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SIBA

Cat No.:V30766 Purity: ≥98%
SIBA (5'-Isobutylthioadenosine) is a Transmethylation inhibitor (SAH analog) with potent antiproliferation activity.
SIBA
SIBA Chemical Structure CAS No.: 35899-54-8
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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5mg
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Product Description
SIBA (5'-Isobutylthioadenosine) is a Transmethylation inhibitor (SAH analog) with potent antiproliferation activity. SIBA reversibly inhibits HSV-1 production by blocking methylation, specifically blocking the 5' end capping of viral mRNA. SIBA also suppresses the growth of tumor cell lines in vitro and metastatic spread in vivo. SIBA may be utilized in cancer, HSV-1 infection and anti-malarial research.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Strong antiproliferative action against 3LL and RMS-J1 tumor cells is demonstrated by SIBA (0.5 mM; 24-96 h) [1]. In HEp2 cells infected with HSV-1, SIBA (1 mM; 12, 24 hours) reversibly reduces HSV production [2]. After ten hours, SIBA reduced the amount of protein synthesis infected with HSV-1 in HEp2 cells by 98% [2]. In HEp2 cells infected with HSV-1, SIBA (1 mM; 8.5 hours) suppresses RNA methylation and protein production [2]. SIBA (0.5, 1.0 mM; 24, 48 hours) interferes with polyamine production, possibly by blocking aminopropyltransferase, and reversibly inhibits the conversion of putrescine to spermidine and/or spermine[3].
ln Vivo
Tumor growth is inhibited in vivo by SIBA (150 mg/kg; intraperitoneal injection; twice weekly for 3 weeks) [1]. In vivo, SIBA (15 mg/kg; intraperitoneal injection; three times a week for four weeks) prevents RMS-J1 cells from spreading metastatically [1].
Cell Assay
Cell proliferation assay [1]
Cell Types: 3 LL and RMS-J1 Cell
Tested Concentrations: 0.5 mM
Incubation Duration: 24-96 hrs (hours)
Experimental Results: Effectively inhibited the growth of 3LL and RMS-J1 tumor cells by 96% and 88%, respectively.

Cell viability assay [2]
Cell Types: HEp2 cells (HSV-1 infection)
Tested Concentrations: 1 mM
Incubation Duration: 12, 24 hrs (hours)
Experimental Results: At 12 hrs (hours) and 24 hrs (hours), virus production was diminished by 88.4% and 98.2%, respectively.

Cell viability assay [2]
Cell Types: HEp2 cells (HSV-1 infection)
Tested Concentrations: 1 mM
Incubation Duration: 8.5 hrs (hours)
Experimental Results: Protein synthesis diminished by 41.3% in normal medium and 63.5% in medium lacking methionine %. Inhibits RNA methylation by 65.4%.

Cell viability assay [3]
Cell Types: Chicken embryo fibroblasts
Tested Concentrations: 0.5, 1.0 mM
Incubation Duration: 24, 48 h
Experimental Results: Inhibition of radioactive diamine uptake, and the inhibition was dose-dependent. Dramatically inhibits the formation of [14C]spermidine and [14C]spermine from [14C]putrescine. Mainly inhibits th
Animal Protocol
Animal/Disease Models: C57BL/6 female mice (4-8 weeks old) [1].
Doses: 150 mg/kg
Route of Administration: intraperitoneal (ip) injection; twice a week for 3 weeks.
Experimental Results: The median number of lung metastases was Dramatically diminished.

Animal/Disease Models: Adult syngeneic Wistar AG rats (8 weeks old; subcutaneously (sc) (sc) transplanted with RMS-J1 cells) [1].
Doses: 15 mg/kg
Route of Administration: intraperitoneal (ip) injection; three times a week for 4 weeks.
Experimental Results: Inhibiting the metastasis and spread of RMS-J1 cells in vivo, the median number of lung metastasis nodules was 26.
References

[1]. 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]. 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]. 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.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H21N5O3S
Molecular Weight
339.41324
Exact Mass
339.137
CAS #
35899-54-8
PubChem CID
123674
Appearance
Off-white to gray solid powder
LogP
0.998
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
5
Heavy Atom Count
23
Complexity
405
Defined Atom Stereocenter Count
4
SMILES
CC(C)CSC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
InChi Key
JDDUQGRUPLKDNT-IDTAVKCVSA-N
InChi Code
InChI=1S/C14H21N5O3S/c1-7(2)3-23-4-8-10(20)11(21)14(22-8)19-6-18-9-12(15)16-5-17-13(9)19/h5-8,10-11,14,20-21H,3-4H2,1-2H3,(H2,15,16,17)/t8-,10-,11-,14-/m1/s1
Chemical Name
(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(2-methylpropylsulfanylmethyl)oxolane-3,4-diol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~294.63 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.37 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.37 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.37 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 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

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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