ZK-756326 dihydrochloride
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MedKoo CAT#: 530328

CAS#: 1780259-94-0 (2HCl)

Description: ZK-756326 is a potent, selective and non-peptide CCR8 chemokine receptor agonist. ZK 756326 inhibited the binding of the CCR8 ligand I-309 (CCL1), with an IC(50) value of 1.8 muM. ZK 756326 was a full agonist of CCR8, dose-responsively eliciting an increase in intracellular calcium and cross-desensitizing the response of the receptor to CCL1.


Price and Availability

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10mg
USD 90
100mg
USD 450
1g
USD 2150
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25mg
USD 150
200mg
USD 750
2g
USD 3650
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50mg
USD 250
500mg
USD 1250
5g
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ZK-756326 dihydrochloride, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530328
Name: ZK-756326 dihydrochloride
CAS#: 1780259-94-0 (2HCl)
Chemical Formula: C21H30Cl2N2O3
Exact Mass:
Molecular Weight: 429.382
Elemental Analysis: C, 58.74; H, 7.04; Cl, 16.51; N, 6.52; O, 11.18


Related CAS #: 1780259-94-0 (2HCl)   874911-96-3 (free base)    

Synonym: ZK-756326; ZK 756326; ZK756326; ZK-756326 dihydrochloride

IUPAC/Chemical Name: 2-[2-[4-[(3-phenoxyphenyl)methyl]-1-piperazinyl]ethoxy]ethanol dihydrochloride

InChi Key: MPACCEKWFGWZHS-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H28N2O3.2ClH/c24-14-16-25-15-13-22-9-11-23(12-10-22)18-19-5-4-8-21(17-19)26-20-6-2-1-3-7-20;;/h1-8,17,24H,9-16,18H2;2*1H

SMILES Code: OCCOCCN1CCN(CC2=CC=CC(OC3=CC=CC=C3)=C2)CC1.[H]Cl.[H]Cl


Technical Data

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

Shelf Life:
>2 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).

Harmonized System Code:
293490


Additional Information

Related CAS#
CAS#1780259-94-0 (ZK-756326 dihydrochloride)
CAS#874911-96-3 (ZK-756326 free base).

ZK 756326 stimulated extracellular acidification in cells expressing human CCR8. The ability of ZK 756326 to induce a response was receptor-specific and mediated through Galpha(i), because it could be blocked by treatment with pertussis toxin. The CCR8 agonist activated cells expressing murine CCR8, eliciting their chemotaxis and inducing phosphorylation of extracellular signal-regulated kinase ERK1/2. Like CCL1, ZK 756326 inhibited human immunodeficiency virus (HIV) fusion of cells expressing CD4 and CCR8. Finally, unlike mCCL1, ZK 756326 bound to and activated a form of mCCR8 that was mutated to eliminate O-linked sulfation at tyrosines 14 and 15. Therefore, ZK 756326 is most probably not binding in the same manner as CCL1 but can activate the switch mechanism involved in transducing signaling events. In summary, we have identified a nonpeptide agonist of CCR8. This compound may be useful in evaluating the physiological role of CCR8 in HIV infection, as well as in the general study of CCR8 biology without the constraints inherent to the use of protein agonists such as its natural ligand.


References

1: Haskell CA, Horuk R, Liang M, Rosser M, Dunning L, Islam I, Kremer L,
Gutiérrez J, Marquez G, Martinez-A C, Biscone MJ, Doms RW, Ribeiro S.
Identification and characterization of a potent, selective nonpeptide agonist of
the CC chemokine receptor CCR8. Mol Pharmacol. 2006 Jan;69(1):309-16. PubMed
PMID: 16221874.

2: Petersen TP, Ritzén A, Ulven T. A multistep continuous-flow system for rapid
on-demand synthesis of receptor ligands. Org Lett. 2009 Nov 19;11(22):5134-7.
doi: 10.1021/ol902101c. PubMed PMID: 19852497.