Squaramides and thiosquaramides
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The document compares the crystal structures and chloride transport abilities of squaramides, thiourea, and urea, with specific data on their stability constants and efficacy in chloride/nitrate transport at pH 7.2. It includes a summary of the EC50 values and other chemical properties of various tested compounds. Overall, thiosquaramides were found to show low chloride/nitrate transport ability.
Squaramides and thiosquaramides
- 1. Squaramides Squaramides vs. Thiourea vs. Urea
- 2. Crystal structures 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.
- 3. 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.
- 4. 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.
- 5. Summary Ka (TBA Cl) EC50 (nitr) EC50 (bicarb) c logP PSA (Å2) phenyl 1 (sq) 260 1.29 3.99 2.024 48.036 2 (thio) 19 - - 3.659 21.3 3 (urea) 30 - - 2.513 32.747 p-trifluoromethylphenyl 4 (sq) 458 0.06 0.50 3.8662 47.606 5 (thio) 43 0.22 1.15 5.5012 21.041 6 (urea) 75 0.43 1.17 4.3551 32.276 m-bis(trifluoromethyl)phenyl 7 (sq) 634 0.01 0.35 5.7084 47.937 8 (thio) 41 0.17 0.54 7.3434 21.61 9 (urea) 88 0.32 0.41 6.1973 32.694 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.
- 6. Summary Ka (TBA Cl) EC50 (nitr) EC50 (bicarb) c logP PSA (Å2) phenyl 1 (sq) 260 1.29 3.99 2.024 48.036 2 (thio) 19 - - 3.659 21.3 3 (urea) 30 - - 2.513 32.747 p-trifluoromethylphenyl 4 (sq) 458 0.06 0.50 3.8662 47.606 5 (thio) 43 0.22 1.15 5.5012 21.041 6 (urea) 75 0.43 1.17 4.3551 32.276 m-bis(trifluoromethyl)phenyl 7 (sq) 634 0.01 0.35 5.7084 47.937 8 (thio) 41 0.17 0.54 7.3434 21.61 9 (urea) 88 0.32 0.41 6.1973 32.694 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.
- 7. Summary Ka (TBA Cl) EC50 (nitr) EC50 (bicarb) c logP PSA (Å2) phenyl 1 (sq) 260 1.29 3.99 2.024 48.036 2 (thio) 19 - - 3.659 21.3 3 (urea) 30 - - 2.513 32.747 p-trifluoromethylphenyl 4 (sq) 458 0.06 0.50 3.8662 47.606 5 (thio) 43 0.22 1.15 5.5012 21.041 6 (urea) 75 0.43 1.17 4.3551 32.276 m-bis(trifluoromethyl)phenyl 7 (sq) 634 0.01 0.35 5.7084 47.937 8 (thio) 41 0.17 0.54 7.3434 21.61 9 (urea) 88 0.32 0.41 6.1973 32.694 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.
- 8. 260 M-1 458 M-1 634 M-1 270 M-1 60 M-1 no interaction Stability constants with chloride in DMSO-d6/0.5% water
- 9. 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 7.2 pH 7.2 Chloride/nitrate – 1% Thiosquaramides display low Cl/NO3 transport ability at pH 7.2 N. 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
- 10. 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 x pH x Switchable anion transport N. 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