8-Aminoadenosine

Modify Date: 2024-01-13 19:12:05

8-Aminoadenosine Structure
8-Aminoadenosine structure
Common Name 8-Aminoadenosine
CAS Number 3868-33-5 Molecular Weight 282.26
Density 2.25g/cm3 Boiling Point 747.1ºC at 760mmHg
Molecular Formula C10H14N6O4 Melting Point 180-185ºC dec.
MSDS Chinese USA Flash Point 405.6ºC
Symbol GHS06
GHS06
Signal Word Danger

 Use of 8-Aminoadenosine


8-Aminoadenosine (8-NH2-Ado), a RNA-directed nucleoside analogue, reduces cellular ATP levels and inhibits mRNA synthesis. 8-Aminoadenosine blocks Akt/mTOR signaling and induces autophagy and apoptosis in a p53-independent manner. 8-Aminoadenosine has antitumor activity[1][2][3].

 Names

Name 8-aminoadenosine
Synonym More Synonyms

 8-Aminoadenosine Biological Activity

Description 8-Aminoadenosine (8-NH2-Ado), a RNA-directed nucleoside analogue, reduces cellular ATP levels and inhibits mRNA synthesis. 8-Aminoadenosine blocks Akt/mTOR signaling and induces autophagy and apoptosis in a p53-independent manner. 8-Aminoadenosine has antitumor activity[1][2][3].
Related Catalog
Target

Akt

mTOR

In Vitro 8-Aminoadenosine (8-NH2-Ado; 0.1-10 μM; for 48 h) has IC50s of 1.5 μM and 8.88 μM in MM.1S and U266 cells, respectively[1]. 8-Aminoadenosine (10 μM; for 24 h) induces significant apoptotic death of MCF-7 cells in p53-independent pathway. 8-Aminoadenosine causes PARP cleavage in MCF-7 cells[2]. 8-Aminoadenosine (3 μM; 0.5-4 h) induces autophagy in the MM.1S cell line[1]. 8-Aminoadenosine (3 μM; 2-16 h) causes a greater drop in ATP levels in the MM.1S cells[1]. 8-Aminoadenosine (3 μM; 5 h) causes a 50% reduction in glucose consumption in MM.1S cells[1]. 8-Aminoadenosine (3 μM; 5 h) indicates a time-dependent decrease in GLUT1 expression at 5 h, whereas at 24 h there was a down-regulation of both transporters (GLUT1 and GLUT4) in MM.1S cells[1]. 8-Aminoadenosine inhibits cell proliferation, activated cell death, and does not activate transcription of the p53 target gene p21 or increase protein levels of either p53 or p21[1]. The toxic effects of 8-Aminoadenosine require adenosine kinase activity to convert 8-Aminoadenosine to 8-NH2-ATP in adenosine kinase-deficient cells[1]. Cell Viability Assay[1] Cell Line: MM.1S and U266 cells Concentration: 0.1, 0.3, 1, 3, 10 μM Incubation Time: For 48 hours Result: Had IC50s of 1.5 μM and 8.88 μM in MM.1S and U266 cells, respectively. Apoptosis Analysis[2] Cell Line: MCF-7 cells Concentration: 10 μM Incubation Time: For 24 hours Result: Induced significant apoptotic death. Apoptosis was not inhibited by knockdown of functional p53. Apoptosis Analysis[1] Cell Line: MM.1S cell line Concentration: 3 μM Incubation Time: 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4 hours Result: Induced the formation of LC3-II protein. Caused the appearance of a population with a high AVO content with 1 μM for 24 hours.
References

[1]. Mala Shanmugam, et al. Targeting glucose consumption and autophagy in myeloma with the novel nucleoside analogue 8-aminoadenosine. J Biol Chem. 2009 Sep 25;284(39):26816-30.

[2]. Alla Polotskaia, et al. 8-Amino-adenosine activates p53-independent cell death of metastatic breast cancers. Mol Cancer Ther. 2012 Nov;11(11):2495-504.

[3]. Jennifer Ann Frey, et al. 8-Amino-adenosine inhibits multiple mechanisms of transcription. Mol Cancer Ther. 2010 Jan;9(1):236-45.

 Chemical & Physical Properties

Density 2.25g/cm3
Boiling Point 747.1ºC at 760mmHg
Melting Point 180-185ºC dec.
Molecular Formula C10H14N6O4
Molecular Weight 282.26
Flash Point 405.6ºC
Exact Mass 282.10800
PSA 165.56000
Appearance of Characters white to beige
Storage condition -20?C Freezer
Water Solubility H2O: soluble2mg/mL, clear (warmed)

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Hazard Codes T
Risk Phrases 25
Safety Phrases 45
RIDADR UN 2811 6.1 / PGIII

 Synthetic Route

~95%

8-Aminoadenosine Structure

8-Aminoadenosine

CAS#:3868-33-5

Literature: Postigo, Al; Kopsov, Sergey; Ferreri, Carla; Chatgilialoglu, Chryssostomos Organic Letters, 2007 , vol. 9, # 25 p. 5159 - 5162

~29%

8-Aminoadenosine Structure

8-Aminoadenosine

CAS#:3868-33-5

Literature: Repkova; Ivanova; Komarova; Meshchaninova; Kuznetsova; Venyaminova Russian Journal of Bioorganic Chemistry, 1999 , vol. 25, # 9 p. 612 - 622

~20%

Detail
Literature: Nilov, Denis I.; Komarov, Dmitry Y.; Panov, Maxim S.; Karabaeva, Kanykey E.; Mereshchenko, Andrey S.; Tarnovsky, Alexander N.; Wilson, R. Marshall Journal of the American Chemical Society, 2013 , vol. 135, # 9 p. 3423 - 3438

~%

8-Aminoadenosine Structure

8-Aminoadenosine

CAS#:3868-33-5

Literature: Liu, Jie; Barrio, Jorge R.; Satyamurthy, Nagichettiar Journal of Fluorine Chemistry, 2006 , vol. 127, # 9 p. 1175 - 1187

~7%

8-Aminoadenosine Structure

8-Aminoadenosine

CAS#:3868-33-5

Literature: Nilov, Denis I.; Komarov, Dmitry Y.; Panov, Maxim S.; Karabaeva, Kanykey E.; Mereshchenko, Andrey S.; Tarnovsky, Alexander N.; Wilson, R. Marshall Journal of the American Chemical Society, 2013 , vol. 135, # 9 p. 3423 - 3438

~%

8-Aminoadenosine Structure

8-Aminoadenosine

CAS#:3868-33-5

Literature: Liu, Jie; Barrio, Jorge R.; Satyamurthy, Nagichettiar Journal of Fluorine Chemistry, 2006 , vol. 127, # 9 p. 1175 - 1187

 Articles10

More Articles
Property editing of peptide nucleic acids (PNA): gem-dimethyl, cyanuryl and 8-aminoadenine PNAs.

Nucleic Acids Symp. Ser. (51) , 17-8, (2007)

We herein describe the introduction of gem-dimethyl substitution into the aminoethylglycyl backbone of PNA to impart steric constraint and pre-organise PNA for selective recognition of nucleic acids. ...

Targeting glucose consumption and autophagy in myeloma with the novel nucleoside analogue 8-aminoadenosine.

J. Biol. Chem. 284(39) , 26816-30, (2009)

Multiple myeloma, an incurable plasma cell malignancy, is characterized by altered cellular metabolism and resistance to apoptosis. Recent connections between glucose metabolism and resistance to apop...

8-Amino-adenosine induces loss of phosphorylation of p38 mitogen-activated protein kinase, extracellular signal-regulated kinase 1/2, and Akt kinase: role in induction of apoptosis in multiple myeloma.

Mol. Cancer Ther. 4(4) , 569-77, (2005)

Multiple myeloma is a slowly proliferating B-cell malignancy that accumulates apoptosis-resistant and replication-quiescent cell populations, posing a challenge for current chemotherapeutics that targ...

 Synonyms

8-Amino-adenosin
8-Amino Adenosine
8-Aminoadenosine
8-Amino-D-adenosine
Top Suppliers:I want be here



Get all suppliers and price by the below link:

8-Aminoadenosine suppliers

8-Aminoadenosine price