A peptide chloride channel inhibitor
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Chlorotoxin (trifluoroacetate salt)

Item No. 35788

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-methionyl-L-cysteinyl-L-methionyl-L-prolyl-L-cysteinyl-L-phenylalanyl-L-threonyl-L-threonyl-L-α-aspartyl-L-histidyl-L-glutaminyl-L-methionyl-L-alanyl-L-arginyl-L-lysyl-L-cysteinyl-L-α-aspartyl-L-α-aspartyl-L-cysteinyl-L-cysteinylglycylglycyl-L-lysylglycyl-L-arginylglycyl-L-lysyl-L-cysteinyl-L-tyrosylglycyl-L-prolyl-L-glutaminyl-L-cysteinyl-L-leucyl-L-cysteinyl-L-argininamide, cyclic (2→19),(5→28),(16→33),(20→35)-tetrakis(disulfide), trifluoroacetate salt
Synonyms
  • CTX
  • TM-601
Molecular Formula
C158H249N53O47S11 • XCF3COOH
Formula Weight
3995.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Peptide Sequence
MCMPCFTTDHQMARKCDDCCGGKGRGKCYGPQCLCR-NH2
Solubility(Learn about Variance in Solubility)
Water: Sparingly soluble: 1-10 mg/ml
SMILES
OC(C[C@H](NC([C@]([H])([C@@H](C)O)NC([C@]([H])([C@@H](C)O)NC([C@@H](NC([C@H]1NC([C@@H]2CCCN2C([C@H](CCSC)NC([C@H]3NC([C@H](CCSC)N[H])=O)=O)=O)=O)=O)CC4=CC=CC=C4)=O)=O)=O)C(N[C@@H](CC5=CNC=N5)C(N[C@@H](CCC(N)=O)C(N[C@@H](CCSC)C(N[C@H](C(N[C@@H](CCCNC(N)=N)C(N[C@@H](CCCCN[H])C(N[C@@H]6C(N[C@@H](CC(O)=O)C(N[C@@H](CC(O)=O)C(N[C@@H](CSSC3)C(N[C@@H]7C(NCC(NCC(N[C@@H](CCCCN[H])C(NCC(N[C@@H](CCCNC(N)=N)C(NCC(N[C@@H](CCCCN[H])C(N[C@@H](CSSC1)C(N[C@@H](CC(C=C8)=CC=C8O)C(NCC(N9CCC[C@H]9C(N[C@@H](CCC(N)=O)C(N[C@@H](CSSC6)C(N[C@H](C(N[C@@H](CSSC7)C(N[C@@H](CCCNC(N)=N)C(N)=O)=O)=O)CC(C)C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)C)=O)=O)=O)=O)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C158H249N53O47S11.C2HF3O2/c1-77(2)55-96-138(241)205-105(144(247)186-86(125(165)228)28-18-47-173-156(166)167)70-264-262-68-103-131(234)177-63-115(217)176-64-116(218)183-87(25-12-15-44-159)128(231)178-65-117(219)184-88(29-19-48-174-157(168)169)129(232)179-66-118(220)185-89(26-13-16-45-160)133(236)202-107-72-267-269-75-110-149(252)195-98(56-81-23-10-9-11-24-81)143(246)208-124(80(5)213)154(257)209-123(79(4)212)153(256)199-102(61-122(226)227)141(244)196-99(58-83-62-172-76-181-83)139(242)189-92(37-39-113(163)215)136(239)190-94(42-53-260-7)132(235)182-78(3)126(229)187-91(30-20-49-175-158(170)171)134(237)188-90(27-14-17-46-161)135(238)203-108(73-266-265-71-106(146(249)193-96)204-137(240)93(38-40-114(164)216)191-151(254)111-31-21-50-210(111)119(221)67-180-130(233)97(194-147(107)250)57-82-33-35-84(214)36-34-82)148(251)198-100(59-120(222)223)140(243)197-101(60-121(224)225)142(245)206-109(150(253)201-103)74-268-263-69-104(200-127(230)85(162)41-52-259-6)145(248)192-95(43-54-261-8)155(258)211-51-22-32-112(211)152(255)207-110;3-2(4,5)1(6)7/h9-11,23-24,33-36,62,76-80,85-112,123-124,212-214H,12-22,25-32,37-61,63-75,159-162H2,1-8H3,(H2,163,215)(H2,164,216)(H2,165,228)(H,172,181)(H,176,217)(H,177,234)(H,178,231)(H,179,232)(H,180,233)(H,182,235)(H,183,218)(H,184,219)(H,185,220)(H,186,247)(H,187,229)(H,188,237)(H,189,242)(H,190,239)(H,191,254)(H,192,248)(H,193,249)(H,194,250)(H,195,252)(H,196,244)(H,197,243)(H,198,251)(H,199,256)(H,200,230)(H,201,253)(H,202,236)(H,203,238)(H,204,240)(H,205,241)(H,206,245)(H,207,255)(H,208,246)(H,209,257)(H,222,223)(H,224,225)(H,226,227)(H4,166,167,173)(H4,168,169,174)(H4,170,171,175);(H,6,7)/t78-,79+,80+,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,123-,124-;/m0./s1
InChi Key
YWSGDBYKBNIEOZ-RXIQVKIDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Chlorotoxin is a peptide originally isolated from the venom of the scorpion L. quinquestriatus.1,2 It inhibits chloride currents in rat colonic enterocyte plasma membrane preparations when used at a concentration of 594 nM.1 Chlorotoxin also binds to, but does not inhibit, matrix metalloproteinase-2 (MMP-2; IC50s = 0.71 and >30 µM, respectively), as well as neuropilin-1 (NRP-1; IC50 = 0.78 µM) in cell-free assays.3 It induces paralysis in crayfish (P. clarkii) but is not cytotoxic to human U87MG glioma, MCF-7 breast cancer, PC3 prostate cancer, and A549 lung cancer cells.1,2 Administration of chimeric antigen receptor (CAR) T cells expressing CAR with chlorotoxin as the targeting domain increase survival and decrease tumor volume in an orthotopic patient-derived xenograft (PDX) mouse model of glioblastoma.4 Liposomes containing chlorotoxin and encapsulating doxorubicin decrease tumor volume in a U87 glioma mouse xenograft model.5 Fluorescently labeled chlorotoxin has been used for tumor imaging in vivo.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. DeBin, J.A., Maggio, J.E., and Strichartz, G.R. Purification and characterization of chlorotoxin, a chloride channel ligand from the venom of the scorpion. Am. J. Physiol. 264(2 Pt 1), C361-C369 (1993).

    2. Ayed, A.S., Omran, M.A.A.A., Nabil, Z.I., et al. C-terminal amidation of chlorotoxin does not affect tumour cell proliferation and has no effect on toxin cytotoxicity. Int. J. Pept. Res. Ther. 27(1), 659-667 (2021).

    3. Farkas, S., Cioca, D., Murányi, J., et al. Chlorotoxin binds to both matrix metalloproteinase 2 and neuropilin 1. The Journal of Biological Chemisty 299(9), 104998 (2023).

    4. Wang, D., Starr, R., Chang, W.C., et al. Chlorotoxin-directed CAR T cells for specific and effective targeting of glioblastoma. Sci. Transl. Med. 12(533), eaaw2672 (2020).

    5. Xiang, Y., Liang, L., Wang, X., et al. Chloride channel-mediated brain glioma targeting of chlorotoxin-modified doxorubicine-loaded liposomes. J. Control Release 152(3), 402-410 (2011).

    6. Veiseh, M., Gabikian, P., Bahrami, S.B., et al. Tumor paint: A chlorotoxin:Cy5.5 bioconjugate for intraoperative visualization of cancer foci. Cancer Res. 67(14), 6882-6888 (2007).