Lophotoxin | CAS#78697-56-0 | neuromuscular toxin

MedKoo Cat#: 599213 | Name: Lophotoxin

Description:

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

Lophotoxin belongs to the cembrene class of diterpenoids; neuromuscular toxin isolated from several pacific gorgonians of the genus Lophogorgia.

Chemical Structure

Lophotoxin

CAS#78697-56-0

Theoretical Analysis

MedKoo Cat#: 599213

Name: Lophotoxin

CAS#: 78697-56-0

Chemical Formula: C22H24O8

Exact Mass: 416.1471

Molecular Weight: 416.42

Elemental Analysis: C, 63.45; H, 5.81; O, 30.74

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lophotoxin;

IUPAC/Chemical Name

(22R,23R,41R,44R,45R,5S,7S)-14-formyl-23-methyl-42-oxo-7-(prop-1-en-2-yl)-43,46-dioxa-1(2,5)-furana-2(2,3)-oxirana-4(4,1)-bicyclo[3.1.0]hexanacyclooctaphane-5-yl acetate

InChi Key

KGRIGHVGXOOCOY-ALYDTWDZSA-N

InChi Code

InChI=1S/C22H24O8/c1-10(2)12-5-14-13(9-23)6-15(27-14)18-21(4,29-18)8-16-19-22(30-19,20(25)28-16)17(7-12)26-11(3)24/h6,9,12,16-19H,1,5,7-8H2,2-4H3/t12-,16-,17+,18+,19-,21-,22-/m1/s1

SMILES Code

O=CC1=C2C[C@@H](C(C)=C)C[C@H](OC(C)=O)[C@@]3(C(O4)=O)O[C@]3([H])[C@@]4([H])C[C@@]5(C)O[C@@]5([H])C(O2)=C1

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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 416.42 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.

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

1: Groebe DR, Abramson SN. Lophotoxin is a slow binding irreversible inhibitor of nicotinic acetylcholine receptors. J Biol Chem. 1995 Jan 6;270(1):281-6. PubMed PMID: 7814387. 2: Atchison WD, Narahashi T, Vogel SM. Endplate blocking actions of lophotoxin. Br J Pharmacol. 1984 Jul;82(3):667-72. PubMed PMID: 6146369; PubMed Central PMCID: PMC1986998. 3: Fenical W, Okuda RK, Bandurraga MM, Culver P, Jacobs RS. Lophotoxin: a novel neuromuscular toxin from Pacific sea whips of the genus Lophogorgia. Science. 1981 Jun 26;212(4502):1512-4. PubMed PMID: 6112796. 4: Sorenson EM, Culver P, Chiappinelli VA. Lophotoxin: selective blockade of nicotinic transmission in autonomic ganglia by a coral neurotoxin. Neuroscience. 1987 Mar;20(3):875-84. PubMed PMID: 2885781. 5: Langdon RB, Jacobs RS. Quantal analysis indicates an alpha-toxin-like block by lophotoxin, a non-ionic marine natural product. Life Sci. 1983 Mar 14;32(11):1223-8. PubMed PMID: 6132312. 6: Culver P, Jacobs RS. Lophotoxin: a neuromuscular acting toxin from the sea whip (Lophogorgia rigida). Toxicon. 1981;19(6):825-30. PubMed PMID: 6121394. 7: Abramson SN, Li Y, Culver P, Taylor P. An analog of lophotoxin reacts covalently with Tyr190 in the alpha-subunit of the nicotinic acetylcholine receptor. J Biol Chem. 1989 Jul 25;264(21):12666-72. PubMed PMID: 2568359. 8: Wipf P, Soth MJ. Synthesis of the C(1)-C(18) segment of lophotoxin and pukalide. Control of 2-alkenylfuran (E/Z)-configuration. Org Lett. 2002 May 16;4(10):1787-90. PubMed PMID: 12000299. 9: Tornøe C, Holden-Dye L, Garland C, Abramson SN, Fleming JT, Sattelle DB. Lophotoxin-insensitive nematode nicotinic acetylcholine receptors. J Exp Biol. 1996 Oct;199(Pt 10):2161-8. PubMed PMID: 8896363. 10: Culver P, Fenical W, Taylor P. Lophotoxin irreversibly inactivates the nicotinic acetylcholine receptor by preferential association at one of the two primary agonist sites. J Biol Chem. 1984 Mar 25;259(6):3763-70. PubMed PMID: 6142893. 11: Culver P, Burch M, Potenza C, Wasserman L, Fenical W, Taylor P. Structure-activity relationships for the irreversible blockade of nicotinic receptor agonist sites by lophotoxin and congeneric diterpene lactones. Mol Pharmacol. 1985 Nov;28(5):436-44. PubMed PMID: 4058423. 12: Abramson SN, Trischman JA, Tapiolas DM, Harold EE, Fenical W, Taylor P. Structure/activity and molecular modeling studies of the lophotoxin family of irreversible nicotinic receptor antagonists. J Med Chem. 1991 Jun;34(6):1798-804. PubMed PMID: 1676426. 13: Abramson SN, Culver P, Kline T, Li Y, Guest P, Gutman L, Taylor P. Lophotoxin and related coral toxins covalently label the alpha-subunit of the nicotinic acetylcholine receptor. J Biol Chem. 1988 Dec 5;263(34):18568-73. PubMed PMID: 2903863. 14: Langdon RB, Jacobs RS. Irreversible autonomic actions by lophotoxin suggest utility as a probe for both C6 and C10 nicotinic receptors. Brain Res. 1985 Dec 16;359(1-2):233-8. PubMed PMID: 3000521. 15: Ortega MJ, Zubía E, Sánchez MC, Carballo JL. Cembrane diterpenes from the gorgonian Leptogorgia laxa. J Nat Prod. 2008 Sep;71(9):1637-9. doi: 10.1021/np8002639. Epub 2008 Aug 13. PubMed PMID: 18698819. 16: Tornøe C, Bai D, Holden-Dye L, Abramson SN, Sattelle DB. Actions of neurotoxins (bungarotoxins, neosurugatoxin and lophotoxins) on insect and nematode nicotinic acetylcholine receptors. Toxicon. 1995 Apr;33(4):411-24. Review. PubMed PMID: 7570627. 17: Kreienkamp HJ, Sine SM, Maeda RK, Taylor P. Glycosylation sites selectively interfere with alpha-toxin binding to the nicotinic acetylcholine receptor. J Biol Chem. 1994 Mar 18;269(11):8108-14. PubMed PMID: 7907588. 18: Hyde EG, Boyer A, Tang P, Xu Y, Abramson SN. Irreversible inhibitors of nicotinic acetylcholine receptors: isolation and structural characterization of the biologically active solvolysis products of bipinnatin-A and bipinnatin-C. J Med Chem. 1995 Jun 9;38(12):2231-8. PubMed PMID: 7783154. 19: Luetje CW, Wada K, Rogers S, Abramson SN, Tsuji K, Heinemann S, Patrick J. Neurotoxins distinguish between different neuronal nicotinic acetylcholine receptor subunit combinations. J Neurochem. 1990 Aug;55(2):632-40. PubMed PMID: 1973456. 20: Ksebati MB, Ciereszko LS, Schmitz FJ. 11 beta, 12 beta-Epoxypukalide, a furanocembranolide from the gorgonian Leptogorgia setacea. J Nat Prod. 1984 Nov-Dec;47(6):1009-12. PubMed PMID: 6152470.