AMI-1 free acid

Modify Date: 2024-01-13 17:35:49

AMI-1 free acid Structure
AMI-1 free acid structure
Common Name AMI-1 free acid
CAS Number 134-47-4 Molecular Weight 504.49000
Density 1.798 g/cm3 Boiling Point N/A
Molecular Formula C21H16N2O9S2 Melting Point 86-88 °C
MSDS N/A Flash Point N/A

 Use of AMI-1 free acid


AMI-1 free acid is a potent, cell-permeable and reversible inhibitor of protein arginine N-methyltransferases (PRMTs), with IC50s of 8.8 μM and 3.0 μM for human PRMT1 and yeast-Hmt1p, respectively. AMI-1 free acid exerts PRMTs inhibitory effects by blocking peptide-substrate binding[1].

 Names

Name 7,7'-(Carbonylbis(azanediyl))bis(4-hydroxynaphthalene-2-sulfonic acid)
Synonym More Synonyms

 AMI-1 free acid Biological Activity

Description AMI-1 free acid is a potent, cell-permeable and reversible inhibitor of protein arginine N-methyltransferases (PRMTs), with IC50s of 8.8 μM and 3.0 μM for human PRMT1 and yeast-Hmt1p, respectively. AMI-1 free acid exerts PRMTs inhibitory effects by blocking peptide-substrate binding[1].
Related Catalog
Target

IC50: 8.8 μM (PRMT1), 3.0 μM (yeast-Hmt1p)[1]

In Vitro AMI-1 free acid can inhibit the in vitro methylation reactions performed by all five recombinantly active PRMTs (PRMT1, -3, -4, and -6 and Hmt1p)[2]. AMI-1 free acid not only inhibits type I PRMTs (PRMT1, 3, 4 and 6) but also type II PRMT5[2]. AMI-1 free acid specifically inhibits arginine, but not lysine, methyltransferase activity in vitro and does not compete for the AdoMet binding site[3]. AMI-1 free acid inhibits methylation of GFP-Npl3 and cellular proteins[3]. AMI-1 free acid (0.6-2.4 mM; 48-96 hours) inhibits the cell viability of sarcoma in S180 and U2OS cells in a time-dependent and dose-dependent manner in vitro[4]. AMI-1 free acid (1.2-2.4 mM; 48-72 hours) reduces S180 cell viability through the induction of cell apoptosis[4]. Cell Viability Assay[4] Cell Line: S180 cells, U2OS cells Concentration: 0.6 mM, 1.2 mM, 2.4 mM Incubation Time: 48 hours, 72 hours, 96 hours Result: Inhibited the cell viability. Apoptosis Analysis[4] Cell Line: S180 cells Concentration: 1.2 mM, 2.4 mM Incubation Time: 48 hours, 72 hours Result: Increased the percentages of cells undergoing apoptosis.
In Vivo AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) inhibits S180 viability in vivo[4]. AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) downregulates PRMT5 but does not regulate the expression of PRMT7 in a tumor xenograft model[4]. AMI-1 free acid (0.5 mg; intratumorally; daily; for 7 days) decreases the levels of H4R3me2s and H3R8me2s in a tumor xenograft model[4]. Animal Model: 6-7 weeks old male Kunming mice (18-22 g), with S180 cells xenograft[4] Dosage: 0.5 mg Administration: Intratumorally, daily, for 7 days Result: Decreased tumor weight.
References

[1]. Donghang Cheng, et al. Small Molecule Regulators of Protein Arginine Methyltransferases. J Biol Chem. 2004 Jun 4;279(23):23892-9.

[2]. Zhang, B., et al. Targeting protein arginine methyltransferase 5 inhibits colorectal cancer growth by decreasing arginine methylation of eIF4E and FGFR3. Oncotarget. 2015 Sep 8;6(26):22799-811.

[3]. Donghang Cheng, et al. Small Molecule Regulators of Protein Arginine Methyltransferases. J Biol Chem. 2004 Jun 4;279(23):23892-9.

[4]. Baolai Zhang, et al. Arginine Methyltransferase inhibitor-1 Inhibits Sarcoma Viability in vitro and in vivo. Oncol Lett. 2018 Aug;16(2):2161-2166.

 Chemical & Physical Properties

Density 1.798 g/cm3
Melting Point 86-88 °C
Molecular Formula C21H16N2O9S2
Molecular Weight 504.49000
Exact Mass 504.03000
PSA 207.09000
LogP 5.84920
Index of Refraction -45 ° (C=1, AcOH)

 MSDS

Material Safety Data Sheet

Section1. Identification of the substance
Product Name: 6,6’-Ureylene-bis(1-naphthol-3-sulfonic acid)
Synonyms:

Section2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

Section3. Composition/information on ingredients.
Ingredient name:6,6’-Ureylene-bis(1-naphthol-3-sulfonic acid)
CAS number:134-47-4

Section4. First aid measures
Skin contact:Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact:Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation:Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion:Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

Section5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

Section6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution:Wear approved mask/respirator
Hand precaution:Wear suitable gloves/gauntlets
Skin protection:Wear suitable protective clothing
Eye protection:Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

Section7. Handling and storage
Handling:This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

Section8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

Section9. Physical and chemical properties
Appearance:Not specified
Boiling point:No data
No data
Melting point:
Flash point:No data
Density:No data
Molecular formula:C21H16N2O9S2
Molecular weight:504.5

Section10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

Section11. Toxicological information
No data.

Section12. Ecological information
No data.

Section13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

Section14. Transportation information
Non-harzardous for air and ground transportation.

Section15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.


SECTION 16 - ADDITIONAL INFORMATION
N/A

 Safety Information

Hazard Codes Xi
Safety Phrases S22-S24/25
WGK Germany 3
HS Code 2922210000

 Synthetic Route

~90%

AMI-1 free acid Structure

AMI-1 free acid

CAS#:134-47-4

Literature: Ragno, Rino; Simeoni, Silvia; Castellano, Sabrina; Vicidomini, Caterina; Mai, Antonello; Caroli, Antonella; Tramontano, Anna; Bonaccini, Claudia; Trojer, Patrick; Bauer, Ingo; Brosch, Gerald; Sbardella, Gianluca Journal of Medicinal Chemistry, 2007 , vol. 50, # 6 p. 1241 - 1253

~%

AMI-1 free acid Structure

AMI-1 free acid

CAS#:134-47-4

Literature: DE116200 ;

 Precursor & DownStream

Precursor  3

DownStream  0

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

6,6'-Ureylene-bis(1-naphthol-3-sulfonic acid)
EINECS 205-142-9
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