Nano- and Microgels Through Addition Reactions of Functional Oligomers and Polymers

Chapter
Part of the Advances in Polymer Science book series (POLYMER, volume 234)

Abstract

Nano- and Microgels are predominantly prepared using radical polymerization techniques. This chapter reviews alternative approaches to microgel preparation based on addition reactions of functional oligomers and polymers. This allows preparation of microgels under physiological conditions and in the presence of biologically active molecules without affecting their function. This method is therefore predominantly used to synthesize microgels for biomedical applications. Different crosslinking chemistries that have been used in this context are presented and discussed with regard to reaction conditions and stability of the reaction product. Microgels that have been prepared by these techniques are divided into two groups. Natural polymers used for the preparation of microgels are described first, followed by artificial prepolymers that are suitable for the preparation of microgels. The different preparation methods as well as the resulting microgels and their properties are presented and discussed.

Keywords

Addition reactions Disulfide bridges Drug delivery Michael addition Microgel Prepolymers 

Abbreviations

BBMEC

Bovine brain microvessel endothelial cell lines

BSA

Bovine serum albumin

CDI

N,N-Carbonyldiimidazole

CHP

Cholesterol-bearing PuL

CHPNG

Cholesterol-bearing PuL nanogels

CL

Cellulose

CS

Chitosan

DDC

N,N-Dicyclohexylcarbodiimide

DLS

Dynamic light scattering

DMSO

Dimethyl sulfoxide

DSP

Dithiobis(succinimidyl propionate)

DTBP

Dimethyl 3, 3-dithiobispropionimidate

DTME

Dithio-bis-maleimidoethane

DTT

Dithiothreitol

DVS

Divinyl sulfone

ECM

Extracellular matrix

EDC

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

EDTADA

Ethylenediaminetetraacetic dianhydride

FATP

5-Fluoroadenine arabinoside

GSH

Glutathione

HA

Hyaluronan

HPC

Hydroxypropylcellulose

LCST

Lower critical solution temperature

NAC

N-Acetylcysteine

ODN

Oligonucleotide

PASP

Poly(aspartic acid)

PEG

Poly(ethylene glycol)

PEG-OVS

Poly(ethylene glycol)-octavinylsulfone

PEI

Poly(ethylene imine)

PG

Poly(glycidol)

PNIPAM

Poly(N-isopropylacrylamide)

p-NPC

p-Nitrophenylcarbonate

PuL

Pullulan

RAFT

Reversible addition-fragmentation chain transfer polymerization

SEM

Scanning electron microscopy

SFM

Scanning force microscopy

STS

Sulfanyl thiocarbonyl sulfanyl

TEM

Transmission electron microscopy

TPP

Tripolyphosphate

References

  1. [1]
    Peppas NA, Hilt JZ, Khademhosseini A, Langer R (2006) Adv Mater 18:1345Google Scholar
  2. [2]
    Kabanov AV, Vinogradov SV (2009) Angew Chem Int Ed Engl 48:5418Google Scholar
  3. [3]
    Pich A, Richtering W (2010) Adv Polym Sci doi: 10.1007/12_2010_70Google Scholar
  4. [4]
    Oh JK, Drumright R, Siegwart DJ, Matyjaszewski (2008) Prog Polym Sci 33:448Google Scholar
  5. [5]
    Landfester K, Musyanovych A (2010) Adv Polym Sci doi: 10.1007/12_2010_68Google Scholar
  6. [6]
    Hennik WE, van Nostrum CF (2002) Adv Drug Deliv Rev 54:13Google Scholar
  7. [7]
    van Tomme SR, Storm G, Hennink WE (2008) Int J Pharm 355:1Google Scholar
  8. [8]
    Hoare TR, Kohane DS (2008) Polymer 49:1993Google Scholar
  9. [9]
    De Geest BG, Dejugnat C, Sukhorukov GB, Braeckmans K, De Smedt SC, Demeester J (2005) Adv Mater 17:2357Google Scholar
  10. [10]
    Oh JK, Lee DI, Park JM (2009) Prog Polym Sci 34:1261Google Scholar
  11. [11]
    Raemdonck K, Demeester J, De Smedt S (2009) Soft Matter 5:707Google Scholar
  12. [12]
    Soussan E, Cassel S, Blanzat M, Rico-Lattes I (2009) Angew Chem Int Ed Engl 48:274Google Scholar
  13. [13]
    Rivest C, Morrison DWG, Ni B, Rubin J, Yadav V, Mahdavi A, Karp JM, Khademhosseini A (2007) J Mech Mater Struct 2:1103Google Scholar
  14. [14]
    Liu Z, Jiao Y, Wang Y, Zhou C, Zhang Z (2008) Adv Drug Deliv Rev 60:1650Google Scholar
  15. [15]
    Voet D, Voet JG (2005) Biochemistry, 3rd edn. Wiley, New YorkGoogle Scholar
  16. [16]
    Gilbert HF (1995) Meth Enzymol 251:8Google Scholar
  17. [17]
    Meister A, Anderson ME (1983) Annu Rev Biochem 52:711Google Scholar
  18. [18]
    Wu G, Fang Y-Z, Yang S, Lupton JR, Turner ND (2004) J Nutr 134:489Google Scholar
  19. [19]
    Saito G, Swanson JA, Lee K-D (2003) Adv Drug Deliv Rev 55:199Google Scholar
  20. [20]
    Meng F, Hennink WE, Zhong Z (2009) Biomaterials 30:2180Google Scholar
  21. [21]
    Kosower NS, Kosower EM (1995) Meth Enzymol 251:123Google Scholar
  22. [22]
    Shu XZ, Liu Y, Luo Y, Roberts MC, Prestwich GD (2002) Biomacromolecules 3:1304Google Scholar
  23. [23]
    Hahn SK, Park JK, Tomimatsu T, Shimobouji T (2007) Int J Biol Macromol 40:374Google Scholar
  24. [24]
    Goessl A, Tirelli N, Hubbell JA (2004) J Biomater Sci Polym Ed 15:895Google Scholar
  25. [25]
    Mather BD, Viswanathan K, Miller KM, Long TE (2006) Prog Polym Sci 31:487Google Scholar
  26. [26]
    Qiu B, Stefanos S, Ma J, Lalloo A, Perry BA, Leibowitz MJ, Sinko PJ, Stein S (2003) Biomaterials 24:11Google Scholar
  27. [27]
    Hiemstra C., van der Aa LJ, Zhong Z, Dijkstra PJ, Feijen J (2007) Macromolecules 40:1165Google Scholar
  28. [28]
    Gehrke SH, Uhden LH, McBride JF (1998) J Control Release 55:21Google Scholar
  29. [29]
    Lutolf MP, Tirelli N, Cerritelli S, Cavalli L, Hubbell JA (2001) Bioconjug Chem 12:1051Google Scholar
  30. [30]
    Metters A, Hubbell J (2005) Biomacromolecules 6:290Google Scholar
  31. [31]
    Kim M-S, Choi Y-J, Noh I, Tae G (2007) J Biomed Mater Res A 83A:674Google Scholar
  32. [32]
    Han S-C, He W-D, Li J, Li L-Y, Sun X-L, Zhang B-Y, Pan T-T (2009) J Polym Sci A Polym Chem 47:4074Google Scholar
  33. [33]
    Yamaguchi N, Kiick KL (2005) Biomacromolecules 6:1921Google Scholar
  34. [34]
    Schultz KM, Baldwin AD, Kiick KL, Furst EM (2009) Macromolecules 42:5310Google Scholar
  35. [35]
    Kratz F, Warnecke A, Riebeseel K, Rodrigues PCA (2002) In: Dumitriu S (ed) Polymeric biomaterials. Marcel Dekker, New York, p 859Google Scholar
  36. [36]
    van Dijk M, Rijkers DTS, Liskamp RM, van Nostrum CF, Hennink WE (2009) Bioconjug Chem 20:2001Google Scholar
  37. [37]
    Hermanson GT (2008) Bioconjugate techniques, 2nd edn. Elsevier, AmsterdamGoogle Scholar
  38. [38]
    Hoare DG, Koshland DE (1966) J Am Chem Soc 88:2057Google Scholar
  39. [39]
    Kunkel GR, Mehrabian M, Martinson HG (1981) Mol Cell Biol 34:3Google Scholar
  40. [40]
    Lomant AJ, Fairbanks G (1976) J Mol Biol 104:243Google Scholar
  41. [41]
    Wang K, Richards F (1974) J Biol Chem 249:8005Google Scholar
  42. [42]
    Paul R, Anderson GW (1960) J Am Chem Soc 82:4596Google Scholar
  43. [43]
    Gasteier P, Reska A, Schulte P, Salber J, Offenhäusser A, Moeller M, Groll J (2007) Macromol Biosci 7:1010Google Scholar
  44. [44]
    Smyth DG (1967) J Biol Chem 242:1592Google Scholar
  45. [45]
    Janes KA, Calvo P, Alonso MJ (2001) Adv Drug Deliv Rev 47:83Google Scholar
  46. [46]
    Agnihotri SA, Mallikarjuna NN, Aminabhavi TM (2004) J Control Release 100:5Google Scholar
  47. [47]
    Prabaharan M, Mano JF (2005) Drug Deliv 12:41Google Scholar
  48. [48]
    Hoffman AS (2002) Adv Drug Deliv Rev 54:3Google Scholar
  49. [49]
    Coviello T, Matricardi P, Marianecci C, Alhaique F (2007) J Control Release 119:5Google Scholar
  50. [50]
    Lee KY, Mooney DJ (2001) Chem Rev 101:1869Google Scholar
  51. [51]
    Payne GF, Raghavan SR (2007) Soft Matter 3:521Google Scholar
  52. [52]
    Illum L (1998) Pharm Res 15:1326Google Scholar
  53. [53]
    Fraser JRE, Laurent TC, Laurent UBG (1997) J Intern Med 242:27Google Scholar
  54. [54]
    Asari A (2004) In: Garg HG, Hales CA (eds) Chemistry and biology of hyaluronan. Elsevier, Amsterdam, pp 457–468Google Scholar
  55. [55]
    Leach JB, Schmidt C (2004) In: Wnek GE, Bowlin GL (eds) Encyclopedia of biomaterials and biomedical engineering. Marcel Dekker, New York, pp 779–788Google Scholar
  56. [56]
    Phillips GO (1992) In: Glasser WG, Hatakayma H (eds) Viscoelasticity of biomaterials. ACS symposium series, vol 489. American Chemical Society, Washington DC, p 168Google Scholar
  57. [57]
    Capila I, Linhardt RJ (2002) Angew Chem Int Ed Engl 41:390Google Scholar
  58. [58]
    Bernkop-Schnürch A, Schwarz V, Steininger S (1999) Pharm Res 16:876Google Scholar
  59. [59]
    Bernkop-Schnürch A, Hornof M, Pinter Y (2003) Int J Pharm 260:229Google Scholar
  60. [60]
    Bernkop-Schnürch A, Guggi D, Pinter Y (2004) J Control Release 94:177Google Scholar
  61. [61]
    Krauland AH, Guggi D, Bernkop-Schnürch A (2006) Int J Pharm 307:270Google Scholar
  62. [62]
    Krauland AH, Leitner VM, Grabovac V, Bernkop-Schnürch A (2006) J Pharm Sci 95:2463Google Scholar
  63. [63]
    Schmitz T, Bravo-Osuna I, Vauthier C, Ponchel G, Loretz B, Bernkop-Schnürch A (2007) Biomaterials 28:524Google Scholar
  64. [64]
    Loretz B, Thaler M, Bernkop-Schnürch A (2007) Bioconjug Chem 18:1028Google Scholar
  65. [65]
    Atyabi F, Talaie F, Dinarvand R (2009) J Nanosci Nanotechnol 9:4593Google Scholar
  66. [66]
    Lee D, Zhang W, Shirley SA, Kong X, Hellermann GR, Lockey RF, Mohapatra SS (2007) Pharm Res 24:157Google Scholar
  67. [67]
    Shu S, Wang X, Zhang X, Zhang, X, Wang Z, Li C (2009) New J Chem 33:1882Google Scholar
  68. [68]
    Hahn SK, Kim JS, Shimobouji T (2006) J Biomed Mater Res 80A:916Google Scholar
  69. [69]
    Lee, H, Mok H, Lee S, Oh Y-K, Park TG (2007) J Control Release 119:245Google Scholar
  70. [70]
    Lee, H, Jeong Y, Park TG (2007) Biomacromolecules 8:3705Google Scholar
  71. [71]
    Morimoto N, Qui X-P, Winnik FM, Akiyoshi K (2008) Macromolecules 41:5985Google Scholar
  72. [72]
    Bae KH, Mok H, Park TG (2008) Biomaterials 29:3376Google Scholar
  73. [73]
    Wong SS (1991) Chemistry of protein conjugation and cross-linking. CRC, Boca RatonGoogle Scholar
  74. [74]
    Gao J, Haidar G, Lu X, Hu Z (2001) Macromolecules 34:2242Google Scholar
  75. [75]
    Xia X, Tang S, Lu X, Hu Z (2003) Macromolecules 36:3695Google Scholar
  76. [76]
    Cai T, Hu Z (2004) Langmuir 20:7355Google Scholar
  77. [77]
    Jha AK, Hule RA, Jiao T, Teller SS, Clifton RJ, Duncan RL, Pochan DJ, Jia X (2009) Macromolecules 42:537Google Scholar
  78. [78]
    Scott EA, Nichols, MD, Cordova, LH, George BJ, Jun Y-S, Elbert DL (2008) Biomaterials 29:4481Google Scholar
  79. [79]
    Hasegawa U, Sawada S-I, Shimizu T, Kishida T, Otsuji E, Mazda O, Akiyoshi K (2009) J Control Release 140:312Google Scholar
  80. [80]
    Monteiro OAC, Airoldi C (1999) Int J Biol Macromol 26:119Google Scholar
  81. [81]
    Denkbas EB, Seyyal M, Piskin E (1999) J Microencapsul 16:741Google Scholar
  82. [82]
    Al-Helw AA, Al-Angary AA, Mahrous GM, Al-Dardari MM (1998) J Microencapsul 15:373Google Scholar
  83. [83]
    Thanoo BC, Sunny MC, Jayakrishnan A (1992) J Pharm Pharmacol 44:283Google Scholar
  84. [84]
    Jameela SR, Kumary TV, Lal AV, Jayakrishnan A (1998) J Control Release 52:17Google Scholar
  85. [85]
    Kumbar SG, Kulkarni A, Aminabhavi TM (2002) J Microencapsul 19:173Google Scholar
  86. [86]
    Mitra A, Gaur U, Ghosh PC, Maitra AN (2001) J Control Release 74:317Google Scholar
  87. [87]
    He P, Davis SS, Illum L (1998) Int J Pharm 166:75Google Scholar
  88. [88]
    He P, Davis SS, Illum L (1999) Int J Pharm 187:53Google Scholar
  89. [89]
    Wang L-Y, Ma G-H, Su Z-G (2005) J Control Release 106:62Google Scholar
  90. [90]
    Wang L-Y, Gu Y-H, Zhou Q-Z, Ma G-H, Wan Y-H, Su Z-G (2006) Colloids Surf B Biointerfaces 50:126Google Scholar
  91. [91]
    Wei W, Wang L-Y, Yuan L, Wei Q, Yang X-D, Su Z-G, Ma G-H (2007) Adv Funct Mater 17:3153Google Scholar
  92. [92]
    Bodnar M, Hartmann JF, Borbely J (2005) Biomacromolecules 6:2521Google Scholar
  93. [93]
    Bodnar M, Hartmann JF, Borbely J (2006) Biomacromolecules 7:3030Google Scholar
  94. [94]
    Yun YH, Goetz DJ, Yellen P, Chen W (2004) Biomaterials 25:147Google Scholar
  95. [95]
    Jia X, Yeo Y, Clifton RJ, Jiao T, Kohane DS, Kobler JB, Zeitels SM, Langer R (2006) Biomacromolecules 7:3336Google Scholar
  96. [96]
    Shen X, Zhang L, Jiang X, Hu Y, Guo J (2007) Angew Chem Int Ed Engl 46:7104Google Scholar
  97. [97]
    Yamaoka T, Tabata Y, Ikada Y (1994) J Pharm Sci 83:601Google Scholar
  98. [98]
    Harris JM, Zalipsky S (eds) (1997) Poly(ethylene glycol): chemistry and biological applications. American Chemical Society, Washington DCGoogle Scholar
  99. [99]
    Prime KL, Whitesides GM (1993) J Am Chem Soc 115:10714Google Scholar
  100. [100]
    Leckband D, Sheth S, Halperin A (1999) J Biomater Sci Polym Ed 10:1125Google Scholar
  101. [101]
    Oral E, Peppas NA (2004) J Biomed Mater Res 68A:439Google Scholar
  102. [102]
    Lutolf MP, Hubbell JA (2003) Biomacromolecules 4:713Google Scholar
  103. [103]
    Dhanasingh A, Salber J, Moeller M, Groll J (2010) Soft Matter. 6:618Google Scholar
  104. [104]
    Vandenberg EJ (1985) J Polym Sci A Polym Chem 23:915Google Scholar
  105. [105]
    Sunder A, Hanselmann R, Frey H, Mülhaupt R (1999) Macromolecules 32:4240Google Scholar
  106. [106]
    Dworak A, Baran G, Trzebicka B, Wałach W (1999) React Funct Polym 42:31Google Scholar
  107. [107]
    Erberich M, Keul H, Möller M (2007) Macromolecules 40:3070Google Scholar
  108. [108]
    Keul H, Möller M (2009) J Polym Sci A Polym Chem 47:3209Google Scholar
  109. [109]
    Kainthan RK Janzen J, Levin E, Devine DV, Brooks DE (2006) Biomacromolecules 7:703Google Scholar
  110. [110]
    Boussif O, Lezoualc’h F, Zanta MA, Mergny MD, Scherman D, Demeneix B, Behr J-P (1995) Proc Natl Acad Sci USA 92:7297Google Scholar
  111. [111]
    Pack DW, Hoffman AS, Pun S, Stayton PS (2005) Nat Rev Drug Discov 4:581Google Scholar
  112. [112]
    Garnett MC (1999) Crit Rev Ther Drug Carrier Syst 16:147Google Scholar
  113. [113]
    Behr J-P (1997) Chimia 51:34Google Scholar
  114. [114]
    Peng Q, Zhong Z, Zhuo R (2008) Bioconjug Chem 19:499Google Scholar
  115. [115]
    Forrest ML, Koerber JT, Pack DW (2003) Bioconjug Chem 14:934Google Scholar
  116. [116]
    Kloeckner J, Wagner E, Ogris M (2006) Eur J Pharm Sci 29:414Google Scholar
  117. [117]
    Gosselin MA, Guo W, Lee RJ (2001) Bioconjug Chem. 12:989Google Scholar
  118. [118]
    Wang Y, Chen P, Shen J (2006) Biomaterials 27:5292Google Scholar
  119. [119]
    Thomas M, Ge Q, Lu JJ, Chen J, Klibanov A (2005) Pharm Res 22:373Google Scholar
  120. [120]
    Schmidt-Wolf GD., Schmidt-Wolf, IGH (2003) Trends Mol Med 9:67Google Scholar
  121. [121]
    Park TG, Jeong JH, Kim SW (2006) Adv Drug Deliv Rev 58:467Google Scholar
  122. [122]
    Bauhuber S, Hozsa C, Breunig M, Göpferich A (2009) Adv Mat 21:3286Google Scholar
  123. [123]
    Luten J, van Nostrum CF, De Smedt SC, Hennink WE (2008) J Control Release 126:97Google Scholar
  124. [124]
    Jere D, Jiang HL, Arote R, Kim YK, Choi YJ, Cho MH, Akaike T, Cho CS (2009) Expert Opin Drug Deliv 6:827Google Scholar
  125. [125]
    Aliyar HA, Hamilton PD, Remsen EE, Ravi N (2005) J Bioact Compat Polym 20:169Google Scholar
  126. [126]
    Groll J, Singh S, Albrecht K, Moeller M (2009) J Polym Sci A Polym Chem 47:5543Google Scholar
  127. [127]
    Nichols MD, Scott EA, Elbert DL (2009) Biomaterials 30:5283Google Scholar
  128. [128]
    Mok H, Park TG (2006) Bioconjug Chem 17:1369Google Scholar
  129. [129]
    Vinogradov S, Batrakova E, Kabanov A (1999) Colloids Surf B Biointerfaces 16:291Google Scholar
  130. [130]
    Vinogradov SV, Bronich TK, Kabanov AV (2002) Adv Drug Deliv Rev 54:135Google Scholar
  131. [131]
    Bronich TK, Vinogradov SV, Kabanov AV (2001) Nano Lett 1:535Google Scholar
  132. [132]
    Vinogradov SV, Batrakova EV, Kabanov AV (2004) Bioconjug Chem 15:50Google Scholar
  133. [133]
    Vinogradov SV (2006) Curr Pharm Res 12:4703Google Scholar
  134. [134]
    Vinogradov SV, Zeman AD, Batrakova EV, Kabanov AV (2005) J Control Release 107:143Google Scholar
  135. [135]
    Vinogradov SV, Kohli E, Zeman AD (2006) Pharm Res 23:920Google Scholar
  136. [136]
    Nimesh S, Goyal A, Pawar V, Jayaraman S, Kumar P, Chandra R, Singh Y, Gupta KC (2006) J Control Release 110:457Google Scholar
  137. [137]
    Swami A, Goyal R, Tripathi SK, Singh N, Katiyar N, Mishra AK, Gupta KC (2009) Int J Pharm 374:125Google Scholar
  138. [138]
    Kohli E, Han H-Y, Zeman AD, Vinogradov SV (2007) J Control Release 121:19Google Scholar
  139. [139]
    Neu M, Sitterberg J, Bakowsky U, Kissel T (2006) Biomacromolecules 7:3428Google Scholar
  140. [140]
    Neu M, Germerhaus O, Mao S, Voigt KH, Behe M, Kissel T (2007) J Control Release 118:370Google Scholar
  141. [141]
    Deng R, Yue Y, Jin F, Chen Y, Kung H-F, Lin MCM, Wu C (2009) J Control Release 140:40Google Scholar
  142. [142]
    Lee Y, Park SY, Kim C, Park TG (2009) J Control Release 135:89Google Scholar
  143. [143]
    Dalton PD, Hostert C, Albrecht K, Moeller M, Groll J (2008) Macromol Biosci 8:923Google Scholar
  144. [144]
    Caraculacu AA, Coseri S (2001) Prog Polym Sci 26:799Google Scholar

Copyright information

© Springer 2010

Authors and Affiliations

  • Krystyna Albrecht
  • Martin Moeller
    • 1
  • Juergen Groll
    • 1
  1. 1.DWI e.V. and Institute of Technical and Macromolecular ChemistryRWTH Aachen UniversityAachenGermany

Personalised recommendations