ChemInform Abstract: Rothemund and Adler‐Longo Reactions Revisited: Synthesis of Tetraphenylporphyrins Under Equilibrium Conditions.

Lindsey, Jonathan S.; Schreiman, Irwin C.; Hsu, Henry C.; Kearney, Patrick C.; Marguerettaz, Anne M.

doi:10.1002/chin.198741321

Cited by 4 publications

(4 citation statements)

References 1 publication

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“…The record player molecules 1f-j (Figure 1) were synthesized by a modular approach described by Heitmann et al [15]. The boronic ester 22 was prepared according to a mixed aldehyde procedure [16,17] For the synthesis of the azopyridines, Baeyer-Mills reactions [18] with 4-substituted 3-aminopyridines were applied [4]. The nitroso compounds 3 and 6 were synthesized by two different methods.…”

Section: Synthesismentioning

confidence: 99%

Synthesis of 4-substituted azopyridine-functionalized Ni(II) porphyrins as molecular spin switches

Ludwig¹,

Moje²,

Röhricht³

et al. 2020

Preprint

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We present the synthesis and the spin switching efficiencies of Ni(II)-porphyrins substituted with azopyridines as covalently attached photoswitchable ligands. The molecules are designed in such a way that the azopyridines coordinate to the Ni ion if the azo unit is in cis configuration. For steric reasons no intramolecular coordination is possible if the azopyridine unit adopts the trans configuration. Photoisomerization of the azo unit between cis and trans is achieved upon irradiation with 505 nm (trans→cis) and 435 nm (cis→trans). Concurrently with the isomerization and coordination/decoordination, the spin state of the Ni ion switches between singlet (low-spin) and triplet (high-spin). Previous studies have shown that the spin switching efficiency is strongly dependent on the solvent and on the substituent at the 4-position of the pyridine unit. We now introduced thiol, disulfide, thioethers, nitrile and carboxylic acid groups and investigated their spin switching efficiency.

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Section: Synthesismentioning

confidence: 99%

Synthesis of 4-substituted azopyridine-functionalized Ni(II) porphyrins as molecular spin switches

Ludwig¹,

Moje²,

Röhricht³

et al. 2020

Preprint

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“…Condensation of ortho-carbomethoxybenzaldehyde with pyrrole acresidue binding the iron, whereas the IgG2a-Fe(ToCPP)complex cording to an already described procedure [21] gave a mixture of 4 was a low-spin hexacoordinate iron(III) complex with two strong atropoisomers of meso-tetrakis-ortho-carbomethoxyphenyl-porphyrligands binding the iron atom. Both IgGI-Fe(ToCPP) complexes ins [22].…”

Section: Spin Hexacoordinate Iron(ill) Complexes With No Amino Acidmentioning

confidence: 99%

Artificial peroxidase‐like hemoproteins based on antibodies constructed from a specifically designed ortho‐carboxy substituted tetraarylporphyrin hapten and exhibiting a high affinity for iron‐porphyrins

et al. 1996

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here that antibodies elicited against a more sophisticated hapAbstract In order to get catalytic antibodies modelling peroxidases BALB/c mice have been immunized with iron(Ill)-ten, the ironllll) -meso-c~,c~,c¢,~-tetrakis-orthocarboxyphenylct,ct,ct,[~-mesotetrakis-orthocarboxyphenyl-porphyrin (Feporphyrin (Fe(ToCPP), 1) bind 1 with the highest affinity (ToCPP))-KLH conjugates. Monocional antibodies have been reported so far for iron-porphyrins. A detailed spectroscopic produced by the hybridoma technology. Three antibodies, 2 IgG1 and kinetic study of the resulting IgG-1 complexes shows that and 1 IgG2a, were found to bind both Fe(ToCPP) and the free they are either high-spin or low-spin Fe(III) complexes and base ToCPPH2 with similar binding constants. None of those only the high spin complexes exhibit a peroxidase activity 5-antibodies was found to bind tetraphenylporphyrin. Those results fold higher than 1 alone and stable until complete conversion suggest that the recognition of Fe(ToCPP) by the antibodies was of the reducing cosubstrate. mainly due to the binding of the carboxylate groups to some amino acid residues of the protein. True Kd values of 2.9 × 10 -9 M and 5.5 × 10 -9 M have been determined for the two IgGi-2. Materials and methods Fe(ToCPP) complexes. Those values are the best ones ever reported for iron-porphyrin-antibody complexes. UV-vis. studies have shown that the two IgGI-Fe(ToCPP) complexes were high- l. Synthesis ~!/' meso-o;,o;,ct,~-tetrakis-orthoearhox.vphenyl-porphvrin 2 and its iron(Ill) complexes 1spin hexacoordinate iron(Ill) complexes, with no amino acid Condensation of ortho-carbomethoxybenzaldehyde with pyrrole acresidue binding the iron, whereas the IgG2a-Fe(ToCPP)complex cording to an already described procedure [21] gave a mixture of 4 was a low-spin hexacoordinate iron(III) complex with two strong atropoisomers of meso-tetrakis-ortho-carbomethoxyphenyl-porphyrligands binding the iron atom. Both IgGI-Fe(ToCPP) complexes ins [22]. The ct,~,t~,[I atropoisomer was isolated by column chromawere found to catalyze the oxidation of 2,2'-azinobis (3-tography on silica gel (eluent: CH2C1.2/Et,_O: 80/20) and identified by ethylbenzothiazoline-6-sulfonic acid (ABTS) 5-fold more effiits UV-visible and 1H NMR spectra which were identical to those ciently than Fe(ToCPP) alone whereas the binding of lgG2a to reported in the literature [22]. 2 was then obtained after hydrolysis this iron-porphyrin had no effect on its catalytic activity, kcat of the methyl esters at 40°C in 50% H2SO4 (v/~ Preparation ~[ monoelonal antibodies1 was activated by N-hydroxy-succinimide and covalently attached to KLH (keyhole limpet hemocyanin) and to BSA (bovine serum albumin) in PBS pH 7.5. The conjugates were then purified by column 1. Introduction chromatography on Biogel P10. Hapten-carrier protein ratios determined spectrophotometrically were in the range of 15/1 to 20/1. Two In the last few years, many monoclonal antibodies elicited 5 week old, female BALB/c mice were immunized with the haptenagainst ca...

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“…hydroxyphenyl)-porphyrin (THPP) 1. 5, 10, 15, 20-Tetrakis (4hydroxyphenyl)-porphyrin (THPP) was synthesized according to the Rothemund and Adler-Longo method 28. In a brief, freshly distilled pyrrole (4.17 mL, 60 mmol) and 4-Hydroxy benzaldehyde (10 g, 60 mmol) were added to refluxing propionic acid (300 mL).…”

mentioning

confidence: 99%

Synthesis and Aggregation of a Porphyrin-Cored Hyperbranched Polyglycidol and Its Application as a Macromolecular Photosensitizer for Photodynamic Therapy

et al. 2019

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Macromolecules are potentially useful delivery systems for cancer drugs as their size allows them to utilize the enhanced permeability and retention effect (EPR), which facilitates selective delivery to (and retention within) tumors. In addition, macromolecular delivery systems can prolong circulation times as well as protecting and solubilizing toxic and hydrophobic drug moieties. Overall these properties and abilities can result in an enhanced therapeutic effect. Photodynamic therapy (PDT) combines the use of oxygen and a photosensitizer (PS), that become toxic upon light-irradiation. We proposed that a PS encapsulated within a water-soluble macromolecule could exploit the EPR effect and safely and selectively deliver the PS to a tumor. In this paper, we describe the synthesis of a porphyrin cored hyperbranched polymer that aggregated into larger micellar structures. DLS and TEM indicated that these aggregated structures had diameters of 45 nm and 20 nm for the solvated and non-solvated species respectively. The porphyrin cored HBP (PC-HBP), along with the non-encapsulated porphyrin (THPP), were screened against EJ bladder carcinoma cells in the dark and light. Both THPP and PC-HBP displayed good toxicity in the light, with LD50 concentrations of 0.5 M and 1.7 M respectively. However, in the dark, the non-incorporated porphyrin (THPP) displayed significant toxicity, generating an LD50 of 4 M. On the other hand, no dark toxicity was observed for the polymer system (PC-HBP) at concentrations of 100 M or less. As such, incorporation within the large polymer aggregate serves to eliminate dark toxicity, whilst maintaining excellent toxicity when irradiated.

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ChemInform Abstract: Rothemund and Adler‐Longo Reactions Revisited: Synthesis of Tetraphenylporphyrins Under Equilibrium Conditions.

Cited by 4 publications

References 1 publication

Synthesis of 4-substituted azopyridine-functionalized Ni(II) porphyrins as molecular spin switches

Synthesis of 4-substituted azopyridine-functionalized Ni(II) porphyrins as molecular spin switches

Artificial peroxidase‐like hemoproteins based on antibodies constructed from a specifically designed ortho‐carboxy substituted tetraarylporphyrin hapten and exhibiting a high affinity for iron‐porphyrins

Synthesis and Aggregation of a Porphyrin-Cored Hyperbranched Polyglycidol and Its Application as a Macromolecular Photosensitizer for Photodynamic Therapy

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