Highly hydrophilic cationic gold nanorods stabilized by novel quaternary ammonium surfactant with negligible cytotoxicity
Language English Country Germany Media print-electronic
Document type Letter, Research Support, Non-U.S. Gov't
Grant support
GA16-13967S
Grant Agency of the Czech Republic - International
RVO 68378050
Institutional Grant - International
Project NV15-31847A - International
Long Term Development plan - 1011 - International
00179906
MH CZ - DRO - International
VT2019-2021
University of Hradec Kralove - International
- Keywords
- N,N,N-trimethyl-3,6,9,12,15-pentaoxaheptadecyl-17-sulfanyl-1-ammonium bromide (POSAB), cytotoxicity, gold nanorods, quaternary ammonium salts,
- MeSH
- Alkylation MeSH
- CHO Cells MeSH
- Cricetulus MeSH
- Hydrophobic and Hydrophilic Interactions * MeSH
- Quaternary Ammonium Compounds chemistry MeSH
- Nanotubes chemistry MeSH
- Surface-Active Agents chemistry MeSH
- Drug Stability MeSH
- Cell Survival drug effects MeSH
- Gold chemistry toxicity MeSH
- Animals MeSH
- Check Tag
- Animals MeSH
- Publication type
- Letter MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Quaternary Ammonium Compounds MeSH
- Surface-Active Agents MeSH
- Gold MeSH
The photothermal cancer therapy using cationic gold nanorods (GNRs) stabilized by quaternary ammonium salts (QAS) have a great potential to enhance conventional cancer treatment as it promises the effective eradication of cancer cells including cells resistant to radio- and chemo-therapy and the stimulation of anti-tumor immune response. However, as the cytotoxicity of the conventional alkanethiol-QAS compounds limits their utility in medicine, here we developed GNRs modified by novel highly hydrophilic cationic surfactant composed of the quaternary ammonium group and ethylene glycol chain N,N,N-trimethyl-3,6,9,12,15-pentaoxaheptadecyl-17-sulfanyl-1-ammonium bromide (POSAB) showing insignificant cytotoxicity in the free state. Surface modification of GNRs by POSAB allowed to prepare nanoparticles with good stability in water, high cellular uptake and localization in lysosomes that are a promising alternative to alkanethiol-stabilized GNRs especially for biomedical applications.
Biomedical Research Center University Hospital Hradec Kralove Hradec Kralove Czech Republic
Charles University 1st Faculty of Medicine Prague Czech Republic
Genome Integrity Unit Danish Cancer Society Research Center Copenhagen Denmark
See more in PubMed
M. Tischer, G. Pradel, K. Ohlsen, U. Holzgrabe, ChemMedChem 2012, 7, 22.
O. Soukup, R. Dolezal, D. Malinak, J. Marek, S. Salajkova, M. Pasdiorova, J. Honegr, J. Korabecny, P. Nachtigal, F. Nachon, D. Jun, K. Kuca, Bioorg. Med. Chem. 2016, 24, 841.
D. Malinak, R. Dolezal, J. Marek, S. Salajkova, O. Soukup, M. Vejsova, J. Korabecny, J. Honegr, M. Penhaker, K. Musilek, K. Kuca, Bioorg. Med. Chem. Lett. 2014, 24, 5238.
R. Dolezal, O. Soukup, D. Malinak, R. M. L. Savedra, J. Marek, M. Dolezalova, M. Pasdiorova, S. Salajkova, J. Korabecny, J. Honegr, T. C. Ramalho, K. Kuca, Eur. J. Med. Chem. 2016, 121, 699.
A. S. Sokolova, C. O. Yarovaya, C. A. Shernyukov, C. E. Pokrovsky, C. A. Pokrovsky, V. A. Lavrinenko, V. V. Zarubaev, T. S. Tretiak, P. M. Anfimov, O. I. Kiselev, A. B. Beklemishev, N. F. Salakhutdinov, Bioorg. Med. Chem. 2013, 21, 6690.
E. Oblak, A. Piecuch, A. Krasowska, J. Luczynski, Microbiol. Res. 2013, 168, 630.
M. C. Jennings, K. P. Minbiole, W. M. Wuest, ACS Infect. Dis. 2015, 1, 288.
O. Damour, S. Z. Hua, F. Lasne, M. Villain, P. Rousselle, C. Collombel, Burns 1992, 18, 479.
C. Augustin, O. Damour, Cell Biol. Toxicol. 1995, 11, 167.
H. Nagamune, T. Maeda, K. Ohkura, K. Yamamoto, M. Nakajima, Toxicol. In Vitro 2000, 14, 139.
G. McDonnell, A. D. Russell, Clin. Microbiol. Rev. 1999, 12, 147.
D. Lichtenberg, E. Opatowski, M. M. Kozlov, Biochim. Biophys. Acta 2000, 1508, 1.
J. A. Castillo, A. Pinazo, J. Carilla, M. R. Infante, M. A. Alsina, I. Haro, P. Clapes, Langmuir 2004, 20, 3379.
A. S. Inacio, K. A. Mesquita, M. Baptista, J. Ramalho-Santos, W. L. Vaz, O. V. Vieira, PLoS One 2011, 6, e19850.
G. Yellen, M. E. Jurman, T. Abramson, R. MacKinnon, Science 1991, 251, 939.
A. S. Inacio, G. N. Costa, N. S. Domingues, M. S. Santos, A. J. Moreno, W. L. Vaz, O. V. Vieira, Antimicrob. Agents Chemother. 2013, 57, 2631.
S. Zhang, S. Ding, J. Yu, X. Chen, Q. Lei, W. Fang, Langmuir 2015, 31, 12161.
M. Zarska, F. Novotny, F. Havel, M. Sramek, A. Babelova, O. Benada, M. Novotny, H. Saran, K. Kuca, K. Musilek, Z. Hvezdova, R. Dzijak, M. Vancurova, K. Krejcikova, B. Gabajova, H. Hanzlikova, L. Kyjacova, J. Bartek, J. Proska, Z. Hodny, Bioconjugate Chem. 2016, 27, 2558.
R. R. Arvizo, O. R. Miranda, M. A. Thompson, C. M. Pabelick, R. Bhattacharya, J. D. Robertson, V. M. Rotello, Y. S. Prakash, P. Mukherjee, Nano Lett. 2010, 10, 2543.
X. Liu, N. Huang, H. Li, Q. Jin, J. Ji, Langmuir 2013, 29, 9138.
L. Vigderman, P. Manna, E. R. Zubarev, Angew. Chem. Int. Ed. Engl. 2012, 51, 636.
K. K. Sandhu, C. M. McIntosh, J. M. Simard, S. W. Smith, V. M. Rotello, Bioconjugate Chem. 2002, 13, 3.
R. Hong, G. Han, J. M. Fernandez, B. J. Kim, N. S. Forbes, V. M. Rotello, J. Am. Chem. Soc. 2006, 128, 1078.
L. Tong, Q. Wei, A. Wei, J. X. Cheng, Photochem Photobiol. 2009, 85, 21.
A. M. Alkilany, L. B. Thompson, S. P. Boulos, P. N. Sisco, C. J. Murphy, Adv. Drug Deliv. Rev. 2011, 64, 190.
L. C. Kennedy, L. R. Bickford, N. A. Lewinski, A. J. Coughlin, Y. Hu, E. S. Day, J. L. West, R. A. Drezek, Small 2011, 7, 169.
R. Mooney, L. Roma, D. Zhao, D. Van Haute, E. Garcia, S. U. Kim, A. J. Annala, K. S. Aboody, J. M. Berlin, ACS Nano 2014, 8, 12450.
S. Kang, S. H. Bhang, S. Hwang, J. K. Yoon, J. Song, H. K. Jang, S. Kim, B. S. Kim, ACS Nano. 2015, 9, 9678.
M. R. Ali, M. A. Rahman, Y. Wu, T. Han, X. Peng, M. A. Mackey, D. Wang, H. J. Shin, Z. G. Chen, H. Xiao, R. Wu, Y. Tang, D. M. Shin, M. A. El-Sayed, Proc. Natl. Acad. Sci. USA 2017, 114, E3110.
K. F. Chu, D. E. Dupuy, Nat. Rev. Cancer 2014, 14, 199.
Y. Qiu, Y. Liu, L. Wang, L. Xu, R. Bai, Y. Ji, X. Wu, Y. Zhao, Y. Li, C. Chen, Biomaterials 2010, 31, 7606.
M. Zarska, M. Sramek, F. Novotny, F. Havel, A. Babelova, B. Mrazkova, O. Benada, M. Reinis, I. Stepanek, K. Musilek, J. Bartek, M. Ursinyova, O. Novak, R. Dzijak, K. Kuca, J. Proska, Z. Hodny, Biomaterials 2018, 154, 275.
X. Wu, J. Y. Chen, A. Brech, C. Fang, J. Wang, P. J. Helm, Q. Peng, Biomaterials 2013, 34, 6157.
S. Link, C. Burda, B. Nikoobakht, M. A. El-Sayed, J. Phys. Chem. B 2000, 104, 6152.
O. G. Mekenyan, G. D. Veith, SAR QSAR Environ Res. 1993, 1, 335.
M. T. D. Cronin, Curr. Comput.-Aided Drug Des. 2006, 2, 405.
K. M. Docherty, J. C. F. Kulpa, Green Chem. 2005, 7, 185.
K. Knop, R. Hoogenboom, D. Fischer, U. S. Schubert, Angew. Chem. Int. Ed. Engl. 2010, 49, 6288.
H. Hakkinen, Nat. Chem. 2012, 4, 443.
T. Mosmann, J. Immunol. Methods 1983, 65, 55.
N. J. Yang, M. J. Hinner, Methods Mol. Biol. 2015, 1266, 29.
N. Bogliotti, B. Oberleitner, A. Di-Cicco, F. Schmidt, J. C. Florent, V. Semetey, J. Colloid Interface Sci. 2011, 357, 75.
X. Cheng, X. Tian, A. Wu, J. Li, J. Tian, Y. Chong, Z. Chai, Y. Zhao, C. Chen, C. Ge, ACS Appl. Mater. Interfaces 2015, 7, 20568.
J. Dausend, A. Musyanovych, M. Dass, P. Walther, H. Schrezenmeier, K. Landfester, V. Mailander, Macromol. Biosci. 2008, 8, 1135.
J. Lin, H. Zhang, Z. Chen, Y. Zheng, ACS Nano 2010, 4, 5421.
P. R. Leroueil, S. A. Berry, K. Duthie, G. Han, V. M. Rotello, D. Q. McNerny, J. R. Baker Jr. , B. G. Orr, M. M. Holl, Nano Lett. 2008, 8, 420.
Wide-Antimicrobial Spectrum of Picolinium Salts
