65148-67-6Relevant articles and documents
Porphyrin and tetrabenzoporphyrin dendrimers: Tunable membrane-impermeable fluorescent pH nanosensors
Finikova, Olga,Galkin, Alexander,Rozhkov, Vladimir,Cordero, Maria,Haegerhaell, Cecilia,Vinogradov, Sergei
, p. 4882 - 4893 (2003)
The pH dependencies of the UV - vis and fluorescent spectra of new water-soluble dendritic porphyrins and tetrabenzoporphyrins were studied. Because of extended π-conjugation and nonplanar distortion, the absorption and the emission bands of tetraaryltetrabenzoporphyrins (Ar4TBP) are red-shifted and do not overlap with those of regular tetraarylporphyrins (Ar4P). When encapsulated inside dendrimers with hydrophilic outer layers, Ar4Ps and Ar4TBPs become water soluble and can serve as pH indicators, with pK's adjustable by the peripheral charges on the dendrimers. Two new dendritic porphyrins, Gen 4 polyglutamic porphyrin dendrimer H2P-Glu4OH (1) with 64 peripheral carboxylates and Gen 1 poly(ester amide) Newkome-type tetrabenzoporphyrin dendrimer H2TBP-Nw1OH (2) with 36 peripheral carboxylates, were synthesized and characterized. The pK's of the encapsulated porphyrins (pKH2P-Glu4OH = 6.2 and pKH2TBP-Nw1OH = 6.3) were found to be strongly influenced by the dendrimers, revealing significant electrostatic shielding of the cores by the peripheral charges. The titration curves obtained by differential excitation using the mixtures of the dendrimers were shown to be identical to those determined for the dendrimers individually. Due to their peripheral carboxylates and nanometric molecular size, porphyrin dendrimers cannot penetrate through phospholipid membranes. Dendrimer 1 was captured inside phospholipid liposomes, which were suspended in a solution containing dendrimer 2. No response from 1 was detected upon pH changes in the bulk solution, while the response from 2 was predictably strong. When proton channels were created in the liposome walls, both compounds responded equally to the bulk pH changes. These results suggest that porphyrin dendrimers can be used as fluorescent pH indicators for proton gradient measurements.
Proteo-dendrimers designed for complementary recognition of cytochrome c: Dendrimer architecture toward nanoscale protein complexation
Paul, Dharam,Miyake, Hiroyuki,Shinoda, Satoshi,Tsukube, Hiroshi
, p. 1328 - 1338 (2007/10/03)
"Proteo-dendrimers" in which polyanionic hepta(glutamic acids), fluorescent zinc porphyrinate cores, hydrophilic polyether surfaces, and nonpeptide hydrophobic dendrons are combined, were developed as a new series of synthetic receptors for protein recogn
The Synthesis of Chiral Dendrimeric Molecules Based on Amino Acid Repeat Units
Twyman, L. J.,Beezer, A. E.,Esfand, R.,Mathews, B. T.,Mitchell, J. C.
, p. 3408 - 3460 (2007/10/03)
The use of simple natural products for the synthesis of chiral dendrimeric molecules is discussed. The synthesis of dendrimeric poly-L-aspartic acid, poly-L-glutamic acid and poly-L-lysine is reported.