Synthesis and Characterization of Regiorandom and Regioregular Poly(3-octylfuran)

Jk, Politis; Jc, Nemes; Curtis,

doi:10.1021/ja003588i

Cited by 116 publications

(141 citation statements)

References 87 publications

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“…To a solution of 22.4 ml of a 0.4 M solution of phenylmagnesium bromide (9 mmol, 1.5 eq) in anhydrous THF was added 502 mg (3 mmol) of isocantharidin (21,22) to afford the intermediate ␥-lactone, (3aR,4R,7S,7aR)-rel-octahydro-3,3-diphenyl-4,7-epoxyisobenzofuran-1-one. The crude ␥-lactone was reduced using 311 mg (8 …”

Section: R2s3s4s)-rel-3-(hydroxymethyl)-7-oxabicyclo[221]heptanmentioning

confidence: 99%

“…The pseudocantharidins A, B, C, and D (Fig. 1A) were synthesized either from commercially available cantharidin or the previously reported isocantharidin (21,22) according to the procedures summarized in Fig. 1B.…”

Section: Cell Viabilitymentioning

confidence: 99%

“…Pseudocantharidin C was synthesized using a three-step procedure: (i) fusion of isocantharidin with urea to afford (3aR,4S,7R,7aS)-rel-octahydro-4,7-epoxy-1H-isoindole-1,3-dione (20); (ii) reduction of this intermediate imide with lithium aluminum hydride to furnish the intermediate pyrrolidine; and (iii) acylation of the pyrrolidine with 4-bromobenzoyl chloride. Pseudocantharidin B was synthesized by the addition of phenylmagnesium bromide to isocantharidin (21,22) and the subsequent reduction of the intermediate ␥-lactone with lithium aluminum hydride. Complete characterization of these products through a combination of infrared and NMR spectroscopy, mass spectrometry, and combustion analyses unequivocally established the assigned structures and purity of these compounds.…”

Section: Cell Viabilitymentioning

confidence: 99%

“…Pseudocantharidins Change Alternative Splicing of the SMN2 pre-mRNA and Exhibit Different Cellular Toxicity-Using cantharidin or isocantharidin (21,22) (27,35) (Fig. 2A) and treated with different pseudocantharidins at a concentration between 0.25 and 1 mM.…”

Section: Cell Viabilitymentioning

confidence: 99%

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Synthesis and Characterization of Pseudocantharidins, Novel Phosphatase Modulators That Promote the Inclusion of Exon 7 into the SMN (Survival of Motoneuron) pre-mRNA

Zhang

Kelemen

Santen

et al. 2011

Journal of Biological Chemistry

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Alternative pre-mRNA splicing is a central element of eukaryotic gene expression. Its deregulation can lead to disease, and methods to change splice site selection are developed as potential therapies. Spinal muscular atrophy is caused by the loss of the SMN1 (survival of motoneuron 1) gene. A therapeutic avenue for spinal muscular atrophy treatment is to promote exon 7 inclusion of the almost identical SMN2 (survival of motoneuron 2) gene. The splicing factor tra2-beta1 promotes inclusion of this exon and is antagonized by protein phosphatase (PP) 1. To identify new compounds that promote exon 7 inclusion, we synthesized analogs of cantharidin, an inhibitor of PP1, and PP2A. Three classes of compounds emerged from these studies. The first class blocks PP1 and PP2A activity, blocks constitutive splicing in vitro, and promotes exon 7 inclusion in vivo. The second class has no measurable effect on PP1 activity but activates PP2A. This class represents the first compounds described with these properties. These compounds cause a dephosphorylation of Thr-33 of tra2-beta1, which promotes exon 7 inclusion. The third class had no detectable effect on phosphatase activity and could promote exon 7 via allosteric effects. Our data show that subtle changes in similar compounds can turn a phosphatase inhibitor into an activator. These chemically related compounds influence alternative splicing by distinct mechanisms.An estimated 95% of human multi-exon genes undergo alternative pre-mRNA splicing (1, 2). Unlike promoter activity that regulates the abundance of transcripts, alternative splicing influences the structure of the mRNAs and their encoded proteins (reviewed in Ref. 3). The high incidence of alternative splicing and its ability to increase the coding capacity of the genome makes it a central element in eukaryotic gene expression.Despite its importance, we do not fully understand how splice sites, especially the alternative ones, are selected. The accurate recognition of splice sites in vivo is the result of a combinatorial mechanism (4 -7) where protein complexes assemble on the nascent pre-mRNA, because of the combination of weak RNA/RNA, RNA/protein, and protein/protein interactions. Transient interaction between the spliceosome and regulatory proteins assembling on the pre-mRNA help in the recognition of splice sites (8). There is increasing evidence that the phosphorylation state of splicing regulatory proteins is a crucial element for this recognition process (reviewed in Ref. 9), because phosphorylation/dephosphorylation often changes the affinity between proteins in these complexes. The spliceosome acts in a stepwise fashion on the pre-mRNA, and four distinct splicing complexes, the H, A, B and C complexes, have been identified (7). The H and E complexes contain the pre-mRNA imbedded with various proteins, among them hnRNPs and SR proteins as well as the U1 snRNP bound to the 5Ј splice site. The entry of U2 snRNP defines the branch point and leads to the formation of the A complex. The entry of the U4/5/6 snRN...

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Section: R2s3s4s)-rel-3-(hydroxymethyl)-7-oxabicyclo[221]heptanmentioning

confidence: 99%

Section: Cell Viabilitymentioning

confidence: 99%

Section: Cell Viabilitymentioning

confidence: 99%

Section: Cell Viabilitymentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Characterization of Pseudocantharidins, Novel Phosphatase Modulators That Promote the Inclusion of Exon 7 into the SMN (Survival of Motoneuron) pre-mRNA

Zhang

Kelemen

Santen

et al. 2011

Journal of Biological Chemistry

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“…[5][6][7] In addition, compared with thiophoene-based materials, they prefer more planar main chain conformation, are more electron-rich and have a slightly larger energy gap. [ 6 ] Furan moiety was successfully introduced into conjugated polymers for fi eld-effect transistor or photovoltaic…”

mentioning

confidence: 99%

Bisfuran‐s‐Tetrazine‐Based Conjugated Polymers: Synthesis, Characterization, and Photovoltaic Properties

Ding

2011

Macro Chemistry & Physics

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Bisfuran-s-tetrazine (FTz) and its copolymers with cyclopenta[2,1-b:3,4-b ′ ]dithiophene (CPDT) and benzo[1,2-b:4,5-b ′ ]dithiophene (BDT) (PCPDTFTz and PBDTFTz) are prepared with the alternating s-tetrazine and CPDT or BDT units bridged by a furan ring. Their optical and electrochemical properties are studied and compared with their thiophene analogs (PCPDTTTz-out and PCPDTTTz-in), in which the bridging unit is 4-hexylthiophene or 3-hexylthiophene, respectively. Bulk heterojunction (BHJ) solar cells fabricated from these polymers with PC 71 BM have a power conversion effi ciency (PCE) of 0.8%, which is much lower than that from the PCPDTTTz-out analog (3.2%), due to the low steric hindrance of the furan polymers in the absence of alkyl substitution on the furan ring. dithienopyrrole have been developed, [ 1 ] while the number of electron-accepting units are relatively limited. Up to now, only benzothiadiazole, diketopyrrolopyrrole, thienothiophene, and recently emerged thieno [3,4-c] pyrrole-4,6-dione units showed a good potential for this application. [ 1 ] Our group introduced s-tetrazine to the family of electron-accepting building blocks and reported the fi rst solution processable s-tetrazine-based conjugated polymers. [ 2 ] Compared with other electron-accepting units, s-tetrazine is very attractive due to its simple synthetic approach, symmetric structure, and high electron affi nity. [ 3 ] Our previous work are mainly based on alkyl chain substituted bisthiophene-s-tetrazine (TTz) units and it was found that polymers from this thiophene based s-tetrazine have relatively poor solubility, [ 4 ] and thus large side groups are required to achieve solution processability.Very recently, furan-based materials attracted our attention, as they usually displayed improved solubility. [5][6][7] In addition, compared with thiophoene-based materials, they prefer more planar main chain conformation, are more electron-rich and have a slightly larger energy gap. [ 6 ] Furan moiety was successfully introduced into conjugated polymers for fi eld-effect transistor or photovoltaic

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Electrically Active Polymers

Zarras

Irvin

2003

Encyclopedia of Polymer Science and Technology

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In the years since the discovery of conductivity in polyacetylene, a tremendous amount of research has been devoted to the synthesis, characterization, and application development of electrically active polymers. This article reviews the theory of conduction in these materials and discusses the syntheses of the major types of electrically active polymers. Electrical conductivities of these polymers are presented along with stability and mechanical and optical properties. The unique combinations of properties in these materials have led to a wide range of practical applications, which are also discussed.

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Synthesis and Characterization of Regiorandom and Regioregular Poly(3-octylfuran)

Cited by 116 publications

References 87 publications

Synthesis and Characterization of Pseudocantharidins, Novel Phosphatase Modulators That Promote the Inclusion of Exon 7 into the SMN (Survival of Motoneuron) pre-mRNA

Synthesis and Characterization of Pseudocantharidins, Novel Phosphatase Modulators That Promote the Inclusion of Exon 7 into the SMN (Survival of Motoneuron) pre-mRNA

Bisfuran‐s‐Tetrazine‐Based Conjugated Polymers: Synthesis, Characterization, and Photovoltaic Properties

Electrically Active Polymers

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