TEI-9647

Alias: TEI 9647; TEI9647; TEI-9647

Cat No.:V12071 Purity: ≥98%

COA Product Data Instructions for use SDS

TEI-9647 (TEI9647) is a vitamin D receptor (VDR) antagonist with immunomodulatory effects.

TEI-9647 Chemical Structure CAS No.: 173388-20-0
Product category: VD VDR

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of TEI-9647:

TEI-9648

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Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

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Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Biological Data

Product Description

TEI-9647 (TEI9647) is a vitamin D receptor (VDR) antagonist with immunomodulatory effects. It prevents the production of osteoclasts from pagetic bone marrow cells that are brought on by 1,25-dihydroxyvitamin D3.

Biological Activity I Assay Protocols (From Reference)

ln Vitro	TEI-9647 (100 nM; 24 hours) treatment distinctly reduces the expression of the p21WAF1,CIP1 gene that is triggered by 1α,25(OH)2D3[1]. TEI-9647 (10-1000 nM; 96 hours) blocks in a dose-dependent manner the reciprocal changes in CD11b and CD71 expression linked to 1α,25(OH)2D3-induced HL-60 cell differentiation. At 100 nM, TEI-9647 totally inhibits both the rise in CD11b and the fall in CD71 expression[1]. TEI-9647 blocks the luciferase reporter's activation in COS-7 cells transfected with the human vitamin D nuclear receptor and rat 25(OH)D3-24-hydroxylase gene's DRE, as well as 1α,25(OH)2D3-mediated HL-60 cell differentiation[1]. TEI-9647 cannot bring about cell differentiation in HL-60 cells, not even after treatment at 1 μM. TEI-9647 is unable to activate α-NB esterase or NBT-reducing activity on its own. On the other hand, 1α,25(OH)2D3 (0.1 nM)-induced up-regulation in HL-60 cells is significantly suppressed by TEI-9647[1]. TEI-9647 (0.001-1 μM; for 10 days) inhibits bone resorption caused by 1α,25(OH)2D3 (1 nM) in a dose-dependent manner. Even at 1 μM, TEI-9647 by itself never causes bone resorption[2]. TEI-9647 (10 nM; 12 h) significantly reduces the expression of the genes TAFII-17 and 25-OH-D3-24-hydroxylase that are brought on in bone marrow cells by 1α,25(OH)2D3 (0.1 nM)[2].
References	[1]. Antagonistic action of novel 1α,25-dihydroxyvitamin D3-26, 23-lactone analogs on differentiation of human leukemia cells (HL-60) induced by 1α,25-dihydroxyvitamin D3. J Biol Chem. 1999 Jun 4;274(23):16392-9. [2]. Vitamin D antagonist, TEI-9647, inhibits osteoclast formation induced by 1α,25-dihydroxyvitamin D3 from pagetic bone marrow cells. J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):331-4. [3]. Synthesis and structure-activity relationships of TEI-9647 derivatives as Vitamin D3 antagonists. J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):31-4.

ln Vitro

TEI-9647 (100 nM; 24 hours) treatment distinctly reduces the expression of the p21WAF1,CIP1 gene that is triggered by 1α,25(OH)2D3[1].
TEI-9647 (10-1000 nM; 96 hours) blocks in a dose-dependent manner the reciprocal changes in CD11b and CD71 expression linked to 1α,25(OH)2D3-induced HL-60 cell differentiation. At 100 nM, TEI-9647 totally inhibits both the rise in CD11b and the fall in CD71 expression[1].
TEI-9647 blocks the luciferase reporter's activation in COS-7 cells transfected with the human vitamin D nuclear receptor and rat 25(OH)D3-24-hydroxylase gene's DRE, as well as 1α,25(OH)2D3-mediated HL-60 cell differentiation[1].
TEI-9647 cannot bring about cell differentiation in HL-60 cells, not even after treatment at 1 μM. TEI-9647 is unable to activate α-NB esterase or NBT-reducing activity on its own. On the other hand, 1α,25(OH)2D3 (0.1 nM)-induced up-regulation in HL-60 cells is significantly suppressed by TEI-9647[1].
TEI-9647 (0.001-1 μM; for 10 days) inhibits bone resorption caused by 1α,25(OH)2D3 (1 nM) in a dose-dependent manner. Even at 1 μM, TEI-9647 by itself never causes bone resorption[2].
TEI-9647 (10 nM; 12 h) significantly reduces the expression of the genes TAFII-17 and 25-OH-D3-24-hydroxylase that are brought on in bone marrow cells by 1α,25(OH)2D3 (0.1 nM)[2].

References

[1]. Antagonistic action of novel 1α,25-dihydroxyvitamin D3-26, 23-lactone analogs on differentiation of human leukemia cells (HL-60) induced by 1α,25-dihydroxyvitamin D3. J Biol Chem. 1999 Jun 4;274(23):16392-9.

[2]. Vitamin D antagonist, TEI-9647, inhibits osteoclast formation induced by 1α,25-dihydroxyvitamin D3 from pagetic bone marrow cells. J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):331-4.

[3]. Synthesis and structure-activity relationships of TEI-9647 derivatives as Vitamin D3 antagonists. J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):31-4.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C27H38O4
Molecular Weight	426.5882
Exact Mass	426.28
Elemental Analysis	C, 76.02; H, 8.98; O, 15.00
CAS #	173388-20-0
Related CAS #	TEI-9648;173388-21-1
Appearance	Solid powder
SMILES	C[C@H](C[C@H]1CC(=C)C(=O)O1)[C@H]2CC[C@@H]\3[C@@]2(CCC/C3=C\C=C/4\C[C@H](C[C@@H](C4=C)O)O)C
InChi Key	SAODSJHDCZTVAT-CZADFQNYSA-N
InChi Code	InChI=1S/C27H38O4/c1-16(12-22-13-17(2)26(30)31-22)23-9-10-24-19(6-5-11-27(23,24)4)7-8-20-14-21(28)15-25(29)18(20)3/h7-8,16,21-25,28-29H,2-3,5-6,9-15H2,1,4H3/b19-7+,20-8-/t16-,21-,22+,23-,24+,25+,27-/m1/s1
Chemical Name	(5S)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-methylideneoxolan-2-one
Synonyms	TEI 9647; TEI9647; TEI-9647
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: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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 (~234.4 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 2.5 mg/mL (5.86 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication. 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 (5.86 mM) 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; with ultrasonication. 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. View More Solubility in Formulation 3: 2.5 mg/mL (5.86 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. 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.)

Solubility (In Vitro)

DMSO: ~100 mg/mL (~234.4 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (5.86 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
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 (5.86 mM) 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; with ultrasonication.
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.

View More

Solubility in Formulation 3: 2.5 mg/mL (5.86 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.
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	2.3442 mL	11.7209 mL	23.4417 mL
	5 mM	0.4688 mL	2.3442 mL	4.6883 mL
	10 mM	0.2344 mL	1.1721 mL	2.3442 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

Mass

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Volume

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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
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See Example

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.

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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

Molecular formula

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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
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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)

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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.

Note： (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.

Biological Data

Antagonistic action of TEI-9647 on 1α,25(OH)2D3( VDR )-mediated expression of the 25(OH)D3-24-hydroxylase gene in a luciferase reporter assay. J Biol Chem . 1999 Jun 4;274(23):16392-9.
Effects of TEI-9647 on 1α,25(OH)2D3-induced HL-60 cell differentiation as examined with cell surface marker expression. J Biol Chem . 1999 Jun 4;274(23):16392-9.
Effects of TEI-9647 and TEI-9648 on KH-1060-induced HL-60 cell differentiation. J Biol Chem . 1999 Jun 4;274(23):16392-9.
Effects of TEI-9647 and TEI-9648 on 1α,25(OH)2D3-induced HL-60 cell differentiation as examined with NBT-reducing activity. J Biol Chem . 1999 Jun 4;274(23):16392-9.