Porphyrin‐Containing Glycodendrimers

Abstract

Two dendrimers, incorporating tetrasubstituted porphyrin units as their cores and, in one case, four perbenzoylated and, in the other case, twelve peracetylated β-D-glucopyranosyl residues at their peripheries, have been synthesized in yields of 39 and 16%, respectively. The deprotection of these dendrimers was achieved quantitatively under Zemplé n conditions. The protected and deprotected dendrimers were characterized by liquid secondary-ion or matrixassisted laser desorption ionization time-of-flight mass spec-

Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics

“…131,200–202 Stoddart and co-workers reported the synthesis of two symmetric tetrasubstituted porphyrin glycoconjugated dendrimers with four and 12 β -D-glucopyranosyl residues present on the periphery of the tetrapyrrolic macrocycle (Figure 19). 203 …”

A Strategy for the Targeting of Photosensitizers. Synthesis, Characterization, and Photobiological Property of Porphyrins Bearing Glycodendrimeric Moieties

“…[29][30][31][32] Recently, Ballardini et al described the synthesis and photophysical properties of two dendrimer macrocycles, incorporating tetrasubstituted porphyrin units as core and, in one case, four benzyloylated or deprotected β-D-glucopyranosyl and in an other case, twelve acetylated-β-D-glucopyranosyl or β-D-glucopyranosyl residues at the peripheries of the tetrapyrrolic macrocycle. 33 These unprotected tetrasubstituted molecules are symmetric and highly water-soluble but no in vitro photoefficiency was described. In another approach, Matsuo et al described the synthesis of glycosylated myoglobin by a reconstitutional method as an The Journal of Organic Chemistry ARTICLE artificial prosthetic group inserted into sperm whale apomyoglobin to afford a β-galactosylated myoglobin.…”

Microsolvation in superfluid helium droplets studied by the electronic spectra of six porphyrin derivatives and one chlorine compound

“…[24][25][26][27][28] It is even more challenging to record dispersed emission spectra where only a fraction of the weak fluorescence is dispersed over the 1024 × 256 pixels of a CCD chip. Therefore, the signal to noise level was much lower as compared to the phthalocyanines.…”

“…For TPC, the oscillator strength and fluorescence quantum yield are known to be much larger than for the corresponding porphyrin derivative. [24][25][26][27][28] Under these conditions, the fluorescence of a minor contamination with TPP could not be detected from the TPC sample while the fluorescence of a minor contami- nation with TPC can even dominate the spectrum of a TPP sample. Further evidence for the contamination of the TPP sample with TPC was provided by the chromatograms which revealed the same two species for both samples, however, with almost inverted abundance.…”