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AB120809

AMD 3465 hexahydrobromide, CXCR4 antagonist

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(5 Publications)

MW 410.6 Da, Purity >97%. Potent and selective CXCR4 antagonist. Shows 8-fold greater affinity than AMD 3100 (ab120718). Potent HIV entry inhibitor (IC50 = ~10 nM). Additionally mobilizes stem cells in vivo.

View Alternative Names

C-X-C chemokine receptor type 4, CD184, CD184 antigen, CXCR4_HUMAN, Chemokine (C X C motif) receptor 4, Chemokine CXC Motif Receptor 4, D2S201E, FB22, Fusin, HM89, HSY3RR, LCR1, LESTR, Leukocyte-derived seven transmembrane domain receptor, Lipopolysaccharide associated protein 3, NPY3R, NPYR, NPYRL, NPYY3, NPYY3R, Neuropeptide Y receptor Y3, Probable G protein coupled receptor lcr1 homolog, SDF-1 receptor, SEVEN-TRANSMEMBRANE-SEGMENT RECEPTOR, Stromal cell-derived factor 1 receptor, WHIM, WHIMS

1 Images
Chemical Structure - AMD 3465 hexahydrobromide, CXCR4 antagonist (AB120809)
  • Chemical Structure

Lab

Chemical Structure - AMD 3465 hexahydrobromide, CXCR4 antagonist (AB120809)

2D chemical structure image of ab120809, AMD 3465 hexahydrobromide, CXCR4 antagonist

Key facts

CAS number

185991-24-6

Purity

>97%

Form

Solid

form

Molecular weight

410.6 Da

Molecular formula

C<sub>2</sub><sub>4</sub>H<sub>3</sub><sub>8</sub>N<sub>6</sub>

PubChem

483559

Nature

Synthetic

Solubility

Soluble in water to 50 mM

Soluble in DMSO to 25 mM

Biochemical name

2-Pyridinemethanamine, N-((4-(1,4,8,11-tetraazacyclotetradec-1-ylmethyl)phenyl)methyl)-

Biological description

Potent and selective CXCR4 antagonist. Shows 8-fold greater affinity than AMD 3100 (ab120718). Potent HIV entry inhibitor (IC50 = ~10 nM). Additionally mobilizes stem cells in vivo.

Canonical smiles

C1CNCCNCCCN(CCNC1)CC2=CC=C(C=C2)CNCC3=CC=CC=N3

InChi

InChI=1S/C24H38N6/c1-2-13-29-24(5-1)20-28-19-22-6-8-23(9-7-22)21-30-17-4-12-26-15-14-25-10-3-11-27-16-18-30/h1-2,5-9,13,25-28H,3-4,10-12,14-21H2

InChiKey

CWJJHESJXJQCJA-UHFFFAOYSA-N

IUPAC Name

N-(pyridin-2-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

CXCR4 also known as C-X-C chemokine receptor type 4 is a G protein-coupled receptor that is involved in signal transduction. It has a molecular weight of approximately 41 kDa. CXCR4 is ubiquitously expressed across various tissues including immune cells like T and B lymphocytes as well as in bone marrow brain and heart. It binds specifically with the ligand CXCL12 also known as stromal cell-derived factor 1 (SDF-1) facilitating responses such as cell migration and proliferation.
Biological function summary

CXCR4 plays an important role in the immune system hematopoiesis and angiogenesis. It does not function alone and is often part of a larger protein complex where it recruits and activates other G proteins. The receptor mediates chemotactic responses directing cells to sites of inflammation or injury. Its interaction with CXCL12 is critical for maintaining immune surveillance aiding in the movement and positioning of immune cells.

Pathways

CXCR4 integrates into significant cellular signaling pathways such as the PI3K/AKT pathway and the MAPK pathway. It collaborates closely with signaling proteins like AKT1 and MAPK1 impacting cell survival and growth. These pathways are essential for various cellular functions including cell cycle progression and apoptosis regulation. The cross-talk between CXCR4 and these pathways underlines its influence on cell fate decisions.

CXCR4 is implicated in cancer metastasis and HIV entry into cells. Overexpression of CXCR4 is observed in several cancers contributing to tumor growth and metastasis. The interaction between CXCR4 and CXCL12 facilitates the infiltration and spread of cancer cells. Additionally in HIV CXCR4 serves as a coreceptor along with CD4 allowing the virus to enter and infect host cells. Both cancer and HIV illustrate CXCR4's central role in disease progression and pathogenesis.

Product protocols

Publications (5)

Recent publications for all applications. Explore the full list and refine your search

Frontiers in physiology 15:1349119 PubMed38370015

2024

Modeling the SDF-1/CXCR4 protein using advanced artificial intelligence and antagonist screening for Japanese anchovy.

Applications

Unspecified application

Species

Unspecified reactive species

Issei Yahiro,Kyle Dominic Eguid Barnuevo,Oga Sato,Sipra Mohapatra,Atsushi Toyoda,Takehiko Itoh,Kaoru Ohno,Michiya Matsuyama,Tapas Chakraborty,Kohei Ohta

Oncotarget 8:2261-2274 PubMed27903985

2016

The tissue inhibitor of metalloproteinases-1 (TIMP-1) promotes survival and migration of acute myeloid leukemia cells through CD63/PI3K/Akt/p21 signaling.

Applications

Unspecified application

Species

Unspecified reactive species

Dorian Forte,Valentina Salvestrini,Giulia Corradi,Lara Rossi,Lucia Catani,Roberto M Lemoli,Michele Cavo,Antonio Curti

Biochemical pharmacology 78:993-1000 PubMed19540208

2009

Pharmacology of AMD3465: a small molecule antagonist of the chemokine receptor CXCR4.

Applications

Unspecified application

Species

Unspecified reactive species

Veronique Bodart,Virginia Anastassov,Marilyn C Darkes,Stefan R Idzan,Jean Labrecque,Gloria Lau,Renee M Mosi,Kathleen S Neff,Kim L Nelson,Melanie C Ruzek,Ketan Patel,Zefferino Santucci,Robert Scarborough,Rebecca S Y Wong,Gary J Bridger,Ron T Macfarland,Simon P Fricker

The American journal of pathology 169:424-32 PubMed16877345

2006

AMD3465, a novel CXCR4 receptor antagonist, abrogates schistosomal antigen-elicited (type-2) pulmonary granuloma formation.

Applications

Unspecified application

Species

Unspecified reactive species

Jerry S Hu,Christine M Freeman,Valerie R Stolberg,Bo Chin Chiu,Gary J Bridger,Simon P Fricker,Nicholas W Lukacs,Stephen W Chensue

Biochemical pharmacology 70:752-61 PubMed16011832

2005

AMD3465, a monomacrocyclic CXCR4 antagonist and potent HIV entry inhibitor.

Applications

Unspecified application

Species

Unspecified reactive species

Sigrid Hatse,Katrien Princen,Erik De Clercq,Mette M Rosenkilde,Thue W Schwartz,Pedro E Hernandez-Abad,Renato T Skerlj,Gary J Bridger,Dominique Schols
View all publications

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