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. 2008 Dec 8;64(50):11440-11448.
doi: 10.1016/j.tet.2008.08.096.

Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins

Ana Z Muresan  1 , Jonathan S Lindsey
Affiliations

Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins

Ana Z Muresan et al. Tetrahedron. .

Abstract

Three free base porphyrins have been prepared that bear a polar and facially encumbering 2,4,6-tris(carboxymethoxy)phenyl motif at one meso (5-) position. The only other substituent (15-position) comprises phenyl, formyl, or p-aminophenyl. The porphyrins exhibit solubility in water (or aqueous buffer solutions) at pH >/=7 and concentrations >1 mM at room temperature. The concise syntheses, water-solubility, and bioconjugatable handle make these porphyrin constructs suitable for biological applications.

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Figures

Figure 1
Figure 1
Molecular model of porphyrin H2P-1 showing conformations (not energy-minimized) of the 2,6-carboxymethoxy units attached to the aryl moiety.
Figure 2
Figure 2
Variable temperature 1H NMR spectra for porphyrin H2P-2 in DMSO-d6.
Figure 3
Figure 3
Absorption spectra of porphyrin H2P-3 at room temperature in water (solid line), THF (dashed line) and DMSO (dotted line).
Figure 4
Figure 4
Absorption spectra of porphyrins in aqueous buffer solution (pH = 7) at room temperature as a function of concentration. (A) Porphyrin H2P-1: (solid line) c = 2.8 mM, l = 1 mm; (dotted line) c = 0.56 mM, l = 5 mm; (dashed line) c = 0.28 mM, l = 10 mm. (B) Porphyrin H2P-2: (solid line) c = 2.5 mM, l = 1 mm; (dotted line) c = 0.5 mM, l = 5 mm; (dashed line) c = 0.25 mM, l = 10 mm. (C) Porphyrin H2P-3: (solid line) c = 3 mM, l = 1 mm; (dotted line) c = 0.6 mM, l = 5 mm; (dashed line) c = 0.3 mM, l = 10 mm.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Chart 1
Chart 1
Chart 2
Chart 2
Chart 3
Chart 3
See this image and copyright information in PMC

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