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Non-distorted visible light-absorbing thiol-PEGylated gold-coated superparamagnetic iron oxide nanoparticles–porphyrin conjugates and their inhibitory effects against nosocomial pathogens

Published online by Cambridge University Press:  28 October 2019

Bamidele M. Amos-Tautua ,
Olayemi J. Fakayode ,
Sandy van Vuuren ,
Sandile P. Songca  and
Oluwatobi S. Oluwafemi
Bamidele M. Amos-Tautua
Affiliation:
Department of Chemical Sciences (formerly Applied Chemistry), University of Johannesburg, P. O. Box 17011, Doornfontein 2028, Johannesburg, South Africa Centre for Nanomaterials Science Research, University of Johannesburg, Johannesburg, South Africa
Olayemi J. Fakayode
Affiliation:
Department of Chemical Sciences (formerly Applied Chemistry), University of Johannesburg, P. O. Box 17011, Doornfontein 2028, Johannesburg, South Africa Centre for Nanomaterials Science Research, University of Johannesburg, Johannesburg, South Africa
Sandy van Vuuren
Affiliation:
Department of Pharmacy and Pharmacology, University of the Witwatersrand, Parktown 2193, Johannesburg, South Africa
Sandile P. Songca
Affiliation:
Department of Chemistry, University of KwaZulu-Natal, Private Bag X 54001, Durban4000, South Africa
Oluwatobi S. Oluwafemi*
Affiliation:
Department of Chemical Sciences (formerly Applied Chemistry), University of Johannesburg, P. O. Box 17011, Doornfontein 2028, Johannesburg, South Africa Centre for Nanomaterials Science Research, University of Johannesburg, Johannesburg, South Africa
*
Address all correspondence to Oluwatobi S. Oluwafemi at oluwafemi.oluwatobi@gmail.com
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Abstract

A low-cost synthesis approach was developed for the fabrication of four symmetric meso-substituted water-soluble thiolated polyethylene glycol gold-coated superparamagnetic iron oxide nanoparticles–porphyrin (p-hydroxyphenyl [THPP], 3,5-dimethoxyphenyl [TdMPP], 3-pyridyl[T-3-PyP], and 1-methylpyridinium-3-yl[T3-Py+P4I−]) conjugates to achieve materials with enhanced absorption and therapeutic properties. After evaluation of their antibacterial inhibition characteristics against four nocosomial pathogens (Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Enterococcus faecalis), THPP and TdMPP conjugates showed some remarkable minimum inhibitory concentration values of 0.104 and 0.625 mg/mL against E. coli and E. faecalis, respectively, making these materials to be alternative agents for the inhibition of these pathogens in the environmental and clinical fields.

Type
Research Letters
Information
MRS Communications , Volume 9 , Issue 4 , December 2019 , pp. 1335 - 1342
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Copyright
Copyright © Materials Research Society 2019

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References

1.Penon, O., Patino, T., Barrios, L., Nogues, C., Amabilino, D.B., Wurst, K., and Perez-Garcia, L.: A new porphyrin for the preparation of functionalized water-soluble gold nanoparticles with low intrinsic toxicity. ChemistryOpen 4, 127–136 (2015).CrossRefGoogle ScholarPubMed
2.Barona-Castaño, J.C., Carmona-Vargas, C.C., Brocksom, T.J., and De Oliveira, K.T.: Porphyrins as catalysts in scalable organic reactions. Molecules 21, 1–27 (2016).CrossRefGoogle ScholarPubMed
3.Allison, R.R. and Moghissi, K.: Photodynamic therapy (PDT): PDT mechanisms. Clin. Endosc. 46, 24–29 (2013).CrossRefGoogle ScholarPubMed
4.La, D.D., Bhosale, S.V., Jones, L.A., and Bhosale, S.V.: Arginine-induced porphyrin-based self-assembled nanostructures for photocatalytic applications under simulated sunlight irradiation. Photochem. Photobiol. Sci. 16, 151–154 (2017).CrossRefGoogle ScholarPubMed
5.Paolesse, R., Nardis, S., Monti, D., Stefanelli, M., and Di Natale, C.: Porphyrinoids for chemical sensor applications. Chem. Rev. 117, 2517–2583 (2017).CrossRefGoogle ScholarPubMed
6.Gao, B., Liu, Y., Yin, H., Li, Y., Bai, Q., and Zhang, L.: Water-soluble dendritic polyaspartic porphyrins: potential photosensitizers for photodynamic therapy. New J. Chem. 36, 28–31 (2012).CrossRefGoogle Scholar
7.Winkler, K., Simon, C., Finke, M., Bleses, K., Birke, M., Szentmáry, N., Hüttenberger, D., Eppig, T., Stachon, T., Langenbucher, A., Foth, H.-J., Herrmann, M., Seitz, B., and Bischoff, M.: Photodynamic inactivation of multidrug-resistant Staphylococcus aureus by chlorin e6 and red light (λ = 670 nm). J. Photochem. Photobiol. B Biol. 162, 340–347 (2016).CrossRefGoogle Scholar
8.Li, Z., Wang, C., Cheng, L., Gong, H., Yin, S., Gong, Q., Li, Y., and Liu, Z.: PEG-functionalized iron oxide nanoclusters loaded with chlorin e6 for targeted, NIR light induced, photodynamic therapy. Biomaterials 34, 9160–9170 (2013).CrossRefGoogle Scholar
9.Dou, Q.Q., Teng, C.P., Ye, E., and Loh, X.J.: Effective near-infrared photodynamic therapy assisted by upconversion nanoparticles conjugated with photosensitizers. Int. J. Nanomed. 10, 419–432 (2015).Google ScholarPubMed
10.Fakayode, O.J., Kruger, C.A., Songca, S.P., Abrahamse, H., and Oluwafemi, O.S.: Photodynamic therapy evaluation of methoxypolyethyleneglycol-thiol-SPIONs-gold-meso-tetrakis(4-hydroxyphenyl)porphyrin conjugate against breast cancer cells. Mater. Sci. Eng. C 92, 737–744 (2018).CrossRefGoogle ScholarPubMed
11.Ormond, A.B. and Freeman, H.S.: Dye sensitizers for photodynamic therapy. Materials 6, 817–840 (2013).CrossRefGoogle ScholarPubMed
12.Fakayode, O.J., Tsolekile, N., Songca, S.P., and Oluwafemi, O.S.: Applications of functionalized nanomaterials in photodynamic therapy. Biophys. Rev. 10, 49–67 (2018).CrossRefGoogle ScholarPubMed
13.Zhou, F., Xing, D., Ou, Z., Wu, B., Resasco, D.E., and Chen, W.R.: Cancer photothermal therapy in the near-infrared region by using single-walled carbon nanotubes. J. Biomed. Opt. 14, 1–7 (2009).CrossRefGoogle ScholarPubMed
14.Vieira, L., Castilho, M.L., Ferreira, I., Ferreira-Strixino, J., Hewitt, K.C., and Raniero, L.: Synthesis and characterization of gold nanostructured Chorin e6 for Photodynamic Therapy. Photodiagnosis Photodyn. Ther. 18, 6–11 (2017).CrossRefGoogle ScholarPubMed
15.Mccarthy, J.R., Bhaumik, J., Merbouh, N., and Weissleder, R.: High-yielding syntheses of hydrophilic conjugatable chlorins and bacteriochlorins. Org. Biomol. Chem. 7, 3430–3436 (2009).CrossRefGoogle ScholarPubMed
16.Aravindu, K., Mass, O., Vairaprakash, P., Springer, J.W., Yang, E., Niedzwiedzki, D.M., Kirmaier, C., Bocian, D.F., Holten, D., and Lindsey, J.S.: Amphiphilic chlorins and bacteriochlorins in micellar environments. Molecular design, de novo synthesis, and photophysical properties. Chem. Sci. 4, 3459–3477 (2013).CrossRefGoogle Scholar
17.Muresan, A.Z. and Lindsey, J.S.: Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins. Tetrahedron 64, 11440–11448 (2008).CrossRefGoogle ScholarPubMed
18.Huan, Y.F., Fei, Q., Shan, H.Y., Wang, B.J., Xu, H., and Feng, G.D.: A novel water-soluble sulfonated porphyrin fluorescence sensor for sensitive assays of H2O2 and glucose. Analyst 140, 1655–1661 (2015).CrossRefGoogle ScholarPubMed
19.Fakayode, O.J., Songca, S.P., and Oluwafemi, O.S.: Neutral red separation property of ultrasmall-gluconic acid capped superparamagnetic iron oxide nanoclusters coprecipitated with goethite and hematite. Sep. Purif. Technol. 192, 475–482 (2018).CrossRefGoogle Scholar
20.Tintoré, M., Mazzini, S., Polito, L., Marelli, M., Latorre, A., Somoza, Á, Aviñó, A., Fàbrega, C., and Eritja, R.: Gold-coated superparamagnetic nanoparticles for single methyl discrimination in DNA aptamers. Int. J. Mol. Sci. 16, 27625–27639 (2015).CrossRefGoogle ScholarPubMed
21.Mohammad, F., Balaji, G., Weber, A., Uppu, R.M., and Kumar, C.S.S.R.: Influence of gold nanoshell on hyperthermia of super paramagnetic iron oxide nanoparticles (SPIONs). J. Phys. Chem. C 114, 19194–19201 (2010).CrossRefGoogle Scholar
22.Anbarasu, M., Anandan, M., Chinnasamy, E., Gopinath, V., and Balamurugan, K.: Synthesis and characterization of polyethylene glycol (PEG) coated Fe3O4 nanoparticles by chemical co-precipitation method for biomedical applications. Spectrochim. Acta A Mol. Biomol. Spectrosc. 135, 536–539 (2015).CrossRefGoogle ScholarPubMed
23.Silva, A.H., Lima, E., Mansilla, M.V., Zysler, R.D., Troiani, H., Pisciotti, M.L.M., Locatelli, C., Benech, J.C., Oddone, N., Zoldan, V.C., Winter, E., Pasa, A.A., and Creczynski-Pasa, T.B.: Superparamagnetic iron-oxide nanoparticles mPEG350- and mPEG2000-coated: cell uptake and biocompatibility evaluation. Nanomed. Nanotechnol. Biol. Med. 12, 909–919 (2016).CrossRefGoogle ScholarPubMed
24.Murray, P.R., Rosenthal, K.S., and Pfaller, M.A.: Medical Microbiology, 5th ed. (Elsevier, Philadelphia, PA, USA, 2005), pp. 106–348.Google Scholar
25.Khan, H.A., Ahmad, A., and Mehboob, R.: Nosocomial infections and their control strategies. Asian Pac. J. Trop. Biomed. 5, 509–514 (2015).CrossRefGoogle Scholar
26.Eloff, J.N.: A sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta Med. 64, 711–713 (1998).CrossRefGoogle ScholarPubMed
27.He, Y.P., Miao, Y.M., Li, C.R., Wang, S.Q., Cao, L., Xie, S.S., Yang, G.Z., Zou, B.S., and Burda, C.: Size and structure effect on optical transitions of iron oxide nanocrystals. Phys. Rev. B 71, 1–9 (2005).CrossRefGoogle Scholar
28.Krishnamurthy, S., Esterle, A., Sharma, N.C., and Sahi, S.V.: Yucca-derived synthesis of gold nanomaterial and their catalytic potential. Nanoscale Res. Lett. 9, 1–9 (2014).CrossRefGoogle ScholarPubMed
29.Wu, W., He, Q., and Jiang, C.: Magnetic iron oxide nanoparticles: synthesis and surface functionalization strategies. Nanoscale Res. Lett. 3, 397–415 (2008).CrossRefGoogle ScholarPubMed
30.Sun, Q., Reddy, B.V., Marquez, M., Jena, P., Gonzalez, C., and Wang, Q.: Theoretical study on gold-coated iron oxide nanostructure: magnetism and bioselectivity for amino acids. J. Phys. Chem. C. 111, 4159–4163 (2007).CrossRefGoogle Scholar
31.Xue, Y., Li, X., Li, H., and Zhang, W.: Quantifying thiol-gold interactions towards the efficient strength control. Nat. Commun. 5, 1–9 (2014).CrossRefGoogle ScholarPubMed
32.Honary, S. and Zahir, F.: Effect of zeta potential on the properties of nano-drug delivery systems - a review (Part 1). Trop. J. Pharm. Res. 12, 255–264 (2013).Google Scholar
33.Hirsch, V., Kinnear, C., Moniatte, M., Rothen-Rutishauser, B., Clift, M.J.D., and Fink, A.: Surface charge of polymer coated SPIONs influences the serum protein adsorption, colloidal stability and subsequent cell interaction in vitro. Nanoscale 5, 3723–3732 (2013).CrossRefGoogle ScholarPubMed
34.Ahmed, W., Neller, R., and Katouli, M.: Host species-specific metabolic fingerprint database for enterococci and Escherichia coli and its application to identify sources of fecal contamination in surface waters. Appl. Environ. Microbiol. 71, 4461–4468 (2005).CrossRefGoogle ScholarPubMed
35.Byappanahalli, M.N., Nevers, M.B., Korajkic, A., Staley, Z.R., and Harwood, V.J.: Enterococci in the environment. Microbiol. Mol. Biol. Rev. 76, 685–706 (2012).CrossRefGoogle ScholarPubMed
36.Edberg, S.C., Rice, E.W., Karlin, R.J., and Allen, M.J.: Escherichia coli: the best biological drinking water indicator for public health protection. J. Appl. Microbiol. 88, 106–116 (2000).CrossRefGoogle Scholar
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