Azoramide

Alias: Azoramide

Cat No.:V3175 Purity: ≥98%

COA Product Data Instructions for use SDS

Azoramide is a small-molecule modulator ofthe unfolded protein response (UPR) and an ER stress alleviator that is reported to haveantidiabetic activity.

Azoramide Chemical Structure CAS No.: 932986-18-0
Product category: Apoptosis

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

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Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2024 Dec 18.

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

Cell 2020,183:1202-1218.e25.

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Nat Metab 2024, 6: 1108-1127.

Cell Stem Cell 2024, 31:106-126.e13.

Nature 597, 119–125 (2021)

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

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

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Science Trans Med 2023, 15: eadd7872.

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Immunity 2024,57:2651-2668.e12.

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

Azoramide is a small-molecule modulator of the unfolded protein response (UPR) and an ER stress alleviator that is reported to have antidiabetic activity. It can improve ER protein-folding ability and activates ER chaperone capacity to protect cells against ER stress. Azoramide also displayed potent antidiabetic efficacy in two mouse models with obesity by improving by improving peripheral insulin sensitivity and pancreatic β-cell function. Therefore, azoramide has the potential to be developed as a drug for type 2 diabete. In addition, a recent study showed that azoramide may serve as an antagonist against GLP-1R in MSC (mesenchymal stem cells) lineage determination, and azoramide favors adipogenesis against osteogenesis through inhibiting the GLP-1 receptor-PKA-β-catenin pathway.

Biological Activity I Assay Protocols (From Reference)

Targets

UPR

ln Vitro

Azoramide may be protective because it increases chaperone expression while decreasing protein synthesis and does not cause cytotoxicity or apoptosis. To fully increase chaperone capacity, azoramide may need the IRE1 and PERK branches of the UPR to be present and functional. Azoramide has been discovered to be a particular type of compound with the dual ability to promote ER homeostasis by activating ER chaperone capacity both acutely and chronically. Its treatment effectively shields cells from ER stress conditions brought on by chemicals. During ER stress brought on by metabolic stress, azoramide maintains beta cell survival and function. Azoramide pretreatment's initial action does not compromise ER function. Treatment with azoramide increases SERCA expression, which improves Ca+2 retention in the ER. Azoramide interacts with UPR pathways to support ER stress resolution and enhance ER functionality[1].

ln Vivo

In mice with genetic obesity and diet-induced obesity, azoramide improves glucose homeostasis. Surprisingly, azoramide treatment significantly increases beta cell function, glucose tolerance, and insulin sensitivity in obese mice in several preclinical models[1].

Cell Assay

In either the absence or presence of 20 mM azoramide, INS1 cells are treated for 60 hours with 25 mM glucose and 500 mM palmitate (G/P). Using the CellTiter-Glo cell viability assay system, viability is evaluated after incubation.

Animal Protocol

i.p. injection; azoramide compound (20 mg/ml, 30 μl per injection) was administered via intraperitoneal injection once a day for 14 consecutive days.

C57BL/6 mice

References

[1]. Phenotypic assays identify azoramide as a small-molecule modulator of the unfolded protein response with antidiabetic activity. Sci Transl Med. 2015 Jun 17;7(292):292ra98.

[2]. Azoramide protects iPSC-derived dopaminergic neurons with PLA2G6 D331Y mutation through restoring ER function and CREB signaling. Cell Death Dis. 2020 Feb 18;11(2):130.

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

Physicochemical Properties

Molecular Formula

C15H17CLN2OS

Molecular Weight

308.83

Exact Mass

308.075

Elemental Analysis

C, 58.34; H, 5.55; Cl, 11.48; N, 9.07; O, 5.18; S, 10.38

CAS #

932986-18-0

Related CAS #

932986-18-0

PubChem CID

7518316

Appearance

White to off-white solid powder

Density

1.2±0.1 g/cm3

Index of Refraction

1.574

LogP

3.97

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Heavy Atom Count

Complexity

308

Defined Atom Stereocenter Count

SMILES

O=C(CCC)NCCC1=CSC(C2C=CC(Cl)=CC=2)=N1

InChi Key

VYBFWKKCWTXCQX-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H17ClN2OS/c1-2-3-14(19)17-9-8-13-10-20-15(18-13)11-4-6-12(16)7-5-11/h4-7,10H,2-3,8-9H2,1H3,(H,17,19)

Chemical Name

N-[2-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]ethyl]butanamide

Synonyms

Azoramide

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: >61 mg/mL (~197.5 mM)

Water: < 1mg/mL

Ethanol: >61 mg/mL (~197.5 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.10 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 (8.10 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 (8.10 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	3.2380 mL	16.1901 mL	32.3803 mL
	5 mM	0.6476 mL	3.2380 mL	6.4761 mL
	10 mM	0.3238 mL	1.6190 mL	3.2380 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

Concentration

Volume

Molecular Weight*

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

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.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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

Total molecular weight

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.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

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.)

% DMSO

% Tween 80

% ddH₂O

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

Reduced BMP2-induced bone formation in azoramide-treated mice.Stem Cell Res Ther. 2018; 9: 57.
Inhibited osteogenic differentiation potential of C3H10T1/2 cells with azoramide treatment in vitro.Stem Cell Res Ther. 2018; 9: 57.
Enhanced adipogenic differentiation potential of C3H10T1/2 cells and mouse-derived MSCs with azoramide treatment in vitro.Stem Cell Res Ther. 2018; 9: 57.
Ex-4 treatment attenuated azoramide effects on suppressing C3H10T1/2 cell osteoblast differentiation and promoting their differentiation into adipocytes.Stem Cell Res Ther. 2018; 9: 57.

Azoramide

GLP-1R silencing abolished the azoramide (Azo) regulatory effects of suppressing C3H10T1/2 cell osteoblast differentiation and promoting their differentiation into adipocytes.Stem Cell Res Ther. 2018; 9: 57.

Decreased expression levels of protein kinase A (PKA) with azoramide (Azo) treatment.Stem Cell Res Ther. 2018; 9: 57.
Stem Cell Res Ther. 2018; 9: 57.
Image depicting the main facts observed of azoramide pre-treatment on ER homeostasis.Ann Transl Med. 2016 Oct; 4(Suppl 1): S45
Azoramideregulates ER folding and secretion capacity without inducing ER stress.Sci Transl Med.2015 Jun 17;7(292):292ra98.
Azoramideprotects against chemically-induced ER stress in vitro.Sci Transl Med.2015 Jun 17;7(292):292ra98.
Azoramideinduces weight loss, changes in energy expenditure and improved metabolic profile in mice with diet-induced obesity.Sci Transl Med.2015 Jun 17;7(292):292ra98.
Azoramideimproves ER function, insulin secretion and survival in beta cells.Sci Transl Med.2015 Jun 17;7(292):292ra98.
Azoramidetreatment alters ER calcium homeostasis.Sci Transl Med.2015 Jun 17;7(292):292ra98.
Azoramidereduces ER stress and improves metabolism inob/obmice.Sci Transl Med.2015 Jun 17;7(292):292ra98.
Reporter systems monitor ER chaperone availability and activity.Sci Transl Med.2015 Jun 17;7(292):292ra98.