Day: November 21, 2022

Saleh, Amer F. published the artcileSynthesis and Splice-Redirecting Activity of Branched, Arginine-Rich Peptide Dendrimer Conjugates of Peptide Nucleic Acid Oligonucleotides, Computed Properties of 186046-81-1, the publication is Bioconjugate Chemistry (2010), 21(10), 1902-1911, database is CAplus and MEDLINE.

Arginine-rich cell-penetrating peptides have found excellent utility in cell and in vivo models for enhancement of delivery of attached charge-neutral PNA or PMO oligonucleotides. The authors report the synthesis of dendrimeric peptides containing 2- or 4-branched arms each having one or more R-Ahx-R (R = Arg; Ahx = aminohexanoic acid) motifs and their disulfide conjugation to a PNA705 splice-redirecting oligonucleotide. Conjugates were assayed in a HeLa pLuc705 cell assay for luciferase up-regulation and splicing redirection. Whereas 8-Arg branched peptide-PNA conjugates showed poor activity compared to a linear (R-Ahx-R)₄-PNA conjugate, 2-branched and some 4-branched 12 and 16 Arg peptide-PNA conjugates showed activity similar to that of the corresponding linear peptide-PNA conjugates. Many of the 12- and 16-Arg conjugates retained significant activity in the presence of serum. Evidence showed that biol. activity in HeLa pLuc705 cells of the PNA conjugates of branched and linear (R-Ahx-R) peptides is associated with an energy-dependent uptake pathway, predominantly clathrin-dependent, but also with some caveolae dependence.

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Computed Properties of 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Saleh, Amer F. published the artcileSynthesis and Splice-Redirecting Activity of Branched, Arginine-Rich Peptide Dendrimer Conjugates of Peptide Nucleic Acid Oligonucleotides, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is Bioconjugate Chemistry (2010), 21(10), 1902-1911, database is CAplus and MEDLINE.

Arginine-rich cell-penetrating peptides have found excellent utility in cell and in vivo models for enhancement of delivery of attached charge-neutral PNA or PMO oligonucleotides. The authors report the synthesis of dendrimeric peptides containing 2- or 4-branched arms each having one or more R-Ahx-R (R = Arg; Ahx = aminohexanoic acid) motifs and their disulfide conjugation to a PNA705 splice-redirecting oligonucleotide. Conjugates were assayed in a HeLa pLuc705 cell assay for luciferase up-regulation and splicing redirection. Whereas 8-Arg branched peptide-PNA conjugates showed poor activity compared to a linear (R-Ahx-R)₄-PNA conjugate, 2-branched and some 4-branched 12 and 16 Arg peptide-PNA conjugates showed activity similar to that of the corresponding linear peptide-PNA conjugates. Many of the 12- and 16-Arg conjugates retained significant activity in the presence of serum. Evidence showed that biol. activity in HeLa pLuc705 cells of the PNA conjugates of branched and linear (R-Ahx-R) peptides is associated with an energy-dependent uptake pathway, predominantly clathrin-dependent, but also with some caveolae dependence.

Bioconjugate Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Della Sala, Giorgio published the artcileSynthesis of uracil derivatives by oxidation of Fischer tungsten-carbene uracil complexes, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione, the publication is Journal of Organometallic Chemistry (2007), 692(8), 1623-1627, database is CAplus.

A study on the oxidation of Fischer tungsten-carbene uracil complexes has been carried out. E.g., oxidation of Fischer tungsten-carbene uracil complex I by Me₃NO gave 78% uracil II. Several commonly used oxidants gave results strongly influenced by the presence of substituents on the nitrogen atoms. In particular, the usual oxidants failed in the oxidation of 3-alkyl uracil carbene complexes. Finally, the authors showed that t-Bu hydroperoxide is able to oxidize successfully 3-alkyl uracil carbene complexes and can be used as a good alternative to the other methods.

Journal of Organometallic Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Recommanded Product: 3-Methylpyrimidine-2,4(1H,3H)-dione.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Krchnak, V. published the artcileNovel pyrimidine derivatives, reactions, and ultraviolet spectra, Name: 5-Aminopyrimidine-2-carbonitrile, the publication is Collection of Czechoslovak Chemical Communications (1975), 40(5), 1396-402, database is CAplus.

The conditions were studied for selective hydrolysis of I (R1 = NH2, NMe2, OH, OAc, OMe, SH, SMe, H, F, Cl, Br, SOME2, SO2Me, CN) and the products characterized by uv spectra. Hydrolysis of I in boiling 0.02M H2SO4 or 0.2M AcOH gave the corresponding II, while treating I with 0.2M H2SO4 at 110° or with boiling 5% K2CO3 solution yielded the appropriate III. In strongly alk. media I (R1 = CN) gave III (R1 = CONH2) and III (R1 = CO2H). Special conditions were required for the hydrolysis of I (R1 = F) (IV) which gave in 3M KHF2 at 75° II (R1 = F) and at 120° afforded III (R1 = F), while heating IV in 5% K2CO3 solution yielded III (R1 = NMe2).

Collection of Czechoslovak Chemical Communications published new progress about 56621-93-3. 56621-93-3 belongs to pyrimidines, auxiliary class Pyrimidine,Nitrile,Amine, name is 5-Aminopyrimidine-2-carbonitrile, and the molecular formula is C5H4N4, Name: 5-Aminopyrimidine-2-carbonitrile.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Krchnak, V. published the artcilePreparation and some reactions of 2,5-substituted pyrimidines, Synthetic Route of 56621-93-3, the publication is Collection of Czechoslovak Chemical Communications (1975), 40(5), 1384-9, database is CAplus.

The title compounds I (X = H, NH2, SH, SMe) were prepared by direct synthesis from [Me2NCH:C(CH:NMe2)N:CHNMe2]+ClO4- and HN:CXNH2. The reactants were reluxed in EtOH with dropwise addition of MeONa and HNEt2 distilled off in vacuo. I (X = H) was accompanied by [Me2NCH:NCH:NMe2]+ClO4- as by-product formed by reaction of liberated HNMe2 with HN:CHNH2. I (X = SMe) gave with NaClO, according to the reaction temperature, I (X = SOMe) or I (X = SO2Me) (II). II was especially ready for nucleophilic substitution of the SO2Me group and gave with alc. MeONa and with KCN in hot DMF, resp., I (X = OMe) and I (X = CN). Reaction of I (X = SH) with Me2SO in the presence of H2SO4 yielded III instead of the expected 2-hydroxypyrimidine derivative The readiness of II to undergo nucleophilic substitution by OMe and CN in the position 2 was compared with 3 addnl. 2-methylsulfonylpyrimidine 5-substituted with NHCHO, NH2, and H. The reaction rate was lowered by electron donating 5-substituents but the order of reactivities was different for OMe and CN.

Collection of Czechoslovak Chemical Communications published new progress about 56621-93-3. 56621-93-3 belongs to pyrimidines, auxiliary class Pyrimidine,Nitrile,Amine, name is 5-Aminopyrimidine-2-carbonitrile, and the molecular formula is C5H4N4, Synthetic Route of 56621-93-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Sabale, Pramod M. published the artcileClickable PNA Probes for Imaging Human Telomeres and Poly(A) RNAs, SDS of cas: 169396-92-3, the publication is ACS Omega (2018), 3(11), 15343-15352, database is CAplus and MEDLINE.

The ability to bind strongly to complementary nucleic acid sequences, invade complex nucleic acid structures and resist degradation by cellular enzymes has made peptide nucleic acid (PNA) oligomers as very useful hybridization probes in mol. diagnosis. For such applications, the PNA oligomers have to be labeled with appropriate reporters as they lack intrinsic labels that can be used in biophys. assays. While solid-phase synthesis is commonly used to attach reporters onto PNA, development of milder and modular labeling methods will provide access to PNA oligomers labeled with a wider range of biophys. tags. Here, the authors describe the establishment of a post-synthetic modification strategy based on bioorthogonal chem. reactions in functionalizing PNA oligomers in solution with variety of tags. A toolbox composed of alkyne- and azide-modified monomers were site-specifically incorporated into PNA oligomers and post-synthetically click-functionalized with various tags ranging from sugar, amino acid, biotin and fluorophores by using copper(I)-catalyzed azide-alkyne cycloaddition, strain-promoted azide-alkyne cycloaddition and Staudinger ligation reactions. As a proof of utility of this method, fluorescent PNA hybridization probes were developed and used in imaging human telomeres in chromosomes and poly(A) RNAs in cells. Taken together, this simple approach of generating a wide range of functional PNA oligomers will expand the use of PNA in mol. diagnosis.

ACS Omega published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, SDS of cas: 169396-92-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Ribeiro da Silva, Manuel A. V. published the artcileExperimental study on the thermochemistry of some amino derivatives of uracil, COA of Formula: C5H6N2O2, the publication is Journal of Chemical Thermodynamics (2011), 43(11), 1763-1767, database is CAplus.

Values of the standard (p = 0.1 MPa) molar enthalpy of combustion, ΔcHm , of four crystalline compounds: 5-aminouracil, 6-aminouracil, 6-amino-1-methyluracil, and 6-amino-1,3-dimethyluracil, were determined, at T = 298.15 K, using a static bomb combustion calorimeter. The values obtained of standard molar enthalpy of combustion were used to derive the standard molar enthalpy of formation of the compounds investigated in their condensed phase and together with literature values of the standard molar enthalpy of sublimation, yielded the standard molar enthalpies of formation in the gaseous phase. These are discussed in terms of the effects of the mol. structure on the relative enthalpic stability.

Journal of Chemical Thermodynamics published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, COA of Formula: C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Roeglin, Lars published the artcileDNA and RNA-controlled switching of protein kinase activity, Computed Properties of 186046-81-1, the publication is ChemBioChem (2009), 10(4), 758-765, database is CAplus and MEDLINE.

Protein switches use the binding energy gained upon recognition of ligands to modulate the conformation and binding properties of protein segments. We explored whether the programmable nucleic acid mediated recognition might be used to design or mimic constraints that limit the conformational freedom of peptide segments. The aim was to design nucleic acid-peptide conjugates in which the peptide portion of the conjugate would change the affinity for a protein target upon hybridization. This approach was used to control the affinity of a PNA-phosphopeptide conjugate for the signal transduction protein Src kinase, which binds the cognate phosphopeptides in a linear conformation. Peptide-nucleic acid arms were attached to known peptide binders. The chimeric mols. were studied in three modes: (1) as single strands, (2) constrained by intermol. hybridization (duplex formation) and (3) constrained by intramol. hybridization (hairpin formation). Of note, duplexes that were designed to accommodate bulged peptide structures (for example, in hairpins or bulges) had lower binding affinities than duplexes in which the peptide was allowed to adopt a more relaxed conformation. Greater than 90-fold differences in binding affinities were observed It was, thus, feasible to make use of DNA hybridization to reversibly switch from no to almost complete inhibition of Src-SH2-peptide binding, and vice versa. A series of DNA and PNA-based hybridization experiments revealed the importance of charges and conformational effects. Nucleic acid mediated switching was extended to the use of RNA; this enabled a regulation of the enzymic activity of the Src kinase. The proof-of-principle results demonstrate for the first time that PNA-peptide chimeras can transduce changes of the concentration of a given RNA mol. to changes of the activity of a signal transduction enzyme.

ChemBioChem published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Computed Properties of 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Silva, F. published the artcileSite and bond selective H- formation in methylated pyrimidine bases driven by potassium molecule collisions, Category: pyrimidines, the publication is Journal of Physics: Conference Series (2012), 388(Part 10), 102032/1, database is CAplus.

In this study we present for the first time site (N₁-H/N₃-H) and bond (N-H/C-H) selectivity of H- formation in 1-methylthymine, 3-methyluracil and deuterated thymine (C positions) triggered by potassium mol. collisions. By comparing the H loss of these mols. with H loss in thymine and uracil and setting the energy one can predict site and bond selectivity in these set of mols.

Journal of Physics: Conference Series published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C23H43NP2, Category: pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Silva, F. published the artcileSite- and bond-selective H- formation in methylated pyrimidine bases driven by potassium-molecule collisions, Category: pyrimidines, the publication is Journal of Physics: Conference Series (2012), 388(Part 1), 012040/1-012040/6, database is CAplus.

Electron transfer in alkali-mol. collisions to gas phase thymine and uracil yielding H- formation is selectively controlled in the energy range between 5 and 65 eV. By tuning the collision energy, electron transfer from the alkali to methylated thymine (at the N1 position), methylated uracil (at the N3 position) and partly deuterated thymine, enables H-formation. Such process proceeds not only through the breaking of the (C-H) against (N-H) bonds but also through N1 against N3 sites. Such selectivity, as far as bond and site are concerned, is here reported for the first time in collision induced dissociation experiments by alkali-mol. interactions.

Journal of Physics: Conference Series published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C17H14O5, Category: pyrimidines.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia