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Documentos Principais

SMB00287

Sigma-Aldrich

Formycin A

from Streptomyces kaniharaensis, ≥98% (HPLC)

Sinônimo(s):

1-C-(7-Amino-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-1,4-anhydro-(1S)-D-Ribitol, 7-Amino-3-(β-D-ribofuranosyl)-1H-pyrazolo[4,3-d]pyrimidine, 8-Aza-9-deazaadenosine, Formycin, NSC 102811

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About This Item

Fórmula empírica (Notação de Hill):
C10H13N5O4
Número CAS:
Peso molecular:
267.24
Beilstein:
624229
Número MDL:
Código UNSPSC:
51102829
ID de substância PubChem:
NACRES:
NA.85

fonte biológica

Streptomyces kaniharaensis

Nível de qualidade

Ensaio

≥98% (HPLC)

Formulário

powder

condição de armazenamento

(Keep container tightly closed in a dry and well-ventilated place.)

cor

white to off-white

solubilidade

DMSO: soluble 1 mg/mL
H2O: soluble 3 mg/mL

espectro de atividade do antibiótico

viruses (Antiretroviral)

Modo de ação

enzyme | inhibits

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

chave InChI

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Informações sobre genes

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Descrição geral

Chemical structure: nucleoside
Formycin A is an adenosine analog, and is cytotoxic in nature. It acts as a substrate for the human enzymes human erythrocytic adenosine deaminase and adenosine kinase.

Ações bioquímicas/fisiológicas

Formycin A (FA) is a C-nucleoside that inhibits the E.coli enzyme purine nucleoside phosphorylase (PNP).
Formycin A (FA) is a C-nucleoside that inhibits the E.coli enzyme purine nucleoside phosphorylase (PNP). FA was found to upsurge insulin release elevated by glucose, and was also shown to inhibit 5′-Methylthioadenosine/S-adenosylhomocysteine (MTA/AdoHcy) nucleosidase, an enzyme important in the recycling of methionine. Research has shown FA is an antiretroviral agent against HIV-1, targeting reverse transcription.
Formycin A possess antitumor function, along with its antibacterial and antiviral activity.

Embalagem

10MG

Outras notas

Keep container tightly closed in a dry and well-ventilated place.
Store the product sealed at –20 °C. Under these conditions the product is stable for at least 4 years.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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Tautomerism of the nucleoside antibiotic formycin, as studied by carbon-13 nuclear magnetic resonance.
T R Krugh
Journal of the American Chemical Society, 95(14), 4761-4762 (1973-07-11)
R P Agarwal et al.
The Journal of clinical investigation, 57(4), 1025-1035 (1976-04-01)
Deficiency of erythrocytic and lymphocytic adenosine deaminase (ADA) occurs in some patients with severe combined immunodeficiency disease (SCID). SCID with ADA deficiency is inherited as an autosomal recessive trait. ADA is markedly reduced or undetectable in affected patients (homozygotes), and
C-4? Truncated carbocyclic formycin derivatives
Zhou J, et al.
Tetrahedron, 62(29), 7009-7013 (2006)
Helmut Rosemeyer et al.
Chemistry & biodiversity, 16(4), e1900012-e1900012 (2019-02-19)
Two lipophilic derivatives of formycin A (1) and formycin B (5) carrying an O-2',3'-(ethyl levulinate) ketal group have been prepared. These were base-alkylated at N(1) (for 1) and N(1) and N(6) (for 5) with both isopentenyl and all-trans-farnesyl residues. Upon
A Bzowska et al.
Biochimica et biophysica acta, 1120(3), 239-247 (1992-04-17)
Formycin B (FB), a moderate inhibitor (Ki approximately 100 microM) of mammalian purine nucleoside phosphorylase (PNP), and formycin A (FA), which is totally inactive vs. the mammalian enzyme, are both effective inhibitors of the bacterial (Escherichia coli) enzyme (Ki approximately

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