[CAS NO. 35899-54-8] SIBA
PRODUCTS SPECIFICATIONS [35899-54-8]
DESCRIPTION [35899-54-8]
Overview
| MDL | MFCD00056008 |
|---|---|
| Molecular Weight | 339.41 |
| Molecular Formula | C14H21N5O3S |
| SMILES | O[C@@H]([C@H]([C@H](N1C=NC2=C1N=CN=C2N)O3)O)[C@H]3CSCC(C)C |
Summary
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] .
IC50 & Target
|
Plasmodium |
HSV-1 |
In Vitro
SIBA (0.5 mM; 24-96 h) shows strong anti-proliferative activity against 3LL and RMS-J1 tumour cells
[1]
.
SIBA (1 mM; 12, 24 h) reversibly inhibits HSV production in HEp2 cells (infected by HSV-1)
[2]
.
SIBA inhibits protein synthesis by 98% after 10 h infection of HEp2 cells (infected by HSV-1)
[2]
.
SIBA (1 mM; 8.5 h) inhibits protein synthesis and RNA methylation in HEp2 cells (infected by HSV-1)
[2]
.
SIBA (0.5, 1.0 mM; 24, 48 h) inhibits the conversion of putrescine into spermidine and/or spermine and that this inhibition is a reversible one (interferes with polyamine biosynthesis, probably by blocking aminopropyltransferase)
[3]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Cell Proliferation Assay [1]
| Cell Line: | 3 LL and RMS-J1 cells |
| Concentration: | 0.5 mM |
| Incubation Time: | 24-96 h |
| Result: | Inhibited 3LL and RMS-J1 tumor cell growth potently by 96% and 88%, respectively. |
Cell Viability Assay [2]
| Cell Line: | HEp2 cells (infected by HSV-1) |
| Concentration: | 1 mM |
| Incubation Time: | 12, 24 h |
| Result: | Decreased virus production by 88.4 and 98.2% when at 12 and 24 h, respectively. |
Cell Viability Assay [2]
| Cell Line: | HEp2 cells (infected by HSV-1) |
| Concentration: | 1 mM |
| Incubation Time: | 8.5 h |
| Result: |
Reduced protein synthesis by 41.3% in normal medium and by 63.5% in medium poor in methionine.
Inhibited RNA methylation by 65.4%. |
Cell Viability Assay [3]
| Cell Line: | chick embryo fibroblasts |
| Concentration: | 0.5, 1.0 mM |
| Incubation Time: | 24, 48 h |
| Result: |
Inhibited the uptake of the radioactive diamine and that the inhibition was dose-dependent.
Markedly inhibited the formation of [ 14 C]spermidine and [ 14 C]spermine from [ 14 C]putrescine. Inhibited the growth of chick embryo fibroblasts mainly after exposure for 48 h. |
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]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| 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. |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
DMSO : ≥ 100 mg/mL ( 294.63 mM )
* "≥" means soluble, but saturation unknown.
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 2.9463 mL | 14.7314 mL | 29.4629 mL |
| 5 mM | 0.5893 mL | 2.9463 mL | 5.8926 mL |
| 10 mM | 0.2946 mL | 1.4731 mL | 2.9463 mL |
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.
- [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.
- [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.