alpha-Conotoxin imi

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 596981

CAS#: 156467-85-5

Description: alpha-Conotoxin imi is a nicotinic acetylcholine receptor ligand isolated from the snail Conus imperialis.

Chemical Structure

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alpha-Conotoxin imi
CAS# 156467-85-5
Instruction

Theoretical Analysis

MedKoo Cat#: 596981
Name: alpha-Conotoxin imi
CAS#: 156467-85-5
Chemical Formula: C52H82N20O15S4
Exact Mass: 1,354.52
Molecular Weight: 1,355.590
Elemental Analysis: C, 46.07; H, 6.10; N, 20.67; O, 17.70; S, 9.46

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: alpha-Conotoxin imi; alpha-Ctx-imi;

IUPAC/Chemical Name: (4R,7R,10S,13S)-13-((S)-2-(((6S,9S,12S,15R,18S)-9-((1H-indol-3-yl)methyl)-1,23-diamino-6-(((R)-1-amino-3-mercapto-1-oxopropan-2-yl)carbamoyl)-1,23-diimino-15-(mercaptomethyl)-12-methyl-8,11,14,17-tetraoxo-2,7,10,13,16,22-hexaazatricosan-18-yl)carbamoyl)pyrrolidine-1-carbonyl)-1-amino-10-(hydroxymethyl)-4,7-bis(mercaptomethyl)-2,5,8,11-tetraoxo-3,6,9,12-tetraazapentadecan-15-oic acid

InChi Key: IFMXNBRHEQLZMI-VAYQAVKTSA-N

InChi Code: 1S/C52H82N20O15S4/c1-24(41(78)66-30(15-25-18-61-27-8-3-2-7-26(25)27)44(81)64-28(9-4-12-59-51(55)56)42(79)69-33(20-88)40(54)77)62-46(83)35(22-90)70-43(80)29(10-5-13-60-52(57)58)65-49(86)37-11-6-14-72(37)50(87)31(16-39(75)76)67-45(82)32(19-73)68-48(85)36(23-91)71-47(84)34(21-89)63-38(74)17-53/h2-3,7-8,18,24,28-37,61,73,88-91H,4-6,9-17,19-23,53H2,1H3,(H2,54,77)(H,62,83)(H,63,74)(H,64,81)(H,65,86)(H,66,78)(H,67,82)(H,68,85)(H,69,79)(H,70,80)(H,71,84)(H,75,76)(H4,55,56,59)(H4,57,58,60)/t24-,28-,29-,30-,31-,32-,33-,34-,35-,36-,37-/m0/s1

SMILES Code: NCC(N[C@@H](CS)C(N[C@@H](CS)C(N[C@@H](CO)C(N[C@@H](CC(O)=O)C(N(CCC1)[C@@H]1C(N[C@@H](CCCNC(N)=N)C(N[C@@H](CS)C(N[C@@H](C)C(N[C@@H](Cc2c3ccccc3[nH]c2)C(N[C@@H](CCCNC(N)=N)C(N[C@@H](CS)C(N)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O

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).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,355.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Mei D, Zhao L, Chen B, Zhang X, Wang X, Yu Z, Ni X, Zhang Q. α-Conotoxin ImI-modified polymeric micelles as potential nanocarriers for targeted docetaxel delivery to α7-nAChR overexpressed non-small cell lung cancer. Drug Deliv. 2018 Nov;25(1):493-503. doi: 10.1080/10717544.2018.1436097. PubMed PMID: 29426250.

2: Padilla A, Keating P, Hartmann JX, Marí F. Effects of α-conotoxin ImI on TNF-α, IL-8 and TGF-β expression by human macrophage-like cells derived from THP-1 pre-monocytic leukemic cells. Sci Rep. 2017 Oct 6;7(1):12742. doi: 10.1038/s41598-017-11586-2. PubMed PMID: 28986583; PubMed Central PMCID: PMC5630575.

3: Gao B, Peng C, Lin B, Chen Q, Zhang J, Shi Q. Screening and Validation of Highly-Efficient Insecticidal Conotoxins from a Transcriptome-Based Dataset of Chinese Tubular Cone Snail. Toxins (Basel). 2017 Jul 6;9(7). pii: E214. doi: 10.3390/toxins9070214. PubMed PMID: 28684723; PubMed Central PMCID: PMC5535161.

4: Taguchi A, Kobayashi K, Kotani A, Muguruma K, Kobayashi M, Fukumoto K, Takayama K, Hakamata H, Hayashi Y. 3-Nitro-2-pyridinesulfenates as Efficient Solution- and Solid-Phase Disulfide Bond Forming Agents. Chemistry. 2017 Jun 16;23(34):8262-8267. doi: 10.1002/chem.201700952. Epub 2017 May 29. PubMed PMID: 28407456.

5: Yu R, Tabassum N, Jiang T. Investigation of α-conotoxin unbinding using umbrella sampling. Bioorg Med Chem Lett. 2016 Feb 15;26(4):1296-300. doi: 10.1016/j.bmcl.2016.01.013. Epub 2016 Jan 7. PubMed PMID: 26796065.

6: Kudryavtsev DS, Shelukhina IV, Son LV, Ojomoko LO, Kryukova EV, Lyukmanova EN, Zhmak MN, Dolgikh DA, Ivanov IA, Kasheverov IE, Starkov VG, Ramerstorfer J, Sieghart W, Tsetlin VI, Utkin YN. Neurotoxins from snake venoms and α-conotoxin ImI inhibit functionally active ionotropic γ-aminobutyric acid (GABA) receptors. J Biol Chem. 2015 Sep 11;290(37):22747-58. doi: 10.1074/jbc.M115.648824. Epub 2015 Jul 28. PubMed PMID: 26221036; PubMed Central PMCID: PMC4566246.

7: Wan J, Huang JX, Vetter I, Mobli M, Lawson J, Tae HS, Abraham N, Paul B, Cooper MA, Adams DJ, Lewis RJ, Alewood PF. α-Conotoxin dendrimers have enhanced potency and selectivity for homomeric nicotinic acetylcholine receptors. J Am Chem Soc. 2015 Mar 11;137(9):3209-12. doi: 10.1021/jacs.5b00244. Epub 2015 Mar 3. PubMed PMID: 25710197.

8: Mei D, Lin Z, Fu J, He B, Gao W, Ma L, Dai W, Zhang H, Wang X, Wang J, Zhang X, Lu W, Zhou D, Zhang Q. The use of α-conotoxin ImI to actualize the targeted delivery of paclitaxel micelles to α7 nAChR-overexpressing breast cancer. Biomaterials. 2015 Feb;42:52-65. doi: 10.1016/j.biomaterials.2014.11.044. Epub 2014 Dec 13. PubMed PMID: 25542793.

9: Kiss T, Krajcs N, Pirger Z, Hernádi L. Nicotinic acetylcholine receptors containing the α7-like subunit mediate contractions of muscles responsible for space positioning of the snail, Helix pomatia L. tentacle. PLoS One. 2014 Oct 10;9(10):e109538. doi: 10.1371/journal.pone.0109538. eCollection 2014. PubMed PMID: 25303328; PubMed Central PMCID: PMC4193815.

10: Baxter JC, Ramachandra R, Mayne DR, Elmslie KS. Functional expression of α7-nicotinic acetylcholine receptors by muscle afferent neurons. J Neurophysiol. 2014 Sep 15;112(6):1549-58. doi: 10.1152/jn.00035.2014. Epub 2014 Jun 25. PubMed PMID: 24966300; PubMed Central PMCID: PMC4137244.

11: White SH, Carter CJ, Magoski NS. A potentially novel nicotinic receptor in Aplysia neuroendocrine cells. J Neurophysiol. 2014 Jul 15;112(2):446-62. doi: 10.1152/jn.00796.2013. Epub 2014 Apr 16. PubMed PMID: 24740855.

12: Yu R, Kaas Q, Craik DJ. Delineation of the unbinding pathway of α-conotoxin ImI from the α7 nicotinic acetylcholine receptor. J Phys Chem B. 2012 May 31;116(21):6097-105. doi: 10.1021/jp301352d. Epub 2012 May 18. PubMed PMID: 22571488.

13: Shigeri Y, Inazumi S, Hagihara Y, Yasuda A, Kawasaki H, Arakawa R, Nakata M. Desorption/ionization efficiency of peptides containing disulfide bonds in matrix-assisted laser desorption/ionization mass spectrometry. Anal Sci. 2012;28(3):295-9. PubMed PMID: 22451371.

14: White SH, Magoski NS. Acetylcholine-evoked afterdischarge in Aplysia bag cell neurons. J Neurophysiol. 2012 May;107(10):2672-85. doi: 10.1152/jn.00745.2011. Epub 2012 Feb 8. PubMed PMID: 22323635.

15: Dekan Z, Vetter I, Daly NL, Craik DJ, Lewis RJ, Alewood PF. α-Conotoxin ImI incorporating stable cystathionine bridges maintains full potency and identical three-dimensional structure. J Am Chem Soc. 2011 Oct 12;133(40):15866-9. doi: 10.1021/ja206408q. Epub 2011 Sep 15. PubMed PMID: 21899353.

16: Lee RH, Liu YQ, Chen PY, Liu CH, Chen MF, Lin HW, Kuo JS, Premkumar LS, Lee TJ. Sympathetic α₃β₂-nAChRs mediate cerebral neurogenic nitrergic vasodilation in the swine. Am J Physiol Heart Circ Physiol. 2011 Aug;301(2):H344-54. doi: 10.1152/ajpheart.00172.2011. Epub 2011 May 2. PubMed PMID: 21536845.

17: Yu R, Craik DJ, Kaas Q. Blockade of neuronal α7-nAChR by α-conotoxin ImI explained by computational scanning and energy calculations. PLoS Comput Biol. 2011 Mar;7(3):e1002011. doi: 10.1371/journal.pcbi.1002011. Epub 2011 Mar 3. PubMed PMID: 21390272; PubMed Central PMCID: PMC3048385.

18: Wagenaar DA, Gonzalez R, Ries DC, Kristan WB Jr, French KA. Alpha-conotoxin ImI disrupts central control of swimming in the medicinal leech. Neurosci Lett. 2010 Nov 26;485(3):151-6. doi: 10.1016/j.neulet.2010.08.078. Epub 2010 Sep 15. PubMed PMID: 20833225; PubMed Central PMCID: PMC2956871.

19: Mejia M, Heghinian MD, Busch A, Armishaw CJ, Marí F, Godenschwege TA. A novel approach for in vivo screening of toxins using the Drosophila Giant Fiber circuit. Toxicon. 2010 Dec;56(8):1398-407. doi: 10.1016/j.toxicon.2010.08.005. Epub 2010 Aug 17. Erratum in: Toxicon. 2011 Feb;57(2):357-8. PubMed PMID: 20723555; PubMed Central PMCID: PMC2967628.

20: Armishaw CJ, Dutton JL, Craik DJ, Alewood PF. Establishing regiocontrol of disulfide bond isomers of alpha-conotoxin ImI via the synthesis of N-to-C cyclic analogs. Biopolymers. 2010;94(3):307-13. doi: 10.1002/bip.21360. PubMed PMID: 20013812.