Synthesis of a fluorescent and star-shaped 4-arm PEG with different functional groups at its ends

Dong-Ik Lee; Chan-Jin Kim; Chang-Ha Lee; Ik-Sung Ahn

Journal of Industrial and Engineering Chemistry, Vol.18, No.3, 1186-1190, May, 2012

DOI10.1016/j.jiec.2012.01.010 Export Citation

Synthesis of a fluorescent and star-shaped 4-arm PEG with different functional groups at its ends

Dong-Ik Lee, Chan-Jin Kim, Chang-Ha Lee , and Ik-Sung Ahn^†

Department of Chemical and Biomolecular Engineering, Yonsei University, Seoul 120-749, South Korea

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Dityrosine (DY), which is fluorescent and biocompatible, has multiple functional groups, including two amine and two carboxylic acid groups. By conjugating PEG arms to DY, we successfully synthesized a star-shaped 4-arm PEG with two carboxylic acid and two amine groups at its four ends. Two different kinds of molecules could be further linked to this 4-arm PEG. The chemical structures and molecular weights of the intermediate 2-arm PEG and 4-arm PEG were determined by 1H NMR spectroscopy and matrix assisted laser desorption ionization-time of flight-mass spectrometry (MALDI-TOF-MS).

Keywords:N,N'-diBoc-dityrosine;Dityrosine;4-arm Polyethylene glycol;Fluorescent core

[References]

Merrill EW, in: Harris JM (Ed.), Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical Applications, Plenum Press, New York, 199 (1992)
Sherman MR, Williams LD, Saifer MGP, French JA, Kwak LW, Oppenheim JJ, in: Harris JM, Zaplisky S (Eds.), ACS Symposium Series, vol. 680, American Chemical Society, Washington, DC, 155 (1997)
Merrill EW, J. Biomater. Sci. Polym. Ed., 5, 1 (1993)
Lapienis G, Prog. Polym. Sci., 34, 852 (2009)
Pasut G, Veronese FM, Adv. Drug Deliver. Rev., 61, 1177 (2009)
Veronese FM, Caliceti P, Schiavon O, J. Bioact. Compat. Polym., 12, 196 (1997)
Monfardini C, Schiavon O, Caliceti P, Morpurgo M, Harris JM, Veronese FM, Bioconjugate Chem., 6, 62 (1995)
Ono K, Kai Y, Maeda H, Samizo F, Sakurai K, Nishimura H, Inada Y, J. Biomater.Sci. Polym. Ed., 2, 61 (1991)
Peleshanko S, Jeong J, Shevchenko VV, Genson KL, Pikus Y, Ornatska M, Petrash S, Tsukruk VV, Macromolecules, 37(20), 7497 (2004)
Gunawidjaja R, Peleshanko S, Tsukruk VV, Macromolecules, 38(21), 8765 (2005)
Hou SJ, Chaikof EL, Taton D, Gnanou Y, Macromolecules, 36(11), 3874 (2003)
Rele SM, Cui WX, Wang LC, Hou SJ, Barr-Zarse G, Tatton D, Gnanou Y, Esko JD, Chaikof EL, J. Am. Chem. Soc., 127(29), 10132 (2005)
Giulivi C, Davies KJA, Methods Enzymol., 233, 363 (1994)
Smail EH, Briza P, Panagos A, Berenfeld L, Infect. Immun., 63, 4078 (1995)
Malencik DA, Anderson SR, Amino Acids., 25, 233 (2003)
Giulivi C, Davies KJA, J. Biol. Chem., 276, 24129 (2001)
Heinecke JW, Free Radic. Biol. Med., 32, 1090 (2002)
Li J, Hodgeman BA, Christensen BM, Insect Biochem. Mol. Biol., 26, 309 (1996)
Nomura K, Suzuki N, Arch. Biochem. Biophys., 319, 525 (1995)
Hanft F, Koehler P, J. Agric. Food Chem., 53, 2418 (2005)
Lee DI, Choi JY, Kim CJ, Ahn IS, Process Biochem., 46, 142 (2011)
Zalipsky S, Albericio F, Barany G, in: Deber CM, Hruby VJ, Kopple KD (Eds.), Peptides: Structure and Function, Pierce Chemical Co, 257 (1985)
Souza JM, Giasson BI, Chen Q, Lee VMY, J. Biol. Chem., 275, 18344 (2000)
Lapienis G, Penczek S, J. Polym. Sci. A: Polym. Chem., 42(7), 1576 (2004)

[Referenced By]

[Related Articles]

[1] Merrill EW, in: Harris JM (Ed.), Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical Applications, Plenum Press, New York, 199 (1992)

[2] Sherman MR, Williams LD, Saifer MGP, French JA, Kwak LW, Oppenheim JJ, in: Harris JM, Zaplisky S (Eds.), ACS Symposium Series, vol. 680, American Chemical Society, Washington, DC, 155 (1997)

[3] Merrill EW, J. Biomater. Sci. Polym. Ed., 5, 1 (1993)

[4] Lapienis G, Prog. Polym. Sci., 34, 852 (2009)

[5] Pasut G, Veronese FM, Adv. Drug Deliver. Rev., 61, 1177 (2009)

[6] Veronese FM, Caliceti P, Schiavon O, J. Bioact. Compat. Polym., 12, 196 (1997)

[7] Monfardini C, Schiavon O, Caliceti P, Morpurgo M, Harris JM, Veronese FM, Bioconjugate Chem., 6, 62 (1995)

[8] Ono K, Kai Y, Maeda H, Samizo F, Sakurai K, Nishimura H, Inada Y, J. Biomater.Sci. Polym. Ed., 2, 61 (1991)

[9] Peleshanko S, Jeong J, Shevchenko VV, Genson KL, Pikus Y, Ornatska M, Petrash S, Tsukruk VV, Macromolecules, 37(20), 7497 (2004)

[10] Gunawidjaja R, Peleshanko S, Tsukruk VV, Macromolecules, 38(21), 8765 (2005)

[11] Hou SJ, Chaikof EL, Taton D, Gnanou Y, Macromolecules, 36(11), 3874 (2003)

[12] Rele SM, Cui WX, Wang LC, Hou SJ, Barr-Zarse G, Tatton D, Gnanou Y, Esko JD, Chaikof EL, J. Am. Chem. Soc., 127(29), 10132 (2005)

[13] Giulivi C, Davies KJA, Methods Enzymol., 233, 363 (1994)

[14] Smail EH, Briza P, Panagos A, Berenfeld L, Infect. Immun., 63, 4078 (1995)

[15] Malencik DA, Anderson SR, Amino Acids., 25, 233 (2003)

[16] Giulivi C, Davies KJA, J. Biol. Chem., 276, 24129 (2001)

[17] Heinecke JW, Free Radic. Biol. Med., 32, 1090 (2002)

[18] Li J, Hodgeman BA, Christensen BM, Insect Biochem. Mol. Biol., 26, 309 (1996)

[19] Nomura K, Suzuki N, Arch. Biochem. Biophys., 319, 525 (1995)

[20] Hanft F, Koehler P, J. Agric. Food Chem., 53, 2418 (2005)

[21] Lee DI, Choi JY, Kim CJ, Ahn IS, Process Biochem., 46, 142 (2011)

[22] Zalipsky S, Albericio F, Barany G, in: Deber CM, Hruby VJ, Kopple KD (Eds.), Peptides: Structure and Function, Pierce Chemical Co, 257 (1985)

[23] Souza JM, Giasson BI, Chen Q, Lee VMY, J. Biol. Chem., 275, 18344 (2000)

[24] Lapienis G, Penczek S, J. Polym. Sci. A: Polym. Chem., 42(7), 1576 (2004)