• Title/Summary/Keyword: Porphyrin derivatives

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Porphyrin Derivatives from a Recombinant Escherichia coli Grown on Chemically Defined Medium

  • Lee, Min Ju;Chun, Se-Jin;Kim, Hye-Jung;Kwon, An Sung;Jun, Soo Youn;Kang, Sang Hyeon;Kim, Pil
    • Journal of Microbiology and Biotechnology
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    • v.22 no.12
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    • pp.1653-1658
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    • 2012
  • We have reported previously that a recombinant Escherichia coli co-expresses aminolevulinic acid (ALA) synthase, an NADP-dependent malic enzyme, and a dicarboxylate transporter-produced heme, an iron-chelated porphyrin, in a succinate-containing complex medium. To develop an industrially plausible process, a chemically defined medium was formulated based on M9 minimal medium. Heme synthesis was enhanced by adding sodium bicarbonate, which strengthened the C4 metabolism required for the precursor metabolite, although a pH change discouraged cell growth. Increasing the medium pH buffering capacity (100mM phosphate buffer) and adding sodium bicarbonate enabled the recombinant E. coli to produce heme at rates 60% greater than those in M9 minimal medium. Adding growth factors (1 mg/l thiamin, 0.01 mg/l biotin, 5 mg/l nicotinic acid, 1 mg/l pantothenic acid, and 1.4 mg/l cobalamin) also induced positive heme production effects at levels twice of heme production in M9-based medium. Porphyrin derivatives and heme were found in the chemically defined medium, and their presence was confirmed by liquid chromatography/mass spectroscopy (LC/MS). The formulated medium allowed for the production of $0.6{\mu}M$ heme, $29{\mu}M$ ALA, $0.07{\mu}M$ coproporphyrin I, $0.21{\mu}M$ coproporphyrin III, and $0.23{\mu}M$ uroporphyrin in a 3 L pH-controlled culture.

Porphyrin-Cored Arylether Dendrimers with Vinyl Groups in the Periphery

  • Lim, So-Yeon;Choi, Dae-Ock;Shin, Eun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.29 no.7
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    • pp.1353-1358
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    • 2008
  • Benzyl arylether dendrimers with zinc porphyrin core and terminal vinyl groups have been synthesized and their photophysical properties and the influence of dendritic environments were investigated. Free base porphyrin-cored benzyl arylether dendrimers 1a-1c and 3a-3c, and their zinc derivatives 2a-2c and 4a-4c have been prepared. Absorption spectra are similar for all porphyrin-cored benzyl arylether dendrimers, except that absorption intensity at 280 nm increases in the higher generation of dendrimer. Fluorescence spectra are similar with two bands for all free base porphyrin dendrimers 1a-1c and 3a-3c, although fluorescence intensity ratio of shorter wavelength emission band to longer wavelength band varies with the generation of dendrimer. Emission efficiencies of 1a-1c and 3a-3c are lower than that of TTP. Emission efficiencies of 2a-2c and 4a-4c are higher than that of ZnTTP. Absorption and emission properties of 1a-1c, 2a-2c, 3a-3c, and 4a-4c were affected negligibly with dendritic environments.

Cycloolefins Oxidation Reaction Catalyzed by Ga(III)-, In(III)- and TI(III)-Porphyrin Derivatives (Ga(III)-, In(III)-, TI(III)-porphyrin 유도체를 촉매제로 한 고리성 올레핀의 산화반응)

  • Na, Hun-Gil
    • Journal of the Korean Applied Science and Technology
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    • v.21 no.1
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    • pp.76-88
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    • 2004
  • The catalytic oxidation reaction of several cycloolefins in $CH_2Cl_2$ have been investigated using non-redox metalloporphyrin(M = Ga(III), In(III) and TI(III) complexes as a catalyst and sodium hypochlorite as a terminal oxidant. Porphyrins were $(p-CH_3O)$TPP, $(p-CH_3)$TPP, TPP, (p-F)TPP, (p-Cl)TPP and $(F_{20})$TPP (TPP=5,10,15,20-tetraphenyl-21H,23H-porphyrin) and olefins were cyclopentene, cyclohexene, cycloheptene and cyclooctene, The substrate conversion yield(%) was investigated according to the radius effect of non-redox metal ion, substituent effect and hindrance effect of metalloporphyrin. The conversion yield of cycloolefin was in the following order : $C_5$ < $C_6$ < $C_7$ = $C_8$.

The Cytotoxic Action of New Ag-Porphyrin as a Potential Chemotherapeutic Agent

  • Nelli, Babayan;Artak, Tovmasyan;Ani, Gevorkyan;Gennadi, Gasparyan;Rouben, Aroutiounian
    • Korean Journal of Environmental Biology
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    • v.26 no.2
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    • pp.115-120
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    • 2008
  • Earlier we have described new water-soluble Ag- and Zn-derivatives of tetrachloride meso-tetra (4-N-oxiethylpyridyl) porphyrin (TOEtPyP) as potential anticancer drugs. In this work the effect of one of these metal porphyrins, TOEtPyP Ag, on the cell population kinetics was studied in vitro using morphological and biochemical techniques. The results suggested that TOEtPyP Ag action consisted in the simultaneous suppression of the cell growth and activation of the cell death. About 40% of the cells were shown to die via apoptotic pathway. So, the porphyrin studied may be attributed to inducers of both necrotic and apoptotic processes. The results obtained support our previous assertion that TOEtPyP Ag may be considered as a potential chemotherapeutic agent.

The Syntheses of Phthalocyanine Hybrid Derivatives and Their Properties (프탈로시아닌계 하이브리드 유도체들의 합성 및 이의 특성에 관한 연구)

  • Kim, Seong Jin;An, Ba Ryong;Lee, Gun-Dae;Park, Seong Soo
    • Applied Chemistry for Engineering
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    • v.24 no.3
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    • pp.266-273
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    • 2013
  • Phthalocyanine (Pc), porphyrin, subphthalocyanine, and perylene compounds can be applicable to the fields of optical storage media, organic solar cell, LCD, PDP, semiconductor, and counterfeit money detection etc. In this study, phthalocyanine hybrid derivatives were synthesized by cross-linking perylene, subphthalocyanine, or porphyrin to the main frame of Pc. Absorbtion band of two different wavelengths appeared simultaneously in the phthalocyanine hybrid derivatives. Compared to phthalocyanine, the solubility was enhanced and the degree of Q-band shift was changed according to the kind of substitute compounds. The chemical and optical properties of samples were analyzed using FT-IR, $^1H-NMR$, and UV-Vis spectroscopic techniques.

Syntheses of Metalloporphyrins and Polymer-bonded Metalloporphyrin and Their Catalytic Effects on Benzoquinone Photoreduction (Metalloporphyrins 와 Polymer-bonded Metalloporphyrin 의 합성 및 Benzoquinone 광환원반응의 촉매효과)

  • Kyu-Ja Whang;Hee-Kyung Lee;Yong-Keun Lee
    • Journal of the Korean Chemical Society
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    • v.35 no.5
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    • pp.569-574
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    • 1991
  • Six free base porphyrins were synthesized by reacting pyrrole with benzaldehyde or its derivatives and then reacted with metal chlorides to prepare corresponding metal complexes. In addition, polymer-bonded porphyrins were synthesized by treating chloromethylated styrene-divinyl benzene (1%) copolymer beads with meso-tetra (p-aminophenyl)porphyrin (TNPP) solution and then treated with cupric chloride to obtain Cu(Res-NH-TPP-$NH_2$). The porphyrin compounds were characterized by visible, inffrared and electron spin resonance spectral analyses. The metal contents of metalloporphyrins were determined by atomic adsorption spectrophotometry. The synthesized porphyrin compounds were subsequently examined for their catalytic strength and found the activity to increase in the following order: free base porphyrins; metalloporphyrins; polymer-bonded metalloporphyrin. Among metalloporphyrins, Cu-TNPP showed the greatest catalytic power.

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NMR Study on Binding Interactions of Cationic Porphyrin Derivatives with double helical $d(CGCGAATTCGCG)_2$

  • Huh, Sungho;Hong, Seokjoo
    • Journal of the Korean Magnetic Resonance Society
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    • v.5 no.2
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    • pp.118-129
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    • 2001
  • Binding interactions of cationic porphyrins, T4MPyP and TMAP with DNA oligomer d(CGCGAATTCGCG), were studied with NMR spectroscopy, W and CD spectroscopic method. Two porphyrins showed significant differences in NMR, UV and CD data upon binding to DNA. T4MPyP was considered to position more closely to DNA bases through partial intercalation as well as ionic intercalation between the positive charges of porphyrin and phosphate group of DNA at 5’-GC-3’steps. Contrast to this, TMAP was thought to bind to phosphate of DNA more or less outside of the groove.

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Facile Syntheses of Modified Tripyrranes and Their Application to the Syntheses fo Regioisomerically Pure Porphyrin Derivatives

  • 허필연;이창희
    • Bulletin of the Korean Chemical Society
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    • v.17 no.6
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    • pp.515-520
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    • 1996
  • Simple conditions were discovered to afford tripyrranes by reaction of 2,5-bis(α-hydroxymethyl)furan or 2,5-bis(α-hydroxy-α-phenylmethyl)thiophene with excess pyrrole in the presence of acid catalyst. Stepwise synthesis of porphyrins with core-ligand modification and synthesis of meso-tetraarylporphyrins bearing two different substituents in cis orientation have developed as building blocks for the various porphyrin-based model systems. Consequently, 21-thia-23-oxa-10,15-diphenylporphyrin (28), 21-oxa-10,15-diphenylporphyrin (29) and 21-oxa-23-carba-12-aza-10,15-diphenylporphyrin (30) were synthesized by acid-catalyzed [3+1] condensation between tripyrranes and 2,5-bis(α-hydroxymethyl)pyrrole or 2,5-bis(α-hydroxy-α-phenylmethyl)thiophene. The synthetic pathway described here gave regioisomerically pure porphyrins and thus overcame the synthetic problems associated with separation and purification of regioisomeric mixture.