Strategy for Detecting Systemic Treatment Sensitivity of Primary Liver Cancer Based on a Novel Infrared-emissive Organic Nanoparticle

Abstract

In this study, we synthesized an organic material with near-infrared emission capabilities: 4-(2-(4-(9-(4-(diphenylamino) phenyl) naphtho[2,3-c] [1,2,5] thiadiazol-4-yl) phenyl)-1H-phenol-1-ylidene) malononitrile (TPA). Furthermore, TPA-PEG2000 fluorescent nanoparticles were prepared via coating the shells with PEG2000. TPA-PEG2000 exhibited strong near-infrared emission near 700 nm, with a photoluminescence quantum yield of 15.09%, indicating a high emission efficiency. Molecular biology experiments have confirmed its low toxicity and excellent biocompatibility. Increased cholesterol and phospholipid levels in liver cancer cell membranes with low sensitivity or high drug resistance lead to increased rigidity, reduced membrane fluidity, reduced endocytic efficiency, and reduced uptake. Therefore, the uptake of TPA-PEG2000 nanoparticles into cells and the near-infrared fluorescence intensity can be used to evaluate the sensitivity of systemic liver cancer treatment in a simple and efficient manner.

Keywords

Nanoparticle / Near-infrared / Fluorescence / Systemic treatment sensitivity / Cell membrane fluidity

References

[1] Fitzmaurice C, Allen C, Barber R M, Barregard L, Bhutta Z A, Brenner H, Dicker D J, Chimed-Orchir O, Dandona R, Dandona L. JAMA Oncology, 2017, 3: 524.

[2] Bukowski K, Kciuk M, Kontek R. Int. J. Mol. Sci., 2020, 21: 9.

[3] Wu Q, Yang Z, Nie Y, Shi Y, Fan D. Cancer Letters, 2014, 347: 159.

[4] Minchinton A I, Tannock I F. Nat. Rev. Cancer, 200, 6: 583.

[5] Mayer L, Bally M, Cullis P. Biochimica Et Biophysica Acta (BBA)-Biomembranes, 198, 857: 123.

[6] Bunea A-I, Harloff-Helleberg S, Taboryski R, Nielsen H M. Advances in Colloid and Interface Science, 2020, 281: 102177.

[7] Dallavalle S, Dobričić V, Lazzarato L, Gazzano E, Machuqueiro M, Pajeva I, Tsakovska I, Zidar N, Fruttero R. Drug Resistance Updates, 2020, 50: 100682.

[8] Goler-Baron V, Assaraf Y G. PloS One, 2011, 6: 16007.

[9] May G L, Wright L C, Dyne M, Mackinnon W B, Fox R M, Mountford C E. Int J Cancer, 1988, 42: 728.

[10] Baritaki S, Apostolakis S, Kanellou P, Dimanche-Boitrel M T, Spandidos D A, Bonavida B. Adv. Cancer Res., 2007, 98: 149.

[11] Peetla C, Bhave R, Vijayaraghavalu S, Stine A, Kooijman E, Labhasetwar V. Mol. Pharm., 2010, 7: 2334.

[12] Lei Z N, Tian Q, Teng Q X, Wurpel J N D, Zeng L, Pan Y, Chen Z S. MedComm, 2023, 4: 265.

[13] Zalba S, Ten Hagen T L. Cancer Treat Rev., 2017, 52: 48.

[14] Sharom F. Frontiers in Oncology, 2014, 4: 41.

[15] Hendrich A B, Michalak K. Curr Drug Targets, 2003, 4: 23.

[16] Kopecka J, Trouillas P, Gašparović A Č, Gazzano E, Assaraf Y G, Riganti C. Drug Resistance Updates, 2020, 49: 100670.

[17] Vijayaraghavalu S, Peetla C, Lu S, Labhasetwar V. Mol. Pharm., 2012, 9: 2730.

[18] Higgins C F. Annual Review of Cell Biology, 1992, 8: 67.

[19] Sinicrope F A, Dudeja P K, Bissonnette B M, Safa A R, Brasitus T A. Journal of Biological Chemistry, 1992, 267: 24995.

[20] Cai C, Zhu H, Chen J. Biochemical and Biophysical Research Communications, 2004, 320: 868.

[21] Wu F, Shao Z Y, Zhai B J, Zhao C L, Shen D M. Ultrasound Med. Biol., 2011, 37: 151.

[22] Yoshida T, Kondo T, Ogawa R, Feril L B Jr., Zhao Q L, Watanabe A, Tsukada K. Cancer Chemother Pharmacol, 2008, 61: 559.

[23] Schuldes H, Dolderer J H, Schoch C, Bickeböller R, Woodcock B G. Int. J. Clin. Pharmacol. Ther., 2000, 38: 204.

[24] Erazo-Oliveras A., Muñoz-Vega M., Salinas M. L., Wang X., Chapkin R. S., Febs. J., 2022, doi: https://doi.org/10.1111/febs.16665

[25] Peetla C, Vijayaraghavalu S, Labhasetwar V. Advanced Drug Delivery Reviews, 2013, 65: 1686.

[26] Lee W K, Kolesnick R N. Cell Signal, 2017, 38: 134.

[27] Vijayaraghavalu S, Peetla C, Lu S, Labhasetwar V. Molecular Pharmaceutics, 2012, 9: 2730.

[28] Cong V T, Houng J L, Kavallaris M, Chen X, Tilley R D, Gooding J J. Chem. Soc. Rev., 2022, 51: 7531.

[29] Nori A, Kopeček J. Advanced Drug Delivery Reviews, 2005, 57: 609.

[30] Banushi B, Joseph S R, Lum B, Lee J J, Simpson F. Nat. Rev. Cancer, 2023, 12: 18.

[31] Kaźmierczak Z, Szostak-Paluch K, Przybyło M, Langner M, Witkiewicz W, Jędruchniewicz N, Dąbrowska K. Bioorganic & Medicinal Chemistry, 2020, 28: 115556.

[32] Rennick J J, Johnston A P R, Parton R G. Nat. Nanotechnol., 2021, 16: 266.

[33] Chen K, Li X, Zhu H, Gong Q, Luo K. Curr. Med. Chem., 2018, 25: 3017.

[34] Ziello J E, Huang Y, Jovin I S. Mol. Med., 2010, 16: 222.

[35] Ha K D, Bidlingmaier S M, Liu B. Frontiers in Physiology, 201, 7: 381.

[36] Kratz F. J. Control Release, 2008, 132: 171.

[37] Kopecka J, Campia I, Olivero P, Pescarmona G, Ghigo D, Bosia A, Riganti C. J. Control Release, 2011, 149: 196.

[38] Pomeroy A E, Schmidt E V, Sorger P K, Palmer A C. Trends in Cancer, 2022, 11: 915.

[39] Ju Y, Guo H, Edman M, Hamm-Alvarez S F. Adv. Drug Deliv. Rev., 2020, 157: 118.

[40] Jin Y, Seo K H, Ko H M, Jung T W, Chung Y H, Lee J H, Park H H, Kim H C, Jeong J H, Lee S H. Arch. Pharm. Res., 2019, 42: 455.

[41] Lu F, Zhao T, Sun X, Wang Z, Fan Q, Huang W. Chem. Res. Chinese Universities, 2021, 37(4): 943.

[42] Li X, Tan W, Bai X, Li F. Chem. Res. Chinese Universities, 2023, 39(2): 192.

[43] Hayashi K, Nakamura M, Miki H, Ozaki S, Abe M, Matsumoto T, Ishimura K. Advanced Functional Materials, 2012, 22: 3539.

[44] Liu W, Zhang Y, Qi J, Qian J, Tang B Z. Chem. Res. Chinese Universities, 2021, 37(1): 171.

[45] Alifu N, Zebibula A, Qi J, Zhang H, Sun C, Yu X, Xue D, Lam J W Y, Li G, Qian J, Tang B Z. ACS Nano, 2018, 12: 11282.

[46] Zhang Z, Liu C, Akakuru O, Xu W, Wu A, Zhang Y. Chem. Res. Chinese Universities, 2021, 37(4): 967.

[47] Gao Y, Yao M, Zhou C, Liu H, Zhang S-T, Yang B. Journal of Materials Chemistry C, 2022, 10: 4579.

[48] Ying G, Sun K, Lv Y, Liu H, Zhang S-T, Yang B. Dyes and Pigments, 2023, 213: 111196.

[49] Xiao S, Gao Y, Wang R, Liu H, Li W, Zhou C, Xue S, Zhang S-T, Yang B, Ma Y. Chemical Engineering Journal, 2022, 440: 135911.