CHIR-090
- Product Name
- CHIR-090
- CAS No.
- 728865-23-4
- Chemical Name
- CHIR-090
- Synonyms
- CS-2285;CHIR-090;CHIR-090 (CHIR 090;CHIR-090, 10 mM in DMSO;N-((2S,3R)-3-Hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide;N-[(1S,2R)-2-Hydroxy-1-[(hydroxyamino)carbonyl]propyl]-4-[[4-(4-morpholinylmethyl)phenyl]ethynyl]benzamide;N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide;Benzamide, N-[(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl]-4-[2-[4-(4-morpholinylmethyl)phenyl]ethynyl]-;N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morphChemicalbookolin-4-ylmethyl)phenyl]ethynyl]benzamide
- CBNumber
- CB62645119
- Molecular Formula
- C24H27N3O5
- Formula Weight
- 437.49
- MOL File
- 728865-23-4.mol
CHIR-090 Property
- Density
- 1.33±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- ≥21.85 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O
- form
- solid
- pka
- 9.11±0.40(Predicted)
- color
- White to off-white
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H315Causes skin irritation
H317May cause an allergic skin reaction
H318Causes serious eye damage
H334May cause allergy or asthma symptoms or breathing difficulties if inhaled
H341Suspected of causing genetic defects
H361Suspected of damaging fertility or the unborn child
H370Causes damage to organs
H413May cause long lasting harmful effects to aquatic life
- Precautionary statements
-
P201Obtain special instructions before use.
P202Do not handle until all safety precautions have been read and understood.
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P272Contaminated work clothing should not be allowed out of the workplace.
P273Avoid release to the environment.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P284Wear respiratory protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313IF exposed or concerned: Get medical advice/attention.
P310Immediately call a POISON CENTER or doctor/physician.
P321Specific treatment (see … on this label).
P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.
P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P363Wash contaminated clothing before reuse.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- SML3092
- Product name
- CHIR-090
- Purity
- ≥98% (HPLC)
- Packaging
- 5MG
- Price
- $158
- Updated
- 2025/07/31
- Product number
- SML3092
- Product name
- CHIR-090
- Purity
- ≥98% (HPLC)
- Packaging
- 25MG
- Price
- $481
- Updated
- 2025/07/31
- Product number
- 22256
- Product name
- CHIR090
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $57
- Updated
- 2024/03/01
- Product number
- 22256
- Product name
- CHIR090
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $166
- Updated
- 2024/03/01
- Product number
- 22256
- Product name
- CHIR090
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $275
- Updated
- 2024/03/01
CHIR-090 Chemical Properties,Usage,Production
Description
CHIR-090 is the first reported compound that in fact kills both E. coli and Pseudomonas aeruginosa in bacterial disk diffusion assays (Liang et al. 2011). Nonetheless, CHIR-090 was about 600-fold less effective against LpxC orthologs from the Rhizobiaceae family than against E. coli LpxC. In this way, studies have shown that the removal of morpholine ring, based on a chemical scaffold of reduced radius, was able to increase affinity by 20-fold for LpxC enzymes from the Rhizobiaceae family of bacteria and enhance the antibiotic activity against E. coli and P. aeruginosa by 2–4 fold over CHIR-090.
Uses
CHIR-090 is a potent, slow, tight-binding inhibitor of the LpxC deacetylase. It binds to E. coli LpxC with a Ki of 4.0 nM. CHIR-090 is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Definition
ChEBI: CHIR-090 is an L-threonine derivative obtained by formal condensation of the carboxy group of 4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzoic acid with the amino group of N-hydroxy-L-threoninamide. It has a role as an antimicrobial agent, a lipopolysaccharide biosynthesis inhibitor and an EC 3.5.1.108 (UDP-3-O-acyl-N-acetylglucosamine deacetylase) inhibitor. It is an acetylenic compound, a member of morpholines, a member of benzamides, a L-threonine derivative and a hydroxamic acid.
Synthesis
728878-12-4
728865-23-4
General procedure for the synthesis of N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide from CHIR090-Intermediate 1: To a stirred anhydrous methanol (5 mL) of hydroxylamine hydrochloride (400 mg, 5.76 mmol) at 0 °C and under nitrogen protection solution was slowly added sodium methanol (25 wt% methanol solution, 1.860 g, 8.60 mmol). After the reaction mixture was stirred at 0 °C for 20 min, a 1:1 methanol/THF (6 mL) solution of methyl ester 4 (829 mg, 1.90 mmol) was added. Subsequently, the reaction mixture was continued to be stirred at 0°C for 1 hr and then brought to room temperature and stirred for 4 hr. Upon completion of the reaction, the reaction was quenched with 1.0 M hydrochloric acid (6 mL), the organic solvent was removed by concentration by rotary evaporation, and the residue was diluted with DMSO (4 mL). Analytical reversed-phase high-performance liquid chromatography (RP-HPLC, C18 column, acetonitrile gradient 5-35% with 0.1% trifluoroacetic acid, UV detection wavelength 300 nm, run time 16 min) showed a purity of 85% for the crude product mixture. Purification of the crude product by preparative RP-HPLC and lyophilization of the collected fractions gave the target compound 5 (701 mg, 81% yield) as a fluffy white solid. Low resolution mass spectrometry (ESI+) m/z 438.1 (calculated value of 438.20 for C24H27N3O5+H); reversed-phase high-performance liquid chromatography (300 nm, 16-minute run time) retention time was 8.7 minutes.
in vivo
CHIR-090 is a potent antibiotic against E. coli and inhibits E. coli LpxC activity in vitro in the low nM range. E. coli W3110 colonies resistant to 1 μg/mL CHIR-090 are not observed without prior chemical mutagenesis. A strain of E. coli W3110 is able to grow on LB agar plates containing 1 to 10 μg/mL CHIR-090, which is 4 to 40 times above the MIC of 0.25 μg/mL under our conditions for wild-type E. coli W3110. The doubling time of W3110RL is 40 min in the presence of 1 μg/mL CHIR-090, which is exactly the same rate as wild-type in the absence of inhibitor. Wild-type cells stopped growing after about 2 h in the presence of 1 μg/mL CHIR-090[1].
target
LpxC
References
[1] Barb AW, et al. Inhibition of lipid A biosynthesis as the primary mechanism of CHIR-090 antibiotic activity in Escherichia coli. Biochemistry. 2007 Mar 27;46(12):3793-802. DOI:10.1021/bi6025165
[2] Barb AW, et al. Structure of the deacetylase LpxC bound to the antibiotic CHIR-090: Time-dependent inhibition and specificity in ligand binding. Proc Natl Acad Sci U S A. 2007 Nov 20;104(47):18433-8. DOI:10.1073/pnas.0709412104
[3] Tan JH, et al. In Vitro and In Vivo Efficacy of an LpxC Inhibitor, CHIR-090, Alone or Combined with Colistin against Pseudomonas aeruginosa Biofilm. Antimicrob Agents Chemother. 2017 Jun 27;61(7). pii: e02223-16. DOI:10.1128/AAC.02223-16
CHIR-090 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from CHIR-090 manufacturers
- Product
- N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide 728865-23-4
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- Min98% HPLC
- Supply Ability
- g/kg/ton
- Release date
- 2019-12-23