Complex formation of Cu(II), Ni(II), Zn(II), Co(II), and Cd(II) acetates with 3,3′,4,4′,5,5′-hexamethyldipyrrolylmethene

Гусева, Г. Б.; Антина, Е. В.; V’yugin, A. I.; Loginova, A. E.

doi:10.1134/s1070328408080071

Cited by 9 publications

(6 citation statements)

References 5 publications

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“…It should be mentioned that the configuration of the double bond in 75 could not be unequivocally determined. The same group also isolated another tri-methylated bis-pyrrole 76 ( Figure 10 ) [ 91 ], which has only been known as a synthetic product before [ 92 , 93 ]. Both compounds 75 and 76 displayed negligible antibacterial activity, whereas the APK 75 showed weak to moderate cytotoxicity against four human cancer cell lines (SF-268, MCF-7, NCI-H460, and HePG-2, with IC 50 values of 56.46 µM ± 0.87 µM, 35.73 µM ± 1.45 µM, 44.62 µM ± 2.49 µM, and 39.22 µM ± 3.00 µM, respectively, Figure 10 ).…”

Section: Non-halogenated Marine Pyrrole Alkaloidsmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

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Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats but can also frequently be found as natural products in the marine environment. This review highlights the important class of marine pyrrole alkaloids, well-known for their diverse biological activities. A broad overview of the marine pyrrole alkaloids with a focus on their isolation, biological activities, chemical synthesis, and derivatization covering the decade from 2010 to 2020 is provided. With relevant structural subclasses categorized, this review shall provide a clear and timely synopsis of this area.

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Section: Non-halogenated Marine Pyrrole Alkaloidsmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

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“…Upon a large scale fermentation of S. albus J1074/pCSG5033 (containing the intact fls gene cluster (Yang et al, 2015 ; Supplementary Figure 1 ) in a 40-L fermentator and the subsequent isolation with various chromatographic methods, FST C ( 1 ) was obtained as the major product, along with several new dimeric FSTs derived from non-enzymatic reactions (Huang et al, 2018 ). In addition, two new decaketide derivatives SEK43F ( 2 ) and fluoquinone ( 3 ), two known non-aketide-derived anthraquinones 2-acetylchrysophanol ( 4 ) (Abdelfattah, 2009 ) and 4-acetylchrysophanol ( 5 ) (Shaaban et al, 2007 ), and a previously synthesized compound 3,3′,4,4′,5,5′-hexamethyl-2,2′-dipyrrolylmethene ( 6 ) (Figure 1 ), were also isolated (Guseva et al, 2008 ; Lund and Thompson, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

“…It was thus deduced that fluoquinone ( 3 ) should also contain a pair of racemic ( S )-(+)- and ( R )-(-)-enantiomers (almost in a ration of 1:1) due to its negligible optical rotation. Analysis of the 1 H NMR and 13 C NMR data of compounds 4 – 6 revealed that they were identical to 2-acetylchrysophanol ( 4 ) (Supplementary Figure 4 , Supplementary Table 1 ) (Abdelfattah, 2009 ), 4-acetylchrysophanol ( 5 ) (Supplementary Figure 5 , Supplementary Table 1 ) (Shaaban et al, 2007 ), and 3,3′,4,4′,5,5′-hexamethyl-2,2′-dipyrrolylmethene ( 6 ) (Supplementary Figure 6 , Supplementary Table 1 ) (Guseva et al, 2008 ; Lund and Thompson, 2014 ).…”

Section: Resultsmentioning

confidence: 99%

Marine Bacterial Aromatic Polyketides From Host-Dependent Heterologous Expression and Fungal Mode of Cyclization

et al. 2018

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The structure diversity of type II polyketide synthases-derived bacterial aromatic polyketides is often enhanced by enzyme controlled or spontaneous cyclizations. Here we report the discovery of bacterial aromatic polyketides generated from 5 different cyclization modes and pathway crosstalk between the host and the heterologous fluostatin biosynthetic gene cluster derived from a marine bacterium. The discovery of new compound SEK43F (2) represents an unusual carbon skeleton resulting from a pathway crosstalk, in which a pyrrole-like moiety derived from the host Streptomyces albus J1074 is fused to an aromatic polyketide SEK43 generated from the heterologous fluostatin type II PKSs. The occurrence of a new congener, fluoquinone (3), highlights a bacterial aromatic polyketide that is exceptionally derived from a characteristic fungal F-mode first-ring cyclization. This study expands our knowledge on the power of bacterial type II PKSs in diversifying aromatic polyketides.

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“…This may be due to the higher binding ability of Cu(II) with PEI. It has been shown that Cu(II) has higher thermodynamic stability in terms of higher complexation constant, enthalpy of complex formation and lower entropy compared to Ni(II) and Zn(II) ions 31–33. Further, it is known that Zn(II) complexes have low ligand‐field stability due to the complete filling of d‐orbitals.…”

Section: Resultsmentioning

confidence: 99%

Transport of copper, nickel and zinc ions across ultrafiltration membrane based on modified polysulfone and cellulose acetate

Arthanareeswaran

Thanikaivelan

2010

Asia-Pacific J Chem Eng

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In this work, an attempt has been made to separate divalent copper, nickel and zinc ions from aqueous solutions by modified polymeric membranes. Membranes from polysulfone (PSf) and cellulose acetate (CA) were prepared in the absence and presence of the hydrophilic polymer, sulfonated poly ether ether ketone (SPEEK) and additive, polyethyleneglycol (PEG 600), in various compositions. Studies were carried out to find the rejection and permeate flux of Cu(II), Ni(II) and Zn(II) ions using polyethyleneimine (PEI) as the chelating ligand. On increasing concentrations of SPEEK and PEG in PSf and CA casting solution, the rejection of metal ions is decreasing while the permeate flux has an increasing trend. These effects are due to the increased pore formation in the PSf and CA membranes because of the hydrophilic polymer and additive. In general, it was found that CA/SPEEK/PEG blend membranes displayed higher permeate flux and lower rejection compared to PSf/SPEEK/PEG blend membranes at all additive concentrations. It has also been demonstrated that the extent of removal of metal ions depend on the affinity of metal ions to PEI to form macromolecular complexes and the thermodynamic stability of the formed complexes. 

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Complex formation of Cu(II), Ni(II), Zn(II), Co(II), and Cd(II) acetates with 3,3′,4,4′,5,5′-hexamethyldipyrrolylmethene

Cited by 9 publications

References 5 publications

Marine Pyrrole Alkaloids

Marine Pyrrole Alkaloids

Marine Bacterial Aromatic Polyketides From Host-Dependent Heterologous Expression and Fungal Mode of Cyclization

Transport of copper, nickel and zinc ions across ultrafiltration membrane based on modified polysulfone and cellulose acetate

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