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Merck
CN

T7154

Tyr-Ile-Gly-Ser-Arg

≥97% (HPLC)

Synonym(s):

Laminin Fragment 929-933

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About This Item

Empirical Formula (Hill Notation):
C26H42N8O8
CAS Number:
110590-64-2
Molecular Weight:
594.66
NACRES:
NA.32
PubChem Substance ID:
24900419
UNSPSC Code:
12352209
MDL number:
MFCD00076472
Form:
powder
Assay:
≥97% (HPLC)
Biological source:
synthetic (organic)

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InChI

1S/C26H42N8O8/c1-3-14(2)21(34-22(38)17(27)11-15-6-8-16(36)9-7-15)24(40)31-12-20(37)32-19(13-35)23(39)33-18(25(41)42)5-4-10-30-26(28)29/h6-9,14,17-19,21,35-36H,3-5,10-13,27H2,1-2H3,(H,31,40)(H,32,37)(H,33,39)(H,34,38)(H,41,42)(H4,28,29,30)/t14-,17-,18-,19-,21-/m0/s1

SMILES string

CC[C@H](C)[C@H](NC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O

InChI key

MWOGMBZGFFZBMK-LJZWMIMPSA-N

biological source

synthetic (organic)

assay

≥97% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

H2O: soluble 1 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

Application

Tyr-Ile-Gly-Ser-Arg (YIGSR) can be used at the interface between the conjugated polymer and the tissue for the engineering of tissue interface. The product can also be used to study the role of integrins β1, α6, and α3 in promoting type II epithelial differentiation during lung maturation in the fetus.

Biochem/physiol Actions

Tyr-Ile-Gly-Ser-Arg (YIGSR) is a pentapeptide of the protein laminin that reduces the lung colony formation in mice administered with melanoma cells as well as can block the invasiveness of the cells in vitro. It inhibits the increased expression of endothelial nitric-oxide synthase in primary porcine aortic endothelial cells.
Tyr-Ile-Gly-Ser-Arg is a fragment of domain III of the laminin B1 chain . It is a major receptor binding site in laminin. It competes with laminin for the cell surface receptor. It is an inhibitor of tumor growth and metastasis.

Preparation Note

Tyr-Ile-Gly-Ser-Arg dissolves in water at 1 mg/ml to yield a clear, colorless solution.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000481319
0000481319
0000261358
0000261358
SLCN4078

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Yamato Kikkawa et al.
Cell adhesion & migration, 7(1), 150-256 (2012-12-25)
Laminin-111 is a large trimeric basement membrane glycoprotein with many active sites. In particular, four peptides active in tumor malignancy studies have been identified in laminin-111 using a systematic peptide screening method followed by various assays. Two of the peptides
Presenting multiple adhesion ligands on hydrogels for control of PC12 phenotype.
Jae-Won Lee et al.
Journal of controlled release : official journal of the Controlled Release Society, 152 Suppl 1, e219-e220 (2011-12-27)
Angelo Bella et al.
Journal of medicinal chemistry, 52(24), 7966-7969 (2009-12-03)
Conformationally constrained mimetics of the laminin cell-adhesion site, YIGSR, are described. The site is the natural antagonist of the integrin-associated laminin receptor 1 (LAMR1) known to mediate metastatic tumor adhesion. The attachment of selected metastatic cell lines toward the constrained
Bart G J Dekkers et al.
Respiratory research, 11, 170-170 (2010-12-07)
Fibroproliferative airway remodelling, including increased airway smooth muscle (ASM) mass and contractility, contributes to airway hyperresponsiveness in asthma. In vitro studies have shown that maturation of ASM cells to a (hyper)contractile phenotype is dependent on laminin, which can be inhibited
Bart G J Dekkers et al.
American journal of respiratory cell and molecular biology, 41(4), 494-504 (2009-02-14)
Airway smooth muscle (ASM) plays a key role in the development of airway hyperresponsiveness and remodeling in asthma, which may involve maturation of ASM cells to a hypercontractile phenotype. In vitro studies have indicated that long-term exposure of bovine tracheal
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Product Information Sheet - T7154

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