WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H406139
CAS#: 185991-07-5 (HBr)
Description: AMD3465, also known as GENZ 644494, is a novel CXCR4 receptor antagonist with potential anticancer and anti-HIV activity. AMD3465 can block infection of T-tropic, CXCR4-using HIV.
Hodoodo Cat#: H406139
Name: AMD3465 HBr
CAS#: 185991-07-5 (HBr)
Chemical Formula: C24H44Br6N6
Exact Mass: 410.32
Molecular Weight: 896.080
Elemental Analysis: C, 32.17; H, 4.95; Br, 53.50; N, 9.38
Related CAS #: 185991-24-6 (free base) 185991-07-5 (HBr)
Synonym: AMD3465 HBr, AMD3465 hydrobromide; AMD3465; AMD-3465; AMD 3465; GENZ 644494; GENZ-644494; GENZ644494;
IUPAC/Chemical Name: N-(4-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)benzyl)-1-(pyridin-2-yl)methanamine hexahydrobromide
InChi Key: ARHBIBDGWDRBJH-UHFFFAOYSA-N
InChi Code: InChI=1S/C24H38N6.6BrH/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;6*1H
SMILES Code: [H]Br.[H]Br.[H]Br.[H]Br.[H]Br.[H]Br.C1(CNCC2=CC=C(CN3CCNCCCNCCNCCC3)C=C2)=NC=CC=C1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 896.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
---|---|---|---|
1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
1: Zhang Z, Wu H, Huang S, Chen L, Chen X, Zhang W, Liao L, Zhang X. AMD3465 (hexahydrobromide) rescues the MG63 osteoblasts against the apoptosis induced by high glucose. Biomed Pharmacother. 2021 Jun;138:111476. doi: 10.1016/j.biopha.2021.111476. Epub 2021 Mar 24. PMID: 33773470.
2: Hatse S, Princen K, De Clercq E, Rosenkilde MM, Schwartz TW, Hernandez-Abad PE, Skerlj RT, Bridger GJ, Schols D. AMD3465, a monomacrocyclic CXCR4 antagonist and potent HIV entry inhibitor. Biochem Pharmacol. 2005 Sep 1;70(5):752-61. doi: 10.1016/j.bcp.2005.05.035. PMID: 16011832.
3: Leung K. 64Cu-{N-[1,4,8,11-Tetraazacyclotetradecanyl-1,4-ph enylenebis(methylene)]-2-(aminomethyl)pyridine}. 2011 Sep 15 [updated 2012 Jan 5]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004–2013. PMID: 22206104.
4: Hu JS, Freeman CM, Stolberg VR, Chiu BC, Bridger GJ, Fricker SP, Lukacs NW, Chensue SW. AMD3465, a novel CXCR4 receptor antagonist, abrogates schistosomal antigen-elicited (type-2) pulmonary granuloma formation. Am J Pathol. 2006 Aug;169(2):424-32. doi: 10.2353/ajpath.2006.051234. PMID: 16877345; PMCID: PMC1599788.
5: Bodart V, Anastassov V, Darkes MC, Idzan SR, Labrecque J, Lau G, Mosi RM, Neff KS, Nelson KL, Ruzek MC, Patel K, Santucci Z, Scarborough R, Wong RS, Bridger GJ, Macfarland RT, Fricker SP. Pharmacology of AMD3465: a small molecule antagonist of the chemokine receptor CXCR4. Biochem Pharmacol. 2009 Oct 15;78(8):993-1000. doi: 10.1016/j.bcp.2009.06.010. Epub 2009 Jun 18. PMID: 19540208.
6: Wu D, Jin L, Xu H. The Effects of the CXCR4 Antagonist, AMD3465, on Human Retinal Vascular Endothelial Cells (hRVECs) in a High Glucose Model of Diabetic Retinopathy. Med Sci Monit. 2019 Sep 16;25:6946-6954. doi: 10.12659/MSM.917186. PMID: 31860633; PMCID: PMC6761849.
7: Hartimath SV, Khayum MA, van Waarde A, Dierckx RAJO, de Vries EFJ. N-[11C]Methyl-AMD3465 PET as a Tool for In Vivo Measurement of Chemokine Receptor 4 (CXCR4) Occupancy by Therapeutic Drugs. Mol Imaging Biol. 2017 Aug;19(4):570-577. doi: 10.1007/s11307-016-1028-8. PMID: 27896627; PMCID: PMC5498639.
8: Hartimath SV, van Waarde A, Dierckx RA, de Vries EF. Evaluation of N-[(11)C]methyl-AMD3465 as a PET tracer for imaging of CXCR4 receptor expression in a C6 glioma tumor model. Mol Pharm. 2014 Nov 3;11(11):3810-7. doi: 10.1021/mp500398r. Epub 2014 Aug 18. PMID: 25094028.
9: Hartimath SV, Draghiciu O, Daemen T, Nijman HW, van Waarde A, Dierckx RAJO, de Vries EFJ. Therapy-Induced Changes in CXCR4 Expression in Tumor Xenografts Can Be Monitored Noninvasively with N-[11C]Methyl-AMD3465 PET. Mol Imaging Biol. 2020 Aug;22(4):883-890. doi: 10.1007/s11307-019-01447-x. PMID: 31802362; PMCID: PMC7343732.
10: Ling X, Spaeth E, Chen Y, Shi Y, Zhang W, Schober W, Hail N Jr, Konopleva M, Andreeff M. The CXCR4 antagonist AMD3465 regulates oncogenic signaling and invasiveness in vitro and prevents breast cancer growth and metastasis in vivo. PLoS One. 2013;8(3):e58426. doi: 10.1371/journal.pone.0058426. Epub 2013 Mar 6. PMID: 23484027; PMCID: PMC3590173.
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19: Ghasemi K, Ghasemi K. MSX-122: Is an effective small molecule CXCR4 antagonist in cancer therapy? Int Immunopharmacol. 2022 Jul;108:108863. doi: 10.1016/j.intimp.2022.108863. Epub 2022 May 25. PMID: 35623288.
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