Metal contaminants promote degradation of lipid/DNA complexes during lyophilization

Biochimica et Biophysica Acta - Biomembranes

Volumn 1768, Issue 3, 2007, Pages 669-677

  Molina, Marion d C ^a   Anchordoquy, Thomas J ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

Chelating agents; Gene delivery; Lyophilization; Metal contamination; Nonviral vectors; Reactive oxygen species

Indexed keywords

CHELATING AGENT; DEFEROXAMINE MESYLATE; DNA; DRUG ADDITIVE; EDETIC ACID; FERROUS ION; FLUORESCAMINE; LIPID; METAL; PENTETIC ACID; REACTIVE OXYGEN METABOLITE; TRANSITION ELEMENT; TREHALOSE; VIRUS VECTOR;

ANIMAL CELL; ARTICLE; CHELATION; DNA DEGRADATION; DNA EXTRACTION; FREEZE DRYING; LIPID DEGRADATION; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL;

ANIMALS; CERCOPITHECUS AETHIOPS; CHELATING AGENTS; COS CELLS; DEFEROXAMINE; DNA; EDETIC ACID; FERRIC COMPOUNDS; FLUORESCAMINE; FREEZE DRYING; INDICATORS AND REAGENTS; IRON CHELATING AGENTS; LIPOSOMES; PENTETIC ACID; PHENANTHROLINES; REACTIVE OXYGEN SPECIES; SOLUTIONS; TRANSFECTION; TREHALOSE; WATER;

EID: 33847057354     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2006.12.004     Document Type: Article

References (53)

1. Allison S.D., and Anchordoquy T.J. Mechanisms of protection of cationic lipid-DNA complexes during lyophilization. J. Pharm. Sci. 89 (2000) 682-691
2. Anchordoquy T.J., Carpenter J.F., and Kroll D.J. Maintenance of transfection rates and physical characterization of lipid/DNA complexes after freeze-drying and rehydration. Arch. Biochem. Biophys. 348 (1997) 199-206
3. Cherng J.-Y., Wetering P.v.d., Talsma H., Crommelin D.J.A., and Hennink W.E. Stabilization of polymer-based gene delivery systems. Int. J. Pharm. 183 (1999) 25-28
4. Talsma H., Cherng J.Y., Lehrmann H., Kursa M., Ogris W., Hennink W.E., Cotten M., and Wagner E. Stabilization of gene delivery systems by freeze-drying. Int. J. Pharm. 157 (1997) 233-238
5. Middaugh C.R., Evans R.K., Montgomery D.L., and Casimiro D.R. Analysis of plasmid DNA from a pharmaceutical perspective. J. Pharm. Sci. 87 (1998) 130-146
6. Pogocki D., and Schoneich C. Chemical stability of nucleic acid-derived drugs. J. Pharm. Sci. 89 (2000) 443-456
7. Evans R.K., Xu Z., Bohannon K.E., Wang B., Brunner M.W., and Volkin D.B. Evaluation of degradation pathways for plasmid DNA in pharmaceutical formulations via accelerated stability studies. J. Pharm. Sci. 89 (2000) 76-87
8. Waterman K.C., Adami R.C., Alsante K.M., Hong J., Landis M.S., Lombardo F., and Roberts C.J. Stabilization of pharmaceuticals to oxidative degradation. Pharm. Dev. Technol. 7 (2002) 1-32
9. Breen A.P., and Murphy J.A. Reactions of oxyl radicals with DNA. Free Radical Biol. Med. 18 (1995) 1033-1077
10. Imlay J.A., and Linn S. DNA damage and oxygen radical toxicity. Science 240 (1988) 1302-1309
11. Kukielka E., and Cederbaum A.I. DNA strand cleavage as a sensitive assay for the production of hydroxyl radicals by microsomes: role of cytochrome P4502E1 in the increased activity after ethanol treatment. Biochem. J. 302 (1994) 773-779
12. Marrot L., and Giacomoni P.U. Enhancement of oxidative DNA degradation by histidine: the role of stereochemical parameters. Mutat. Res. 275 (1992) 69-79
13. Buettner G.R., and Jurkiewicz B.A. Catalytic metals, ascorbate and free radicals: combinations to avoid. Radiat. Res. 145 (1996) 532-541
14. Valko M., Morris H., and Cronin M.T.D. Metals, toxicity and oxydative stress. Curr. Med. Chem. 12 (2005) 1161-1208
15. Adami R.C., Collard W.T., Gupta S.A., Kwok K.Y., Bonadio J., and Rice K.G. Stability of peptide-condensed plasmid DNA formulations. J. Pharm. Sci. 87 (1998) 678-683
16. Molina M.d.C., Allison D.S., and Anchordoquy T.J. Maintenance of particle size during the freezing step of the lyophilization process is insufficient for preservation of activity: insight from other structural indicators. J. Pharm. Sci. 90 (2001) 1445-1455
17. Anchordoquy T.J., Girouard L.G., Carpenter J.F., and Kroll D.J. Stability of lipid/DNA complexes during agitation and freeze-thawing. J. Pharm. Sci. 87 (1998) 1046-1051
18. Allison S.D., Molina M.d.C., and Anchordoquy T.J. Stabilization of lipid/DNA complexes during the freezing step of the lyophilization process: The particle isolation hypothesis. Biochim. Biophys. Acta 1468 (2000) 127-138
19. Zhang Y., and Anchordoquy T.J. The role of lipid charge density in the serum stability of cationic lipid/DNA complexes. Biochim. Biophys. Acta 1663 (2004) 143-157
20. Lloyd R.S., Haidle C.W., and Robberson D.L. Bleomycin-specific fragmentation of double-stranded DNA. Biochemistry 17 (1978) 1890-1896
21. 2+ and Cu+ with dioxygen; comparison with the Fenton chemistry. Acta Biochim. Pol. 47 (2000) 951-962
22. Qian S.Y., and Buettner G.R. Iron and dioxygen chemistry is an important route to initiation of biological free radical oxidations: an electron paramagnetic resonance spin trapping study. Free Radic. Biol. Med. 26 (1999) 1447-1456
23. Pou S., Huang Y.-I., Bhan A., Bhadti V.S., Hosmane R.S., Wu S.Y., Cao G.-L., and Rosen G.M. A fluorophore-containing nitroxide as a probe to detect superoxide and hydroxyl radical generated by stimulated neutrofils. Anal. Biochem. 212 (1993) 85-90
24. Li B., Gutierrez P.L., and Blough N.V. Trace determination of hydroxyl radical in biological systems. Anal. Chem. 69 (1997) 4295-4302
25. +3, and oxygen react with DNA-derived radicals formed during iron-mediated Fenton reaction. Biochemistry 35 (1996) 12212-12219
26. Aruoma O.I., Halliwell B., Gajewski E., and Dizdaroglu M. Copper-ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem. J. 273 (1991) 601-604
27. Stoewe R., and Prutz W.A. Copper-catalyzed DNA damage by ascorbate and hydrogen peroxide: kinetics and yield. Free Radic. Biol. Med. 3 (1987) 97-105
28. Izatt R.M., Christensen J.J., and Rytting J.H. Sites and thermodynamic quantities associated with proton and metal ion interaction with ribonucleic acid, deoxyribonucleic acid, and their constituent bases, nucleosides, and nucleotides. Chem. Rev. 71 (1971) 439-481
29. Ouameur A.A., Arakawa H., Ahmad R., Naoui M., and Tajmir-Riahi H.A. A comparative study of Fe(II) and Fe(III) interactions with DNA duplex: major and minor grooves bindings. DNA Cell Biol. 24 (2005) 394-401
30. Pezzano H., and Podo F. Structure of binary complexes of mono- and polynucleotides with metal ions of the first transition group. Chem. Rev. 80 (1980) 366-401
31. Sagripanti J.L., and Kraemer K.H. Site-specific oxidative DNA damage at polyguanosines produced by copper plus hydrogen peroxide. J. Biol. Chem. 264 (1989) 1729-1734
32. Halliwell B., and Gutteridge J.M.C. Free Radicals in Biology and Medicine. 3rd ed. (1999), Oxford Univ. Press, Oxford
33. Pedreno E., Lopez-Contreras A.J., Cremades A., and Penafiel R. Protecting or promoting effects of spermine on DNA strand breakage induced by iron or copper ions as a function of metal concentration. J. Inorg. Biochem. 99 (2005) 2074-2080
34. Srinivasan A., Lehmler H.-J., Robertson L.W., and Ludewig G. Production of DNA strand breaks in vitro and reactive oxygen species in vitro and HL-60 cells by PCB metabolites. Toxicol. Sci. 60 (2001) 92-102
35. Dokka S., Toledo D., Shi X., Castranova V., and Rojanasakul Y. Oxygen radical-mediated pulmonary toxicity induced by some cationic liposomes. Pharm. Res. 17 (2000) 521-525
36. Graf E., Mahoney J.R., Bryant R.G., and Eaton J.W. Iron-catalyzed hydroxyl radical formation. Stringent requirement for free iron coordination site. J. Biol. Chem. 259 (1984) 3620-3624
37. Buettner G.R., Doherty T.P., and Patterson L.K. The kinetics of the reaction of superoxide radical with Fe(III) complexes of EDTA, DETAPAC, and HEDTA. FEBS Lett. 158 (1983) 143-146
38. Miller D.M., Buettner G.R., and Aust S.D. Transition metals as catalysts of "autoxidation" reactions. Free Radic. Biol. Med. 8 (1990) 95-108
39. Buettner G.R., Oberley L.W., and Leuthauser S.W.H.C. The effect of iron on the distribution of superoxide and hydroxyl radicals as seen by spin trapping and on the superoxide dismutase assay. Photochem. Photobiol. 28 (1978) 693-695
40. Dean R.T., and Nicholson P. The action of nine chelators on iron-dependent radical damage. Free Radic. Res. 20 (1994) 83-101
41. Zhu B.Z., Kitrossky N., and Chevion M. Evidence for production of hydroxyl radicals by pentachlorophenol metabolites and hydrogen peroxide: a metal-independent organic Fenton reaction. Biochem. Biophys. Res. Commun. 270 (2000) 942-946
42. Engelmann M.D., Bobier R.T., Hiatt T., and Cheng I.F. Variability of the Fenton reaction characteristics of the EDTA, DTPA, and citrate complexes of iron. BioMetals 16 (2003) 519-527
43. Yamazaki I., and Piette L.H. EPR spin-traping study on the oxidizing species formed in the reaction of the ferrous ion with hydrogen peroxide. J. Am. Chem. Soc. 113 (1991) 7588-7593
44. Lloyd D.R., and Phillips D.H. Oxidative DNA damage mediated by copper(II), iron(II) and nickel(II) Fenton reactions: evidence for site-specific mechanisms in the formation of double-strands breaks, 8-hydroxydeoxyguanosine and putative intrastrand cross-links. Mutat. Res. 424 (1999) 23-36
45. Hancock B.C., and Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci 86 (1997) 1-12
46. Halliwell B. Use of desferrioxamine as a 'probe' for iron-dependent formation of hydroxyl radicals. Evidence for a direct reaction between desferal and the superoxide radical. Biochem. Pharmacol. 34 (1985) 229-233
47. Burkitt M.J., and Mason R.P. Direct evidence for in vivo hydroxyl-radical generation in experimental iron overload: an ESR spin-trapping investigation. Proc. Natl. Acad. Sci. U. S. A. 88 (1991) 8440-8444
48. Halliwell B. Protection against tissue damage in vivo by desferrioxamine: what is its mechanism of action?. Free Radical Biol. Med. 7 (1989) 645-651
49. Gutteridge J.M.C., Quinlan G.J., Swain J., and Cox J. Ferrous ion formation by ferrioxamine prepared from aged desferrioxamine: a potential prooxidant property. Free Radical Biol. Med. 16 (1994) 733-739
50. Schaich K.M., and Borg D.C. Fenton reactions in lipid phases. Lipids 23 (1988) 570-579
51. Toyokuni S., and Sagripanti J.L. Association between 8-hydroxy-2′-deoxyguanosine formation and DNA strand breaks mediated by copper and iron. Free Radical Biol. Med. 20 (1996) 859-864
52. Anchordoquy T.J., Armstrong T.K., Molina M.C., Allison D.S., Zhang Y., Patel M.M., Lentz Y.K., and Koe G.S. Formulation considerations for DNA-based therapeutics. In: Lu D.R., and Oie S. (Eds). Cellular Drug Delivery: Principles and Practice (2004), Humana Press, New Jersey 237-264
53. Molina M.C., Armstrong T.K., Zhang Y., Patel M.M., Lentz Y.K., and Anchordoquy T.J. The stability of lyophilized lipid/DNA complexes during prolonged storage. J. Pharm. Sci. 93 (2004) 2259-2273