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Chemical Compound Review:

Isophthalamide benzene-1,3-dicarboxamide

Synonyms: m-Phthalamide, SureCN36694, AG-E-23638, ACMC-209e7q, CHEBI:38801, ...

Brooks, S.J. et al., Yue, Z. et al., Eccleston, M.E. et al., Chen, R. et al., Hom, R.K. et al.

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High impact information on isophthalamide

Compound 20 with the N-terminal isophthalamide proved to be the most potent HE inhibitor (IC(50) = 30 nM) toward BACE [1].
Steric interactions in 1,3-dicarboxamidoanthraquinones have been employed to 'twist' isophthalamide-like anion binding sites; the crystal structure of the fluoride complex of a bis-3,5-dichlorophenylamide derivative shows the receptor acting as a 'hydrogen-bonding corner' in a '2 + 2' fluoride containing molecular box [2].
A pH responsive pseudopeptide, poly(L-lysine iso-phthalamide), has been modified with a hydrophilic poly(ethylene glycol) analogue, Jeffamine M-1000 and the effect of grafting ratio on the pH responsive behaviour of the grafted polymers in aqueous solution investigated using fluorescence and 1H NMR spectroscopy [3].
However, at pH 5.5, relative to poly (L-lysine iso-phthalamide), the grafted polymers displayed a better ability to rupture the outer membranes of these cells [4].
5. Relative to the degree of lysis displayed by poly(L-lysine iso-phthalamide), lysis was reduced by partial esterification and increased by replacing the aromatic iso-phthaloyl moiety with a long chain aliphatic dodecyl moiety [5].

References

Design and synthesis of hydroxyethylene-based peptidomimetic inhibitors of human beta-secretase. Hom, R.K., Gailunas, A.F., Mamo, S., Fang, L.Y., Tung, J.S., Walker, D.E., Davis, D., Thorsett, E.D., Jewett, N.E., Moon, J.B., John, V. J. Med. Chem. (2004) [Pubmed]
'Twisted' isophthalamide analogues. Brooks, S.J., Evans, L.S., Gale, P.A., Hursthouse, M.B., Light, M.E. Chem. Commun. (Camb.) (2005) [Pubmed]
Modulation of the pH-responsive properties of poly(L-lysine iso-phthalamide) grafted with a poly(ethylene glycol) analogue. Yue, Z., Eccleston, M.E., Slater, N.K. Biomaterials (2005) [Pubmed]
Modulation of cell membrane disruption by pH-responsive pseudo-peptides through grafting with hydrophilic side chains. Chen, R., Yue, Z., Eccleston, M.E., Williams, S., Slater, N.K. Journal of controlled release : official journal of the Controlled Release Society. (2005) [Pubmed]
pH-responsive pseudo-peptides for cell membrane disruption. Eccleston, M.E., Kuiper, M., Gilchrist, F.M., Slater, N.K. Journal of controlled release : official journal of the Controlled Release Society. (2000) [Pubmed]

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