The spectroscopic characterisation of proline derivatives of tolyl-porphyrins and their iron and cobalt complexes

Skrzypek, D.; Madejska, I.; Habdas, Jan; Dudkowiak, Alina

doi:10.1016/j.molstruc.2007.06.016

Cited by 9 publications

(18 citation statements)

References 41 publications

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“…We were able to separate the two A 2 B 2 -type isomers 29 and 30 through column chromatography using gradient elution. 1 H NMR, 13 C NMR, and MALDI-TOF analyses confirmed the identify of all compounds. We also attempted to expand the porphyrin library by reacting m-THPP with different heterocyclic reagents such as coumarin-3carboxylic acid (22) and 3-(bromoacetyl)coumarin (23) under similar conditions but without success.…”

Section: Synthesis Of Porphyrin Heterocycle Conjugatesmentioning

confidence: 58%

“…The target lipoporphyrin amino acid derivatives 11─17 were purified via column chromatography and preparative TLC. All the compounds were characterized by 1 H NMR, 13 C NMR, MALDI-TOF and UV-vis spectroscopy (see S.I. ).…”

Section: Synthesis Of Porphyrin Amino Acid Conjugatesmentioning

confidence: 99%

“…The organic layer was separated, dried over anhydrous MgSO 4 , filtered, and the solvent removed under reduced pressure. The residue was purified with column chromatography using a solvent system of CH 2 Cl 2 /petroleum ether 60-80 °C/MeOH (3:1:0.5 to 3: 13 C NMR (100 MHz, CDCl 3 ): δ c = 168.9, 153. 6, 150.1, 143.5, 127.7, 121.8, 119.5, 114.4, 65.7, 61.6, 29.9, 13.…”

Section: Synthesis Of Carboxylic Monoacid Porphyrin Derivativesmentioning

confidence: 99%

“…Tyrosine-porphyrins 9 are potentially selective for tumor cells by targeting the estrogen receptor alpha (ERα) that is over-expressed in breast cancer cells 10 and, unlike estradiol itself, does not trigger tumor progression. 11 Proline-linked porphyrins have been used as chiral molecular materials and catalysts, 12 possess a high triplet state quantum yield, 13 nonporphyrin-conjugates were reported as non-steroidal anti-inflammatory drugs, 14 while the natural amino acid glycine can suppress cell proliferation and blocks the mitogenic cytokines responsible for hepatocyte proliferation. 15 Different synthetic approaches have been utilized to covalently link porphyrins with amino acids.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of amphiphilic meso-tetrasubstituted porphyrin-L-amino acid and -heterocyclic conjugates based on m-THPP

Sweed

Senge

Atta

et al. 2018

J. Porphyrins Phthalocyanines

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Two series of amphiphilic meso-tetrasubstituted porphyrin conjugates based on 5,10,15,20-tetrakis(3-hydroxyphenyl)porphyrin ([Formula: see text]-THPP) covalently linked to L-amino acids and heterocycles were synthesized efficiently in the context of a program targeting new photosensitizers for PDT. 5,10,15-Tris(3-hydroxyphenyl)-20-(3-oxyacetic acid)phenyl]porphyrin and the respective trihexyl ether derivatives were conjugated with polar and non-polar natural L-amino acids such as glycine, L-proline, and L-tyrosine via an amide bond linker using [Formula: see text]-tetramethyl-[Formula: see text]-(1H-benzotriazol-1-yl)uroniumhexafluorophosphate in diisopropylethylamine (HBTU/DIPEA). [Formula: see text]-THPP was also conjugated with heterocyclic systems such as indole 3-acetic acid, 4-methylthiazole-5-carboxylic acid, and thiophene-2-carboxylic acid via ester linker using [Formula: see text]-(3-dimethylaminopropyl)-[Formula: see text]-ethylcarbodiimide hydrochloride in [Formula: see text]-hydroxysuccinamide or 1-hydroxybenzotriazole (EDCI, NHS or HOBt). The members of the two series were obtained in good yields and characterized by UV-vis, HRMS MALDI-TOF, 1H NMR and 13C NMR spectroscopy.

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Section: Synthesis Of Porphyrin Heterocycle Conjugatesmentioning

confidence: 58%

Section: Synthesis Of Porphyrin Amino Acid Conjugatesmentioning

confidence: 99%

Section: Synthesis Of Carboxylic Monoacid Porphyrin Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of amphiphilic meso-tetrasubstituted porphyrin-L-amino acid and -heterocyclic conjugates based on m-THPP

Sweed

Senge

Atta

et al. 2018

J. Porphyrins Phthalocyanines

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“…The metalloporphyrin, 5,10,15,20-tetrakis(3,4-dimethoxy-phenyl)-porphyrin Fe(III) chloride, compound 1 , represented in Figure 2a, was obtained by adapting the procedure of metallation of the porphyrin base described in literature [54,55] using large excess of iron (III) chloride [40]. …”

Section: Methodsmentioning

confidence: 99%

Trace Oxygen Sensitive Material Based on Two Porphyrin Derivatives in a Heterodimeric Complex

et al. 2017

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The successful preparation of a novel dimer complex formed between 5,10,15,20-tetrakis(3,4-dimethoxyphenyl)-porphyrin Fe(III) chloride and (5,10,15,20-tetraphenylporphinato) dichlorophosphorus(V) chloride using the well-known reactivity of the P–X bond is reported. The obtained complex was characterized by UV-vis, Fourier transform infrared spectroscopy (FT-IR), fluorescence, 1H-NMR, 13C-NMR, and 31P-NMR spectroscopic techniques and also by additional Heteronuclear Single Quantum Coherence (HSQC) and Heteronuclear Multiple Bond Correlation (HMBC) experiments in order to correctly assign the NMR signals. Scanning electron microscopy (SEM) and EDX quantifications completed the characterizations. This novel porphyrin dimer complex demonstrated fluorescence sensing of H2O2 in water for low oxygen concentrations in the range of 40–90 µM proving medical relevance for early diagnosis of diseases such as Alzheimer’s, Parkinson’s, Huntington’s, and even cancer because higher concentrations of H2O2 than 50 μM are consideredcytotoxic for life. Due to its optical properties, this novel metalloporphyrin–porphyrin based complex is expected to show PDT and bactericidal activity under visible-light irradiation.

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Fluorescence Spectroscopy in Optoelectronics, Photomedicine, and Investigation of Biomolecular Systems

Wróbel

Dudkowiak

Goc

2009

Reviews in Fluorescence 2008

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The spectroscopic characterisation of proline derivatives of tolyl-porphyrins and their iron and cobalt complexes

Cited by 9 publications

References 41 publications

Synthesis of amphiphilic meso-tetrasubstituted porphyrin-L-amino acid and -heterocyclic conjugates based on m-THPP

Synthesis of amphiphilic meso-tetrasubstituted porphyrin-L-amino acid and -heterocyclic conjugates based on m-THPP

Trace Oxygen Sensitive Material Based on Two Porphyrin Derivatives in a Heterodimeric Complex

Fluorescence Spectroscopy in Optoelectronics, Photomedicine, and Investigation of Biomolecular Systems

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