Synthesis and Characterization of Uncharged Water-Soluble Star Polymers Containing a Porphyrin Core

Mineo, Placido; Scamporrino, Emilio; Vitalini, Daniele

doi:10.1002/1521-3927(20020801)23:12<681::aid-marc681>3.0.co;2-i

Cited by 56 publications

(55 citation statements)

References 9 publications

(13 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5,10,15,20-tetrakis{p-[ω-methoxy poly(oxyethylene)]phenyl}-porphyrin (H 2 -P), having an average molecular mass of 3600 Da with a narrow polydispersity (M w /M n ) 1.01), was prepared by reaction between tetrakis(p-hydroxyphenyl)porphyrin (obtained from pyrrole and p-acetoxybenzaldheyde in boiling propionic acid 30 ) and chlorinated poly(ethyleneglycol)methyl ether [PEGMEC, formed by reaction of poly(ethyleneglycol)-methyl ether with thionyl chloride in tetrahydrofuran (THF)] having an average molecular mass of 750 Da. 24 In a 10 mL flask, 1.07 g of PEGMEC-750 (about 1.43 mmol) was dissolved in 6 mL of a H 2 O/THF (1:1) solution; after the addition of 0.12 g of tetrakis(p-hydroxyphenyl)porphyrin (0.177 mmol, half of the required stoichiometric quantity) dissolved in 1.42 mL of a 0.5 M NaOH aqueous solution, the mixture was refluxed for 24 h. Then, 1.42 mL of 0.5 M NaOH and 1.5 mL of THF were further added and the solution was continuously refluxed. After 24 h, the reaction was stopped by the addition of CH 3 COOH, dried under vacuum and the residue, dissolved in CHCl 3 , and fractionated by column chromatography using silica gel as the stationary phase and a solution of CHCl 3 / C 2 H 5 OH/N(C 2 H 5 ) 3 (96.5:2.0:1.5) as the eluant.…”

Section: Methodsmentioning

confidence: 99%

“…[20][21][22] However, although the presence of the free charges does not seem to modify the ligand properties of the porphyrin, in some cases (as an example, the crossing through cellular membranes), the possibility of undesirable effects with respect to the uncharged species cannot be excluded. 23 Consequently, our research [24][25][26][27] has been directed to the design, synthesis, and characterization of new porphyrin derivatives (and their metal complexes) in which the presence of uncharged hydrophilic and biocompatible poly(ethylene glycol) units, bound to the meso porphyrin positions, makes these molecules hydrosoluble.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Uncharged Water-Soluble Co(II)−Porphyrin: A Receptor for Aromatic α-Amino Acids

et al. 2005

Self Cite

View full text Add to dashboard Cite

Changes in the UV-vis spectra and induced circular dichroism (ICD) signals observed, in correspondence with the porphyrin Soret region, for aqueous solutions of achiral 5,10,15,20-tetrakis{p-[omega-methoxy poly(oxy-ethylene)]phenyl}porphyrin cobalt (II) (Co-P) and aromatic alpha-L-amino acids (Trp and Phe) give direct evidence for the coordination between the Co-P and amino acids. Considering that Co-P, besides the Co atom (one-fixation-point system), does not contain in the molecule active ligand groups and that no ICD signals have been observed in the case of Co-P/Ala, it has been concluded that hydrophobic interactions or stacking interactions between the aromatic rings of the porphyrin and those of Trp or Phe, acting as further amino acid (AA) fixation points, can strongly reduce the mobility of the chiral guest, thus permitting the generation of ICD signals. The effects of changes of both pH (in the range 2-9) and amino acid structure on the ICD phenomenon have also been investigated. In particular, the following have been observed: (i) strong ICD signals for all of the Co-P/N-acetyl amino acid aqueous solutions at pH 7, (ii) an unexpected ICD band with a bisignate form for the Co-P/Ala solution at pH 9 after long aging, and (iii) an opposite ICD signal when alpha-D-Phe and alpha-D-Trp enantiomers have been used. The data reported in this paper show how the binding mechanism between receptor and AAs changes by modulating properly the pH or the molecular structures and indicate that in these aqueous solutions the coordination Co-N is not the fundamental mechanism giving rise to the formation of the complexes and that the binding can be driven by hydrophobic interactions. These occurrences, through the analysis of the spectroscopic response (and, in particular, the form of the ICD band), can allow the recognition of AAs.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Uncharged Water-Soluble Co(II)−Porphyrin: A Receptor for Aromatic α-Amino Acids

et al. 2005

Self Cite

View full text Add to dashboard Cite

show abstract

“…The meso-aryl substituents presence in the porphyrins allows to carry out the immobilization on polymeric matrixes, [2,3] the linkage to the surface of gold nanoparticles, [4] the receiving of hybrids with DNA oligonucleotides, [5] etc. For these purposes the symmetric tetrakis(4-hydroxyphenyl)-porphyrin is widely used.…”

mentioning

confidence: 99%

Improved Method of 5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrins Synthesis

Rumyantseva¹,

Gorshkova²,

Mironov³

2013

MHC

View full text Add to dashboard Cite

show abstract

“…Under similar conditions, single PEG chains or PEG-dendrimers (Scheme 41) [134] can also be introduced into asymmetric meso-hydroxyphenylporphyrins [135,136]. Vitalini and coworkers prepared PEGylated derivatives of 76 by alkylation of the phenolic oxygens with a chlorinated PEG [137]. The PEG-functionalized porphyrins could be purified by adding a solution of the compound in CH2Cl2 to a cold solution of Et2O to induce precipitation (for larger PEGs) [129,135]; porphyrins bearing smaller PEG-chains could also be purified by column chromatography (CH2Cl2-acetone-MeOH or CH2Cl2/EtOH mixtures) [129,134].…”

Section: Pegylation Of Meso-aryl Porphyrinsmentioning

confidence: 99%

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

Luciano

Brückner

2017

Preprint

View full text Add to dashboard Cite

Abstract:The increasing popularity of porphyrins and hydroporphyrins for application in a variety of biomedical (photodynamic therapy, fluorescence tagging and imaging, photoacoustic imaging) and technical (chemosensing, catalysis, light harvesting) applications is also associated with the growing number of methodologies that enable their solubilization in aqueous media. Natively, the vast majority of synthetic porphyrinic compounds are not water-soluble. Moreover, any water-solubility imposes several restrictions on the synthetic chemist on when to install solubilizing groups in the synthetic sequence, and how to isolate and purify these compounds. This review summarizes the chemical modifications to render synthetic porphyrins water-soluble, with a focus on the work since 2000. Where available, practical data such as solubility, indicators for the degree of aggregation, and special notes for the practicioner are listed. We hope that this review will guide synthetic chemists through the many strategies known to make porphyrins and hydroporphyrins water soluble.

show abstract

Synthesis and Characterization of Uncharged Water-Soluble Star Polymers Containing a Porphyrin Core

Cited by 56 publications

References 9 publications

Uncharged Water-Soluble Co(II)−Porphyrin: A Receptor for Aromatic α-Amino Acids

Uncharged Water-Soluble Co(II)−Porphyrin: A Receptor for Aromatic α-Amino Acids

Improved Method of 5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrins Synthesis

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

Contact Info

Product

Resources

About