Induced Circular Dichroism of Methylene Blue in Self-Assembled Pullulan Nanoparticles

Seo-Kyung Kim; Soo Kyung Hwang; Cheol Gyun Kim; Hyun-Joong Kim; Chong-Su Cho

Macromolecular Research, Vol.28, No.13, 1198-1203, December, 2020

DOI10.1007/s13233-020-8173-2 Export Citation

Induced Circular Dichroism of Methylene Blue in Self-Assembled Pullulan Nanoparticles

Seo-Kyung Kim¹, Soo Kyung Hwang², Cheol Gyun Kim¹, Hyun-Joong Kim^{2, 3, †}, and Chong-Su Cho^{1, 2, †}

¹Department of Agricultural Biotechnology, Seoul National University, Seoul 08824, Korea
²Research Institute of Agriculture and Life Sciences, Seoul National University, Seoul 08824, Korea
³Program in Environmental Materials Science, Department of Agriculture, Forestry and Bioresources, Seoul National University, Seoul 08824, Korea

E-mail:,

This study reports self-assembled pullulan nanoparticles (PUNPs) obtained by the diafiltration method after dissolving phthalic pullulan in dimethylformamide, which was prepared by esterification between the primary hydroxyl groups of the pullulan and carboxylic acids of phthalic anhydride. The morphologies of the PUNPs observed by transmission electron microscopy (TEM) were spherical shapes. The particle sizes of the PUNPs measured by dynamic light scattering (DLS) were around 75.3 nm with -49.32 mV zeta potential. The ordered structure of pullulan measured by circular dichroism (CD) spectroscopy and X-ray diffraction (XRD) was enhanced by the formation of self-assembled polymeric NPs. Methylene blue (MB) used in tissue imaging agent was loaded into PUNPs via ionic bonding of cationic MB and anionic PUNPs, the CD of MB was induced in the PUNPs in the range of 500-700 nm whose crossing point matched.

Keywords:nanoparticle;methylene blue;pullulan;induced circular dichroism

[References]

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Im W, Kim HS, Tissue Eng. Regen. Med., 16, 213 (2019)
Kim KJ, Choi MS, Shim JH, Rhie JW, Tissue Eng. Regen. Med., 16, 395 (2019)
Yoon SY, Kang SK, Lee HB, Oh SH, Kim WS, Li HS, Bok JD, Cho CS, Choi YJ, Tissue Eng. Regen. Med., 17, 33 (2020)
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[1] Portney NG, Ozkan M, Anal. Bioanal. Chem., 384, 620 (2006)

[2] Petros RA, DeSimone JM, Nat. Rev. Drug Discov., 9, 615 (2010)

[3] Elsabahy M, Wooley KL, Chem. Soc. Rev., 41, 2545 (2012)

[4] Murahari MS, Yergeri MC, Curr. Pharm. Des., 19, 4622 (2013)

[5] Kim WS, Lee JY, Singh B, Maharjan S, Hong L, Lee SM, Cui LH, et al., Sci. Rep., 8, 5878 (2018)

[6] Im W, Kim HS, Tissue Eng. Regen. Med., 16, 213 (2019)

[7] Kim KJ, Choi MS, Shim JH, Rhie JW, Tissue Eng. Regen. Med., 16, 395 (2019)

[8] Yoon SY, Kang SK, Lee HB, Oh SH, Kim WS, Li HS, Bok JD, Cho CS, Choi YJ, Tissue Eng. Regen. Med., 17, 33 (2020)

[9] Ko KW, Yoo YI, Kim JY, Choi B, Park SB, Park W, Rhim WK, Han DK, Tissue Eng. Regen. Med., 17, 155 (2020)

[10] Yang CG, Park GK, McDonald EJ, Choi HS, Tissue Eng. Regen. Med., 16, 433 (2019)

[11] Jung JS, Jo D, Jo G, Hyun H, Tissue Eng. Regen. Med., 16, 443 (2019)

[12] Pillarisetti S, Uthaman S, Huh KM, Koh YS, Lee S, Park IK, Tissue Eng. Regen. Med., 16, 451 (2019)

[13] Miyagawa T, Yamamoto M, Muraki R, Onouchi H, Yashima E, J. Am. Chem. Soc., 129(12), 3676 (2007)

[14] Nishimura T, Shinoda S, Tsukube H, Chirality, 14, 555 (2002)

[15] Yoshida N, Yamaguchi H, Higashi M, J. Chem. Soc.-Faraday Trans., 2, 2507 (1994)

[16] Buss V, Angew. Chem.-Int. Edit., 30, 869 (1991)

[17] Krois D, Brinker UH, J. Am. Chem. Soc., 120(45), 11627 (1998)

[18] Lightner DA, Gawronska JK, Gawronska K, J. Am. Chem. Soc., 107, 2456 (1985)

[19] Owen DJ, VanDerveer D, Schuster GB, J. Am. Chem. Soc., 120(8), 1705 (1998)

[20] Chung TW, Kim BJ, Park SY, Akaike T, Nah JW, Cho CS, Macromolecules, 33(24), 8921 (2000)

[21] Chung TW, Nah JW, Akaike T, Park YH, Cho CS, Polymer, 41(16), 6415 (2000)

[22] Jo J, Yamamoto M, Matsumoto K, Nakamura T, Tabata Y, J. Nanosci. Nanotechnol., 6, 2853 (2006)

[23] Tabata Y, Matsui Y, Uno K, Sokawa Y, Ikada Y, J. Interferon Cytokine Res., 19, 287 (1999)

[24] Kanatani I, Ikai T, Okazaki A, Jo JI, Yamamoto M, Imamura M, Kanematsu A, Yamamoto S, Ito M, Ogawa O, Tabata Y, J. Control. Release, 116, 75 (2006)

[25] Matsui A, Tanaka E, Choi HS, Kianzad V, Gioux S, Lomnes SJ, Frangioni JV, Surgery, 148, 78 (2010)

[26] Hong L, Kim WS, Lee SM, Kang SK, Choi YJ, Cho CS, Front. Microbiol., 10, 142 (2019)

[27] Yoo MK, Park MY, Lee SW, Choi YJ, Park IK, Cho CS, J. Nanosci. Nanotechnol., 10, 3551 (2010)

[28] Tao X, Xie Y, Zhang Q, Qiu X, Yuan L, Wen Y, Li M, Yang X, Tao T, Xie M, Lv Y, Wang Q, Feng X, Nanomaterials, 6, 165 (2016)

[29] Kono H, Kondo N, Isono T, Ogata M, Hirabayashi K, Int. J. Biol. Macromol., 154, 1382 (2019)

[30] Kony DB, Damm W, Stoll S, van Gunsteren WF, Hunenberger PH, Biophys. J., 93, 442 (2007)

[31] Karmakar M, Mahapatra M, Dutta A, Chattopadhyay PK, Singha NR, Int. J. Biol. Macromol., 102, 438 (2017)

[32] Arndt ER, Stevens ES, Carbohydr. Polym., 303, 73 (1997)

[33] Forget A, Christensen J, Ludeke S, Kohler E, Tobias S, Matloubi M, Thomann R, Shastri VP, Proc. Natl. Acad. Sci. U.S.A., 110, 12887 (2013)