2-Aminopurine

Names

[ CAS No. ]:
452-06-2

[ Name ]:
2-Aminopurine

[Synonym ]:
2-Aminoperin
iso-Adenine
2-Aminopurine
3H-Purin-2-amine
MFCD07357244
7H-Purin-2-amine
9H-Purin-2-amine
2-amino purine
EINECS 207-197-4
9H-purin-2-ylamine
Purine, 2-amino-
2-amino-6-purine
1H-Purin-2-amine
4-aminopurine
2-amino-purin
SQ 22,451

Biological Activity

[Description]:

2-Aminopurine, a fluorescent analog of guanosine and adenosine, is a widely used fluorescence-decay-based probe of DNA structure. When 2-Aminopurine is inserted in anoligonucleotide, its fluorescence is highly quenched by stacking with the natural bases. 2-Aminopurine has been used to probe nucleic acid structure and dynamics[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

2-Aminopurine (2AP) is not valuable as afluorescent label because its fluorescence is highly quenched by stacking with the natural bases, when it is inserted in anoligonucleotide. However, it is this very susceptibility to interbase quenching that makes 2AP an exquisitely sensitivefluorescent probe of nucleic acid structure[1]. 2-Aminopurine differs from adenine (6-aminopurine) only in the position of the exocyclic amine group, and yet its fluorescence intensity is one thousand times that of adenine[1].

[References]

[1]. J M Jean, et al. 2-Aminopurine fluorescence quenching and lifetimes: role of base stacking. Proc Natl Acad Sci U S A. 2001 Jan 2;98(1):37-41.

[2]. Dehong Tan, et al. Decreased glycation and structural protection properties of γ-glutamyl-S-allyl-cysteine peptide isolated from fresh garlic scales (Allium sativum L.). Nat Prod Res. 2015;29(23):2219-22.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
328.2±25.0 °C at 760 mmHg

[ Melting Point ]:
280-282 °C(lit.)

[ Molecular Formula ]:
C₅H₅N₅

[ Molecular Weight ]:
135.127

[ Flash Point ]:
152.3±23.2 °C

[ Exact Mass ]:
135.054489

[ PSA ]:
80.48000

[ LogP ]:
-1.33

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.954

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UO7475000

CHEMICAL NAME :: Purine, 2-amino-

CAS REGISTRY NUMBER :: 452-06-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 28

MOLECULAR FORMULA :: C5-H5-N5

MOLECULAR WEIGHT :: 135.15

WISWESSER LINE NOTATION :: T56 BN DM FN HNJ GZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 723 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 270 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: Specific locus test

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Embryo

DOSE/DURATION :: 100 mg/L

REFERENCE :: PNASA6 Proceedings of the National Academy of Sciences of the United States of America. (National Academy of Sciences, Printing & Pub. Office, 2101 Constitution Ave., Washington, DC 20418) V.1- 1915- Volume(issue)/page/year: 78,5685,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UO7475000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Site-specific fluorescence dynamics in an RNA 'thermometer' reveals the role of ribosome binding in its temperature-sensitive switch function.

Nucleic Acids Res. 43(1) , 493-503, (2015)

RNA thermometers control the translation of several heat shock and virulence genes by their temperature-sensitive structural transitions. Changes in the structure and dynamics of MiniROSE RNA, which r...

Pro-inflammatory cytokine/chemokine production by reovirus treated melanoma cells is PKR/NF-κB mediated and supports innate and adaptive anti-tumour immune priming.

Mol. Cancer 10 , 20, (2011)

As well as inducing direct oncolysis, reovirus treatment of melanoma is associated with activation of innate and adaptive anti-tumour immune responses.Here we characterise the effects of conditioned m...

Ligand-induced evolution of intrinsic fluorescence and catalytic activity from cobalt ferrite nanoparticles.

ChemPhysChem 16 , 1627-34, (2015)

To develop CoFe(2)O(4) as magneto-fluorescent nanoparticles (NPs) for biomedical applications, it would be advantageous to identify any intrinsic fluorescence of this important magnetic material by si...