Advertisement

Hyperbranched Polyamines for Transfection

  • Wiebke Fischer
  • Marcelo Calderón
  • Rainer HaagEmail author
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 296)

Abstract

The successful application of gene therapy through DNA transfection into the cell is still a great challenge in ongoing research. Hyperbranched polyamines are highly branched macromolecules, and have gained significant attention in the last two decades, due to their relative ease of preparation, their shape, and their multi-functionality.

This review deals with the syntheses of various hyperbranched polyamines that are prepared through a one-step polymerization process. Furthermore, we present the current status of polyamines as gene carriers and describe their versatility, and their properties such as structure-property dependency, gene transfection efficiency, and cytotoxicity profiles of hyperbranched polyamines.

Keywords

Applications Cytotoxicity profile Gene delivery Hyperbranched polyamines Poly(amido amine) Poly(amido ester) Poly(ethylene imine) Polyglycerol amines Structure-property dependence Synthesis Transfection efficiency 

List of Abbreviations

293T

Cell line

Ǻ

Angström

A549

Cell line (carcinomic human alveolar basal epithelial cell)

AEPZ

1-(2-Aminoethyl) piperazine

AFM

Atomic force microscope

AlCl3

Aluminum chloride

AMP

4-(Aminomethyl)piperidine

ATPase

Enzyme which catalyzes the degradation of adenosine triphosphate

B16F10

Cell line (murine melanoma cell)

BDDA

1,4-Butanediol diacrylate

bis-MPA

2,2-Bis-(methylol)propionic acid

bPEI-g-lPEG

Poly(ethyleneimine)-graft-poly(ethyleneglycol) copolymers

C2C12

Cell line (mouse myoblast cell)

C6

Rat glioma cell line

CBA

N,N′-Cystamine bisacrylamide

Cbz

Benzyl carbamate

CDC2

Cell line (cell division control protein 2)

CHCl3

Chloroform

CHO-K1

Cell line (Chinese hamster ovary-K1)

COS-7

Cell line (African green monkey)

D

Dendritic unit

Da

Dalton

DB

Degree of branching

DEAPA

Diethylaminopropylamine

DETA

Diethylenetriamine

DMDPTA

N,N-Dimethylaminodipropylene-triamine

DNA

Deoxyribonucleic acid

dPG

Dendritic polyglycerols

DTT

Dithiothreitol

EGDA

Ethylene glycol diacrylate

EI

Ethylene imine

FA

Folic acid

G

Generation

g

Graft

GSH

Reduced glutathione

h

Hour

H2

Hydrogen

HDDA

1,6-Hexanediol diacrylate

HEEI

N-(2-Hydroxyethyl) ethylene imine

HEK 293

Cell line (human embryonic kidney 293 cells)

HeLa

Cell line (Henrietta Lacks, immortal cell line)

HepG2

Cell line (human hepatocellular carcinoma)

HMBA

N,N′-Hexamethylene bisacrylamide

HMW

High molecular weight

HPAMAM

Hyperbranched PAMAM

HPB

Hyperbranched polymer

IC

Inhibitory concentration

kDa

Kilo Dalton

L

Linear unit

LiAlH4

Lithium aluminum hydride

LMW

Low molecular weight

MA

Methyl acrylate

MAPK2

Cell line (mitogen-activated kinase 2)

MDD-MB-231

Cell line (breast cancer cells)

MEDA

N-Methylethylenediamine

MeOH

Methanol

Mn

Number average molecular weight

MTT

3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide

MW

Molecular weight

MWD

Molecular weight distribution (Mw/Mn)

N/P ratio

Ratio of nitrogen versus phosphate

N2a

Cell line (Mouse neuroblastoma cells)

NIH/3T3

Cell line (House embryonic fibroblast)

NMR

Nuclear magnetic resonance

OH

Hydroxyl groups

PAMAM

Poly(amido amine)

Pd

Palladium

PD

Polydispersity

PEG

Poly(ethylene glycol)

pEGFP-C1

Plasmid (encodes a red-shifted variant of wild-type GFP)

PEG-PEI

PEGylated poly(ethylene imine)

PEI

Poly(ethylene imine)

PG

Polyglycerol

pGL3-Luc

Luciferase reporter vector

PG-PEHA

Polyglycerol pentaethylenhexamine carbamate

PG-Q-n

PG functionalized with quaternary amines

PG-T-n

PG functionalized with tertiary amines

PHE

Phenylalanine

PPI

Poly(propyl imine)

RHB

Reducible hyperbranched polymer

RNA

Ribonucleic acid

ROP

Ring opening polymerization

SCID

Severe combined immunodeficiency

SEC

Size exclusion chromatography

SIM MC 7721

Cell line (human normal hep-atocyte cells)

siRNA

Small interfering RNA

T

Terminal unit

TEM

Transmission electron microscopy

THF

Tetrahydrofuran

TMPTA

Trimethylol-propane triacrylate

XTT

Cell proliferation kit

References

  1. 1.
    Mintzer MA, Simanek EE (2009) Chem Rev 109:259PubMedGoogle Scholar
  2. 2.
    Park TG, Jeong JH, Kim SW (2006) Adv Drug Deliv Rev 58:467PubMedGoogle Scholar
  3. 3.
    Yang ZR, Wang HF, Zhao J, Peng YY, Wang J, Guinn BA, Huang LQ (2007) Cancer Gene Ther 14:599PubMedGoogle Scholar
  4. 4.
    Schaffer DV, Lauffenburger DA (1998) J Biol Chem 273:28004PubMedGoogle Scholar
  5. 5.
    Merdan T, Kopecek J, Kissel T (2002) Adv Drug Deliv Rev 54:715PubMedGoogle Scholar
  6. 6.
    Wang JY, Casero RA, Jr. (2006) Polyamine Cell Signaling Physiology, Pharmacology, and Cancer Research. Humana Press Inc., Totowa, NJGoogle Scholar
  7. 7.
    Verma IM, Somia N (1997) Nature 389:239PubMedGoogle Scholar
  8. 8.
    Luo D, Saltzman WM (2000) Nat Biotechnol 18:33PubMedGoogle Scholar
  9. 9.
    Li S, Huang L (2000) Gene Ther 7:31PubMedGoogle Scholar
  10. 10.
    Pack DW, Hoffman AS, Pun S, Stayton PS (2005) Nat Rev Drug Discov 4:581PubMedGoogle Scholar
  11. 11.
    Green JJ, Zugates GT, Tedford NC, Huang Y-H, Griffith LG, Lauffenburger DA, Sawicki JA, Langer R, Anderson DG (2007) Adv Mater 19:2836Google Scholar
  12. 12.
    Itaka K, Kanayama N, Nishiyama N, Jang WD, Yamasaki Y, Nakamura K, Kawaguchi H, Kataoka K (2004) J Am Chem Soc 126:13612PubMedGoogle Scholar
  13. 13.
    Minakuchi Y, Takeshita F, Kosaka N, Sasaki H, Yamamoto Y, Kouno M, Honma K, Nagahara S, Hanai K, Sano A, Kato T, Terada M, Ochiya T (2004) Nucleic Acids Res 32:e109PubMedGoogle Scholar
  14. 14.
    Khalil IA, Kogure K, Akita H, Harashima H (2006) Pharmacol Rev 58:32PubMedGoogle Scholar
  15. 15.
    Carmichael GG (2002) Nature 418:379PubMedGoogle Scholar
  16. 16.
    Karmali PP, Chaudhuri A (2007) Med Res Rev 27:696PubMedGoogle Scholar
  17. 17.
    Martin B, Sainlos M, Aissaoui A, Oudrhiri N, Hauchecorne M, Vigneron JP, Lehn JM, Lehn P (2005) Curr Pharm Des 11:375PubMedGoogle Scholar
  18. 18.
    Vijayanathan V, Thomas T, Shirahata A, Thomas TJ (2001) Biochemistry 40:13644PubMedGoogle Scholar
  19. 19.
    Wilson RW, Bloomfield VA (1979) Biochemistry 18:2192PubMedGoogle Scholar
  20. 20.
    Yessine M-A, Lafleur M, Meier C, Petereit H-U, Leroux J-C (2003) Biochim Biophys Acta Biomembr 1613:28Google Scholar
  21. 21.
    Guy J, Drabek D, Antoniou M (1995) Mol Biotechnol 3:237PubMedGoogle Scholar
  22. 22.
    Seymour LW (1992) Crit Rev Ther Drug Carrier Syst 9:135PubMedGoogle Scholar
  23. 23.
    Kim TH, Cooka SE, Arote RB, Cho M-H, Nah JW, Choi YJ, Cho CS (2007) Macromol Biosci 7:611PubMedGoogle Scholar
  24. 24.
    Brissault B, Kichler A, Guis C, Leborgne C, Danos O, Cheradame H (2003) Bioconjug Chem 14:581PubMedGoogle Scholar
  25. 25.
    Sonawane ND, Szoka FC Jr, Verkman AS (2003) J Biol Chem 278:44826PubMedGoogle Scholar
  26. 26.
    Behr JP (1997) Chimica 51:34Google Scholar
  27. 27.
    Thomas TJ, Bloomfield VA (1983) Biopolymers 22:1097PubMedGoogle Scholar
  28. 28.
    Wolff JA, Rozema DB (2008) Mol Ther 16:8PubMedGoogle Scholar
  29. 29.
    Boussif O, Lezoualc’h F, Zanta MA, Mergny MD, Scherman D, Demeneix B, Behr JP (1995) Proc Natl Acad Sci USA 92:7297PubMedGoogle Scholar
  30. 30.
    Dunlap DD, Maggi A, Soria MR, Monaco L (1997) Nucleic Acids Res 25:3095PubMedGoogle Scholar
  31. 31.
    Kichler A, Leborgne C, Coeytaux E, Danos O (2001) J Gene Med 3:135PubMedGoogle Scholar
  32. 32.
    Wightman L, Kircheis R, Rossler V, Carotta S, Ruzicka R, Kursa M, Wagner E (2001) J Gene Med 3:362PubMedGoogle Scholar
  33. 33.
    Kabanov AV, Kabanov VA (1995) Bioconjug Chem 6:7PubMedGoogle Scholar
  34. 34.
    Hartmann L, Häfele S, Peschka-Süss R, Antonietti M, Börner Hans G (2008) Chem Eur J 14:2025PubMedGoogle Scholar
  35. 35.
    Fischer W, Brissault B, Prévost S, Kopaczynska M, Andreou I, Janosch A, Gradzielski M, Haag R (2010) Macromol Biosci acceptedGoogle Scholar
  36. 36.
    Akinc A, Anderson DG, Lynn DM, Langer R (2003) Bioconjug Chem 14:979PubMedGoogle Scholar
  37. 37.
    Esfand R, Tomalia DA (2001) Drug Discov Today 6:427PubMedGoogle Scholar
  38. 38.
    Buhleier E, Wehner W, Vögtle F (1978) Synthesis 155Google Scholar
  39. 39.
    Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1985) Polymer Journal 17:117Google Scholar
  40. 40.
    Tomalia DA, Baker E, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P (1986) Macromolecules 19:2466Google Scholar
  41. 41.
    Newkome GR, Yao Z, Baker GR, Gupta VK (1985) J Org Chem 50:2003Google Scholar
  42. 42.
    Fischer M, Vögtle F (1999) Angew Chem Int Ed 38:884Google Scholar
  43. 43.
    Bosman AW, Janssen HM, Meijer EW (1999) Chem Rev 99:1665PubMedGoogle Scholar
  44. 44.
    Frechet JMJ, Tomalia DA (2001) Dendrimers and other dendritic polymers. Wiley, Chichester, p 155Google Scholar
  45. 45.
    Newkome GR, Moorefield CN, Vögtle F (2001) Dendrimers and dendrons: concepts, syntheses, applictions. Wiley-VCH, WeinheimGoogle Scholar
  46. 46.
    Frechet JM (1994) Science 263:1710PubMedGoogle Scholar
  47. 47.
    Uppuluri S, Keinath SE, Tomalia DA, Dvornic PR (1998) Macromolecules 31:4498Google Scholar
  48. 48.
    Krause W, Hackmann-Schlichter N, Maier FK, Müller R (2000) Top Curr Chem 210:261Google Scholar
  49. 49.
    Stiriba SE, Frey H, Haag R (2002) Angew Chem Int Ed Engl 41:1329PubMedGoogle Scholar
  50. 50.
    Barth RF, Adams DM, Soloway AH, Alam F, Darby MV (1994) Bioconjug Chem 5:58PubMedGoogle Scholar
  51. 51.
    Chen CZ, Beck-Tan NC, Dhurjati P, van Dyk TK, LaRossa RA, Cooper SL (2000) Biomacromolecules 1:473PubMedGoogle Scholar
  52. 52.
    Kojima C, Kono K, Maruyama K, Takagishi T (2000) Bioconjug Chem 11:910PubMedGoogle Scholar
  53. 53.
    Nishiyama N, Stapert HR, Zhang GD, Takasu D, Jiang DL, Nagano T, Aida T, Kataoka K (2003) Bioconjug Chem 14:58PubMedGoogle Scholar
  54. 54.
    Malik N, Wiwattanapatapee R, Klopsch R, Lorenz K, Frey H, Weener JW, Meijer EW, Paulus W, Duncan R (2000) J Control Release 65:133PubMedGoogle Scholar
  55. 55.
    Wiener EC, Brechbiel MW, Brothers H, Magin RL, Gansow OA, Tomalia DA, Lauterbur PC (1994) Magn Reson Med 31:1PubMedGoogle Scholar
  56. 56.
    Chen CZ, Cooper SL (2000) Adv Mater 12:843Google Scholar
  57. 57.
    Lünig U (2000) Nachr Chem 48:134Google Scholar
  58. 58.
    Jansen JF, de Brabander-van den Berg EM, Meijer EW (1994) Science 266:1226PubMedGoogle Scholar
  59. 59.
    Baars MW, Kleppinger R, Koch MH, Yeu SL, Meijer EW (2000) Angew Chem Int Ed Engl 39:1285PubMedGoogle Scholar
  60. 60.
    Stephan H, Spies H, Johannsen B, Kauffmann C, Vögtle F (2000) Org Lett 2:2343PubMedGoogle Scholar
  61. 61.
    Kleij AW, van de Coevering R, Klein Gebbink RJ, Noordman AM, Spek AL, van Koten G (2001) Chemistry 7:181PubMedGoogle Scholar
  62. 62.
    Teobaldi G, Zerbetto F (2003) J Am Chem Soc 125:7388PubMedGoogle Scholar
  63. 63.
    Naylor AM, Goddard WA III, Kiefer GE, Tomalia DA (1989) J Am Chem Soc 111:2339Google Scholar
  64. 64.
    Kim YH, Webster OW (1990) J Am Chem Soc 112:4593Google Scholar
  65. 65.
    Stevelmans S, van Hest JCM, Jansen JFGA, van Boxtel DAFJ, de Brabander-van den Berg EMM, Meijer EW (1996) J Am Chem Soc 7398Google Scholar
  66. 66.
    Chechik V, Zhao M, Crooks RM (1999) J Am Chem Soc 121:4910Google Scholar
  67. 67.
    Pistolis G, Malliaris A, Tsiourvas D, Paleos CM (1999) Chem Eur J 5:1440Google Scholar
  68. 68.
    Schmitzer A, Perez E, Rico-Lattes I, Lattes A, Rosca S (1999) Langmuir 15:4397Google Scholar
  69. 69.
    Chen S, Yu Q, Li L, Boozer CL, Homola J, Yee SS, Jiang S (2002) J Am Chem Soc 124:3395PubMedGoogle Scholar
  70. 70.
    Kojima C, Haba Y, Fukui T, Kono K, Takagishi T (2003) Macromolecules 36:2183Google Scholar
  71. 71.
    Sideratou Z, Tsiourvas D, Paleos CM (2000) Langmuir 16:1766Google Scholar
  72. 72.
    Ghosh SK, Kawaguchi S, Jinbo Y, Izumi Y, Yamaguchi K, Taniguchi T, Nagai K, Koyama K (2003) Macromolecules 36:9162Google Scholar
  73. 73.
    Gillies ER, Fréchet JMJ (2005) Drug Discovery Today 10:35PubMedGoogle Scholar
  74. 74.
    Luger K, Mader AW, Richmond RK, Sargent DF, Richmond TJ (1997) Nature 389:251PubMedGoogle Scholar
  75. 75.
    Joester D, Losson M, Pugin R, Heinzelmann H, Walter E, Merkle HP, Diederich F (2003) Angew Chem Int Ed Engl 42:1486PubMedGoogle Scholar
  76. 76.
    Uyemura M, Aida T (2002) J Am Chem Soc 124:11392PubMedGoogle Scholar
  77. 77.
    Hecht S, Fréchet JMJ (2001) Angew Chem Int Edit 40:74Google Scholar
  78. 78.
    Tomalia DA, Dewald JR (1985) U.S. Patent 4 507 466Google Scholar
  79. 79.
    Tomalia DA, Dewald JR (1986) U.S. Patent 4 568 737Google Scholar
  80. 80.
    Haensler J, Szoka FC Jr (1993) Bioconjug Chem 4:372PubMedGoogle Scholar
  81. 81.
    Vlasov GP, Korol’kov VI, Pankova GA, Tarasenko I, Baranov AN, Glazkov PB, Kiselev AV, Ostapenko OV, Lesina EA, Baranov VS (2004) Bioorg Khim 30:15PubMedGoogle Scholar
  82. 82.
    Service RF (2003) Science 300:243PubMedGoogle Scholar
  83. 83.
    Nel A, Xia T, Madler L, Li N (2006) Science 311:622PubMedGoogle Scholar
  84. 84.
    Guillot-Nieckowski M, Joester D, Stohr M, Losson M, Adrian M, Wagner B, Kansy M, Heinzelmann H, Pugin R, Diederich F, Gallani JL (2007) Langmuir 23:737PubMedGoogle Scholar
  85. 85.
    Gebhart CL, Kabanov AV (2001) J Control Release 73:401PubMedGoogle Scholar
  86. 86.
    Tang MX, Redemann CT, Szoka FC Jr (1996) Bioconjug Chem 7:703PubMedGoogle Scholar
  87. 87.
    Jikei M, Kakimoto M (2001) Prog Polym Sci 26:1233Google Scholar
  88. 88.
    Lyulin AV, Adolf DB, Davies GR (2001) Macromolecules 34:3783Google Scholar
  89. 89.
    Roller S, Zhou H, Haag R (2005) Mol Divers 9:305PubMedGoogle Scholar
  90. 90.
    Haag R, Sunder A, Hebel A, Roller S (2002) J Comb Chem 4:112PubMedGoogle Scholar
  91. 91.
    Krämer M, Stumbé JF, Grimm G, Kaufmann B, Krüger U, Weber M, Haag R (2004) Chembiochem 5:1081PubMedGoogle Scholar
  92. 92.
    Wörner C, Mülhaupt R (1993) Angew Chem 105:1367Google Scholar
  93. 93.
    De Brabander-Van Den Berg M, Meijer EW (1993) Angew Chem Int Ed 32:1308Google Scholar
  94. 94.
    Moors R, Vögtle F (1993) Chem Ber 126:2133Google Scholar
  95. 95.
    Fischer D, von Harpe A, Kunath K, Petersen H, Li Y, Kissel T (2002) Bioconjug Chem 13:1124PubMedGoogle Scholar
  96. 96.
    von Harpe A, Petersen H, Li Y, Kissel T (2000) J Control Release 69:309Google Scholar
  97. 97.
    Dick CR, Ham GE (1970) J Macromol Sci A Pure Appl Chem 4:1301Google Scholar
  98. 98.
    Dick CR, Potter JL, Coker WP (1971) US Patent 3 565 941Google Scholar
  99. 99.
    Horn D, Linhart F (1991) In: Roberts JC (ed) Paper chemistry. Blackie, London, p 44Google Scholar
  100. 100.
    Frey H, Haag R, Buschow KHJ, Robert WC, Merton CF, Bernard I, Edward JK, Subhash M, Patrick V (2001) Encyclopedia of materials: science and technology. Elsevier, Oxford, p 3998Google Scholar
  101. 101.
    Kobayashi S, Hiroishi K, Tokunoh M, Saegusa T (1987) Macromolecules 20:1496Google Scholar
  102. 102.
    Fischer D, Bieber T, Youxin L, Elsässer H-P, Kissel T (1999) Pharm Res 16:1273PubMedGoogle Scholar
  103. 103.
    Kunath K, von Harpe A, Fischer D, Petersen H, Bickel U, Voigt K, Kissel T (2003) J Control Release 89:113PubMedGoogle Scholar
  104. 104.
    Allen TM, Cullis PR (2004) Science 303:1818PubMedGoogle Scholar
  105. 105.
    Petersen H, Fechner PM, Martin AL, Kunath K, Stolnik S, Roberts CJ, Fischer D, Davies MC, Kissel T (2002) Bioconjug Chem 13:845PubMedGoogle Scholar
  106. 106.
    Mao S, Neu M, Germershaus O, Merkel O, Sitterberg J, Bakowsky U, Kissel T (2006) Bioconjug Chem 17:1209PubMedGoogle Scholar
  107. 107.
    Liang B, He M-L, Chan C-y, Chen Y-c, Li X-P, Li Y, Zheng D, Lin MC, Kung H-F, Shuai X-T, Peng Y (2009) Biomaterials 30:4014PubMedGoogle Scholar
  108. 108.
    Baker JR Jr (2009) Hematology 2009:708Google Scholar
  109. 109.
    Putnam D, Langer R (1999) Macromolecules 32:3658Google Scholar
  110. 110.
    Reul R, Nguyen J, Kissel T (2009) Biomaterials 30:5815PubMedGoogle Scholar
  111. 111.
    Lim YB, Han SO, Kong HU, Lee Y, Park JS, Jeong B, Kim SW (2000) Pharm Res 17:811PubMedGoogle Scholar
  112. 112.
    Lim Y, Choi YH, Park JS (1999) J Am Chem Soc 121:5633Google Scholar
  113. 113.
    Forrest ML, Koerber JT, Pack DW (2003) Bioconjug Chem 14:934PubMedGoogle Scholar
  114. 114.
    Lee JH, Lim YB, Choi JS, Lee Y, Kim TI, Kim HJ, Yoon JK, Kim K, Park JS (2003) Bioconjug Chem 14:1214PubMedGoogle Scholar
  115. 115.
    Luo D, Haverstick K, Belcheva N, Han E, Saltzman WM (2002) Macromolecules 35:3456Google Scholar
  116. 116.
    Wang X, He Y, Wu J, Gao C, Xu Y (2009) Biomacromolecules 11:245Google Scholar
  117. 117.
    Dennig J, Duncan E (2002) Rev Mol Biotechnol 90:339Google Scholar
  118. 118.
    Chen J, Wu C, Oupicky D (2009) Biomacromolecules 10:2921PubMedGoogle Scholar
  119. 119.
    Inoue Y, Kurihara R, Tsuchida A, Hasegawa M, Nagashima T, Mori T, Niidome T, Katayama Y, Okitsu O (2008) J Control Release 126:59PubMedGoogle Scholar
  120. 120.
    Voit B (2000) J Polym Sci A Polym Chem 38:2505Google Scholar
  121. 121.
    Meister A, Anderson ME (1983) Annu Rev Biochem 52:711PubMedGoogle Scholar
  122. 122.
    Lynn DM, Langer R (2000) J Am Chem Soc 122:10761Google Scholar
  123. 123.
    Li X, Su Y, Chen Q, Lin Y, Tong Y, Li Y (2005) Biomacromolecules 6:3181PubMedGoogle Scholar
  124. 124.
    Zhong Z, Song Y, Engbersen JF, Lok MC, Hennink WE, Feijen J (2005) J Control Release 109:317PubMedGoogle Scholar
  125. 125.
    Luten J, van Nostrum CF, De Smedt SC, Hennink WE (2008) J Control Release 126:97PubMedGoogle Scholar
  126. 126.
    Lim Y-b, Kim S-M, Lee Y, Lee W-k, Yang T-g, Lee M-j, Suh H, Park J-s (2001) J Am Chem Soc 123:2460PubMedGoogle Scholar
  127. 127.
    Wu D, Liu Y, Jiang X, Chen L, He C, Goh SH, Leong KW (2005) Biomacromolecules 6:3166PubMedGoogle Scholar
  128. 128.
    Arote RB, Lee E-S, Jiang H-L, Kim Y-K, Choi Y-J, Cho M-H, Cho C-S (2009) Bioconjug Chem 20:2231PubMedGoogle Scholar
  129. 129.
    Haag R, Kratz F (2006) Angew Chem Int Ed Engl 45:1198Google Scholar
  130. 130.
    Frey H, Haag R (2002) J Biotechnol 90:257PubMedGoogle Scholar
  131. 131.
    Calderón M, Quadir MA, Sharma SK, Haag R Advanced Materials 22:190Google Scholar
  132. 132.
    Kainthan RK, Gnanamani M, Ganguli M, Ghosh T, Brooks DE, Maiti S, Kizhakkedathu JN (2006) Biomaterials 27:5377Google Scholar
  133. 133.
    Kainthan RK, Hester SR, Levin E, Devine DV, Brooks DE (2007) Biomaterials 28:4581Google Scholar
  134. 134.
    Kainthan RK, Brooks DE (2007) Biomaterials 28:4779Google Scholar
  135. 135.
    Kainthan RK, Mugabe C, Burt HM, Brooks DE (2008) Biomacromolecules 9:886Google Scholar
  136. 136.
    Xu S, Luo Y, Graeser R, Warnecke A, Kratz F, Hauff P, Licha K, Haag R (2009) Bioorg Med Chem Lett 19:1030Google Scholar
  137. 137.
    Calderón M, Graeser R, Kratz F, Haag R (2009) Bioorg Med Chem Lett 19:3725Google Scholar
  138. 138.
    Kolhe P, Khandare J, Pillai O, Kannan S, Lieh-Lai M, Kannan R (2004) Pharm Res 21:2185Google Scholar
  139. 139.
    Khandare J, Mohr A, Calderón M, Welker P, Licha K, Haag R Biomaterials 31:4268Google Scholar
  140. 140.
    Ganguli M, Jayachandran KN, Maiti S (2004) J Am Chem Soc 126:26Google Scholar
  141. 141.
    Tziveleka LA, Psarra AM, Tsiourvas D, Paleos CM (2008) Int J Pharm 356:314Google Scholar
  142. 142.
    Zhang L, Hu C-H, Cheng S-X, Zhuo R-X (2009) Colloids and Surfaces B: Biointerfaces 76:427Google Scholar
  143. 143.
    Fischer W, Calderón M, Schulz A, Andreou I, Weber W, Haag R submittedGoogle Scholar
  144. 144.
    Ofek P, Fischer W, Calderon M, Haag R, Satchi-Fainaro R FASEB J.: fj.09Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • Wiebke Fischer
    • 1
  • Marcelo Calderón
    • 1
  • Rainer Haag
    • 1
    Email author
  1. 1.Institute of Chemistry and BiochemistryFreie Universität BerlinBerlinGermany

Personalised recommendations