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SML2079

ATN-161

Name: ATN-161
Brand: SIGMA

≥98% (HPLC), integrin α5β1 receptor antagonist, powder

Synonym(s):

1-Acetyl-L-prolyl-L-histidyl-L-seryl-L-cysteinyl-L-aspartamide, Ac-PHSCN-NH2, Ac-Pro-His-Ser-Cys-Asn-NH2, PHSCN (Modifications: Pro-1 = N-terminal Ac, Asn-5 = C-terminal amide)

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₃₅N₉O₈S

CAS Number:

262438-43-7

Molecular Weight:

597.64

UNSPSC Code:

12171501

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

powder

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Product Name

ATN-161, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

white to beige

shipped in

wet ice

storage temp.

−20°C

SMILES string

SC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(CCC2)C(=O)C)Cc1nc[nH]c1)CO)C(=O)N[C@@H](CC(=O)N)C(=O)N

InChI

1S/C23H35N9O8S/c1-11(34)32-4-2-3-17(32)23(40)29-14(5-12-7-26-10-27-12)20(37)30-15(8-33)21(38)31-16(9-41)22(39)28-13(19(25)36)6-18(24)35/h7,10,13-17,33,41H,2-6,8-9H2,1H3,(H2,24,35)(H2,25,36)(H,26,27)(H,28,39)(H,29,40)(H,30,37)(H,31,38)/t13-,14-,15-,16-,17-/m0/s1

InChI key

MMHDBUJXLOFTLC-WOYTXXSLSA-N

Related Categories

Bioactive Small Molecules

Application

ATN-161 has been used as an inhibitor of integrin α5β1 and αvβ3 in cultured platelet endothelial cell adhesion molecule (PECAM1)-positive endothelial cells isolated from AL (CECAL).

Biochem/physiol Actions

ATN-161 is a non-RGD based integrin binding peptide derived from the synergy region of fibronectin that inhibits the receptors for integrins alpha-v beta-3 and integrin alpha-5 beta-1. Integrin alpha-5 beta-1 is expressed on endothelial cells and plays a key role in endothelial cell adhesion and migration and may also play a key role in cancer cell invasion and metastasis. ATN-161 was shown to have antiangigenic and antitumor activity.

Antagonist of integrin α5β1 receptor

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Penta-peptide ATN-161 based neutralization mechanism of SARS-CoV-2 spike protein.

Gulam Rabbani et al.

Biochemistry and biophysics reports, 28, 101170-101170 (2021-11-16)

SARS-CoV-2 has become a big challenge for the scientific community worldwide. SARS-CoV-2 enters into the host cell by the spike protein binding with an ACE2 receptor present on the host cell. Developing safe and effective inhibitor appears an urgent need

Fibronectin-integrin signaling regulates PLVAP localization at endothelial fenestrae by microtubule stabilization.

Takashi Nakakura et al.

Cell and tissue research, 384(2), 449-463 (2021-01-16)

Endothelial fenestrae are the transcellular pores existing on the capillary walls which are organized in clusters referred to as sieve plates. They are also divided by a diaphragm consisting of plasmalemma vesicle-associated protein (PLVAP). In this study, we examined the

αvβ3 Integrins Mediate Flow-Induced NF-κB Activation, Proinflammatory Gene Expression, and Early Atherogenic Inflammation.

Jie Chen et al.

The American journal of pathology, 185(9), 2575-2589 (2015-07-28)

Endothelial cell interactions with transitional matrix proteins, such as fibronectin, occur early during atherogenesis and regulate shear stress-induced endothelial cell activation. Multiple endothelial cell integrins bind transitional matrix proteins, including α5β1, αvβ3, and αvβ5. However, the role these integrins play

Joint Antiangiogenic Effect of ATN-161 and Anti-VEGF Antibody in a Rat Model of Early Wet Age-Related Macular Degeneration.

Wen-Qiu Wang et al.

Molecular pharmaceutics, 13(9), 2881-2890 (2016-04-19)

The wet form of age-related macular degeneration (AMD) is a leading cause of blindness among elderly Americans and is characterized by abnormal vessel growth, termed choroidal neovascularization (CNV). Integrin α5β1 is a transmembrane receptor that binds matrix macromolecules and proteinases

Phase 1 trial of the antiangiogenic peptide ATN-161 (Ac-PHSCN-NH(2)), a beta integrin antagonist, in patients with solid tumours.

M E Cianfrocca et al.

British journal of cancer, 94(11), 1621-1626 (2006-05-18)

To evaluate the toxicity, pharmacological and biological properties of ATN-161, a five -amino-acid peptide derived from the synergy region of fibronectin, adult patients with advanced solid tumours were enrolled in eight sequential dose cohorts (0.1-16 mg kg(-1)), receiving ATN-161 administered

Global Trade Item Number

SKU	GTIN
SML2079-5MG	04061835502288
SML2079-25MG	04061835502271

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