Chlorotoxin

Chlorotoxin is a 36 amino-acid peptide from the venom of the Israeli scorpion Leiurus quinquestriatus with anticancer activity. Chlorotoxin is a chloride channel blocker.

Product information

CAS Number: 163515-35-3

Molecular Weight: 3995.71

Formula: C158H249N53O47S11

Chemical Name: 2-[(1R,4R,9R,12S,18S,21R,24S,27S,30S,33S,36S,39S,42S,45S,48S,51S,54R,59R,62S,65S,74S,77R,80S,86S,92S,105R,108S,117S,120S)-9-[(2S)-2-amino-4-(methylsulfanyl)butanamido]-51,80,92-tris(4-aminobutyl)-24-benzyl-105-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-48,86-bis(3-carbamimidamidopropyl)-39,62-bis(2-carbamoylethyl)-33,120-bis(carboxymethyl)-27,30-bis[(1R)-1-hydroxyethyl]-74-[(4-hydroxyphenyl)methyl]-36-[(1H-imidazol-4-yl)methyl]-45-methyl-108-(2-methylpropyl)-12,42-bis[2-(methylsulfanyl)ethyl]-3,10,13,19,22,25,28,31,34,37,40,43,46,49,52,61,64,70,73,76,79,82,85,88,91,94,97,100,107,110,115,118,121-tritriacontaoxo-6,7,56,57,102,103,112,113-octathia-2,11,14,20,23,26,29,32,35,38,41,44,47,50,53,60,63,69,72,75,78,81,84,87,90,93,96,99,106,109,116,119,122-tritriacontaazahexacyclo[57.41.10.8⁴,⁵⁴.4²¹,⁷⁷.0¹⁴,¹⁸.0⁶⁵,⁶⁹]122n-117-yl]acetic acid

Smiles: CC(C)C[C@@H]1NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC4=CNC=N4)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@@H]4CSSC[C@H](NC(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)CNC(=O)CNC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](N)CCSC)C(=O)N[C@@H](CCSC)C(=O)N1CCC[C@H]1C(=O)N4)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(O)=O)NC3=O)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N2)[C@@H](C)O)[C@@H](C)O

InChiKey: QPAKKWCQMHUHNI-GQIQPHNSSA-N

InChi: InChI=1S/C158H249N53O47S11/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/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)/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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Chlorotoxin (Chlorotoxin) preferentially binds to tumor cells and has been harnessed to develop an imaging agent to help visualize tumors during surgical resection. In addition, chlorotoxin has potential as a vehicle to deliver anti-cancer drugs specifically to cancer cells. Chlorotoxin is shown to bind glioma cells, but is unable to bind normal rat astrocytes and Te671, a human rhabdomyosarcoma cell line. Chlorotoxin inhibits the migration of U251MG (glioma) cells, with an IC50 of 600 nM. Chlorotoxin binds to glioma cells is specific and involves high affinity (Kd=4.2 nM) and low affinity (Kd=660 nM) binding sites.Small conductance chloride channels are shown to be potently blocked by Chlorotoxin. Chlorotoxin has been used as a general pharmacological tool to investigate the function of chloride channels.

In Vivo:

Chlorotoxin shows insecticidal activity on insects and other invertebrates. After the administration of I-Chlorotoxin to tumor-bearing mice, the peptides accumulated within the tumor.Chlorotoxin selectively accumulates in the brain of tumor-bearing mice with calculated brain: muscle ratios of 36.4% of injected dose/g (ID/g), as compared to 12.4%ID/g in control animals.

Products are for research use only. Not for human use.