TY  - JOUR
T1  - INVESTIGATION OF ANTIMICROBIAL AND ANTI-QUORUM SENSING PROPERTIES OF SOME DERIVATIVES OF CEPHALOSPORANIC ACID, CIPROFLOXACIN, NORFLOXACIN, AND PENICILLANIC ACID
TT  - BAZI SEFALOSPORANİK ASİT, SİPROFLOKSASİN, NORFLOKSASİN VE PENİCİLLANİK ASİT TÜREVLERİNİN ANTİMİKROBİYAL VE ANTI-QUORUM SENSING ÖZELLİKLERİNİN ARAŞTIRILMASI
AU  - Tüfekci, Enis Fuat
AU  - Hamidi, Sanaz
AU  - Demirbaş, Neslihan
AU  - Ünver, Yasemin
AU  - Kılıç, Ali Osman
PY  - 2020
DA  - January
Y2  - 2019
DO  - 10.30934/kusbed.604829
JF  - Kocaeli Üniversitesi Sağlık Bilimleri Dergisi
JO  - KOU Sag Bil Derg
PB  - Kocaeli Üniversitesi
WT  - DergiPark
SN  - 2149-8571
SP  - 28
EP  - 33
VL  - 6
IS  - 1
LA  - en
AB  - Objective: The rapid increase ofantibiotic resistance among bacteria is a serious public health problem.Studies have focused on the discovery of new antibiotic molecules and thedevelopment of new therapeutic strategies to combat these resistant bacteria.Once it was known that pathogenic bacteria regulate synthesis of virulencefactors by the quorum sensing (QS) mechanism, QS inhibition became anattractive target for antibacterial treatment. This study aimed to investigatethe antimicrobial activities and anti-QS properties of 16 derivatives ofcephalosporanic acid, ciprofloxacin, norfloxacin, and penicillanic acid. Methods: Antimicrobial activity of thederivatives was tested by the agar well diffusion method against variousmicroorganisms. The minimum inhibitory concentration (MIC) of effectivederivatives was assessed by the broth microdilution method. Anti-QS propertieswere investigated using the soft agar method, observing inhibition of violaceinproduction in Chromobacterium violaceum.The data were compared statistically.Results: Six norfloxacin derivativesdisplayed antimicrobial activity against a number of organisms, three of whichwere more effective than control antibiotics (p<0.05) against some organisms. One ciprofloxacin derivativedemonstrated antimicrobial activity against all tested bacteria and was moreeffective against some bacteria than control antibiotic (p<0.05). The MIC valuesof these six norfloxacin and one ciprofloxacin derivatives were between0.04–6.25 µg/mL and 0.04–3.12 µg/mL, respectively. A cephalosporanic acid and apenicillanic acid derivative displayed anti-QS properties.Conclusion: This study shows that some newderivatives of cephalosporanic acid, ciprofloxacin, norfloxacin, andpenicillanic acid may have potential for development of new antibacterial andanti-QS agents.
KW  - Chromobacterium violaceum
KW  - antibiotic resistance
KW  - derivatives
KW  - antimicrobial tests
N2  - Amaç: Bakteriler arasında antibiyotik direncinin hızlaartışı halk sağlığı açısından ciddi bir problem oluşturmaktadır. Çalışmalar,yeni antimikrobiyal moleküllerin keşfi ve dirençli bakterilerle mücadelede yenitedavi stratejilerinin geliştirilmesi üzerine yoğunlaşmıştır. Patojenikbakterilerin, quorum sensing (QS) mekanizmasını kullanarak virülansfaktörlerinin sentezini düzenlediği bulunduktan sonra, QS inhibisyonuantibakteriyel tedavi için cazip bir hedef haline gelmiştir. Bu çalışmadasefalosporanik asit, siprofloksasin, norfloksasin ve penisillanik asit türevi16 maddenin antimikrobiyal aktivitelerinin ve anti-QS özelliklerininaraştırılması amaçlandı.Yöntem: Maddelerin antimikrobiyal aktiviteleri çeşitlimikroorganizmalara karşı agar kuyucuk diffüzyon yöntemi ile test edildi. Etkigösteren maddelerin minimum inhibisyon konsantrasyon (MİK) değerleri sıvımikrodilüsyon yöntemi ile belirlendi. Maddelerin anti-QS özellikleri Chromobacterium violaceum raportörsuşunda viyolasin inhibisyonu üzerine yarı-katı agar yöntemi ile araştırıldı.Veriler istatistiksel olarak karşılaştırıldı.Bulgular: Altı norfloksasin türevi test edilen bakterilerinbir kısmına karşı antimikrobiyal aktivite göstermiş olup üç türevin bazıorganizmalara karşı kontrol antibiyotiklerden daha etkili olduğu tespit edildi(p<0,05). Bir siprofloksasintürevi, test edilen tüm bakterilere karşı antimikrobiyal aktiviteye sahip olupbakterilerin bir kısmına karşı kontrol antibiyotiğinden daha etkili olduğubelirlendi (p<0,05). Altınorfloksasin ve bir siprofloksasin türevinin MİK değerleri, sırasıyla 0,04–6,25µg/mL ve 0,04–3,12 µg/mL aralığında tespit edildi. Bir sefalosporanik asit vebir penisillanik asit türevinin anti-QS özellik gösterdiği belirlendi.Sonuç: Bu sonuçlar, bazı yeni sefalosporanik asit,siprofloksasin, norfloksasin ve penicillanik asit türevlerinin yeni antibakteriyelve anti-QS ajanların geliştirilmesinde potansiyel moleküller olabileceğinigöstermiştir.
CR  - 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).
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - Kalia VC. Quorum sensing inhibitors: an overview. Biotechnol Adv. 2013; 31:224–245. doi: 10.1016/j.biotechadv.2012.10.004
CR  - 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
CR  - 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
CR  - The European Committee on Antimicrobial Susceptibility Testing. EUCAST disk diffusion method, version 4.0, 2014. http://www.eucast.org.
CR  - The European Committee on Antimicrobial Susceptibility Testing. Routine internal quality control as recommended by EUCAST, version 3.1, 2013. http://www.eucast.org.
CR  - 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.
CR  - Carlton RM. Phage therapy: past history and future prospects. Arch Immunol Ther Exp (Warsz). 1999;47:267–274.
CR  - Demain AL, Sanchez S. Microbial drug discovery: 80 years of progress. J Antibiot (Tokyo). 2009;62:5–16. doi: 10.1038/ja.2008.16
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - Gonzalez JE, Keshavan ND. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev. 2006;70:859–875. doi: 10.1128/MMBR.00002-06
CR  - 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
CR  - 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
CR  - Abudoleh SM, Mahasneh AM. Anti-quorum sensing activity of substances isolated from wild berry associated bacteria. Avicenna J Med Biotechnol. 2017;9:23–30.
CR  - 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
CR  - 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
UR  - https://doi.org/10.30934/kusbed.604829
L1  - https://dergipark.org.tr/tr/download/article-file/928035
ER  -