A CXCR4 antagonist and CXCR7 agonist
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Alternative(s)
11974TC 14012 (trifluoroacetate salt)
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TC 14012 (hydrochloride)

Item No. 38140

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclic (4→13)-disulfide L-arginyl-L-arginyl-3-(2-naphthalenyl)-L-alanyl-L-cysteinyl-L-tyrosyl-N5-(aminocarbonyl)-L-ornithyl-L-lysyl-N5-(aminocarbonyl)-D-ornithyl-L-prolyl-L-tyrosyl-L-arginyl-N5-(aminocarbonyl)-L-ornithyl-L-cysteinyl-L-argininamide, hydrochloride
Synonyms
  • H-Arg-Arg-Nal-Cys-Tyr-Cit-Lys-D-Cit-Pro-Tyr-Arg-Cit-Cys-Arg-NH2
Molecular Formula
C90H140N34O19S2 • XHCl
Formula Weight
2066.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
227 nm
SMILES
O=C(N[C@H](C(N[C@@](C(N[C@H](C(N[C@](CSSC[C@H](NC([C@@H](NC([C@H](CCCNC(N)=N)NC([C@@H](N)CCCNC(N)=N)=O)=O)CC1=CC(C=CC=C2)=C2C=C1)=O)C3=O)([H])C(N[C@H](C(N)=O)CCCNC(N)=N)=O)=O)CCCNC(N)=O)=O)([H])CCCNC(N)=N)=O)CC4=CC=C(O)C=C4)[C@@](CCC5)([H])N5C([C@@](NC([C@@H](NC([C@](NC([C@@H](N3)CC6=CC=C(O)C=C6)=O)([H])CCCNC(N)=O)=O)CCCCN)=O)([H])CCCNC(N)=O)=O.Cl
InChi Code
InChI=1S/C90H140N34O19S2.ClH/c91-34-4-3-16-58-74(131)118-63(22-11-41-111-90(104)143)83(140)124-42-12-23-69(124)82(139)121-65(45-50-27-32-55(126)33-28-50)78(135)117-60(19-8-38-108-87(100)101)73(130)115-62(21-10-40-110-89(103)142)76(133)122-67(80(137)112-57(70(93)127)17-6-36-106-85(96)97)47-144-145-48-68(81(138)120-64(44-49-25-30-54(125)31-26-49)77(134)116-61(72(129)114-58)20-9-39-109-88(102)141)123-79(136)66(46-51-24-29-52-13-1-2-14-53(52)43-51)119-75(132)59(18-7-37-107-86(98)99)113-71(128)56(92)15-5-35-105-84(94)95;/h1-2,13-14,24-33,43,56-69,125-126H,3-12,15-23,34-42,44-48,91-92H2,(H2,93,127)(H,112,137)(H,113,128)(H,114,129)(H,115,130)(H,116,134)(H,117,135)(H,118,131)(H,119,132)(H,120,138)(H,121,139)(H,122,133)(H,123,136)(H4,94,95,105)(H4,96,97,106)(H4,98,99,107)(H4,100,101,108)(H3,102,109,141)(H3,103,110,142)(H3,104,111,143);1H/t56-,57-,58-,59-,60-,61-,62-,63+,64-,65-,66-,67-,68-,69-;/m0./s1
InChi Key
FILJDMXNCMSIKH-IXLOEVBISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    TC 14012 is a peptidomimetic antagonist of chemokine (C-X-C motif) receptor 4 (CXCR4; IC50 = 2.9 nM) and CXCR7 agonist.1,2 It induces β-arrestin recruitment in HEK293T cells expressing CXCR7 (EC50 = 350 nM).1 TC 14012 reduces the cytopathic effect of HIV in infected MT-4 cells (EC50 = 0.4 nM) and inhibits HIV entry in vitro in a CXCR4-dependent manner (IC50 = 19.3 nM).3 It inhibits migration induced by chemokine (C-X-C motif) ligand 12 (CXCL12) in MDA-MB-231 breast cancer cells and human umbilical vein endothelial cells (HUVECs) when used at concentrations ranging from 10 to 1,000 nM.2 TC 14012 (10 mg/kg) decreases infarct size in a mouse model of acute myocardial infarction induced by left anterior descending (LAD) coronary artery ligation.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gravel, S., Malouf, C., Boulais, P.E., et al. The peptidomimetic CXCR4 antagonist TC14012 recruits β-arrestin to CXCR7: Roles of receptor domains. The Journal of Biological Chemisty 285(49), 37939-37943 (2010).

    2. Tamamura, H., Hori, A., Kanzaki, N., et al. T140 analogs as CXCR4 antagonists identified as anti-metastatic agents in the treatment of breast cancer. FEBS Lett. 550(1-3), 79-83 (2003).

    3. Tamamura, H., Omagari, A., Hiramatsu, K., et al. Development of specific CXCR4 inhibitors possessing high selectivity indexes as well as complete stability in serum based on an anti-HIV peptide T140. Bioorg. Med. Chem. Lett. 11(14), 1897-1902 (2001).

    4. Zhang, S., Yue, J., Ge, Z., et al. Activation of CXCR7 alleviates cardiac insufficiency after myocardial infarction by promoting angiogenesis and reducing apoptosis. Biomed. Pharmacother. 127, 110168 (2020).