by bullfrog saccular hair cells in vitro Journal of the Association for Research in Otolaryngology 4 2003 565 578 (Pubitemid 38112638)
19. C.F. Dai, D. Mangiardi, D.A. Cotanche, and P.S. Steyger Uptake of fluorescent gentamicin by vertebrate sensory cells in vivo Hearing Research 213 2006 64 78 (Pubitemid 43356630)
20. C.F. Dai, and P.S. Steyger A systemic gentamicin pathway across the stria vascularis Hearing Research 235 2008 114 124 (Pubitemid 50016732)
21. Q. Wang, and P.S. Steyger Trafficking of systemic fluorescent gentamicin into the cochlea and hair cells Journal of the Association for Research in Otolaryngology 10 2009 205 219
22. Q. Wang, A. Kachelmeier, and P.S. Steyger Competitive antagonism of fluorescent gentamicin uptake in the cochlea Hearing Research 268 2010 250 259
23. P. Brandt-Rauf, R. Vince, R. LeMahieu, and S. Pestka Fluorescent assay for estimating the binding of erythromycin derivatives to ribosomes Antimicrobial Agents and Chemotherapy 14 1978 88 94 (Pubitemid 8370712)
24. R. Vince, D. Weiss, and S. Pestka Binding of N-substituted erythromycyclamines to ribosomes Antimicrobial Agents and Chemotherapy 9 1976 131 136
25. K. Yan, E. Hunt, J. Berge, E. May, R.A. Copeland, and R.R. Gontarek Fluorescence polarization method to characterize macrolide-ribosome interactions Antimicrobial Agents and Chemotherapy 49 2005 3367 3372 (Pubitemid 41060584)
26. L.T. Gooljarsingh, C. Fernandes, K. Yan, H. Zhang, M. Grooms, and K. Johanson A biochemical rationale for the anticancer effects of Hsp90 inhibitors: slow, tight binding inhibition by geldanamycin and its analogues Proceedings of the National Academy of Sciences of the United States of America 103 2006 7625 7630
27. L. Llauger-Bufi, S.J. Felts, H. Huezo, N. Rosen, and G. Chiosis Synthesis of novel fluorescent probes for the molecular chaperone Hsp90 Bioorganic and Medicinal Chemistry Letters 13 2003 3975 3978 (Pubitemid 37338430)
28. S. Tsutsumi, B. Scroggins, F. Koga, M.J. Lee, J. Trepel, and S. Felts A small molecule cell-impermeant Hsp90 antagonist inhibits tumor cell motility and invasion Oncogene 27 2008 2478 2487 (Pubitemid 351521101)
29. L. Silva, A. Coutinho, A. Fedorov, and M. Prieto Conformation and self-assembly of a nystatin nitrobenzoxadiazole derivative in lipid membranes Biochimica et Biophysica Acta 1617 2003 69 79 (Pubitemid 37456714)
30. V. Stepanic, S. Kostrun, I. Malnar, M. Hlevnjak, K. Butkovic, and I. Caleta Modeling cellular pharmacokinetics of 14- and 15-membered macrolides with physicochemical properties Journal of Medicinal Chemistry 54 2011 719 733
31. I.J. Fuss, M.E. Kanof, P.D. Smith, and H. Zola Isolation of whole mononuclear cells from peripheral blood and cord blood. Current Protocols in Immunology 2009 Wiley Hoboken (Chapter 7: Unit 7.1)
32. Clinical Laboratory Standard Institute (CLSI) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically 8th ed. 2009 Clinical Laboratory Standard Institute Wayne, PA
33. V. Munic, M. Banjanac, S. Kostrun, K. Nujic, M. Bosnar, and N. Marjanovic Intensity of macrolide anti-inflammatory activity in J774A.1 cells positively correlates with cellular accumulation and phospholipidosis Pharmacological Research 64 2011 298 307
34. V. Munic, Z. Kelneric, L. Mikac, and V. Erakovic Haber Differences in assessment of macrolide interaction with human MDR1 (ABCB1, P-gp) using rhodamine-123 efflux, ATPase activity and cellular accumulation assays European Journal of Pharmaceutical Sciences 41 2010 86 95
35. M. Bosnar, Z. Kelneric, V. Munic, V. Erakovic, and M.J. Parnham Cellular uptake and efflux of azithromycin, erythromycin, clarithromycin, telithromycin, and cethromycin Antimicrobial Agents and Chemotherapy 49 2005 2372 2377 (Pubitemid 40734469)
36. H. Nikaido Molecular basis of bacterial outer membrane permeability revisited Microbiology and Molecular Biology Reviews 67 2003 593 656 (Pubitemid 37549772)
37. I. Johnson, and M. Spence Molecular probes: the handbook - a guide to fluorescent probes and labeling technologies 11th ed. 2010
38. A. Ianaro, A. Ialenti, P. Maffia, L. Sautebin, L. Rombola, and R. Carnuccio Anti-inflammatory activity of macrolide antibiotics Journal of Pharmacology and Experimental Therapeutics 292 2000 156 163 (Pubitemid 30026366)
39. B.S. Murphy, V. Sundareshan, T.J. Cory, D. Hayes Jr., M.I. Anstead, and D.J. Feola Azithromycin alters macrophage phenotype Journal of Antimicrobial Chemotherapy 61 2008 554 560 (Pubitemid 351321127)
40. P.J. McDonald, and H. Pruul Phagocyte uptake and transport of azithromycin European Journal of Clinical Microbiology and Infectious Diseases 10 1991 828 833
41. M. Duvvuri, Y. Gong, D. Chatterji, and J.P. Krise Weak base permeability characteristics influence the intracellular sequestration site in the multidrug-resistant human leukemic cell line HL-60 Journal of Biological Chemistry 279 2004 32367 32372 (Pubitemid 39014690)
42. A.M. Kaufmann, and J.P. Krise Lysosomal sequestration of amine-containing drugs: analysis and therapeutic implications Journal of Pharmaceutical Sciences 96 2007 729 746 (Pubitemid 46657864)
43. K. Yokogawa, J. Ishizaki, S. Ohkuma, and K. Miyamoto Influence of lipophilicity and lysosomal accumulation on tissue distribution kinetics of basic drugs: a physiologically based pharmacokinetic model Methods and Findings in Experimental and Clinical Pharmacology 24 2002 81 93 (Pubitemid 34310988)
44. O. Culic, V. Erakovic, I. Cepelak, K. Barisic, K. Brajsa, and Z. Ferencic Azithromycin modulates neutrophil function and circulating inflammatory mediators in healthy human subjects European Journal of Pharmacology 450 2002 277 289 (Pubitemid 35246071)