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Chemical Structure| 58-61-7 Chemical Structure| 58-61-7

Structure of Adenosine
CAS No.: 58-61-7

Chemical Structure| 58-61-7

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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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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 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 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 monitored hydrolytic consumption of (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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Product Details of Adenosine

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

Safety of Adenosine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Adenosine

GPCR

Isoform Comparison

Biological Activity

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 <<

Protocol

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.
Protocol 1

References

 

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