1867-73-8

Basic information

• Product Name: 6-METHYLAMINOPURINE 9-RIBOFURANOSIDE
• Synonyms: 6-METHYLAMINOPURINE 9-RIBOFURANOSIDE;(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-methylaminopurin-9-yl)oxolane-3,4-diol;N-Methyladenosine;NSC-29409;6-Methylaminopurine D-riboside;6-Methylaminopurine ribonucleoside;6-Methylaminopurinosine;Adenosine, N-methyl-
• CAS NO: 1867-73-8
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 297.2673
• EINECS: 200-001-2
• Product Categories: Inhibitors
• Mol File: 1867-73-8.mol
• Article Data: 40

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 649.1 °C at 760 mmHg
• Flash Point: 346.3 °C
• Appearance: /
• Density: 1.85 g/cm³
• Vapor Pressure: 9.86E-18mmHg at 25°C
• Refractive Index: 1.814
• Storage Temp.: −20°C
• PKA: 13.12±0.70(Predicted)
• CAS DataBase Reference: 6-METHYLAMINOPURINE 9-RIBOFURANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYLAMINOPURINE 9-RIBOFURANOSIDE(1867-73-8)
• EPA Substance Registry System: 6-METHYLAMINOPURINE 9-RIBOFURANOSIDE(1867-73-8)

Safety Data

• Hazardous Substances Data: 1867-73-8(Hazardous Substances Data)

Usage

Description

N6-Methyladenosine is an adenosine analog. It inhibits epinephrine-induced contraction of isolated guinea pig ileum and thoracic aorta when used at a concentration of 10 μM. N6-Methyladenosine (1 mg/kg, i.v.) decreases arterial blood pressure and renal blood flow and increases peripheral resistance in anesthetized dogs. It also inhibits tumor growth in the C3H/ST and C3HB/ST mouse models of spontaneous mammary adenocarcinomas. N6-Methyladenosine is also the most prevelant mRNA modification in eukaryotes and has roles in cell viability and development.

Uses

N6-Methyladenosine is the most common internal modification of eukaryotic mRNA. The result of this modification is specifically recognized mRNA in the cytoplasm which regulates mRNA stability.N6-Methyladenosine is made when a protein complex containin the writer enzyme METTL3 adds a methyl group to adenosine. Two different eraser enzymes ALKBH5 and FTO can remove a methyl group to turn m6A bach into adenosine.

Definition

ChEBI: A methyladenosine compound with one methyl group attached to N6 of the adenine nucleobase.

InChI:InChI=1/C11H15N5O4/c1-12-9-6-10(14-3-13-9)16(4-15-6)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11,17-19H,2H2,1H3,(H,12,13,14)/t5-,7-,8-,11+/m0/s1

Upstream product

• 56787-20-3 2',3',5'-tri-O-acetyl-N⁶-methyl-adenosine 
• 17287-03-5 trimethylsulphonium hydroxide 
• 58-61-7 adenosine 
• 17331-15-6 N⁶-(N,N'-Dimethylaminomethylene)adenosine 
• 53821-43-5 (2R,3R,4S,5R)-2-(6-azido-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol 
• 74-89-5 methylamine 
• 171075-00-6 6-N-acetyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)adenosine 
• 171075-05-1 6-N-acetyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)-6-N-methyladenosine 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 
• 1359697-47-4 6-N-methyladenosine 5'-acetate 
• 87-42-3 6-chloro-7H-purine 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 74-83-9 methyl bromide 
• 14426-53-0 6-Iodo-purine riboside 

Downstream Products

• 4229-50-9 N₆-methyl AMP 
• 1359697-50-9 C₁₁H₁₇N₅O₁₀P₂ 
• 3130-39-0 N₆-Methyl-ATP 
• 41111-73-3 N⁶-methyl-O^{2'_,O3'_{-phenylboranediyl-O}5'}-(toluene-4-sulfonyl)-adenosine 
• 161001-94-1 2',3',5'-tri-O-acetyl-N⁶-methyl-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 161001-99-6 N⁶-methyl-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 661471-87-0 5'-O-(4,4'-dimethoxytrityl)-N⁶-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine 
• 588698-75-3 5’-O-(4,4’-dimethoxytrityl)-2’-O-dimethyl(tert-butyl)silyl-N6-methyladenosine 
• 588698-71-9 5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine 
• 443-72-1 N-methyladenine 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 58-61-7 adenosine 
• 1394956-18-3 C₂₅H₃₅N₇O₄S 

Relevant articles and documents

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Structure-activity relationship of leucyladenylate sulfamate analogues as leucyl-tRNA synthetase (LRS)-targeting inhibitors of Mammalian target of rapamycin complex 1 (mTORC1)

Leucyl-tRNA synthetase (LRS) plays an important role in amino acid-dependent mTORC1 signaling, which is known to be associated with cellular metabolism and proliferation. Therefore, LRS-targeting small molecules that can suppress mTORC1 activation may provide an alternative strategy to current anticancer therapy. In this work, we developed a library of leucyladenylate sulfate analogues by extensively modifying three different pharmacophoric regions comprising adenine, ribose and leucine. Several effective compounds were identified by cell-based mTORC1 activation assays and further tested for anticancer activity. The selected compounds mostly exhibited selective cytotoxicity toward five different cancer cell lines, supporting the hypothesis that the LRS-mediated mTORC1 pathway is a promising alternative target to current therapeutic approaches.

Studies of nucleosides and nucleotides. XXVI. Further studies on the chlorination of inosine derivatives with dimethylformamide-thionyl chloride complex.

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Nucleotide Analog ARL67156 as a Lead Structure for the Development of CD39 and Dual CD39/CD73 Ectonucleotidase Inhibitors

Nucleoside triphosphate diphosphohydrolase1 (NTPDase1, CD39) inhibitors have potential as novel drugs for the (immuno)therapy of cancer. They increase the extracellular concentration of immunostimulatory ATP and reduce the formation of AMP, which can be further hydrolyzed by ecto-5’-nucleotidase (CD73) to immunosuppressive, cancer-promoting adenosine. In the present study, we synthesized analogs and derivatives of the standard CD39 inhibitor ARL67156, a nucleotide analog which displays a competitive mechanism of inhibition. Structure-activity relationships were analyzed at the human enzyme with respect to substituents in the N6- and C8-position of the adenine core, and modifications of the triphosph(on)ate chain. Capillary electrophoresis coupled to laser-induced fluorescence detection employing a fluorescent-labeled ATP derivative was employed to determine the compounds’ potency. Selected inhibitors were additionally evaluated in an orthogonal, malachite green assay versus the natural substrate ATP. The most potent CD39 inhibitors of the present series were ARL67156 and its derivatives 31 and 33 with Ki values of around 1 μM. Selectivity studies showed that all three nucleotide analogs additionally blocked CD73 acting as dual-target inhibitors. Docking studies provided plausible binding modes to both targets. The present study provides a full characterization of the frequently applied CD39 inhibitor ARL67156, presents structure-activity relationships, and provides a basis for future optimization towards selective CD39 and dual CD39/CD73 inhibitors.

Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations

The RNA-world hypothesis assumes that life on Earth started with small RNA molecules that catalyzed their own formation. Vital to this hypothesis is the need for prebiotic routes towards RNA. Contemporary RNA, however, is not only constructed from the four canonical nucleobases (A, C, G, and U), it also contains many chemically modified (noncanonical) bases. A still open question is whether these noncanonical bases were formed in parallel to the canonical bases (chemical origin) or later, when life demanded higher functional diversity (biological origin). Here we show that isocyanates in combination with sodium nitrite establish methylating and carbamoylating reactivity compatible with early Earth conditions. These reactions lead to the formation of methylated and amino acid modified nucleosides that are still extant. Our data provide a plausible scenario for the chemical origin of certain noncanonical bases, which suggests that they are fossils of an early Earth.