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35899-54-8

35899-54-8 Structure

35899-54-8 Structure
IdentificationBack Directory
[Name]

5'-ISOBUTYLTHIO-5'-DEOXYADENOSINE
[CAS]

35899-54-8
[Synonyms]

SIBA
5'-Isobutylthioadenosine
5'-S-Isobutylthioadenosine
5'-S-Isobutyl-5'-deoxyadenosine
5'-Deoxy-5'-isobutylthioadenosine
5'-ISOBUTYLTHIO-5'-DEOXYADENOSINE
5''-Deoxy-5''-S-isobutyladenosine
5’-deoxy-5’-s-isobutylthioadenosine
5'-S-(2-Methylpropyl)-5'-thioadenosine
Adenosine, 5'-S-(2-methylpropyl)-5'-thio-
5'-ISOBUTYLTHIOADENOSINE;5'-DEOXY-5'-ISOBUTYLTHIOADENOSINE
5μ-Deoxy-5μ-S-isobutylthioadenosine, 5μ-S-(2-Methylpropyl)-5μ-thioadenosine
[Molecular Formula]

C14H21N5O3S
[MDL Number]

MFCD00056008
[MOL File]

35899-54-8.mol
[Molecular Weight]

339.41
Chemical PropertiesBack Directory
[Boiling point ]

631.2±65.0 °C(Predicted)
[density ]

1.63±0.1 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Inert atmosphere,2-8°C
[solubility ]

DMSO : ≥ 100 mg/mL (294.63 mM)
[form ]

Solid
[pka]

13.13±0.70(Predicted)
[color ]

Off-white to gray
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

2938909090
Hazard InformationBack Directory
[Uses]

SIBA (5'-Isobutylthioadenosine) is a transmethylation inhibitor (SAH (HY-19528) analogue), with potent anti-proliferative activity. SIBA reversibly inhibits the production of HSV-1 by blocking methylation, specifically by blocking the 5' end-capping of viral mRNA. SIBA also inhibits the growth of tumour cells in vitro and metastatic spread in vivo. SIBA can be used in cancer, HSV-1 infection and anti-malaria studies[1][2][3].
[in vivo]

SIBA (150 mg/kg; i.p.; twice weekly for 3 weeks) inhibits tumor growth in vivo[1].
SIBA (15 mg/kg; i.p.; thrice weekly for 4 weeks) inhibits metastatic spread of RMS-J1 cells in vivo[1].

Animal Model:C57BL/6 female mice (4-8 weeks old)[1].
Dosage:150 mg/kg
Administration:Intraperitoneal injection; twice weekly for 3 weeks.
Result:Significantly reduced the median number of lung metastases.
Animal Model:Adult syngeneic Wistar AG rats (8-week-old; subcutaneously grafted with RMS-J1 cells)[1].
Dosage:15 mg/kg
Administration:Intraperitoneal injection; thrice weekly for 4 weeks.
Result:Inhibited in vivo metastatic spread of RMS-J1 cells, and showed median numbers of lung metastatic nodules was 26.
[IC 50]

Plasmodium; HSV-1
[References]

[1] F Breillout , et al. Association of SIBA treatment and a Met-depleted diet inhibits in vitro growth and in vivo metastatic spread of experimental tumor cell lines. Clin Exp Metastasis. Jan-Feb 1988;6(1):3-16. DOI:10.1007/BF01580402
[2] B Jacquemont, et al. Inhibition of viral RNA methylation in herpes simplex virus type 1-infected cells by 5' S-isobutyl-adenosine. J Virol. 1977 Apr;22(1):160-7. DOI:10.1128/JVI.22.1.160-167.1977
[3] Lawrence F, et al. Effect of 5'-deoxy-5'-isobutylthioadenosine on putrescine uptake and polyamine biosynthesis by chick embryo fibroblasts. Biochem J. 1982 Jun 15;204(3):853-9. DOI:10.1042/bj2040853
Spectrum DetailBack Directory
[Spectrum Detail]

5'-ISOBUTYLTHIO-5'-DEOXYADENOSINE(35899-54-8)1HNMR
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