Novel Perylene-Based Antimicrobial PDI Chromophores

Year 2023, Volume: 10 Issue: 3, 633 - 640, 30.08.2023

Cansu Yılmaz , Pınar Güner , Tülin Aşkun , Funda Yükrük

https://doi.org/10.18596/jotcsa.1292068

Abstract

The main goal of the study was to monitor the Antimicrobial activity of two novel perylene diimides which were synthesized and characterized. Antimicrobial activity was investigated against Four Mycobacterium tuberculosis strains (MT) (Mt-H37Rv, Mt-H37Ra and two clinical isolates) and two Staphylococcus aureus strains [Methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus aureus (SA)]. Minimum inhibitory concentrations (MICs) and minimum bactericidal activity (MBCs) were determined. Both compounds exhibited bactericidal effects and MICs were found to be changing in the range of 48-96 µg/mL for four MT-strains. Compounds were also effective on Staphylococcus strains at MIC = 96 µg/mL.

Keywords

Perylene diimide, Antimicrobial activity, Mycobacterium tuberculosis, Methicillin resistant, Staphylococcus aureus, MIC, MBC

Supporting Institution

This work was supported by grants from Balikesir University (BAP2013/19), The Scientific and Technological Research Council of Turkey (TUBITAK-110T026)

Project Number

BAP2013/19, TUBITAK-110T026

References

• 1. Sapagovas VJ, Gaidelis V, Kovalevskij V, Undzenos A. Perylenetetracarboxylicacid derivatives and photophysical properties. Dyes Pigm.2016;71:178-187.
• 2. Cormier RA, Gregg BA. Synthesis and characterization of liquid crystalline perylene diimide. Chem Mater. 1998;10:1309-1319.
• 3. Angadi MA, Gosztola D, Wasielewski MR. Organic light emitting diodes usig poly (phenylenevinylene) doped with perylenediimide electron acceptors. Mater  Sci Eng B. 1999;63:191-194.
• 4. Ranke P, Bleyl I, Simmerer J, Haarer D, Bacher A, Schmidt HW. Electroluminescence and electron transport in a perylene dye. Appl Phys Lett. 1997;71:1332-1334.
• 5. Hayes RT, Wasielewski MR, Gosztola DJ. Organic dyes with excited state transformations (electron, charge, and proton transfers). Am Chem Soc. 2000;122:5563-5567.
• 6.Davis WV, Svec WA, Ratner MA. Wasielewski MR Molecular wire behaviour in p-phenylenevinylene oligomers. Nature.1998;396:60-63.
• 7. Tornizaki K, Loewe RS, Kirmaier C, Schwartz JK, Retsek JL, Bocian DF, Holten DLindsey JS. Synthesis and Photophysical Properties of Light Harvesting Arrays Comprised of a Porphyrin Bearing Multiple Perylene-Accessory Pigments. J Org Chem. 2002;67:6519-6534.   8. Fuller MJ, Wasielewski M. Photorefractivity in Nematic Liquid Crystals Using a Donor−AcceptorDyadwith a Low Lying Excited Singlet State for Charge Generation. J Phys Chem B.2001;105:7216-7219.
• 9.Fuller MJ, Walsh CJ, Zhao Y, Wasielewski MR. Hybrid Photorefractive Material Composed of Layered Conjugated Polymer and Dye Doped Liquid Crystal Films. Chem Mater. 2002;14:952-953.   10. Ozcan O, Yukruk F, Akkaya EU, Uner D. Dye sensitized artificial photosynthesis in the gas phase over thin and thick TiO2 films under UV and visible light irradiation. Appl Catal B Environ. 2006;71:291-297.   11. Acikbas Y, Capan R, Erdogan M, Yukruk F. Thin film characterization and vapor sensing properties of a novel perylene diimide material. Sensor Actuat B-Chem. 2011;160: 65-71.
• 12. Gregg BA, Cormier RA. Doping Molecular Semiconductors:  n-Type Doping of a Liquid Crystal Perylene Diimide. J Am Chem Soc. 2001;123:7959-7960.   13. Breeze AJ, Salomon A, Ginley DS, Gregg BA, Tillmann H, Horhold HH.Polymer perylenediimide heterojunction solar cells. Appl Phys Lett. 2002;81:3085-3087.   14. Sadrai M, Hadel L, Sauers RR, Husain S, Krogh-Jespersen K, Westbrook JD, Bird FR. Lasing action in a family of perylene derivatives: single absorption and emission spectra, triplet absorption and oxygen quenching constants, and molecular mechanics and semiempirical molecular orbital calculations. J Phys Chem. 1992;96:7988-7996.   15. Gvishi R, Reisfeld R, Brushtein Z. Spectroscopy and laser action of the “red Perylimide dye” in various solvents. Chem Phys Lett.1993;213:338-344.   16. Yukruk F, Dogan AL, Canpinar H, Guc D,Akkaya EU. Water soluble green perylene diimide (PDI) dyes as potential sensitizers for photo dynamic therapy. OrgLett. 2005;7(14):2885-2887.
• 17.Tuna G, Kulaksiz Erkmen G, Dalmizrak O, Dogan A, Ogus IH. Inhibition characteristics of hypericin on rats mallintestine glutathione-Stransferases. N Chem Biol Interact. 2010;188(1):59–65.
• 18. Ma GY, Khan SI, Jacob MR, Tekwani BL, Li ZQ, Pasco DS, Walker LA, Khan LA. Antimicrobial and antileishmanial activities of hypocrellins A and B. Antimic Agents Chemother. 2004;48(11):4450-4452.
• 19. Feyzioglu B, Demircili ME, Ozdemir M, Dogan M, Baykan M, Baysal B. Antibacterial effect of hypericin. Afr J Microbiol Res. 2013;7(11):979-982.
• 20. WHO, World Health Organization, Guidance on ethics of tuberculosis prevention, care and control. WHO/HTM/TB/2010.16. Geneva, 2010.
• 21. WHO, World Health Organisation, Multidrug-resistant tuberculosis (MDR-TB). World Health Organization. 2013.
• 22. WHO, World Health Organization. Tuberculosis MDR-TB & XDR-TB 2011 progress report, WHO Report: Towards universal access to diagnosis and treatment of MDR-TB & XDR-TB by 2015, 23 March 2011, p.2, ISBN 978 92 4 150133 0. 2011.   23. WHO, World Health Organisation, Drug-resistant TB Surveillance &Response, Supplement Global Tuberculosis Report. 2014.   24. Egea AL, Gagetti P, Lamberghini R, Faccone D, Lucero C, Vindel A, Tosoroni D,Garnero A, Saka HA, Galas M, Bocco JL, Corso A, Sola C. New patterns of methicillin-resistant Staphylococcus aureus (MRSA) clones, community-associated MRSA genotypes behave like healthcare-associated MRSA genotypes within hospitals, Argentina. Int J Med Microbiol. 2014; 304:1086–99. 25. Kursunlu A.N, Sahin E, Guler E. Cu (II) chemosensor based on a fluorogenic bodipy-salophen combination: sensitivity and selectivity studies. J. Fluoresc. 2016; 26, 1997-2004.
• 26. Alizada M, Gul A, Oguz M, Kursunlu A.N., Yilmaz M. Ion sensing of sister sensors based-on calix [4] arene in aqueous medium and their bioimaging applications, Dyes Pigm 2020; 184, 108741.
• 27. Oguz M., Gul A., Kursunlu A.N., Yilmaz M. A bifunctional and multi-responsive fluorescent sensor for toxic analytes in the aqueous medium: Easy synthesis, NIR-visible effect, imaging in living cells, J. Mol. 2021; 336, 116861.
• 28. NCCLS National Committee for Clinical Laboratory Standards (NCCLS). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard. Seventh Edition NCCLS Document M7-A7., Wayne, Pennsylvania 2006;26(2):1-16.   29. NCCLS Methods for Determining Bactericidal Activity of Antimicrobial Agents; Approved Guideline, NCCLS document M26-A [ISBN 1-56238-384-1]. NCCLS, 940 West Valley Road, Suite 1400, Wayne, Pennsylvania 19087 USA, Agents; Approved Guideline 1999. 30. BD, Becton, Dickinson and Company Newsletter BD Bactec MGIT 960 SIRE kit now FDA-cleared for susceptibility testing of Mycobacterium tuberculosis. Microbiology News &Ideas 2002;13:4-4.
• 31. Chaudhuri S, Chung SW, Hockney G, Lykken J, Reisner BS, Gatson AM et al. Evaluation of Mycobacteria growth indicator tubes for susceptibility testing of Mycobacterium tuberculosis to isoniazid and rifampin. Diag Microbiol Infect Dis 1995;22(4):325–329.
• 32. Collins L, Franzbla SG Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chemother 1997; 41:1004–1009.
• 33. NCCLS Susceptibility Testing of Mycobacteria, Nocardiae, and Other Aerobic Actinomycetes; Approved Standard. NCCLS document M24-A [ISBN 1-56238-500-3]. NCCLS, 940 West Valley Road, Suite 1400, Wayne, Pennsylvania 19087-1898 USA 2003.
• 34. Molina-Salinas GM, Ramos-Guerra MC, Vargas-Villarreal J, Mata-Cárdenas BD, Becerril-Montes P, Said-Fernández S.Bactericidal Activity of Organic Extracts from Flourensiacernua DC against Strains of Mycobacterium tuberculosis. Archives of Medical Research. 2006;37(1):45-49.
• 35. Yagan S, Yukruk F, Unlu G.V., Antimicrobial Activities of Four Perylene diimides, Afr J Microbiol Res.; 9(7), 427-432. 36. Keskin T, Isgor BS, Isgor YG, Yukruk F.Evaluation of Perylene diimide Derivatives for Potential Therapeutic Benefits on Cancer Chemotherapy. Chem Biol Drug Des. 2012;80(5):675-681.
• 37. Liu K, Xu Z, Yin M, Yang W, He B, Wie W, Shen J.Towards rational design of organic electron acceptors for photovoltaics: A study based on perylene diimide derivatives. J Mater Chem. 2014; 2(15):2093-2096.   38. Ohlsen K, Donat S. The impact of serine/threonine phosphorylation in Staphylococcus aureus. Int J Med Microbiol. 2010;300:137–141.