Poly(amidoamine) dendrimer-drug conjugates with disulfide linkages for intracellular drug delivery

Biomaterials

Volumn 30, Issue 11, 2009, Pages 2112-2121

  Kurtoglu, Yunus E ^a,b   Navath, Raghavendra S ^a,b   Wang, Bing ^b,c   Kannan, Sujatha ^b,c   Romero, Robert ^b   Kannan, Rangaramanujam M ^a,b  

^a Wayne State University   (United States)

^b EUNICE KENNEDY SHRIVER NATIONAL INSTITUTE OF CHILD HEALTH AND HUMAN DEVELOPMENT   (United States)

^c CHILDREN'S HOSPITAL OF MICHIGAN   (United States)

Author keywords

Dendrimers; Glutathione sensitive release; Intracellular drug delivery; N Acetyl cysteine; Neuroinflammation; PAMAM dendrimers

Indexed keywords

GLUTATHIONE-SENSITIVE RELEASE; INTRACELLULAR DRUG DELIVERY; N-ACETYL CYSTEINE; NEUROINFLAMMATION; PAMAM DENDRIMERS;

BODY FLUIDS; DRUG DELIVERY; INTERNET; OXYGEN; PH; PH EFFECTS; PLASMA STABILITY; PLASMAS;

DENDRIMERS;

ACETYLCYSTEINE; BOVINE SERUM ALBUMIN; CYSTEINE; DENDRIMER; DISULFIDE; GLUTATHIONE; POLYAMIDOAMINE; REACTIVE OXYGEN METABOLITE;

ANIMAL CELL; ARTICLE; CELL ACTIVATION; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STABILITY; INTRACELLULAR SPACE; KINETICS; LYSOSOME; MICROGLIA; MOUSE; NONHUMAN; PH; PRIORITY JOURNAL;

ACETYLCYSTEINE; ANIMALS; CATTLE; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTEINE; DENDRIMERS; DRUG DELIVERY SYSTEMS; FLOW CYTOMETRY; GLUTATHIONE; HYDROGEN-ION CONCENTRATION; MICE; POLYAMINES; REACTIVE OXYGEN SPECIES; SERUM ALBUMIN, BOVINE;

BOVINAE;

EID: 59849100122     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2008.12.054     Document Type: Article

References (40)

1. Lee C.C., MacKay J.A., Fréchet J.M.J., and Szoka F.C. Designing dendrimers for biological applications. Nat Biotechnol 23 (2005) 1517-1526
2. Svenson S., and Tomalia D.A. Dendrimers in biomedical applications & reflections on the field. Adv Drug Deliv Rev 57 (2005) 2106-2129
3. Esfand R., and Tomalia D.A. Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications. Drug Discov Today 6 (2001) 427-436
4. Duncan R., and Izzo L. Dendrimer biocompatibility and toxicity. Adv Drug Deliv Rev 57 (2005) 2215-2237
5. Sato N., Kobayashi H., Hiraga A., Saga T., Togashi K., Konishi J., et al. Pharmacokinetics and enhancement patterns of macromolecular MR contrast agents with various sizes of polyamidoamine dendrimer cores. Magn Reson Med 46 (2001) 1169-1173
6. 125I-labelled polyamidoamine dendrimers in vivo. J Control Release 65 (2000) 133-148
7. Matsumura Y., and Maeda H. A new concept for macromolecular therapeutics in cancer chemotherapy: mechanism of tumoritropic accumulation of proteins and the antitumour agent. Cancer Res 46 (1986) 6387-6392
8. Kukowska-Latallo J.F., Candido K.A., Cao Z., Nigavekar S.S., Majoros I.J., Thomas T.P., et al. Nanoparticle targeting of anticancer drug improves therapeutic response in animal model of human epithelial cancer. Cancer Res 65 (2005) 5317-5324
9. Malik N., Evagorou E.G., and Duncan R. Dendrimer-platinate: a novel approach to cancer chemotherapy. Anticancer Drugs 10 (1999) 767-776
10. Zhuo R.X., Du B., and Lu Z.R. In vitro release of 5-fluorouracil with cyclic core dendritic polymer. J Control Release 57 (1999) 249-257
11. Gurdag S., Khandare J., Stapels S., Matherly L.H., and Kannan R.M. Activity of dendrimer-methotrexate conjugates on methotrexate-sensitive and -resistant cell lines. Bioconjug Chem 17 (2006) 275-283
12. Lee C.C., Gillies E.R., Fox M.E., Guillaudeu S.J., Fréchet J.M.J., Dy E.E., et al. A single dose of doxorubicin-functionalized bow-tie dendrimer cures mice bearing C-26 colon carcinomas. Proc Natl Acad Sci U S A 103 (2006) 16649-16656
13. Wiwattanapatapee R., Lomlim L., and Saramunee K. Dendrimers conjugates for colonic delivery of 5-aminosalicylic acid. J Control Release 88 (2003) 1-9
14. Kolhe P., Khandare J., Pillai O., Kannan S., Lieh-Lai M., and Kannan R.M. Preparation, cellular transport, and activity of polyamidoamine-based dendritic nanodevices with a high drug payload. Biomaterials 27 (2006) 660-669
15. Najlah M., Freeman S., Attwood D., and D'Emanuele A. Synthesis, characterization and stability of dendrimer prodrugs. Int J Pharm 308 (2006) 175-182
16. Khandare J., Kolhe P., Pillai O., Kannan S., Lieh-Lai M., Kannan R.M., et al. Cellular transport, and activity of polyamidoamine dendrimer-methylprednisolone conjugates. Bioconjug Chem 16 (2005) 330-337
17. Navath R.S., Kurtoglu Y.E., Wang B., Kannan S., Romero R., and Kannan R.M. Dendrimers-drug conjugates for tailored intracellular drug release based on glutathione levels. Bioconjug Chem 19 (2008) 2446-2455
18. Zafarullah M., Li W.Q., Sylvester J., and Ahmad M. Molecular mechanisms of N-acetyl cysteine actions. Cell Mol Life Sci 60 (2003) 6-20
19. Khan M., Sekhon B., Jatana M., Giri S., Gilg A.G., Sekhon C., et al. Administration of N-acetyl cysteine after focal cerebral ischemia protects brain and reduces inflammation in a rat model of experimental stroke. J Neurosci Res 4 (2004) 519-527
20. Dekhuijzen P.N.R. Antioxidant properties of N-acetyl cysteine: their relevance in relation to chronic obstructive pulmonary disease. Eur Respir J 23 (2004) 629-636
21. Harada D., Naito S., and Otagiri M. Kinetic analysis of covalent binding between N-acetyl-l-cysteine and albumin through the formation of mixed disulfides in human and rat serum in vitro. Pharm Res 19 (2002) 1648-1654
22. Yip L., Dart R.C., and Hurlbut K.M. Intravenous administration of oral N-acetyl cysteine. Crit Care Med 26 (1998) 40-43
23. Kannan RM, Iezzi R, Rajaguru B, Kannan S. Dendrimer-containing particles for sustained release of compounds. International Patent Application Number: PCT/US2008/078988; 2007.
24. Kolhe P., Misra E., Kannan R.M., Kannan S., and Lieh-Lai M. Drug complexation, in vitro release and cellular entry of dendrimers and hyperbranched polymers. Int J Pharm 259 (2003) 143-160
25. Patri A.K., Kukowska-Latallo J.F., and Baker Jr. J.R. Targeted drug delivery with dendrimers: comparison of the release kinetics of covalently conjugated drug and non-covalent drug inclusion complex. Adv Drug Deliv Rev 57 (2005) 2203-2214
26. De Jesus O.L.P., Ihre H.R., Gagne L., Frechet J.M.J., and Szoka Jr. F.C. Polyester dendritic systems for drug delivery applications: in vitro and in vivo evaluation. Bioconjug Chem 13 (2002) 453-461
27. Bracci L., Falciani C., Lelli B., Lozzi L., Runci Y., Pini A., et al. Synthetic peptides in the form of dendrimers become resistant to protease activity. J Biol Chem 278 (2003) 46590-46595
28. Meister A., and Anderson M.E. Glutathione. Annu Rev Biochem 52 (1983) 711-760
29. Arrick B.A., and Nathan C.F. Glutathione metabolism as a determinant of therapeutic efficacy: a review. Cancer Res 44 (1984) 4224-4232
30. Saito G., Swanson J.A., and Lee K. Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities. Adv Drug Deliv Rev 55 (2003) 199-215
31. Zhang W., Tichy S.E., Perez L.M., Maria G.C., Lindahl P.A., and Simanek E.E. Evaluation of multivalent dendrimers based on melamine: kinetics of thiol-disulfide exchange depends on the structure of the dendrimer. J Am Chem Soc 25 (2003) 5086-5094
32. 6 conjugates. Macromol Biosci 8 (2008) 375-383
33. Saadani-Makki F., Kannan S., Lu X., Janisse J., Dawe E., Edwin S., et al. Intrauterine administration of endotoxin leads to motor deficits in a rabbit model: a link between prenatal infection and cerebral palsy. Am J Obstet Gynecol 199 (2008) 651-659
34. Roy A., Jana A., Yatich K., Freidt M.B., Fung Y.K., Martinson J.A., et al. Reactive oxygen species up-regulate CD11b in microglia via nitric oxide: implications for neurodegenerative diseases. Free Radic Biol Med 45 (2008) 686-699
35. Winterbourn C.C., and Metodiewa D. Reactivity of biologically important thiol compounds with superoxide and hydrogen peroxide. Free Radic Biol Med 27 (1999) 322-328
36. Perumal O.P., Inapagolla R., Kannan S., and Kannan R.M. The effect of surface functionality on cellular trafficking of dendrimers. Biomaterials 29 (2008) 3469-3476
37. Kitchens K.M., Foraker A.B., Kolhatkar R.B., Swaan P.W., Eddington N.D., and Ghandehari H. Endocytosis and interaction of poly(amidoamine) dendrimers with caco-2 cells. Pharm Res 24 (2007) 2138-2145
38. Min K.J., Jou I., and Joe E. Plasminogen-induced IL-1beta and TNF-alpha production in microglia is regulated by reactive oxygen species. Biochem Biophys Res Commun 312 (2003) 969-974
39. Flora S.J., Poande M., Kannan G.M., and Mehta A. Lead induced oxidative stress and its recovery following co-administration of melatonin or N-acetyl cysteine during chelation with succimer in male rats. Cell Mol Biol 50 (2004) 543-545
40. Paintlia M.K., Paintlia A.S., Contreras M.A., Singh I., and Singh A.K. Lipopolysaccharide-induced peroxisomal dysfunction exacerbates cerebral white matter injury: attenuation by N-acetyl cysteine. Exp Neurol 210 (2008) 560-576