Evaluation of lipopeptide (daptomycin) aggregation using fluorescence, light scattering, and nuclear magnetic resonance spectroscopy

Journal of Pharmaceutical Sciences

Volumn 103, Issue 3, 2014, Pages 853-861

  Qiu, Jiang ^a   Kirsch, Lee E ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

analytical chemistry; daptomycin; dynamic light scattering; fluorescence spectroscopy; lipopeptide antibiotic; NMR spectroscopy; peptide aggregation; spectroscopy; static light scattering; zwitterion

Indexed keywords

CALCIUM ION; DAPTOMYCIN; KYNURENINE; PHOSPHATE BUFFERED SALINE; ANTIINFECTIVE AGENT; IONOPHORE; KYNURENIC ACID; TRYPTOPHAN;

AQUEOUS SOLUTION; ARTICLE; CONFORMATIONAL TRANSITION; CRITICAL AGGREGATION CONCENTRATION; DRUG CONFORMATION; DRUG SCREENING; DYNAMIC LIGHT SCATTERING; FLUORESCENCE; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENCE SPECTROSCOPY; HYDRODYNAMIC RADIUS; HYDRODYNAMICS; LIGHT SCATTERING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; PH; PHARMACOLOGICAL PARAMETERS; PROTEIN AGGREGATION; RADIATION ABSORPTION; RADIUS; REFRACTION INDEX; STATIC LIGHT SCATTERING; TEMPERATURE SENSITIVITY; ULTRAVIOLET RADIATION; CALCIUM SIGNALING; CHEMISTRY; DRUG STABILITY; HEAT; KINETICS; METABOLISM; NUCLEAR MAGNETIC RESONANCE; OSMOLARITY; PHOTOMETRY; PROTEIN STABILITY; SOLUBILITY; ULTRAVIOLET SPECTROPHOTOMETRY;

ANTI-BACTERIAL AGENTS; CALCIUM SIGNALING; DAPTOMYCIN; DRUG STABILITY; FLUORESCENCE RESONANCE ENERGY TRANSFER; HOT TEMPERATURE; HYDROGEN-ION CONCENTRATION; IONOPHORES; KINETICS; KYNURENIC ACID; KYNURENINE; NEPHELOMETRY AND TURBIDIMETRY; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OSMOLAR CONCENTRATION; PARTICLE SIZE; PROTEIN STABILITY; SOLUBILITY; SPECTROPHOTOMETRY, ULTRAVIOLET; TRYPTOPHAN;

EID: 84894495085     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23859     Document Type: Article

References (41)

1. Enoch DA, Bygott JM, Daly M-L, Karas JA,. 2007. Daptomycin. J Infection 55 (3): 205-213.
2. Raja A, LaBonte J, Lebbos J, Kirkpatrick P,. 2003. Daptomycin. Nat Rev Drug Discov 2 (12): 943-944.
3. Debono M, Abbott B, Molloy R, Fukuda D, Hunt A, Daupert V, Counter F, Ott J, Carrell C, Howard L, Boeck L, Hamill R,. 1988. Enzymatic and chemical modifications of lipopeptide antibiotic A21978C: The synthesis and evaluation of daptomycin (LY146032). J Antibiot 41 (8): 1093-1105.
4. Tally FP, DeBruin MF,. 2000. Development of daptomycin for Gram-positive infections. J Antimicrob Chemother 46 (4): 523-526.
5. Tenover FC,. 2006. Mechanisms of antimicrobial resistance in bacteria. Am J Med 119 (6A): S3-S10.
6. Silverman JA, Perlmutter NG, Shapiro HM,. 2003. Correlation of daptomycin bactericidal activity and membrane depolarization in Staphylococcus aureus. Antimicrob Agents Chemother 47 (8): 2538-2544.
7. Steenbergen JN, Alder J, Thorne GM, Tally FP,. 2005. Daptomycin: A lipopeptide antibiotic for the treatment of serious Gram-positive infections. J Antimicrob Chemother 55 (3): 283-288.
8. Straus SK, Hancock REW,. 2006. Mode of action of the new antibiotic for Gram-positive pathogens daptomycin: Comparison with cationic antimicrobial peptides and lipopeptides. Biochim Biophys Acta Biomembr 1758 (9): 1215-1223.
9. Eliopoulos GM,. 2008. Antimicrobial resistance in the enterococcus. 2nd ed. New York: CRC Press, p 264.
10. Ho SW, Jung D, Calhoun JR, Lear JD, Okon M, Scott WRP, Hancock REW, Straus SK,. 2008. Effect of divalent cations on the structure of the antibiotic daptomycin. Eur Biophys J 37 (4): 421-433.
11. Scott WRP, Baek S-B, Jung D, Hancock REW, Straus SK,. 2007. NMR structural studies of the antibiotic lipopeptide daptomycin in DHPC micelles. Biochim Biophys Acta Biomembr 1768 (12): 3116-3126.
12. Ball L-J, Goult CM, Donarski JA, Micklefield J, Ramesh V,. 2004. NMR structure determination and calcium binding effects of lipopeptide antibiotic daptomycin. Org Biomol Chem 2 (13): 1872-1878.
13. Jung D, Rozek A, Okon M, Hancock REW,. 2004. Structural transitions as determinants of the action of the calcium-dependent antibiotic daptomycin. Chem Biol 11 (7): 949-957.
14. Rotondi KS, Gierasch LM,. 2005. A well-defined amphipathic conformation for the calcium-free cyclic lipopeptide antibiotic, daptomycin, in aqueous solution. Biopolymers 80 (2-3): 374-385.
15. Wang W,. 1999. Instability, stabilization, and formulation of liquid protein pharmaceuticals. Int J Pharm 185 (2): 129-188.
16. Wang W,. 2005. Protein aggregation and its inhibition in biopharmaceutics. Int J Pharm 289 (1-2): 1-30.
17. Lakey JH, Ptak M,. 1988. Fluorescence indicates a calcium-dependent interaction between the lipopeptide antibiotic LY146032 and phospholipid membranes. Biochem 27 (13): 4639-4645.
18. Muangsiri W, Kirsch LE,. 2001. The kinetics of the alkaline degradation of daptomycin. J Pharm Sci 90 (8): 1066-1075.
19. Ostrowsky N, Sornette D, Parker P, Pike ER,. 1981. Exponential sampling method for light scattering polydispersity analysis. Opt Acta 28 (8): 1059-1070.
20. Provencher SW., 1982. A constrained regularization method for inverting data represented by linear algebraic or integral equations. Comput Phys Commun 27 (3): 213-227.
21. Provencher SW., 1982. CONTIN: A general purpose constrained regularization program for inverting noisy linear algebraic and integral equations. Comput Phys Commun 27 (3): 229-242.
22. Riek R, Pervushin K, Wüthrich K,. 2000. TROSY and CRINEPT: NMR with large molecular and supramolecular structures in solution. Trends Biochem Sci 25 (10): 462-468.
23. Ferguson WE, Smith CM, Adams Jr ET, Barlow GH,. 1974. The temperature-dependent self-association of adenosine 5′ triphosphate in 0.154M NaCl. Biophys Chem 1 (5): 325-337.
24. Muraih JK, Harris J, Taylor SD, Palmer M,. 2012. Characterization of daptomycin oligomerization with perylene excimer fluorescence: Stoichiometric binding of phosphatidylglycerol triggers oligomer formation. Biochim Biophys Acta 1818 (3): 673-678.
25. He F, Phan DH, Hogan S, Bailey R, Becker GW, Narhi LO, Razinkov VI,. 2010. Detection of IgG aggregation by a high throughput method based on extrinsic fluorescence. J Pharm Sci 99 (6): 2598-2608.
26. Mahler H-C, Friess W, Grauschopf U, Kiese S,. 2009. Protein aggregation: Pathways, induction factors and analysis. J Pharm Sci 98 (9): 2909-2934.
27. Hawe A, Sutter M, Jiskoot W,. 2008. Extrinsic fluorescent dyes as tools for protein characterization. Pharm Res 25 (7): 1487-1499.
28. Grunewald J, Kopp F, Mahlert C, Linne U, Sieber SA, Marahiel MA,. 2005. Fluorescence resonance energy transfer as a probe of peptide cyclization catalyzed by nonribosomal thioesterase domains. Chem Biol 12 (8): 873-881.
29. Lakowicz JR,. 1999. Energy transfer. In Principles of fluorescence spectroscopy;, Lakowicz JR, Ed. 2nd ed. New York: Kluwer Academic/Plenum Publishers, pp 367-388.
30. a values for specific amino acid residues in daptomycin. J Pharm Sci 100 (10): 4225-4233.
31. Muangsiri W., 2000. The kinetics of the alkaline degradation of daptomycin. Iowa City, Iowa: University of Iowa, pp 25-30.
32. Lamp KC, Rybak MJ,. 1993. Teicoplanin and daptomycin bactericidal activities in the presence of albumin or serum under controlled conditions of pH and ionized calcium. Antimicrob Agents Chemother 37 (3): 605-609.
33. Lamp KC, Rybak MJ, Bailey EM, Kaatz GW,. 1992. In vitro pharmacodynamic effects of concentration, pH, and growth-phase on serum bactericidal activities of daptomycin and vancomycin. Antimicrob Agents Chemother 36 (12): 2709-2714.
34. Larsson L, Öhman S,. 1978. Serum ionized calcium and corrected total calcium in borderline hyperparathyroidism. Clin Chem 24 (11): 1962-1965.
35. Bahte SK, Bertram A, Burkhardt O, Martens-Lobenhoffer J, Goedecke V, Bode-Böger SM, Hiss M, Kielstein JT,. 2010. Therapeutic serum concentrations of daptomycin after intraperitoneal administration in a patient with peritoneal dialysis-associated peritonitis. J Antimicrob Chemother 65 (6): 1312-1314.
36. Benvenuto M, Benziger DP, Yankelev S, Vigliani G,. 2006. Pharmacokinetics and tolerability of daptomycin at doses up to 12 milligrams per kilogram of body weight once daily in healthy volunteers. Antimicrob Agents Chemother 50 (10): 3245-3249.
37. Dvorchik BH, Brazier D, DeBruin MF, Arbeit RD,. 2003. Daptomycin pharmacokinetics and safety following administration of escalating doses once daily to healthy subjects. Antimicrob Agents Chemother 47 (4): 1318-1323.
38. Goedecke VA, Clajus C, Burkhardt O, Martens-Lobenhoffer J, Bode-Böger SM, Kielstein JT, Hiss M,. 2009. Pharmacokinetics and dialysate levels of daptomycin given intravenously in a peritoneal dialysis patient. Scand J Infect Dis 41 (2): 155-157.
39. Khadzhynov D, Slowinski T, Lieker I, Spies C, Puhlmann B, König T, Uhrig A, Eggers K, Neumayer H, TraunmGreek small letter upsilon with dialytikaller F, Joukhadar C, Peters H,. 2011. Plasma pharmacokinetics of daptomycin in critically ill patients with renal failure and undergoing CVVHD. Int J Clin Pharmacol Ther 49 (11): 656-665.
40. Vilay AM, Grio M, DePestel DD, Sowinski KM, Gao L, Heung M, Salama NN, Mueller BA,. 2011. Daptomycin pharmacokinetics in critically ill patients receiving continuous venovenous hemodialysis. Crit Care Med 39 (1): 19-25.
41. Wenisch JM, Meyer B, Fuhrmann V, Saria K, Zuba C, Dittrich P, Thalhammer F,. 2012. Multiple-dose pharmacokinetics of daptomycin during continuous venovenous haemodiafiltration. J Antimicrob Chemother 67 (4): 977-983.