New Semiconducting Polymer Nanoparticles for Antibacterial Agent by the Synergetic Effect of Positive Charge and Photothermal Conversion

doi:10.7503/cjcu20190715

Abstract

Abstract:

Because of the abuse of antibiotics and the emergence of bacterial resistance, the new antibacterial agents are required urgently. Herein, we prepared semiconducting polymer nanoparticles(SP-PPh₃ NPs) with synergistic antibacterial activity due to photothermal properties and positive charge. SP-PPh₃ NPs have broad-spectrum antibacterial properties against Gram-negative Escherichia coli(E. coli) and Gram-positive Staphylococcus aureus(S. aureus). The photothermal conversion efficiency of SP-PPh₃ NPs is 43.8%. Moreover, the positive charge of SP-PPh₃ NPs can adhere to bacteria, which is helpful to transmit heat to bacteria effectively. Under the synergistic effect of heat and positive charge, the antibacterial rates of E. coli and S. aureustreated with SP-PPh₃ NPs are 99.9% and 98.6% in vitro, respectively. In addition, SP-PPh₃ NPs have good biocompatibility and have almost no side effects on the major organs of mice. The bacteria-infected skin wounds on mice can completely heal after 12 d treated with SP-PPh₃ NPs.

Key words: Semiconducting polymer, Positively charged nanoparticles, Photothermal conversion, Antibacterial

CLC Number:

O633

TrendMD:

PAN Guoyong,LI Yawen,MA Lijun,MA Yufan,AI Wenting,WANG Zhenguo,HOU Xinhui,Grigory V·Zyryanov,WANG Zhuo. New Semiconducting Polymer Nanoparticles for Antibacterial Agent by the Synergetic Effect of Positive Charge and Photothermal Conversion[J]. Chem. J. Chinese Universities, 2020, 41(4): 670.

Figures/Tables 7

Fig.1 Synthetic route of SP-PPh3

Fig.2 1H NMR(A, B) and FTIR(C, D) spectra of SP-Br(A) and SP-PPh3(B) (D) is the amplification of the marked part in (C).

Fig.3 Characterization and photothermal activity of materials(A) UV-Vis absorption spectra of SP-PPh3 and SP-PPh3 NPs; (B) DLS and TEM image(inset) of SP-PPh3 NPs; (C) temperature elevation of SP-PPh3 NPs aqueous solution(10, 15, 20, 30 μg/mL) and water under 808 nm laser(1.0 W/cm2); (D) temperature change of SP-PPh3 NPs aqueous solution(20 μg/mL) under irradiation of 808 nm laser(1.0 W/cm2) and turn off laser follow by natural cooling; (E) time-dependent natural logarithm of the temperature of SP-PPh3 NPs during the natural cooling after 16 min; (F) cyclic heating curve of SP-PPh3 NPs(20 μg/mL) under laser irradiation for five circles.

Fig.4 IC50 of SP-PPh3 NPs for E. coli(A) and S. aureus(B)

Fig.5 In vitro antibacterial activity evaluation and SEM images(A) Photographs of bacterial colony formation in the presence of E. coli(A1—A4) and S. aureus(A5—A8). (A1) PBS; (A2) laser; (A3) SP-PPh3 NPs; (A4) SP-PPh3 NPs+laser; (A5) PBS; (A6) laser; (A7) SP-PPh3 NPs; (A8) SP-PPh3 NPs+laser. (B) The relative bacterial viability of the control group(a), the laser group(b), the SP-PPh3 NPs group(c), the SP-PPh3 NPs+laser group(d). The concentration of SP-PPh3 NPs is 20 μg/mL and 808 nm laser power is 1.0 W/cm2. (C) SEM images of E. coli(C1—C3) and S. aureus(C4—C6) contacting with control(C1, C4), 20 μg/mL SP-PPh3 NPs(C2, C5), SP-PPh3 NPs+laser(C3, C6). The 808 nm laser power is 1.0 W/cm2.

Fig.6 Cytotoxicity and mice model experiments(A) Photographs of wounds in mice treated with PBS(control), SP-PPh3 NPs and SP-PPh3 NPs+laser on days 0, 3, 6, 9, 12; (B) IR thermal images of the wound treated without SP-PPh3 NPs and with SP-PPh3 NPs respectively under the laser irradiation(808 nm, 1.5 W/cm2); (C) cytotoxicity of SP-PPh3 NPs(10, 20, 30, 40, 50 μg/mL); (D) wounds area value on day 0, 3, 6, 9, and 12 during antibacterial therapy; (E) the body mass of mice treated with PBS(control), SP-PPh3 NPs and SP-PPh3 NPs+laser; (F) analysis of liver function in mice after 12 d by blood, including alanine aminotransferase(a, U/L), aspartate aminotransferase(b, U/L), alkaline phosphatase(c, U/L), total protein(d, g/L), albumin(e, g/L).

Fig.7 H&E staining analysis of skin and major organs(A) H & E staining slices of wound skin tissue on days 3, 6, 9, and 12; (B) mouse organ H & E staining sections(heart, liver, spleen, lung and kidney) of the control group and the SP-PPh3 NPs treated group.

References 39

[1]	Schulz E., Goes A., Garcia R., Panter F., Koch M., Müllerr., Fuhrmann K., Fuhrmann G., J. Controlled Release, 2018, 290, 46— 55
[2]	Lobritz M. A., Belenky P., Porter C. B. M., Gutierrez A., Yang J. H., Schwarz E. G., Dwyer D. J., Khalil A. S., Collins J. J ., Proc. Natl. Acad. Sci. USA, 2015, 112( 27), 8173— 8180
[3]	Wei X. L., Gao J., Wang F., Man Y., Angsantikul P., Kroll A. V., Zhou J. R., Gao W. W., Lu W. Y., Fang R. H., Zhang L. F., Adv. Mater., 2017, 29( 33), 1701644
[4]	Zhai L. W., Zhang Z. Q., Zhao Y. T., Tang Y. L ., Macromolecules, 2018, 51( 18), 7239— 7247
[5]	Li L. L., Xu J. H., Qi G. B., Zhao X. Z., Yu F. Q., Wang H., ACS Nano, 2014, 8( 5), 4975— 4983
[6]	Xu Q. H., Li J. Z., He J. H., Zhao X., Huo Q. S., Chem. Res. Chinese Universities, 2013, 29( 4), 695— 698
[7]	Hoque J., Adhikary U., Yadav V., Samaddar S., Konai M. M., Prakash R. G., Paramanandham K., Shome B. R., Sanyal K., Haldar J., Mol. Pharmaceutics, 2016, 13( 10), 3578— 3589
[8]	Brown E., Wright G. D ., Nature, 2016, 529( 7586), 336— 343
[9]	Wu S. M., Li A. H., Zhao X. Y., Zhang C. L., Yu B. R., Zhao N., Xu F. J., ACS Appl. Mater. Interfaces, 2019, 11( 19), 17177— 17183
[10]	Zhao Q., Zhao Y. T., Lu Z. N., Tang Y. L., ACS Appl. Mater. Interfaces, 2019, 11( 18), 16320— 16327
[11]	Liu G. Y., Zou J. H., Tang Q. Y., Yang X. Y., Zhang Y. W. Zhang Q., Huang W., Chen P., Shao J. J., Dong X. C., ACS Appl. Mater. Interfaces, 2017, 9( 46), 4007740086
[12]	Li J. C., Rao J. H., Pu K. Y ., Biomaterials, 2018, 155, 217— 235
[13]	Zhang S. H., Sun C. X., Zeng J. F., Sun Q., Wang G. L., Wang Y., Wu Y., Dou S. X., Gao M. Y., Li Z., Adv. Mater., 2016, 28( 40), 8927— 8936
[14]	Levi-Polyachenko N., Young C., MacNeill C., Braden A., Argenta L., Reid S., Int. J. Hyperthermia, 2014, 30( 7), 490— 501
[15]	Hong L., Liu X.M., Tan L., Cui Z. D., Yang X. J., Liang Y. Q., Li Z. Y., Zhu S. L., Zheng Y. F., Yeung K. W. K., Jing D. D., Zheng D., Wang X. B., Wu S. L., Adv. Healthcare Mater., 2019,1900835
[16]	Ma K., Li Y. M., Wang Z. G., Chen Y. Z., Zhang X., Chen C. Y., Yu H., Huang J., Yang Z. Y., Wang X. F., Wang Z., ACS Appl. Mater. Interfaces, 2019, 11( 33), 29630— 29640
[17]	Wang L., Wang L. P., Xu T. S., Guo C. R., Liu C. Z., Zhang H., Li J., Liang Z. Q., Chem. Res. Chinese Universities, 2014, 30( 6), 959— 964
[18]	Guo B., Huang Z. M., Shi Q., Middha E., Xu S. D., Li L., Wu M., Jiang J. W., Hu Q. L., Fu Z. W., Liu B., Adv. Funct. Mater., 2019, 30( 5), 1907093
[19]	Chen Y. Z ., Ai W. T., Guo X., Li Y. W., Ma Y. F., Chen L. F., Zhang H., Wang T. X., Zhang X., Wang Z., Small, 2019,1902352
[20]	Pu K. Y., Shuhendler A. J., Jokerest J. V., Mei J. G., Gambhir S. S., Bao Z. N., Rao J. H., Nat. Nanotechnol., 2014, 9( 3), 233
[21]	Rong Y., Yu. J. B., Zhang X. J., Sun W., Ye F. M., Wu I. C., Zhang Y., Hayden S., Zhang Y., Wu C. F., Chiu D. T., ACS Macro Letters, 2014, 3( 10), 1051— 1054
[22]	Li Y. W., Liu Z. T., Ma Y. F., Chen Y. Z., Ma K., Wang X. F., Zhang D. Q., Wang Z., Adv. Funct. Mater., 2019, 29( 38), 1903733
[23]	Pu K. Y., Mei J. G., Jokerst J. V., Hong G. S., Antaris A. L., Chattopadhyay N., Shuhendler A. J., Kurosawa T., Zhou Y., Gambhir S. S., Bao Z. N., Rao J. H., Adv. Mater., 2015, 27( 35), 5184— 5190
[24]	Peccati F., Wi s ' niewska M. , Solans-Monfort X., Sodupe M., Phys. Chem. Chem. Phys., 2016, 18, 11634— 11643
[25]	Yao L., Zhang S. T., Wang R., Li W. J., Shen F. Z., Yang B., Ma Y. G., Angew. Chem. Int. Ed., 2014, 53( 8), 2119— 2123
[26]	Qi P. L., Wang Z. J., Liu Z. T., Yang S. F., Yang Y., Yao J. J., Zhang G. X., Zhang D. Q., Polym. Chem., 2016, 7, 3838— 3847
[27]	Wang Y., Jett S. D., Crum J., Schanze K. S., Chi E. Y., Whitten D. G ., Langmuir, 2013, 29( 2), 781— 792
[28]	Zhou C. C., Wang F. Y., Chen H., Li M., Qiao F. L., Liu Z., Hou Y. B., Wu C. X., Fan Y. X., Liu L. B., Wang S., Wang Y. L., ACS Appl. Mater. Interfaces, 2016, 8( 6), 4242— 4249
[29]	Jiang G. Y., Wang J. G., Yang Y., Zhang G. X., Liu Y. L., Lin H., Zhang G. L., Li Y. D., Fan X. L., Biosens. Bioelectron., 2016, 85, 62— 67
[30]	Li Q. Y ., Li YMin T. L., Gong J. Y., Du L. L., Phillips D. L., Liu J. K., Lam J. W. Y., Sung H. H. Y., Williams I. D., Kwok T. K., Ho C. L., Li K., Wang J. G., Tang B. Z., Angew. Chem. Int. Ed , doi: 10.1002/anie.201909706
[31]	Qi G. B., Li L. L., Yu F. Q., Wang H., ACS Appl. Mater. Interfaces, 2013, 5( 21), 10874— 10881
[32]	Zehra N., Dutta D., Malik A. H., Ghosh S. S. lyer P. K., ACS Appl. Mater. Interfaces., 2018, 10( 33), 27603— 27611
[33]	Zhu Y. J., Ramasamy M., Yi D. K., ACS Appl. Mater. Interfaces, 2014, 6( 17), 15078— 15085
[34]	Khantamat O., Li C. H., Yu F., Jamison A. C., Shih W. C., Cai C. Z., Lee R., ACS Appl. Mater. Interfaces, 2015, 7( 7), 3981— 3993
[35]	Kim Y. K., Kang E. B., Kim S. M., Park C. P., In I., Park S. Y., ACS Appl. Mater. Interfaces, 2017, 9( 3), 3192— 3200
[36]	Tan L., Li J., Liu X. M., Cui Z. D., Yang X. J., Zhu S. L., Li Z. Y., Yuan X. B., Zheng Y. F., Yeung K. W. K., Pan H. B., Wang X. B., Wu S. L., Adv. Mater., 2018, 30( 31), 1801808
[37]	Xiao L. H., Sun J. H., Liu L. B., Hu R. Lu H., Cheng C. G., Huang Y., Wang S., Geng J. X., ACS Appl. Mater. Interfaces, 2017, 9( 6), 5382— 5391
[38]	Ramasamy M., Lee S. S., Yi D. K., Kim K., J. Mater. Chem. B, 2014, 2( 8), 981— 988
[39]	Jeong C. J., Sharker S. M., In I., Park S. Y., ACS Appl. Mater. Interfaces, 2015, 7( 18), 9469— 9478

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