A peptide inhibitor of HIV-1 fusion
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Enfuvirtide

Item No. 24097

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-acetyl-L-tyrosyl-L-threonyl-L-seryl-L-leucyl-L-isoleucyl-L-histidyl-L-seryl-L-leucyl-L-isoleucyl-L-α-glutamyl-L-α-glutamyl-L-seryl-L-glutaminyl-L-asparaginyl-L-glutaminyl-L-glutaminyl-L-α-glutamyl-L-lysyl-L-asparaginyl-L-α-glutamyl-L-glutaminyl-L-α-glutamyl-L-leucyl-L-leucyl-L-α-glutamyl-L-leucyl-L-α-aspartyl-L-lysyl-L-tryptophyl-L-alanyl-L-seryl-L-leucyl-L-tryptophyl-L-asparaginyl-L-tryptophyl-L-phenylalaninamide
CAS Number
159519-65-0
Molecular Formula
C204H301N51O64
Formula Weight
4491.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
279 nm
SMILES
NC([C@@H](NC([C@@H](NC([C@H](CC(N)=O)NC([C@@H](NC([C@H](CC(C)C)NC([C@H](CO)NC([C@@H](NC([C@@H](NC([C@H](CCCCN)NC([C@@H](NC([C@H](CC(C)C)NC([C@H](CCC(O)=O)NC([C@H](CC(C)C)NC([C@H](CC(C)C)NC([C@H](CCC(O)=O)NC([C@H](CCC(N)=O)NC([C@H](CCC(O)=O)NC([C@H](CC(N)=O)NC([C@H](CCCCN)NC([C@H](CCC(O)=O)NC([C@H](CCC(N)=O)NC([C@H](CCC(N)=O)NC([C@H](CC(N)=O)NC([C@H](CCC(N)=O)NC([C@H](CO)NC([C@H](CCC(O)=O)NC([C@H](CCC(O)=O)NC([C@@]([C@H](CC)C)([H])NC([C@H](CC(C)C)NC([C@H](CO)NC([C@@H](NC([C@@]([C@H](CC)C)([H])NC([C@H](CC(C)C)NC([C@H](CO)NC([C@@]([C@@H](C)O)([H])NC([C@@H](NC(C)=O)CC1=CC=C(O)C=C1)=O)=O)=O)=O)=O)CC2=CN=CN2)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CC(O)=O)=O)=O)CC3=CNC4=C3C=CC=C4)=O)C)=O)=O)=O)CC5=CNC6=C5C=CC=C6)=O)=O)CC7=CNC8=C7C=CC=C8)=O)CC9=CC=CC=C9)=O
InChi Code
InChI=1S/C204H301N51O64/c1-20-102(15)166(253-195(310)137(75-100(11)12)239-200(315)150(93-258)251-190(305)143(82-112-90-215-95-219-112)248-203(318)167(103(16)21-2)254-196(311)138(76-101(13)14)240-201(316)151(94-259)252-204(319)168(105(18)260)255-197(312)139(221-106(19)261)78-108-45-47-113(262)48-46-108)202(317)233-131(58-68-164(280)281)178(293)228-130(57-67-163(278)279)182(297)250-149(92-257)198(313)232-125(52-62-155(210)266)179(294)245-145(84-157(212)268)191(306)229-124(51-61-154(209)265)175(290
InChi Key
PEASPLKKXBYDKL-FXEVSJAOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Enfuvirtide is a biomimetic peptide inhibitor of HIV-1 fusion with CD4+ cells.1 It inhibits HIV-1 infectivity of HeLa cells stably expressing CD4 by the HXB2 strain (IC50 = 692 pM) and by clinical isolates (IC90s = 6.1-61 nM) in a single-cycle infectivity assay. It also inhibits genomic integration of HIV-1 into human intraepithelial vaginal cells and peripheral blood mononuclear cells (PBMCs; IC50s = 51.2 and 13.58 μM, respectively).2 Enfuvirtide binds to a recombinant molecular mimic of HIV-1 glycoprotein gp41 that contains three N-terminal heptad and two C-terminal heptad repeat regions (Kd = 32 nM).3 It also binds to recombinant formyl peptide receptors (FPR) expressed in rat basophilic leukemia cells (IC50 = 5 nM) and attracts and activates human peripheral blood phagocytes, but not T lymphocytes, in vitro when used at a concentration of 100 nM.4 Formulations containing enfuvirtide have been used in combination therapy for the treatment of HIV-1/AIDS.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ingallinella, P., Bianchi, E., Ladwa, N.A., et al. Addition of a cholesterol group to an HIV-1 peptide fusion inhibitor dramatically increases its antiviral potency. Proc. Natl. Acad. Sci. USA 106(14), 5801-5806 (2009).

    2. McElrath, M.J., Ballweber, L., Terker, A., et al. Ex vivo comparison of microbicide efficacies for preventing HIV-1 genomic integration in intraepithelial vaginal cells. Antimicrob. Agents Chemother. 54(2), 763-772 (2010).

    3. Champagne, K., Shishido, A., and Root, M.J. Interactions of HIV-1 inhibitory peptide T20 with the gp41 N-HR coiled coil. The Journal of Biological Chemisty 284(6), 3619-3627 (2009).

    4. Sun, S.B., Gong, W.H., Gao, J.L., et al. T20/DP178, an ectodomain peptide of human immunodeficiency virus type 1 gp41, is an activator of human phagocyte N-formyl peptide receptor. Blood 93(11), 3885-3892 (1999).