Kalkitoxin | CAS#247184-89-0 | ichthyotoxin

MedKoo Cat#: 462103 | Name: Kalkitoxin

Description:

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

Kalkitoxin is an ichthyotoxin derived from the cyanobacterium Lyngbya majuscula. It induces NMDA receptor mediated neuronal necrosis, blocks voltage-dependent sodium channels, and induces cellular hypoxia by inhibiting the electron transport chain (ETC) complex 1.

Chemical Structure

Kalkitoxin

CAS#247184-89-0

Theoretical Analysis

MedKoo Cat#: 462103

Name: Kalkitoxin

CAS#: 247184-89-0

Chemical Formula: C21H38N2OS

Exact Mass: 366.2705

Molecular Weight: 366.61

Elemental Analysis: C, 68.80; H, 10.45; N, 7.64; O, 4.36; S, 8.75

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 #

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Synonym

Kalkitoxin

IUPAC/Chemical Name

(2R)-N-((3S,5S,6R)-7-((4R)-4-Ethenyl-4,5-dihydro-2-thiazolyl)-3,5,6-trimethylheptyl)-N,2-dimethylbutanamide

InChi Key

PHYRFZDJEDWWKT-UJWQCDCRSA-N

InChi Code

InChI=1S/C21H38N2OS/c1-8-16(4)21(24)23(7)11-10-15(3)12-17(5)18(6)13-20-22-19(9-2)14-25-20/h9,15-19H,2,8,10-14H2,1,3-7H3/t15-,16-,17+,18-,19-/m1/s1

SMILES Code

CC[C@@H](C)C(N(CC[C@@H](C)C[C@H](C)[C@H](C)CC1=N[C@H](C=C)CS1)C)=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

>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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 366.61 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: Kalkitoxin Inhibits Angiogenesis, Disrupts Cellular Hypoxic Signaling, and Blocks Mitochondrial Electron Transport in Tumor Cells J. Brian Morgan, Yang Liu, Veena Coothankandaswamy, Fakhri Mahdi, Mika B. Jekabsons, William H. Gerwick, Frederick A. Valeriote, Yu-Dong Zhou, Dale G. Nagle Mar Drugs. 2015 Mar; 13(3): 1552–1568. Published online 2015 Mar 20. doi: 10.3390/md13031552 PMCID: PMC4377999 2: Shellfish Toxins Targeting Voltage-Gated Sodium Channels Fan Zhang, Xunxun Xu, Tingting Li, Zhonghua Liu Mar Drugs. 2013 Dec; 11(12): 4698–4723. Published online 2013 Nov 28. doi: 10.3390/md11124698 PMCID: PMC3877881 3: Marine Toxins That Target Voltage-gated Sodium Channels Ahmed Al-Sabi, Jeff McArthur, Vitaly Ostroumov, Robert J. French Mar Drugs. 2006 Apr; 4(3): 157–192. Published online 2006 Apr 6. PMCID: PMC3663416 4: The Diversity of Cyanobacterial Toxins on Structural Characterization, Distribution and Identification: A Systematic Review Xingde Du, Haohao Liu, Le Yuan, Yueqin Wang, Ya Ma, Rui Wang, Xinghai Chen, Michael D. Losiewicz, Hongxiang Guo, Huizhen Zhang Toxins (Basel) 2019 Sep; 11(9): 530. Published online 2019 Sep 12. doi: 10.3390/toxins11090530 PMCID: PMC6784007 5: Chemical Compounds Toxic to Invertebrates Isolated from Marine Cyanobacteria of Potential Relevance to the Agricultural Industry Magbubah Essack, Hanin S. Alzubaidy, Vladimir B. Bajic, John A. C. Archer Toxins (Basel) 2014 Nov; 6(11): 3058–3076. Published online 2014 Oct 29. doi: 10.3390/toxins6113058 PMCID: PMC4247248 6: Marine Natural Product Peptides with Therapeutic Potential: Chemistry, Biosynthesis, and Pharmacology Vedanjali Gogineni, Mark T. Hamann Biochim Biophys Acta. Author manuscript; available in PMC 2019 Jan 1.Published in final edited form as: Biochim Biophys Acta. 2018 Jan; 1862(1): 81–196. Published online 2017 Aug 24. doi: 10.1016/j.bbagen.2017.08.014 PMCID: PMC5918664 7: Toward Generalization of Iterative Small Molecule Synthesis Jonathan W. Lehmann, Daniel J. Blair, Martin D. Burke Nat Rev Chem. Author manuscript; available in PMC 2018 Apr 23.Published in final edited form as: Nat Rev Chem. 2018 Feb; 2(2): 0115. Published online 2018 Mar 7. doi: 10.1038/s41570-018-0115 PMCID: PMC5912323 8: Diversity and Impact of Prokaryotic Toxins on Aquatic Environments: A Review Elisabete Valério, Sandra Chaves, Rogério Tenreiro Toxins (Basel) 2010 Oct; 2(10): 2359–2410. Published online 2010 Oct 18. doi: 10.3390/toxins2102359 PMCID: PMC3153167 9: Bloom Dynamics of Cyanobacteria and Their Toxins: Environmental Health Impacts and Mitigation Strategies Rajesh P. Rastogi, Datta Madamwar, Aran Incharoensakdi Front Microbiol. 2015; 6: 1254. Published online 2015 Nov 17. doi: 10.3389/fmicb.2015.01254 PMCID: PMC4646972 10: Synthesis and Evaluation of Hermitamides A and B as Human Voltage-Gated Sodium Channel Blockers Eliseu O. De Oliveira, Kristin M. Graf, Manoj K. Patel, Aparna Baheti, Hye-Sik Kong, Linda H. MacArthur, Sivanesan Dakshanamurthy, Kan Wang, Milton L. Brown, Mikell Paige Bioorg Med Chem. Author manuscript; available in PMC 2012 Jul 15.Published in final edited form as: Bioorg Med Chem. 2011 Jul 15; 19(14): 4322–4329. Published online 2011 May 30. doi: 10.1016/j.bmc.2011.05.043 PMCID: PMC3134794