Month: November 2022

Yang, Tianming published the artcileA methylation-switchable conformational probe for the sensitive and selective detection of RNA demethylase activity, SDS of cas: 608-34-4, the publication is Chemical Communications (Cambridge, United Kingdom) (2016), 52(36), 6181-6184, database is CAplus and MEDLINE.

We describe a novel methylation-sensitive nucleic acid (RNA) probe which switches conformation according to its methylation status. When combined with a differential scanning fluorimetry technique, it enables highly sensitive and selective detection of demethylase activity at a single methylated-base level. The approach is highly versatile and may be adapted to a broad range of RNA demethylases.

Chemical Communications (Cambridge, United Kingdom) 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 C21H20BrNO4S, SDS of cas: 608-34-4.

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

Riand, Jacques published the artcileProton and carbon-13 nmr study of substituted pyrimidines. IV. Hindered rotation of N,N-dimethylamino-4-pyrimidines in the monoproton state, Product Details of C6H9N3, the publication is Canadian Journal of Chemistry (1980), 58(5), 466-71, database is CAplus.

The free energy of activation for hindered rotation about the C-N exocyclic bond in some N,N-dimethylaminopyrimidine hydrochlorides was determined by ¹H and ¹³C NMR. Monoprotonation of N,N-dimethylaminopyrimidines induces a large increase in the free energy of activation. This increase is larger for the 4-dimethylamino group than for the 2-dimethylamino group due to the predominance of the monoprotonated (N-1 H) form.

Canadian Journal of Chemistry published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, Product Details of C6H9N3.

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

Riand, Jacques published the artcileProton and carbon-13 nuclear magnetic resonance studies of substituted pyrimidines. Part 3. Hindered internal rotation in some 4-(NN-dimethylamino)pyrimidines, Application In Synthesis of 31401-45-3, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) (1979), 1248-52, database is CAplus.

The free energy of activation for internal rotation about the C-N exocyclic bond of substituted 4-(N,N-dimethylamino)pyrimidines was determined using ¹H and ¹³C NMR line-shape anal. Substituent effects on the rotational barrier of the NMe₂ group were evaluated. The rotational barrier is higher for a NMe₂ group in the 4-position than for one in the 2 position. There is a linear correlation between the free energies of activation and ¹J(C,H) coupling constants for the 4-NMe₂ group.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) published new progress about 31401-45-3. 31401-45-3 belongs to pyrimidines, auxiliary class Pyrimidine,Amine, name is N,N-Dimethylpyrimidin-4-amine, and the molecular formula is C6H9N3, Application In Synthesis of 31401-45-3.

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

Meng, Qing published the artcileDesign, synthesis and evaluation of novel HIV-1 NNRTIs with dual structural conformations targeting the entrance channel of the NNRTI binding pocket, Computed Properties of 56-05-3, the publication is European Journal of Medicinal Chemistry (2016), 53-62, database is CAplus and MEDLINE.

On the basis of structure-based bioisosteric replacement and mol. hybridization strategy, a series of novel dual structural-conformation inhibitors targeting the “entrance channel” of HIV-1 NNRTIs binding pocket (NNIBP) were designed and synthesized. All of the new compounds were evaluated for their anti-HIV activities in MT-4 cells using the MTT method. Five compounds exhibited moderate to excellent potencies inhibiting wild-type (weight) HIV-1 replication with EC₅₀ values ranging from 31.36 μM to 0.11 μM. Among them, compound I was identified as the most potent inhibitor with EC₅₀ values of 0.11 μM and 2.18 μM against weight and K103N/Y181C double mutant HIV-1 strain (RES056), resp. In addition, preliminary structure-activity relationships (SARs) and mol. simulation studies were discussed, which may provide valuable insights for further optimization.

European Journal of Medicinal Chemistry published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Computed Properties of 56-05-3.

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

Zhang, C. F. published the artcileDensity functional theory studies of methylated uracil: geometries and energies, HPLC of Formula: 608-34-4, the publication is Chemical Physics (2000), 256(3), 275-287, database is CAplus.

D. functional theory studies on the geometries and energies of the methylated derivatives of uracil yield two stable conformations, α and β, for each single-methylated uracil. They are different in the spatial orientation of the substituting Me group and the mol. total energy. Analyzing the calculated structural parameters, we also found an elongation effect in the methylated uracil, which contributes to the increase of dipole moment and mol. size of mols. such as the methylated derivatives of nucleic acid bases.

Chemical Physics 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 C3H9ClOS, HPLC of Formula: 608-34-4.

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

Cheng, Yuan published the artcileSupramolecular structures constructed by 3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol monohydrate and 3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-dimethylprop-2-yn-1-ol, Safety of 2-Amino-4,6-dichloropyrimidine, the publication is Acta Crystallographica, Section C: Crystal Structure Communications (2011), 67(7), o244-o248, database is CAplus and MEDLINE.

The mol. of 3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol monohydrate, C₉H₁₀ClN₃O·H₂O, (I), shows a very polarized mol.-electronic structure, while the polarization is slight for 3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-dimethylprop-2-yn-1-ol, C₁₄H₁₇N₃O₂, (II). In the supramol. structure of (I), a combination of hard N-H…N H bonds and soft C-H…N H bonds creates a mol. column. Aromatic π-π stackings between the pyrimidine rings stabilize the column with perpendicular and centroid-centroid distances of 3.283(3) and 3.588(1) Å, resp. Short Cl…Cl contacts further link neighboring mol. columns, creating a hydrophilic tube in which H₂O mols. are fixed by various H bonds. In the packing of (II), a 1-dimensional mol. chain is formed through several contacts involving hard N-H…O(N) and O-H…O(N) and soft C-H…O H bonds. Interchain O-H…O H bonds link the chains giving a two-dimensional stepped network. It is anticipated that study of the influence of H bonding on the patterns of base pairing and mol. packing in aminopyrimidine structures will shed significant light on nucleic acid structures as well as their functions. Crystallog. data are given.

Acta Crystallographica, Section C: Crystal Structure Communications published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, Safety of 2-Amino-4,6-dichloropyrimidine.

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

Sethi, Dalip published the artcileFluorescent Peptide-PNA Chimeras for Imaging Monoamine Oxidase A mRNA in Neuronal Cells, HPLC of Formula: 186046-81-1, the publication is Bioconjugate Chemistry (2012), 23(2), 158-163, database is CAplus and MEDLINE.

Monoamine oxidases (MAO) catalyze the oxidative deamination of many biogenic amines and are integral proteins found in the mitochondrial outer membrane. Changes in MAO-A levels are associated with depression, trait aggression, and addiction. Here we report the synthesis, characterization, and in vitro evaluation of novel fluorescent peptide-peptide nucleic acid (PNA) chimeras for MAOA mRNA imaging in live neuronal cells. The probes were designed to include MAOA-specific PNA dodecamers, separated by an N-terminal spacer to a μ-opioid receptor targeting peptide (DAMGO), with a spacer and a fluorophore on the C-terminus. The probe was successfully delivered into human SH-SY5Y neuroblastoma cells through μ-opioid receptor-mediated endocytosis. The K_d by flow cytometry was 11.6±0.8 nM. Uptake studies by fluorescence microscopy showed ∼5-fold higher signal in human SH-SY5Y neuroblastoma cells than in neg. control CHO-K1 cells that lack μ-opioid receptors. Moreover, a peptide-mismatch control sequence showed no significant uptake in SH-SY5Y cells. Such mRNA imaging agents with near-IR fluorophores might enable real time imaging and quantitation of neuronal mRNAs in live animal models.

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 C6H6N2O, HPLC of Formula: 186046-81-1.

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

Sethi, Dalip published the artcileFluorescent Peptide-PNA Chimeras for Imaging Monoamine Oxidase A mRNA in Neuronal Cells, Application In Synthesis of 169396-92-3, the publication is Bioconjugate Chemistry (2012), 23(2), 158-163, database is CAplus and MEDLINE.

Monoamine oxidases (MAO) catalyze the oxidative deamination of many biogenic amines and are integral proteins found in the mitochondrial outer membrane. Changes in MAO-A levels are associated with depression, trait aggression, and addiction. Here we report the synthesis, characterization, and in vitro evaluation of novel fluorescent peptide-peptide nucleic acid (PNA) chimeras for MAOA mRNA imaging in live neuronal cells. The probes were designed to include MAOA-specific PNA dodecamers, separated by an N-terminal spacer to a μ-opioid receptor targeting peptide (DAMGO), with a spacer and a fluorophore on the C-terminus. The probe was successfully delivered into human SH-SY5Y neuroblastoma cells through μ-opioid receptor-mediated endocytosis. The K_d by flow cytometry was 11.6±0.8 nM. Uptake studies by fluorescence microscopy showed ∼5-fold higher signal in human SH-SY5Y neuroblastoma cells than in neg. control CHO-K1 cells that lack μ-opioid receptors. Moreover, a peptide-mismatch control sequence showed no significant uptake in SH-SY5Y cells. Such mRNA imaging agents with near-IR fluorophores might enable real time imaging and quantitation of neuronal mRNAs in live animal models.

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 C7H5Cl2NO, Application In Synthesis of 169396-92-3.

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

Gorai, Ananta published the artcileThiazole Containing PNA Mimic Regulates c-MYC Gene Expression through DNA G-Quadruplex, Application In Synthesis of 186046-81-1, the publication is Bioconjugate Chemistry (2022), 33(6), 1145-1155, database is CAplus and MEDLINE.

Peptide nucleic acids (PNAs), besides hybridization to complementary DNA and RNAs, bind and stabilize DNA secondary structures. Herein, we illustrate the design and synthesis of PNA like scaffolds by incorporating five membered thiazole rings as modified bases instead of nucleobases and their subsequent effects on gene regulation by biophys. and in vitro assays. A thiazole modified PNA trimer selectively recognizes c-MYC G-quadruplex (G4) DNA over other G4s and duplex DNA. It displays high stabilization potential for the c-MYC G4 DNA and shows remarkable fluorescence enhancement with the c-MYC G4. It is flexible enough to bind at 5′ and 3′ ends as well as in the groove region of c-MYC G4. Furthermore, the PNA trimer easily permeates cellular membrane and suppresses c-MYC mRNA expression in HeLa cells by targeting the promoter G4. This study illuminates modified PNAs as flexible mol. tools for selective targeting of noncanonical nucleic acids and modulating gene function.

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, Application In Synthesis of 186046-81-1.

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

Odell, Luke R. published the artcilePyrimidyn-Based Dynamin Inhibitors as Novel Cytotoxic Agents, COA of Formula: C4H3Cl2N3, the publication is ChemMedChem (2022), 17(1), e202100560, database is CAplus and MEDLINE.

Five focused libraries of pyrimidine-based dynamin GTPase inhibitors, in total 69 compounds were synthesized, and their dynamin inhibition and broad-spectrum cytotoxicity examined Dynamin plays a crucial role in mitosis, and as such inhibition of dynamin was expected to broadly correlate with the observed cytotoxicity. The pyrimidines synthesized ranged from mono-substituted to trisubstituted. The highest levels of dynamin inhibition were noted with di- and tri- substituted pyrimidines, especially those with pendent amino alkyl chains. Short chains and simple heterocyclic rings reduced dynamin activity. There were three levels of dynamin activity noted: 1-10, 10-25 and 25-60 μM. Screening of these compounds in a panel of cancer cell lines: SW480 (colon), HT29 (colon), SMA (spontaneous murine astrocytoma), MCF-7 (breast), BE2-C (glioblastoma), SJ-G2 (neuroblastoma), MIA (pancreas), A2780 (ovarian), A431 (skin), H460 (lung), U87 (glioblastoma) and DU145 (prostate) cell lines reveal a good correlation between the observed dynamin inhibition and the observed cytotoxicity. The most active analogs (31 a,b) developed returned average GI₅₀ values of 1.0 and 0.78 μM across the twelve cell lines examined These active analogs were: N²-(3-dimethylaminopropyl)-N⁴-dodecyl-6-methylpyrimidine-2,4-diamine (31 a) and N⁴-(3-dimethylaminopropyl)-N²-dodecyl-6-methylpyrimidine-2,4-diamine (31 b).

ChemMedChem published new progress about 56-05-3. 56-05-3 belongs to pyrimidines, auxiliary class Pyrimidine,Chloride,Amine,API, name is 2-Amino-4,6-dichloropyrimidine, and the molecular formula is C4H3Cl2N3, COA of Formula: C4H3Cl2N3.

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