Lyngbyatoxin A

We are open as normal during COVID-19 pandemic. Order online, same day shipping out from North Carolina, USA

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

MedKoo CAT#: 530285

CAS#: 70497-14-2

Description: Lyngbyatoxin A is an indole alkaloid from blue-green alga Lyngbya majuscula Gomont; responsible for dermatitis known as "swimmers' itch" in Hawaii.


Price and Availability

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2020-10-26. Prices are subject to change without notice.

Lyngbyatoxin A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 530285
Name: Lyngbyatoxin A
CAS#: 70497-14-2
Chemical Formula: C27H39N3O2
Exact Mass: 437.3042
Molecular Weight: 437.628
Elemental Analysis: C, 74.10; H, 8.98; N, 9.60; O, 7.31


Synonym: Lyngbyatoxin A

IUPAC/Chemical Name: 3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-9-(1-ethenyl-1,5-dimethyl-4-hexenyl)-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-

InChi Key: KISDGNGREAJPQR-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)

SMILES Code: O=C(NC(CO)C1)C(C(C)C)N(C)C2=CC=C(C(C)(C=C)CC/C=C(C)\C)C3=C2C1=CN3


Technical Data

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


References

1: Wells KN, Videau P, Nelson D, Eiting JE, Philmus B. The influence of sigma factors and ribosomal recognition elements on heterologous expression of cyanobacterial gene clusters in Escherichia coli. FEMS Microbiol Lett. 2018 Aug 1;365(15). doi: 10.1093/femsle/fny164. PubMed PMID: 29982530; PubMed Central PMCID: PMC6279124.

2: Zhang L, Hoshino S, Awakawa T, Wakimoto T, Abe I. Structural Diversification of Lyngbyatoxin A by Host-Dependent Heterologous Expression of the tleABC Biosynthetic Gene Cluster. Chembiochem. 2016 Aug 3;17(15):1407-11. doi: 10.1002/cbic.201600229. Epub 2016 Jun 17. PubMed PMID: 27194569.

3: Videau P, Wells KN, Singh AJ, Gerwick WH, Philmus B. Assessment of Anabaena sp. Strain PCC 7120 as a Heterologous Expression Host for Cyanobacterial Natural Products: Production of Lyngbyatoxin A. ACS Synth Biol. 2016 Sep 16;5(9):978-88. doi: 10.1021/acssynbio.6b00038. Epub 2016 Jun 1. PubMed PMID: 27176641.

4: Zhao Z, deMayo JA, West AM, Balunas MJ, Zweifach A. Development of an Enhanced Phenotypic Screen of Cytotoxic T-Lymphocyte Lytic Granule Exocytosis Suitable for Use with Synthetic Compound and Natural Product Collections. J Biomol Screen. 2016 Jul;21(6):556-66. doi: 10.1177/1087057116643260. Epub 2016 Apr 5. PubMed PMID: 27048485.

5: Doucette J, Zhao Z, Geyer RJ, Barra MM, Balunas MJ, Zweifach A. Flow Cytometry Enables Multiplexed Measurements of Genetically Encoded Intramolecular FRET Sensors Suitable for Screening. J Biomol Screen. 2016 Jul;21(6):535-47. doi: 10.1177/1087057116634007. Epub 2016 Feb 23. PubMed PMID: 26908592.

6: Jiang W, Tan S, Hanaki Y, Irie K, Uchida H, Watanabe R, Suzuki T, Sakamoto B, Kamio M, Nagai H. Two new lyngbyatoxin derivatives from the Cyanobacterium, Moorea producens. Mar Drugs. 2014 Dec 1;12(12):5788-800. doi: 10.3390/md12125788. PubMed PMID: 25470181; PubMed Central PMCID: PMC4278201.

7: Youssef DT, Shaala LA, Mohamed GA, Ibrahim SR, Banjar ZM, Badr JM, McPhail KL, Risinger AL, Mooberry SL. 2,3-seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens. Nat Prod Res. 2015;29(8):703-9. doi: 10.1080/14786419.2014.982647. Epub 2014 Nov 25. PubMed PMID: 25421266.

8: Kyadari M, Fatma T, Velpandian T, Malliga P, Bharat N, Fareha B. Antiangiogenic and antiproliferative assessment of cyanobacteria. Indian J Exp Biol. 2014 Aug;52(8):835-42. PubMed PMID: 25141548.

9: Nathel NF, Shah TK, Bronner SM, Garg NK. Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2. Chem Sci. 2014 Jun 1;5(6):2184-2190. PubMed PMID: 24839542; PubMed Central PMCID: PMC4019407.

10: Jiang W, Zhou W, Uchida H, Kikumori M, Irie K, Watanabe R, Suzuki T, Sakamoto B, Kamio M, Nagai H. A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens. Mar Drugs. 2014 May 12;12(5):2748-59. doi: 10.3390/md12052748. PubMed PMID: 24824022; PubMed Central PMCID: PMC4052313.

11: Taylor MS, Stahl-Timmins W, Redshaw CH, Osborne NJ. Toxic alkaloids in Lyngbya majuscula and related tropical marine cyanobacteria. Harmful Algae. 2014 Jan;31:1-8. doi: 10.1016/j.hal.2013.09.003. Epub 2013 Oct 2. PubMed PMID: 28040098.

12: Ongley SE, Bian X, Zhang Y, Chau R, Gerwick WH, Müller R, Neilan BA. High-titer heterologous production in E. coli of lyngbyatoxin, a protein kinase C activator from an uncultured marine cyanobacterium. ACS Chem Biol. 2013 Sep 20;8(9):1888-93. doi: 10.1021/cb400189j. Epub 2013 Jun 17. PubMed PMID: 23751865; PubMed Central PMCID: PMC3880125.

13: Jones AC, Ottilie S, Eustáquio AS, Edwards DJ, Gerwick L, Moore BS, Gerwick WH. Evaluation of Streptomyces coelicolor A3(2) as a heterologous expression host for the cyanobacterial protein kinase C activator lyngbyatoxin A. FEBS J. 2012 Apr;279(7):1243-51. doi: 10.1111/j.1742-4658.2012.08517.x. Epub 2012 Mar 1. PubMed PMID: 22314229.

14: Westrick JA, Szlag DC, Southwell BJ, Sinclair J. A review of cyanobacteria and cyanotoxins removal/inactivation in drinking water treatment. Anal Bioanal Chem. 2010 Jul;397(5):1705-14. doi: 10.1007/s00216-010-3709-5. Epub 2010 May 26. Review. PubMed PMID: 20502884.

15: Harr KE, Szabo NJ, Cichra M, Phlips EJ. Debromoaplysiatoxin in Lyngbya-dominated mats on manatees (Trichechus manatus latirostris) in the Florida King's Bay ecosystem. Toxicon. 2008 Aug 1;52(2):385-8. doi: 10.1016/j.toxicon.2008.05.016. Epub 2008 Jun 5. PubMed PMID: 18585400.

16: Paul VJ, Arthur KE, Ritson-Williams R, Ross C, Sharp K. Chemical defenses: from compounds to communities. Biol Bull. 2007 Dec;213(3):226-51. Review. PubMed PMID: 18083964.

17: Vital P, Tanner D. Efficient and highly enantioselective formation of the all-carbon quaternary stereocentre of lyngbyatoxin A. Org Biomol Chem. 2006 Dec 7;4(23):4292-8. Epub 2006 Oct 20. PubMed PMID: 17102874.

18: Capper A, Tibbetts IR, O'Neil JM, Shaw GR. The fate of Lyngbya majuscula toxins in three potential consumers. J Chem Ecol. 2005 Jul;31(7):1595-606. PubMed PMID: 16222795.

19: Edwards DJ, Gerwick WH. Lyngbyatoxin biosynthesis: sequence of biosynthetic gene cluster and identification of a novel aromatic prenyltransferase. J Am Chem Soc. 2004 Sep 22;126(37):11432-3. PubMed PMID: 15366877.

20: Tønder JE, Hosseini M, Ahrenst AB, Tanner D. Studies of the formation of all-carbon quaternary centres, en route to lyngbyatoxin A. A comparison of phenyl and 7-substituted indole systems. Org Biomol Chem. 2004 May 21;2(10):1447-55. Epub 2004 Apr 20. PubMed PMID: 15136800.