Synthesis and characterization of novel flavonoid-substituted phthalocyanines using (±)naringenin

Yıldız, Salih; Küçükislamoğlu, Mustafa; Tuna, Murat

doi:10.1016/j.jorganchem.2009.09.012

Cited by 14 publications

(4 citation statements)

References 35 publications

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“…The separation of AABB and ABAB structures is inherently problematic, however, since these isomers have identical molecular weights and usually have similar molecular properties. There are some examples of the complete resolution and characterization of the four products for both peripheral substitution 87,192,195,[197][198][199][200] and fused ring modification, 93,181,182,184,[187][188][189][190][191]201 but most recent low symmetry Pc studies have focused on the relatively easily separated AAAB products formed through partial peripheral substitution of Pz, 100,[202][203][204][205][206][207][208][209][210][211][212] Nc, 213 unsubstituted Pc, [213][214][215][216][217][218][219][220][221][222][223][224][225][226][227][228]…”

Section: Mixed and Cross-condensationsmentioning

confidence: 99%

“…The separation of AABB and ABAB structures is inherently problematic, however, since these isomers have identical molecular weights and usually have similar molecular properties. There are some examples of the complete resolution and characterization of the four products for both peripheral substitution ,,,− and fused ring modification, ,,,,− , but most recent low symmetry Pc studies have focused on the relatively easily separated AAAB products formed through partial peripheral substitution of Pz, ,− Nc, unsubstituted Pc, − α-substituted Pc, ,− β-substituted tetrapyrazoporphyrazine, β-substituted P c, − ,− ,− ,,,,− ,− …”

Section: Peripheral Substitution and Fused Ring Modificationmentioning

confidence: 99%

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Low Symmetry Phthalocyanines and Their Analogues

2010

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Section: Mixed and Cross-condensationsmentioning

confidence: 99%

“…The separation of AABB and ABAB structures is inherently problematic, however, since these isomers have identical molecular weights and usually have similar molecular properties. There are some examples of the complete resolution and characterization of the four products for both peripheral substitution ,,,− and fused ring modification, ,,,,− , but most recent low symmetry Pc studies have focused on the relatively easily separated AAAB products formed through partial peripheral substitution of Pz, ,− Nc, unsubstituted Pc, − α-substituted Pc, ,− β-substituted tetrapyrazoporphyrazine, β-substituted P c, − ,− ,− ,,,,− ,− …”

Section: Peripheral Substitution and Fused Ring Modificationmentioning

confidence: 99%

Low Symmetry Phthalocyanines and Their Analogues

2010

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“…It encompasses natural occurring and synthetic phenolic compounds having various potential health benefits. Altogether 300 compounds were collected from over 30 publications [7,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,85,86,87,88,89,90,91,92,93], see Table S2 (Supplementary Material). Compounds were arranged according to their structural similarity into 12 groups: flavones/isoflavones, flavonols, flavanones/ isoflavanones, flavanonols, flavanols, xanthones, chromones, coumarins, chalcones, phenolic acid derivatives, simple phenols and other compounds.…”

Section: Methodsmentioning

confidence: 99%

An In Silico Approach for Assessment of the Membrane Transporter Activities of Phenols: A Case Study Based on Computational Models of Transport Activity for the Transporter Bilitranslocase

Venko

Novič

2019

Molecules

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Phenols are the most abundant naturally accessible antioxidants present in a human normal diet. Since numerous beneficial applications of phenols as preventive agents in various diseases were revealed, the evaluation of phenols bioavailability is of high interest of researchers, consumers and drug manufacturers. The hydrophilic nature of phenols makes a cell membrane penetration difficult, which imply an alternative way of uptake via membrane transporters. However, the structural and functional data of membrane transporters are limited, thus the in silico modelling is really challenging and urgent tool in elucidation of transporter ligands. Focus of this research was a particular transporter bilitranslocase (BTL). BTL has a broad tissue expression (vascular endothelium, absorptive and excretory epithelia) and can transport wide variety of poly-aromatic compounds. With available BTL data (pKi [mmol/L] for 120 organic compounds) a robust and reliable QSAR models for BTL transport activity were developed and extrapolated on 300 phenolic compounds. For all compounds the transporter profiles were assessed and results show that dietary phenols and some drug candidates are likely to interact with BTL. Moreover, synopsis of predictions from BTL models and hits/predictions of 20 transporters from Metrabase and Chembench platforms were revealed. With such joint transporter analyses a new insights for elucidation of BTL functional role were acquired. Regarding limitation of models for virtual profiling of transporter interactions the computational approach reported in this study could be applied for further development of reliable in silico models for any transporter, if in vitro experimental data are available.

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“…18 Alternatively, the properties of the flavonoids can be altered upon conjugation with other molecules. For example, conjugates with phthalocyanine, 19 fullerene, 20 and paclitaxel 21 have been reported, which lead to distinct spectroscopic, antioxidant, and cytotoxic properties, respectively.…”

Section: ■ Introductionmentioning

confidence: 99%

Peptoid Helix Displaying Flavone and Porphyrin: Synthesis and Intramolecular Energy Transfer

Yang

et al. 2019

J. Org. Chem.

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Natural light-harvesting complexes (LHCs) absorb a broad spectrum of sunlight using a collection of photosynthetic pigments whose spatial arrangement is controlled by a protein matrix and exhibit efficient energy transfer. We constructed a novel light-harvesting protein mimic, which absorbs light in the UV to visible region (280–700 nm) by displaying flavone and porphyrin on a peptoid helix. First, an efficient synthesis of 4′-derivatized 7-methoxyflavone (7-MF, 3 and 4) was developed. The flavone–porphyrin–peptoid conjugate (FPPC) was then prepared via Miyaura borylation on a resin-bound peptoid followed by Suzuki coupling between the peptoid and pigment. Circular dichroism spectroscopy indicated that the FPPC underwent helix-to-loop conversion of the peptoid scaffold upon changing the solvent conditions. A distinct intramolecular energy transfer was observed from 7-MF to porphyrin with greater efficiency in the helix than that in the loop conformation of the peptoid, whereas no clear evidence of energy transfer was obtained for unstructured FPPC. We thus demonstrate the value of the helical peptoid, which provided a controlled orientation for 7-MF and porphyrin and modulated the energy transfer efficiency via conformational switching. Our work provides a way to construct a sophisticated LHC mimic with enhanced coverage of the solar spectrum and controllable energy transfer efficiency.

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Synthesis and characterization of novel flavonoid-substituted phthalocyanines using (±)naringenin

Cited by 14 publications

References 35 publications

Low Symmetry Phthalocyanines and Their Analogues

Low Symmetry Phthalocyanines and Their Analogues

An In Silico Approach for Assessment of the Membrane Transporter Activities of Phenols: A Case Study Based on Computational Models of Transport Activity for the Transporter Bilitranslocase

Peptoid Helix Displaying Flavone and Porphyrin: Synthesis and Intramolecular Energy Transfer

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