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INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID

Year 2020, Volume: 6 Issue: 1, 28 - 33, 12.01.2020
https://doi.org/10.30934/kusbed.604829

Abstract

Objective: The rapid increase of
antibiotic resistance among bacteria is a serious public health problem.
Studies have focused on the discovery of new antibiotic molecules and the
development of new therapeutic strategies to combat these resistant bacteria.
Once it was known that pathogenic bacteria regulate synthesis of virulence
factors by the quorum sensing (QS) mechanism, QS inhibition became an
attractive target for antibacterial treatment. This study aimed to investigate
the antimicrobial activities and anti-QS properties of 16 derivatives of
cephalosporanic acid, ciprofloxacin, norfloxacin, and penicillanic acid.

Methods: Antimicrobial activity of the
derivatives was tested by the agar well diffusion method against various
microorganisms. The minimum inhibitory concentration (MIC) of effective
derivatives was assessed by the broth microdilution method. Anti-QS properties
were investigated using the soft agar method, observing inhibition of violacein
production in Chromobacterium violaceum.
The data were compared statistically.

Results: Six norfloxacin derivatives
displayed antimicrobial activity against a number of organisms, three of which
were more effective than control antibiotics (p<0.05) against some organisms. One ciprofloxacin derivative
demonstrated antimicrobial activity against all tested bacteria and was more
effective against some bacteria than control antibiotic (p<0.05).  The MIC values
of these six norfloxacin and one ciprofloxacin derivatives were between
0.04–6.25 µg/mL and 0.04–3.12 µg/mL, respectively. A cephalosporanic acid and a
penicillanic acid derivative displayed anti-QS properties.

Conclusion: This study shows that some new
derivatives of cephalosporanic acid, ciprofloxacin, norfloxacin, and
penicillanic acid may have potential for development of new antibacterial and
anti-QS agents.

References

  • World Health Organization (2018, February 15). Antimicrobial resistance. Available from: https://www.who.int/en/news-room/fact-sheets/detail/antimicrobial-resistance (accessed on 11 November 2019).
  • Alanis AJ. Resistance to antibiotics: are we in the post-antibiotic era? Arch Med Res. 2005;36:697–705. doi: 10.1016/j.arcmed.2005.06.009
  • El-Sharer S, Shaaban M, Barwa R, Hassan R. Control of quorum sensing and virulence factors of Pseudomonas aeruginosa using phenylalanine arginyl β-naphthylamide. J Med Microbiol. 2016;65:1194–1204. doi: 10.1099/jmm.0.000327
  • Papenfort K, Bassler BL. Quorum sensing signal-response systems in gram-negative bacteria. Nat Rev Microbiol. 2016;14:576–588. doi: 10.1038/nrmicro.2016.89
  • Eberl L, Winson MK, Sternberg C, et al. Involvement of N-acyl-L-hormoserine lactone autoinducers in controlling the multicellular behaviour of Serratia liquefaciens. Mol Microbiol. 1996;20:127–136. doi: 10.1111/j.1365-2958.1996.tb02495.x
  • McClean KH, Winson MK, Fish L, et al. Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiol. 1997;143:3703–3711. doi: 10.1099/00221287-143-12-3703
  • Rice SA, Koh KS, Queck SY, Labbate M, Lam KW, Kjelleberg S. Biofilm formation and sloughing in Serratia marcescens are controlled by quorum sensing and nutrient cues. J Bacteriol. 2005;187:3477–3485. doi: 10.1128/JB.187.10.3477-3485.2005
  • Tinaz-Bosgelmez G, Ulusoy S, Ugur A, Ceylan O. Inhibition of quorum sensing-regulated behaviors by Scorzonera sandrasica. Curr Microbiol. 2007;55:114–118. doi: 10.1007/s00284-006-0624-2
  • Kalia VC. Quorum sensing inhibitors: an overview. Biotechnol Adv. 2013; 31:224–245. doi: 10.1016/j.biotechadv.2012.10.004
  • Morohoshi T, Kato M, Fukamachi K, Kato N, Ikeda T. N-acylhomoserine lactone regulates violacein production in Chromobacterium violaceum type strain ATCC 12472. FEMS Microbiol Lett. 2008;279:124–130. doi: 10.1111/j.1574-6968.2007.01016.x
  • McLean RJC, Pierson LS, Fuqua CA. Simple screening protocol for the identification of quorum signal antagonists. J Microbiol Methods. 2004;58:351–360. doi: 10.1016/j.mimet.2004.04.016
  • The European Committee on Antimicrobial Susceptibility Testing. EUCAST disk diffusion method, version 4.0, 2014. http://www.eucast.org.
  • The European Committee on Antimicrobial Susceptibility Testing. Routine internal quality control as recommended by EUCAST, version 3.1, 2013. http://www.eucast.org.
  • Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard-Tenth Edition. CLSI document M07-A10, 2015. Wayne, PA.
  • Carlton RM. Phage therapy: past history and future prospects. Arch Immunol Ther Exp (Warsz). 1999;47:267–274.
  • Demain AL, Sanchez S. Microbial drug discovery: 80 years of progress. J Antibiot (Tokyo). 2009;62:5–16. doi: 10.1038/ja.2008.16
  • Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng CC. Synthesis and antibacterial evaluation of certain quinolone derivatives. J Med Chem. 2001;44:2374–2377. doi: 10.1021/jm0100335
  • Foroumadi A, Soltani F, Moshafi MH, Ashraf-Askari R. Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl) piperazinyl quinolone derivatives. Farmaco. 2003;58:1023–1028. doi: 10.1016/S0014-827X(03)00191-5
  • Foroumadi A, Ghodsi S, Emami S, et al. Synthesis and antibacterial activity of new fluoroquinolones containing a substituted N-(phenethyl)piperazine moiety. Bioorg Med Chem Lett. 2006;16:3499–3503. doi: 10.1016/j.bmcl.2006.03.103
  • Wang S, Jia XD, Liu ML, Lu Y, Guo HY. Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety. Bioorg Med Chem Lett. 2012;22:5971–5975. doi: 10.1016/j.bmcl.2012.07.040
  • Abdelrahman MA, Salama I, Gomaa MS, Elaasser MM, Abdel-Aziz MM, Soliman DH. Design, synthesis and 2D QSAR study of novel pyridine and quinolone hydrazone derivatives as potential antimicrobial and antitubercular agents. Eur J Med Chem. 2018;138:698–714. doi: 10.1016/j.ejmech.2017.07.004
  • Wang LL, Battini N, Bheemanaboina RRY, Zhang SL, Zhou CH. Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation. Eur J Med Chem. 2019;167:105–123. doi: 10.1016/j.ejmech.2019.01.072
  • Gonzalez JE, Keshavan ND. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev. 2006;70:859–875. doi: 10.1128/MMBR.00002-06
  • Rasch M, Rasmussen TB, Andersen JB, et al. Well-known quorum sensing inhibitors do not affect bacterial quorum sensing-regulated bean sprout spoilage. J Appl Microbiol. 2007;102:826–837. doi: 10.1111/j.1365-2672.2006.03121.x
  • Truchado P, López-Gálvez F, Gil MI, Tomás-Barberán FA, Allende A. Quorum sensing inhibitory and antimicrobial activities of honeys and the relationship with individual phenolics. Food Chem. 2009;155:1337–1344. doi: 10.1016/j.foodchem.2009.01.065
  • Abudoleh SM, Mahasneh AM. Anti-quorum sensing activity of substances isolated from wild berry associated bacteria. Avicenna J Med Biotechnol. 2017;9:23–30.
  • Rasmussen TB, Skindersoe ME, Bjarnsholt T et al. Identity and effects of quorum-sensing inhibitors produced by Penicillium species. Microbiol. 2005;151:1325–1340. doi: 10.1099/mic.0.27715-0
  • Skindersoe ME, Alhede M, Phipps R, et al. Effects of antibiotics on quorum sensing in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2008;52:3648–3663. doi: 10.1128/AAC.01230-07

BAZI SEFALOSPORANİK ASİT, SİPROFLOKSASİN, NORFLOKSASİN VE PENİCİLLANİK ASİT TÜREVLERİNİN ANTİMİKROBİYAL VE ANTI-QUORUM SENSING ÖZELLİKLERİNİN ARAŞTIRILMASI

Year 2020, Volume: 6 Issue: 1, 28 - 33, 12.01.2020
https://doi.org/10.30934/kusbed.604829

Abstract

Amaç: Bakteriler arasında antibiyotik direncinin hızla
artışı halk sağlığı açısından ciddi bir problem oluşturmaktadır. Çalışmalar,
yeni antimikrobiyal moleküllerin keşfi ve dirençli bakterilerle mücadelede yeni
tedavi stratejilerinin geliştirilmesi üzerine yoğunlaşmıştır. Patojenik
bakterilerin, quorum sensing (QS) mekanizmasını kullanarak virülans
faktörlerinin sentezini düzenlediği bulunduktan sonra, QS inhibisyonu
antibakteriyel tedavi için cazip bir hedef haline gelmiştir. Bu çalışmada
sefalosporanik asit, siprofloksasin, norfloksasin ve penisillanik asit türevi
16 maddenin antimikrobiyal aktivitelerinin ve anti-QS özelliklerinin
araştırılması amaçlandı.



Yöntem: Maddelerin antimikrobiyal aktiviteleri çeşitli
mikroorganizmalara karşı agar kuyucuk diffüzyon yöntemi ile test edildi. Etki
gösteren maddelerin minimum inhibisyon konsantrasyon (MİK) değerleri sıvı
mikrodilüsyon yöntemi ile belirlendi. Maddelerin anti-QS özellikleri Chromobacterium violaceum raportör
suşunda viyolasin inhibisyonu üzerine yarı-katı agar yöntemi ile araştırıldı.
Veriler istatistiksel olarak karşılaştırıldı.



Bulgular: Altı norfloksasin türevi test edilen bakterilerin
bir kısmına karşı antimikrobiyal aktivite göstermiş olup üç türevin bazı
organizmalara karşı kontrol antibiyotiklerden daha etkili olduğu tespit edildi
(p<0,05). Bir siprofloksasin
türevi, test edilen tüm bakterilere karşı antimikrobiyal aktiviteye sahip olup
bakterilerin bir kısmına karşı kontrol antibiyotiğinden daha etkili olduğu
belirlendi (p<0,05). Altı
norfloksasin ve bir siprofloksasin türevinin MİK değerleri, sırasıyla 0,04–6,25
µg/mL ve 0,04–3,12 µg/mL aralığında tespit edildi. Bir sefalosporanik asit ve
bir penisillanik asit türevinin anti-QS özellik gösterdiği belirlendi.



Sonuç: Bu sonuçlar, bazı yeni sefalosporanik asit,
siprofloksasin, norfloksasin ve penicillanik asit türevlerinin yeni antibakteriyel
ve anti-QS ajanların geliştirilmesinde potansiyel moleküller olabileceğini
göstermiştir.

References

  • World Health Organization (2018, February 15). Antimicrobial resistance. Available from: https://www.who.int/en/news-room/fact-sheets/detail/antimicrobial-resistance (accessed on 11 November 2019).
  • Alanis AJ. Resistance to antibiotics: are we in the post-antibiotic era? Arch Med Res. 2005;36:697–705. doi: 10.1016/j.arcmed.2005.06.009
  • El-Sharer S, Shaaban M, Barwa R, Hassan R. Control of quorum sensing and virulence factors of Pseudomonas aeruginosa using phenylalanine arginyl β-naphthylamide. J Med Microbiol. 2016;65:1194–1204. doi: 10.1099/jmm.0.000327
  • Papenfort K, Bassler BL. Quorum sensing signal-response systems in gram-negative bacteria. Nat Rev Microbiol. 2016;14:576–588. doi: 10.1038/nrmicro.2016.89
  • Eberl L, Winson MK, Sternberg C, et al. Involvement of N-acyl-L-hormoserine lactone autoinducers in controlling the multicellular behaviour of Serratia liquefaciens. Mol Microbiol. 1996;20:127–136. doi: 10.1111/j.1365-2958.1996.tb02495.x
  • McClean KH, Winson MK, Fish L, et al. Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiol. 1997;143:3703–3711. doi: 10.1099/00221287-143-12-3703
  • Rice SA, Koh KS, Queck SY, Labbate M, Lam KW, Kjelleberg S. Biofilm formation and sloughing in Serratia marcescens are controlled by quorum sensing and nutrient cues. J Bacteriol. 2005;187:3477–3485. doi: 10.1128/JB.187.10.3477-3485.2005
  • Tinaz-Bosgelmez G, Ulusoy S, Ugur A, Ceylan O. Inhibition of quorum sensing-regulated behaviors by Scorzonera sandrasica. Curr Microbiol. 2007;55:114–118. doi: 10.1007/s00284-006-0624-2
  • Kalia VC. Quorum sensing inhibitors: an overview. Biotechnol Adv. 2013; 31:224–245. doi: 10.1016/j.biotechadv.2012.10.004
  • Morohoshi T, Kato M, Fukamachi K, Kato N, Ikeda T. N-acylhomoserine lactone regulates violacein production in Chromobacterium violaceum type strain ATCC 12472. FEMS Microbiol Lett. 2008;279:124–130. doi: 10.1111/j.1574-6968.2007.01016.x
  • McLean RJC, Pierson LS, Fuqua CA. Simple screening protocol for the identification of quorum signal antagonists. J Microbiol Methods. 2004;58:351–360. doi: 10.1016/j.mimet.2004.04.016
  • The European Committee on Antimicrobial Susceptibility Testing. EUCAST disk diffusion method, version 4.0, 2014. http://www.eucast.org.
  • The European Committee on Antimicrobial Susceptibility Testing. Routine internal quality control as recommended by EUCAST, version 3.1, 2013. http://www.eucast.org.
  • Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard-Tenth Edition. CLSI document M07-A10, 2015. Wayne, PA.
  • Carlton RM. Phage therapy: past history and future prospects. Arch Immunol Ther Exp (Warsz). 1999;47:267–274.
  • Demain AL, Sanchez S. Microbial drug discovery: 80 years of progress. J Antibiot (Tokyo). 2009;62:5–16. doi: 10.1038/ja.2008.16
  • Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng CC. Synthesis and antibacterial evaluation of certain quinolone derivatives. J Med Chem. 2001;44:2374–2377. doi: 10.1021/jm0100335
  • Foroumadi A, Soltani F, Moshafi MH, Ashraf-Askari R. Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl) piperazinyl quinolone derivatives. Farmaco. 2003;58:1023–1028. doi: 10.1016/S0014-827X(03)00191-5
  • Foroumadi A, Ghodsi S, Emami S, et al. Synthesis and antibacterial activity of new fluoroquinolones containing a substituted N-(phenethyl)piperazine moiety. Bioorg Med Chem Lett. 2006;16:3499–3503. doi: 10.1016/j.bmcl.2006.03.103
  • Wang S, Jia XD, Liu ML, Lu Y, Guo HY. Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety. Bioorg Med Chem Lett. 2012;22:5971–5975. doi: 10.1016/j.bmcl.2012.07.040
  • Abdelrahman MA, Salama I, Gomaa MS, Elaasser MM, Abdel-Aziz MM, Soliman DH. Design, synthesis and 2D QSAR study of novel pyridine and quinolone hydrazone derivatives as potential antimicrobial and antitubercular agents. Eur J Med Chem. 2018;138:698–714. doi: 10.1016/j.ejmech.2017.07.004
  • Wang LL, Battini N, Bheemanaboina RRY, Zhang SL, Zhou CH. Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation. Eur J Med Chem. 2019;167:105–123. doi: 10.1016/j.ejmech.2019.01.072
  • Gonzalez JE, Keshavan ND. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev. 2006;70:859–875. doi: 10.1128/MMBR.00002-06
  • Rasch M, Rasmussen TB, Andersen JB, et al. Well-known quorum sensing inhibitors do not affect bacterial quorum sensing-regulated bean sprout spoilage. J Appl Microbiol. 2007;102:826–837. doi: 10.1111/j.1365-2672.2006.03121.x
  • Truchado P, López-Gálvez F, Gil MI, Tomás-Barberán FA, Allende A. Quorum sensing inhibitory and antimicrobial activities of honeys and the relationship with individual phenolics. Food Chem. 2009;155:1337–1344. doi: 10.1016/j.foodchem.2009.01.065
  • Abudoleh SM, Mahasneh AM. Anti-quorum sensing activity of substances isolated from wild berry associated bacteria. Avicenna J Med Biotechnol. 2017;9:23–30.
  • Rasmussen TB, Skindersoe ME, Bjarnsholt T et al. Identity and effects of quorum-sensing inhibitors produced by Penicillium species. Microbiol. 2005;151:1325–1340. doi: 10.1099/mic.0.27715-0
  • Skindersoe ME, Alhede M, Phipps R, et al. Effects of antibiotics on quorum sensing in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2008;52:3648–3663. doi: 10.1128/AAC.01230-07
There are 28 citations in total.

Details

Primary Language English
Subjects Medical Microbiology
Journal Section Original Article
Authors

Sanaz Hamidi This is me 0000-0002-3648-9560

Enis Fuat Tüfekci 0000-0001-5051-2694

Neslihan Demirbaş 0000-0002-8444-2011

Yasemin Ünver 0000-0001-5834-3223

Ali Osman Kılıç This is me 0000-0002-5506-0866

Publication Date January 12, 2020
Submission Date August 9, 2019
Acceptance Date December 23, 2019
Published in Issue Year 2020 Volume: 6 Issue: 1

Cite

APA Hamidi, S., Tüfekci, E. F., Demirbaş, N., Ünver, Y., et al. (2020). INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID. Kocaeli Üniversitesi Sağlık Bilimleri Dergisi, 6(1), 28-33. https://doi.org/10.30934/kusbed.604829
AMA Hamidi S, Tüfekci EF, Demirbaş N, Ünver Y, Kılıç AO. INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID. KOU Sag Bil Derg. January 2020;6(1):28-33. doi:10.30934/kusbed.604829
Chicago Hamidi, Sanaz, Enis Fuat Tüfekci, Neslihan Demirbaş, Yasemin Ünver, and Ali Osman Kılıç. “INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID”. Kocaeli Üniversitesi Sağlık Bilimleri Dergisi 6, no. 1 (January 2020): 28-33. https://doi.org/10.30934/kusbed.604829.
EndNote Hamidi S, Tüfekci EF, Demirbaş N, Ünver Y, Kılıç AO (January 1, 2020) INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID. Kocaeli Üniversitesi Sağlık Bilimleri Dergisi 6 1 28–33.
IEEE S. Hamidi, E. F. Tüfekci, N. Demirbaş, Y. Ünver, and A. O. Kılıç, “INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID”, KOU Sag Bil Derg, vol. 6, no. 1, pp. 28–33, 2020, doi: 10.30934/kusbed.604829.
ISNAD Hamidi, Sanaz et al. “INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID”. Kocaeli Üniversitesi Sağlık Bilimleri Dergisi 6/1 (January 2020), 28-33. https://doi.org/10.30934/kusbed.604829.
JAMA Hamidi S, Tüfekci EF, Demirbaş N, Ünver Y, Kılıç AO. INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID. KOU Sag Bil Derg. 2020;6:28–33.
MLA Hamidi, Sanaz et al. “INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID”. Kocaeli Üniversitesi Sağlık Bilimleri Dergisi, vol. 6, no. 1, 2020, pp. 28-33, doi:10.30934/kusbed.604829.
Vancouver Hamidi S, Tüfekci EF, Demirbaş N, Ünver Y, Kılıç AO. INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID. KOU Sag Bil Derg. 2020;6(1):28-33.