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SML2497

Sigma-Aldrich

BIO 1211 trifluoroacetate salt

≥97% (HPLC)

Synonym(s):

2-MPUPA-LDVP trifluoroacetate, 4-(N′-(2-Methylphenyl)urea)-phenylacetyl-LDVP trifluoroacetate, BIO-1211 trifluoroacetate, BIO1211 trifluoroacetate, N-[2-[4-[[[(2-Methylphenyl)amino]carbonyl]amino]phenyl]acetyl]-L-leucyl-L-α-aspartyl-L-valyl-L-proline trifluoroacetate, N-[[4-[[[(2-Methylphenyl)amino]carbonyl]amino]-phenyl]acetyl]-LDVP trifluoroacetate, N-[[4-[[[(2-Methylphenyl)amino]carbonyl]amino]-phenyl]acetyl]-Leu-Asp-Val-Pro trifluoroacetate, N-[[4-[[[(2-Methylphenyl)amino]carbonyl]amino]-phenyl]acetyl]-fibronectin CS-1 fragment (1980-1983) trifluoroacetate

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About This Item

Empirical Formula (Hill Notation):
C36H48N6O9 · xC2HF3O2
CAS Number:
187735-94-0
Molecular Weight:
708.80 (free base basis)
MDL number:
MFCD02259692
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

form

film
lyophilized powder

storage condition

desiccated

color

white to beige

shipped in

wet ice

storage temp.

−20°C

SMILES string

N3([C@@H](CCC3)C(=O)O)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)Cc1ccc(cc1)NC(=O)Nc2c(cccc2)C)CC(C)C)CC(=O)O)C(C)C

InChI

1S/C36H48N6O9/c1-20(2)17-26(38-29(43)18-23-12-14-24(15-13-23)37-36(51)40-25-10-7-6-9-22(25)5)32(46)39-27(19-30(44)45)33(47)41-31(21(3)4)34(48)42-16-8-11-28(42)35(49)50/h6-7,9-10,12-15,20-21,26-28,31H,8,11,16-19H2,1-5H3,(H,38,43)(H,39,46)(H,41,47)(H,44,45)(H,49,50)(H2,37,40,51)/t26-,27-,28-,31-/m0/s1

InChI key

NVVGCQABIHSJSQ-KFZSMJGVSA-N

Biochem/physiol Actions

BIO 1211 is a selective, tight-binding α4β1 (VLA-4, very late antigen-4; koff = 1.4 x 10-4/s, KD = 70 pM) integrin antagonist (VCAM-Ig Jurkat surface binding IC50 = 1 nM; integrin-mediated cell adhesion IC50 = 4 nM/α4β1, 2 μM/α4β7, >100 μM/α1β1, α5β1, α6β1, αLβ2, αIIBβ3) based on the Leu-Asp-Val (LDV) sequence from the alternatively spliced connecting segment-1 (CS-1) of fibronectin (aa 1980-1983). In addition to probing α4β1-mediated cellular responses, BIO 1211 is also widely used in animal disease models in vivo, including MS (5-10 mg/kg; murine EAE) and asthma (1-10 mg/kg via intranasal or nebulizer to mice, rats, sheep; 3 mg/sheep iv.).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Nourollah Ramroodi et al.
Immunological investigations, 44(7), 694-712 (2015-10-06)
Some functional limitations and economic burden of therapeutic antibodies indicated that introducing of alternative therapeutic compounds with same or different mechanism of action could be worthwhile. In this regard small-molecule antagonists can have a wide range of impacts, so in
Wei-Sheng Chen et al.
Nature communications, 7, 11302-11302 (2016-04-14)
Lymphangiogenesis plays a pivotal role in diverse pathological conditions. Here, we demonstrate that a carbohydrate-binding protein, galectin-8, promotes pathological lymphangiogenesis. Galectin-8 is markedly upregulated in inflamed human and mouse corneas, and galectin-8 inhibitors reduce inflammatory lymphangiogenesis. In the mouse model
B V Karanam et al.
Xenobiotica; the fate of foreign compounds in biological systems, 37(5), 487-502 (2007-05-25)
BIO1211 is a small peptidyl potent antagonist of the activated form of alpha4beta1 integrin. The effect of enalapril on the in vitro and in vivo cleavage of BIO1211 was investigated. In heparinized blood, plasma and rat liver, lung and intestinal
Gloria C Koo et al.
American journal of respiratory and critical care medicine, 167(10), 1400-1409 (2003-02-06)
A nonpeptidyl small molecule antagonist, compound A, to nonactivated very late antigen-4 (VLA4) was examined in lung inflammation induced by a single dose of ovalbumin challenge. Compound A presented a good pharmacokinetic property, when given intratracheally, and the blood cells
Olli-Pekka Pulkka et al.
Journal of cellular and molecular medicine, 22(4), 2220-2230 (2018-01-30)
The molecular mechanisms for the dissemination and metastasis of gastrointestinal stromal tumours (GIST) are incompletely understood. The purpose of the study was to investigate the clinical relevance of integrin alpha 4 (ITGA4) expression in GIST. GIST transcriptomes were first compared
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