Abstract
A covalent conjugate between an antibacterial ionic liquid and an antimicrobial peptide was produced via “click” chemistry, and found to retain the parent peptide’s activity against multidrug-resistant clinical isolates of Gram-negative bacteria, and antibiofilm action on a resistant clinical isolate of Klebsiella pneumoniae, while exhibiting much improved stability towards tyrosinase-mediated modifications. This unprecedented communication is a prelude for the promise held by ionic liquids -based approaches as tools to improve the action of bioactive peptides.
Highlights
Ionic Liquids (ILs), though mostly known for their potential role as “green solvents”, are becoming increasingly attractive as customizable and tunable organic salts for diverse specific purposes
In view of the above, and based on our recent disclosure of a collagenesis-inducing peptide with potent antibacterial and antibiofilm properties [12], we investigated the effect of coupling an antimicrobial methylimidazolium IL to the N-terminus of that peptide on antibacterial and antibiofilm activities, as well as on stability
In face of the excellent antibacterial properties exhibited by the MeIm-3.1-PP4 conjugate, especially against Gram-negative bacteria, we evaluated its antibiofilm activity using the
Summary
Ionic Liquids (ILs), though mostly known for their potential role as “green solvents”, are becoming increasingly attractive as customizable and tunable organic salts for diverse specific purposes (task-specific ILs). In view of the above, and based on our recent disclosure of a collagenesis-inducing peptide with potent antibacterial and antibiofilm properties [12], we investigated the effect of coupling an antimicrobial methylimidazolium IL to the N-terminus of that peptide on antibacterial and antibiofilm activities, as well as on stability. To this end, we opted to use the well-known copper(I)-catalyzed. SSyynntthheessiiss rroouuttee ttoowwaarrddss MMeeIImm◦ --33..11--PPPP44:: ((ii)) 11..11 mmoollaarr eeqquuiivvaalleennttss((eeqq))ooffMMeeIImm,,11.0.0eeqqooff pproropparagrgyyl lbbrorommididee((8800%%iinn ttoolluueennee)),, 4400 °CC,,2244hh; (;ii()ii5) e5qeoqf oFfmFomc-opcr-optreoctteecdteadmainmoinaocida,ci1d0, e1q0oefqNo-f Ne-tehtyhly-lN-N,N,N-d-diiisiosopproroppyylalammininee (D(IDEAIE)Aan) d 5 aenqdof O-5(benzeoqtriazoofl-1-yOl)--N(b,eNn,zNot,rNia-ztoelt-r1a-myle)t-hNy,lNu,rNon′,iNu′mhteextaraflmuoertohpylhuorsopnhiuatme (HheBxTaUflu) oinroNp,hNo-sdpihmaettehy(HlfoBrTmUa)minideN(,ND-MdiFm),e1thhy, lrfooormmatmemidpeer(aDtuMreF)(,r.t1.);h(,iirio) o2m0% ptiepmerpideirnaetuirne D(Mr.tF.,);15(imii)in, 2r0.t%.; (ivp)ipterirfilduionreoacineticDaMcidF, (T1F5A)/mtriiins,oprro.tp.;yls(iivla)netr(iTflIuSo)/rdoiastciellteicd wacaitder (9(5T:F2A.5):2/t.r5iivs/ovp/vr)o,p2yhls,irl.at.n; e(v()T5ISe)q/doisftailzleiddowaacteetric(9a5c:i2d.,51:20.5eqv/ov/fvD),I2EAh,,ra.tn.;d(v5)e5qeoqfoHf BazTiUdoinacDeMticFa, c1idh,, 1r.0t.; (veiq) 1ofeDq IsEoAdi,uamndL5- aesqcoofrbHaBteT, U10ineqDoMf DF,IE1Ah,, 1r.0t.;eq(voi)f 12,e6q-lusotiddiiunme, 1L-eqasocforPbra-Mte,eI1m0 ,eaqnodf 1DeIEqAo,fc1o0pepqero(fI) b2ro,6m-liudteidiinnDe,M1 Feq:acoeftPonr-iMtrieleIm(M, aenCdN1) e(3q:1ofvc/ovp).per(I) bromide in DMF:acetonitrile (MeCN) (3:1 v/v)
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