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2′,3′,5′-Tri-O-acetyl-6-chloroguanosine

Cat No.:V55821 Purity: ≥98%
2′,3′,5′-Tri-O-acetyl-6-chloroguanosine diacetate is an analogue of purine nucleoside.
2′,3′,5′-Tri-O-acetyl-6-chloroguanosine
2′,3′,5′-Tri-O-acetyl-6-chloroguanosine Chemical Structure CAS No.: 16321-99-6
Product category: Nucleoside Antimetabolite/Analog
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
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Product Description
2′,3′,5′-Tri-O-acetyl-6-chloroguanosine diacetate is an analogue of purine nucleoside. Purine nucleoside analogues have broad-spectrum anticancer effect targeting indolent lymphoid malignancies. The anti-cancer mechanism in this process relies on inhibiting DNA synthesis and inducing apoptosis.
2',3',5'-Tri-O-acetyl-6-chloroguanosine (also known as 2-amino-6-chloro-9-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)purine) is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. The anticancer mechanism involves inhibition of DNA synthesis and induction of apoptosis. It is a research-grade compound not approved for human therapeutic use.
Biological Activity I Assay Protocols (From Reference)
Targets
Purine nucleoside metabolism pathways, including DNA synthesis. As a purine nucleoside analog, 2',3',5'-Tri-O-acetyl-6-chloroguanosine is incorporated into DNA or RNA, disrupting nucleic acid synthesis. The compound targets rapidly dividing cells, particularly lymphoid malignancies. The acetyl groups may improve cellular uptake and stability.
ln Vitro
2',3',5'-Tri-O-acetyl-6-chloroguanosine demonstrates activity as a purine nucleoside analog in cellular assays. Purine nucleoside analogs have broad-spectrum anticancer effects. The compound inhibits DNA synthesis and induces apoptosis in cancer cells. Detailed IC50 values against specific cancer cell lines have not been disclosed in publicly available literature.
ln Vivo
In vivo activity of 2',3',5'-Tri-O-acetyl-6-chloroguanosine has not been extensively characterized in published literature. As a purine nucleoside analog, it would be expected to have antitumor activity in animal models of lymphoid malignancies. In vivo studies would be needed to evaluate its therapeutic potential. Currently, limited in vivo data are available.
Enzyme Assay
In vitro assays for purine nucleoside analogs typically involve measuring inhibition of DNA synthesis using radiolabeled thymidine incorporation. The compound is incubated with cancer cells at varying concentrations, and incorporation of labeled nucleosides is measured. Cell viability is assessed by MTT or CellTiter-Glo assays. Apoptosis is evaluated by caspase activation or Annexin V staining.
Cell Assay
Cells (e.g., lymphoid malignancy cell lines such as Jurkat, Raji, or other cancer cell lines) are cultured and treated with 2',3',5'-Tri-O-acetyl-6-chloroguanosine at concentrations typically ranging from 0.1–100 μM for 24–72 hours. DNA synthesis inhibition is measured by BrdU incorporation. Cell viability is assessed by standard assays. Apoptosis is evaluated by flow cytometry or Western blot for cleaved caspases.
Animal Protocol
In vivo animal studies for 2',3',5'-Tri-O-acetyl-6-chloroguanosine have not been reported in publicly available literature. The compound is primarily used as a research tool for nucleoside analog studies. Future studies in xenograft models of lymphoid malignancies would be needed to evaluate in vivo efficacy.
ADME/Pharmacokinetics
Pharmacokinetic data for 2',3',5'-Tri-O-acetyl-6-chloroguanosine have not been published. The compound has a molecular weight of 427.79 and formula C16H18ClN5O7. The acetyl groups may improve cellular permeability and stability. In vivo PK parameters such as half-life, bioavailability, and tissue distribution have not been characterized.
Toxicity/Toxicokinetics
Toxicology data for 2',3',5'-Tri-O-acetyl-6-chloroguanosine have not been published. The compound is for research use only and not approved for human therapeutic applications. No systematic toxicological evaluation has been performed. Standard safety precautions for handling nucleoside analogs should be observed.
References
[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.
Additional Infomation
2',3',5'-Tri-O-acetyl-6-chloroguanosine (CAS: 16321-99-6, molecular formula C16H18ClN5O7, molecular weight 427.79) is a purine nucleoside analog. It has broad antitumor activity targeting indolent lymphoid malignancies. It is not in clinical trials and has no regulatory approval. The compound is supplied as a research-grade nucleoside analog for laboratory use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H18CLN5O7
Molecular Weight
427.80
Exact Mass
427.089
CAS #
16321-99-6
PubChem CID
10788628
Appearance
Typically exists as solid at room temperature
Density
1.7g/cm3
Boiling Point
637ºC at 760mmHg
Melting Point
146.0 to 150.0 °C
Flash Point
339ºC
Vapour Pressure
4E-16mmHg at 25°C
Index of Refraction
1.69
LogP
0.967
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
8
Heavy Atom Count
29
Complexity
655
Defined Atom Stereocenter Count
4
SMILES
ClC1C2=C(N=C(N([H])[H])N=1)N(C([H])=N2)[C@@]1([H])[C@@]([H])([C@@]([H])([C@@]([H])(C([H])([H])OC(C([H])([H])[H])=O)O1)OC(C([H])([H])[H])=O)OC(C([H])([H])[H])=O
InChi Key
HLVGVJFVAKPFOZ-SDBHATRESA-N
InChi Code
InChI=1S/C16H18ClN5O7/c1-6(23)26-4-9-11(27-7(2)24)12(28-8(3)25)15(29-9)22-5-19-10-13(17)20-16(18)21-14(10)22/h5,9,11-12,15H,4H2,1-3H3,(H2,18,20,21)/t9-,11-,12-,15-/m1/s1
Chemical Name
[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2-amino-6-chloropurin-9-yl)oxolan-2-yl]methyl acetate
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3375 mL 11.6877 mL 23.3754 mL
5 mM 0.4675 mL 2.3375 mL 4.6751 mL
10 mM 0.2338 mL 1.1688 mL 2.3375 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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
  • Click the “Calculate” button
  • 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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