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Squaramides quaramides vs. Thiourea vs. Urea

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Squaramides

SquaramidesSquaramides vs. Thiourea vs. Urea

Crystal structuresN. Busschaert, I.L. Kirby, S. Young, S.J. Coles, P.N. Horton, M.E. Light and P.A. Gale, Angew. Chem. Int. Ed. 2012, 51, 4426.

Chloride/nitrate 1%

N. Busschaert, I.L. Kirby, S. Young, S.J. Coles, P.N. Horton, M.E. Light and P.A. Gale, Angew. Chem. Int. Ed. 2012, 51, 4426.

Chloride/bicarbonate 1%

N. Busschaert, I.L. Kirby, S. Young, S.J. Coles, P.N. Horton, M.E. Light and P.A. Gale, Angew. Chem. Int. Ed. 2012, 51, 4426.

SummaryKa (TBA Cl)EC50 (nitr)EC50 (bicarb)c logPPSA (2)phenyl1 (sq)2601.293.992.02448.0362 (thio)19--3.65921.33 (urea)30--2.51332.747p-trifluoromethylphenyl4 (sq)4580.060.503.866247.6065 (thio)430.221.155.501221.0416 (urea)750.431.174.355132.276m-bis(trifluoromethyl)phenyl7 (sq)6340.010.355.708447.9378 (thio)410.170.547.343421.619 (urea)880.320.416.197332.694

N. Busschaert, I.L. Kirby, S. Young, S.J. Coles, P.N. Horton, M.E. Light and P.A. Gale, Angew. Chem. Int. Ed. 2012, 51, 4426.

SummaryKa (TBA Cl)EC50 (nitr)EC50 (bicarb)c logPPSA (2)phenyl1 (sq)2601.293.992.02448.0362 (thio)19--3.65921.33 (urea)30--2.51332.747p-trifluoromethylphenyl4 (sq)4580.060.503.866247.6065 (thio)430.221.155.501221.0416 (urea)750.431.174.355132.276m-bis(trifluoromethyl)phenyl7 (sq)6340.010.355.708447.9378 (thio)410.170.547.343421.619 (urea)880.320.416.197332.694

N. Busschaert, I.L. Kirby, S. Young, S.J. Coles, P.N. Horton, M.E. Light and P.A. Gale, Angew. Chem. Int. Ed. 2012, 51, 4426.

SummaryKa (TBA Cl)EC50 (nitr)EC50 (bicarb)c logPPSA (2)phenyl1 (sq)2601.293.992.02448.0362 (thio)19--3.65921.33 (urea)30--2.51332.747p-trifluoromethylphenyl4 (sq)4580.060.503.866247.6065 (thio)430.221.155.501221.0416 (urea)750.431.174.355132.276m-bis(trifluoromethyl)phenyl7 (sq)6340.010.355.708447.9378 (thio)410.170.547.343421.619 (urea)880.320.416.197332.694

N. Busschaert, I.L. Kirby, S. Young, S.J. Coles, P.N. Horton, M.E. Light and P.A. Gale, Angew. Chem. Int. Ed. 2012, 51, 4426.

260 M-1458 M-1634 M-1270 M-160 M-1no interactionStability constants with chloride in DMSO-d6/0.5% water

Chloride transport by thiosquaramides (1 mol%) in POPC vesicles loaded with 489 mM NaCl, dispersed in 489 mM NaNO3 and buffered to pH 7.2. Vesicles were lysed at t = 300 s.NO3-pH 7.2pH 7.2

Chloride/nitrate 1%Thiosquaramides display low Cl/NO3 transport ability at pH 7.2N. Busschaert, R.B.P. Elmes, D.D. Czech, X. Wu, I.L. Kirby, E.M. Peck, K.D. Hendzel, S. K. Shaw, B. Chan, B.D. Smith, K.A. Jolliffe, and P.A. Gale, Chem. Sci., 2014, DOI:10.1039/c4sc01629g

Chloride transport after 60s by thiosquaramides (1 mol%) in POPC vesicles loaded with 489 mM NaCl, dispersed in 489 mM NaNO3 and buffered to various pH.

NO3-pH xpH xSwitchable anion transportN. Busschaert, R.B.P. Elmes, D.D. Czech, X. Wu, I.L. Kirby, E.M. Peck, K.D. Hendzel, S. K. Shaw, B. Chan, B.D. Smith, K.A. Jolliffe, and P.A. Gale, Chem. Sci., 2014, DOI:10.1039/c4sc01629g


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