Structure of Adenosine
CAS No.: 58-61-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Adenosine is a nucleoside that is composed of adenine and d-ribose and plays many important biological roles in addition to being components of DNA and RNA.
Synonyms: Adenine riboside; D-Adenosine; NSC 627048
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Fluorescent ratiometric supramolecular tandem assays for phosphatase and phytase enzymes
Kirk M. Atkinson ; Bradley D. Smith ;
Abstract: Ratiometric fluorescent assays have a built-in correction factor which enhances assay accuracy and reliability. We have developed fluorescent ratiometric supramolecular tandem assays for phosphatase and phytase enzymes using a mixture of three molecular components. One of the molecules is a tetra-cationic fluorescence quencher called CalixPyr which can bind and quench the polyanionic pyrene fluorophore, CMP, that emits at 430 nm. Polyphosphates can disrupt the CMP/CalixPyr complex and alter the fluorescence intensity (responsive signal). CalixPyr has no effect on the fluorescence emission of cationic pentamethine cyanine fluorophore, cCy5, which emits at 665 nm and acts as a non-responsive reference signal. The continuous ratiometric fluorescent assay for alkaline phosphatase monitored hydrolytic consumption of adenosine triphosphate (ATP). The continuous ratiometric fluorescent assay for phytase activity monitored hydrolytic consumption of phytate. With further development this latter assay may be useful for high throughput assessment of phytase activity in individual batches of fortified animal feed. It is likely that the three-molecule mixture (CMP, CalixPyr, cCy5) can become a general assay platform for other enzymes that catalyse addition/removal of phosphate groups from appropriate molecular substrates.
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Zhou, Jujun ; Deng, Youchao ; Iyamu, Iredia D. ; Horton, John R. ; Yu, Dan ; Hajian, Taraneh , et al.
Abstract: S-Adenosyl-L-methionine (SAM) analogs are adaptable tools for studying and therapeutically inhibiting SAM-dependent methyltransferases (MTases). Some MTases play significant roles in host-pathogen interactions, one of which is Clostridioides difficile-specific DNA adenine MTase (CamA). CamA is needed for efficient sporulation and alters persistence in the colon. To discover potent and selective CamA inhibitors, we explored modifications of the solvent-exposed edge of the SAM adenosine moiety. Starting from the two parental compounds (6e and 7), we designed an adenosine analog (11a) carrying a 3-phenylpropyl moiety at the adenine N6-amino group, and a 3-(cyclohexylmethyl guanidine)-Et moiety at the sulfur atom off the ribose ring. Compound 11a (IC50 = 0.15 μM) is 10x and 5x more potent against CamA than 6e and 7, resp. The structure of the CamA-DNA-inhibitor complex revealed that 11a adopts a U-shaped conformation, with the two branches folded toward each other, and the aliphatic and aromatic rings at the two ends interacting with one another. 11a occupies the entire hydrophobic surface (apparently unique to CamA) next to the adenosine binding site. Our work presents a hybrid knowledge-based and fragment-based approach to generating CamA inhibitors that would be chem. agents to examine the mechanism(s) of action and therapeutic potentials of CamA in C. difficile infection.
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Purchased from AmBeed: 2086772-26-9 ; 29908-03-0 ; 73-24-5 ; 83948-53-2 ; 39684-80-5 ; 58-61-7 ; 2004-06-0 ; 2038-57-5 ; 199915-38-3 ; 2040291-27-6 ; 3218-02-8 ; 1561178-17-3 ; 58944-73-3
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CAS No. : | 58-61-7 |
Formula : | C10H13N5O4 |
M.W : | 267.24 |
SMILES Code : | O[C@H]1[C@H](N2C=NC3=C(N)N=CN=C23)O[C@H](CO)[C@H]1O |
Synonyms : |
Adenine riboside; D-Adenosine; NSC 627048
|
MDL No. : | MFCD00005752 |
InChI Key : | OIRDTQYFTABQOQ-KQYNXXCUSA-N |
Pubchem ID : | 60961 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
Human monocyte-derived macrophages (MoMF) | 100 nM | 48 h | To validate the impact of ADA2 on macrophage phenotype, results showed ADA2 upregulated PDGF-B expression and secretion | PMC8606247 |
U937 monocytes | 100 nM | 48 h | To study the impact of ADA2 on macrophage differentiation, results showed ADA2 upregulated pro-inflammatory and pro-fibrotic genes, including PDGF-B | PMC8606247 |
human adipocytes | 150 nM | Used to study the role of CD248 in insulin signaling in human adipocytes. Results showed that adipocytes with lower CD248 levels responded more strongly to insulin. | PMC10750038 | |
preadipocytes | 209 μM | 45 min | Used for isolating and culturing primary murine preadipocytes to study the role of CD248 in insulin signaling. Results showed that preadipocytes lacking CD248 exhibited increased sensitivity to insulin. | PMC10750038 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
C57Bl/6J mice | Non-ischemic saphenous artery occlusion model | Topical superfusion | 10^-4 M | 30 minutes | For muscle fixation prior to immunochemistry | PMC2809787 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT06578234 | Chronic Coronary Syndrome|Coro... More >>nary Artery Disease|Ischemic Heart Disease Less << | PHASE4 | RECRUITING | 2026-12-31 | Clinical Physiology, Departmen... More >>t of Clinical Sciences Lund, Lund University, Sk?ne University Hospital, Lund, Sweden Less << |
NCT03218137 | Premature Ventricular Contract... More >>ion (PVC) Less << | PHASE4 | RECRUITING | 2025-12-31 | Weill Cornell Medicine, New Yo... More >>rk, New York, 10065, United States Less << |
NCT01690884 | Coronary Artery Disease | PHASE1 | COMPLETED | 2025-01-17 | Autonomic Dysfunction Center, ... More >>Nashville, Tennessee, 37232, United States Less << |
NCT00612521 | Coronary Artery Stenosis|Coron... More >>ary Artery Disease Less << | PHASE3 | TERMINATED | 2025-09-08 | University of Ottawa Heart Ins... More >>titute, Ottawa, Ontario, K1Y 4W7, Canada Less << |
NCT02681913 | Pathological Processes|Cardiom... More >>yopathies Less << | PHASE2 | UNKNOWN | 2025-12-18 | Amphia Hospital, Breda, Noord-... More >>Brabant, 4818CK, Netherlands Less << |
NCT03231371 | Orthotopic Heart Transplant | PHASE3 | COMPLETED | 2025-01-11 | University of MIchigan-Congeni... More >>tal Heart Center, Ann Arbor, Michigan, 48109, United States Less << |
NCT00284323 | Acute ST Elevation Myocardial ... More >>Infarction Less << | PHASE2 | UNKNOWN | - | Universitaire Ziekenhuizen Leu... More >>ven, Leuven, 3000, Belgium Less << |
NCT05014061 | Myocardial Ischemia | PHASE3 | WITHDRAWN | 2025-12-25 | - |
NCT01939912 | Heart Failure|Peripheral Chemo... More >>receptor Hypersensitivity Less << | COMPLETED | 2025-09-16 | Centrum Choro?b Serca - Klinik... More >>a Kardiologii, 4. Wojskowy Szpital Kliniczny, Wroclaw, 50-981, Poland Less << | |
NCT00781404 | Acute Myocardial Infarction | PHASE3 | COMPLETED | 2025-07-12 | ValldHebron Hospital, Barcelon... More >>a, 08035, Spain Less << |
NCT04588441 | Acute Respiratory Distress | PHASE2 | WITHDRAWN | 2025-12-25 | - |
NCT04392362 | Supra-ventricular Tachycardia | PHASE3 | COMPLETED | 2020-12-16 | Steve Biko hospital, Pretoria,... More >> Gauteng, 0001, South Africa Less << |
NCT01123525 | Angina Pectoris | PHASE1|PHASE2 | COMPLETED | 2025-09-11 | University Hospital of North N... More >>orway, Trooms?, 9038, Norway Less << |
Bio Calculators | ||||
Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
3.74mL 0.75mL 0.37mL |
18.71mL 3.74mL 1.87mL |
37.42mL 7.48mL 3.74mL |
|
Dissolving Methods |
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
|
Tags: Adenosine | Adenine riboside | D-Adenosine | Nucleoside Antimetabolite/Analog | Autophagy | Apoptosis | Endogenous Metabolite | GPCR | endogenous | nadenine riboside | purine nucleoside | cellular energy | ATP | ADP | AMP | neurotransmitter | anti-inflammatory | vasodilation | 58-61-7
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P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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