Highly photostable rylene-encapsulated polymeric nanoparticles for fluorescent labeling in biological system

Mingyeong Kang; Hanseong Kim; Tae Hyeong Lee; Yang Hoon Huh; Young Sang Kim; Sun Joo Park; Jun-O Jin; Peter C.W. Lee; Minseok Kwak

Journal of Industrial and Engineering Chemistry, Vol.80, 239-246, December, 2019

DOI10.1016/j.jiec.2019.08.001 Export Citation

Highly photostable rylene-encapsulated polymeric nanoparticles for fluorescent labeling in biological system

Mingyeong Kang^{1, 2}, Hanseong Kim¹, Tae Hyeong Lee³, Yang Hoon Huh⁴, Young Sang Kim¹, Sun Joo Park¹, Jun-O Jin⁵, Peter C.W. Lee³, and Minseok Kwak^{1, †}

¹Department of Chemistry, Pukyong National University, Busan 48513, Republic of Korea
²Interdisciplinary Program of Marine Convergence Design, Pukyong National University, Busan 48513, Republic of Korea
³Department of Biomedical Sciences, University of Ulsan College of Medicine, ASAN Medical Center Seoul 05505, Republic of Korea
⁴Center for Microscopy Research, Korea Basic Science Institute, Chungcheongbuk-do 28119, Republic of Korea
⁵Department of Medical Biotechnology, Yeungnam University, Gyeongbuk 38541, Republic of Korea

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Rylene dyes exhibit superior photophysical properties including outstanding chemical and photochemical stabilities as well as high fluorescence quantum yields (FQYs). However, the rylene chromophores have some limitations, such as high hydrophobicity and low solubility in aqueous solution, as a fluorescent tag for biological system. Herein, we present a general method to load the rylene dyes into triblock copolymer nanoparticles (NPs) and stabilize the core. The rylene dyes in confined hydrophobic core fairly preserve their FQYs in aqueous environment. Lumogen probe nanoparticles (PNPs) were prepared with four different commercial rylenes (Lumogen Violet, Yellow, Orange and Red) in the spectral region of visible and infrared (400-750 nm) and their photophysical properties were characterized. They exhibited enhanced photostability compared to commercial fluorescent dyes. Also the internalization of Lumogen PNPs in HeLa cell was confirmed by cell uptake test. These results indicate the Lumogen PNPs can be widely applicable in fluorescence detection and imaging such as flow cytometry and fluorescence microscopy.

Keywords:sIPN;PNPs;Nanoprobe;Bioimaging

[References]

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Zhong YL, Peng F, Bao F, Wang SY, Ji XY, Yang L, Su YY, Lee ST, He Y, J. Am. Chem. Soc., 135(22), 8350 (2013)
Gui R, Jin H, Wang Z, Li J, Chem. Soc. Rev., 47, 6795 (2018)
Nagao Y, Misono T, Dyes Pigment., 5, 171 (1984)
Rademacher A, Markle S, Langhals H, Chem. Ber., 115, 2927 (1982)
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[Referenced By]

[1] Gui R, Jin H, Bu X, Fu Y, Wang Z, Liu Q, Coord. Chem. Rev., 383, 82 (2019)

[2] Grossi M, Morgunova M, Cheung S, Scholz D, Conroy E, Terrile M, Panarella A, Simpson JC, Gallagher WM, O’Shea DF, Nat. Commun., 7, 10855 (2016)

[3] Zhang X, Wang S, Xu L, Feng L, Ji Y, Tao L, Lia S, Wei Y, Nanoscale, 4, 5581 (2012)

[4] Xu K, Zhong GS, Zhuang XW, Science, 339(6118), 452 (2013)

[5] Huber O, Brunner A, Maier P, Kaufmann R, Couraud PO, Cremer C, Fricker G, PLoS One, 7, e44776 (2012)

[6] Nyk M, Kumar R, Ohulchanskyy TY, Bergey EJ, Prasad PN, Nano Lett., 8, 3834 (2008)

[7] He H, Xie C, Ren J, Anal. Chem., 80, 5951 (2008)

[8] Larson DR, Zipfel WR, Williams RM, Clark SW, Bruchez MP, Wise FW, Webb WW, Science, 300, 1434 (2003)

[9] Zhong YL, Peng F, Bao F, Wang SY, Ji XY, Yang L, Su YY, Lee ST, He Y, J. Am. Chem. Soc., 135(22), 8350 (2013)

[10] Gui R, Jin H, Wang Z, Li J, Chem. Soc. Rev., 47, 6795 (2018)

[11] Nagao Y, Misono T, Dyes Pigment., 5, 171 (1984)

[12] Rademacher A, Markle S, Langhals H, Chem. Ber., 115, 2927 (1982)

[13] Bullock JE, Vagnini MT, Ramanan C, Co DT, Wilson TM, Dicke JW, Marks TJ, Wasielewski MR, J. Phys. Chem. B, 114(5), 1794 (2010)

[14] Huang C, Barlow S, Marder SR, J. Org. Chem., 76, 2386 (2011)

[15] Battagliarin G, Davies M, Mackowiak S, Li C, Mullen K, ChemphysChem, 13, 923 (2012)

[16] Margineanu A, Hofkens J, Cotlet M, Habuchi S, Stefan A, Qu JQ, Kohl C, Mullen K, Vercammen J, Engelborghs Y, Gensch T, De Schryver FC, J. Phys. Chem. B, 108(32), 12242 (2004)

[17] Avlasevich Y, Li C, Mullen K, J. Mater. Chem., 20, 3814 (2010)

[18] Weil T, Abdalla MA, Jatzke C, Hengstler J, Mullen K, Biomacromolecules, 6(1), 68 (2005)

[19] Zhang X, Wang S, Liu M, Hui J, Yang B, Tao L, Wei Y, Nanoscale, 2, 335 (2013)

[20] Bhattacharjee J, Verma G, Aswal VK, Hassan PA, Pramana, 71, 991 (2008)

[21] Huang Z, Zhang X, Zhang X, Fu C, Wang K, Yuan J, Tao L, Wei Y, Polym. Chem., 6, 607 (2015)

[22] Huang Z, Chen Q, Wan Q, Wang K, Yuan J, Zhang X, Tao L, Wei Y, Polym. Chem., 8, 4805 (2017)

[23] Alexandridis P, Holzwarth JF, Hatton TA, Macromolecules, 27(9), 2414 (1994)

[24] Arranja A, Schroder AP, Schmutz M, Waton G, Schosseler F, Mendes E, J. Control. Release, 196, 87 (2014)

[25] Online VA, Zhang X, Zhang X, Wang S, Liu M, Tao L, Wei Y, Nanoscale., 5, 147 (2013)

[26] Petrov P, Bozukov M, Tsvetanov CB, J. Mater. Chem., 15, 1481 (2005)

[27] Lee H, Lee YS, Lee KD, Park SY, Macromol. Biosci., 11, 1264 (2011)

[28] Doycheva M, Petrova E, Stamenova R, Tsvetanov C, Riess G, Macromol. Mater. Eng., 289, 676 (2004)

[29] Oktavia L, Jeong SM, Kang MY, Kim HS, Lee TH, Zhang JB, Seo HW, Lee JH, Han DH, An YJ, Yang CD, Kim JH, Je JT, Song SM, Cho EA, Kim SY, Jin JO, Lee PCW, Kwak MS, J. Ind. Eng. Chem., 73, 87 (2019)

[30] Schneider CA, Rasband WS, Eliceiri KW, Nat. Methods., 9, 671 (2012)

[31] Yoo H, Yang J, Yousef A, Wasielewski MR, Kim D, J. Am. Chem. Soc., 132(11), 3939 (2010)

[32] Hwang J, Kang M, Sari MI, Lee TH, Kim K, Ryu J, Baek SK, Ahn DJ, Lee PCW, Kwak M, Macromol. Res., 1 (2019)

[33] Shirmanova MV, Druzhkova IN, Lukina MM, Matlashov ME, Belousov VV, Snopova LB, Prodanetz NN, Dudenkova VV, Lukyanov SA, Zagaynova EV, BBA - Gen. Subj., 1850, 1905 (2015)

[34] Anderson M, Moshnikova A, Engelman DM, Reshetnyak YK, Andreev OA, Proc. Natl. Acad. Sci., 113, 1 (2016)