MedKoo Cat#: 598437 | Name: Latrunculin M

Description:

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

Latrunculin M is a novel marine toxin that disrupt microfilament organization in cultured cells.

Chemical Structure

Latrunculin M
Latrunculin M
CAS#122876-49-7

Theoretical Analysis

MedKoo Cat#: 598437

Name: Latrunculin M

CAS#: 122876-49-7

Chemical Formula: C21H33NO5S

Exact Mass: 411.2079

Molecular Weight: 411.55

Elemental Analysis: C, 61.29; H, 8.08; N, 3.40; O, 19.44; S, 7.79

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Latrunculin M;
IUPAC/Chemical Name
methyl (S,2Z,6Z)-10-((2S,6R)-6-hydroxy-6-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-3,8-dimethyldeca-2,6-dienoate
InChi Key
ZDGSZBCCKDDREV-FQGBDBPUSA-N
InChi Code
InChI=1S/C21H33NO5S/c1-15(7-4-5-8-16(2)13-19(23)26-3)10-11-17-9-6-12-21(25,27-17)18-14-28-20(24)22-18/h4,7,13,15,17-18,25H,5-6,8-12,14H2,1-3H3,(H,22,24)/b7-4-,16-13-/t15-,17+,18+,21-/m1/s1
SMILES Code
O=C(SC1)N[C@@H]1[C@@](O2)(O)CCC[C@H]2CC[C@H](C)/C=C\CC/C(C)=C\C(OC)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 411.55 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
1: Sierra-Paredes G, Loureiro AI, Wright LC, Sierra-Marcuño G, Soares-da-Silva P. Effects of eslicarbazepine acetate on acute and chronic latrunculin A-induced seizures and extracellular amino acid levels in the mouse hippocampus. BMC Neurosci. 2014 Dec 20;15:134. doi: 10.1186/s12868-014-0134-2. PubMed PMID: 25526768; PubMed Central PMCID: PMC4279694. 2: Fürstner A, De Souza D, Turet L, Fenster MD, Parra-Rapado L, Wirtz C, Mynott R, Lehmann CW. Total syntheses of the actin-binding macrolides latrunculin A, B, C, M, S and 16-epi-latrunculin B. Chemistry. 2007;13(1):115-34. PubMed PMID: 17091520. 3: Himaki T, Mizobe Y, Tsuda K, Suetomo M, Yamakuchi H, Miyoshi K, Takao S, Yoshida M. Effect of postactivation treatment with latrunculin A on in vitro and in vivo development of cloned embryos derived from kidney fibroblasts of an aged Clawn miniature boar. J Reprod Dev. 2012;58(4):398-403. Epub 2012 Apr 13. PubMed PMID: 22498812. 4: Mallol A, Santaló J, Ibáñez E. Improved development of somatic cell cloned mouse embryos by vitamin C and latrunculin A. PLoS One. 2015 Mar 6;10(3):e0120033. doi: 10.1371/journal.pone.0120033. eCollection 2015. PubMed PMID: 25749170; PubMed Central PMCID: PMC4352067. 5: Lu YY, Lin YK, Wen ZH, Chen YC, Chen SA, Chen YJ. Latrunculin B modulates electrophysiological characteristics and arrhythmogenesis in pulmonary vein cardiomyocytes. Clin Sci (Lond). 2016 May;130(9):721-32. doi: 10.1042/CS20150593. Epub 2016 Feb 2. PubMed PMID: 26839418. 6: Ketelaar T, Meijer HJ, Spiekerman M, Weide R, Govers F. Effects of latrunculin B on the actin cytoskeleton and hyphal growth in Phytophthora infestans. Fungal Genet Biol. 2012 Dec;49(12):1014-22. doi: 10.1016/j.fgb.2012.09.008. Epub 2012 Oct 2. PubMed PMID: 23036581. 7: Moccia F. Latrunculin A depolarizes starfish oocytes. Comp Biochem Physiol A Mol Integr Physiol. 2007 Dec;148(4):845-52. Epub 2007 Sep 5. PubMed PMID: 17897856. 8: Wood JA, McKee CT, Thomasy SM, Fischer ME, Shah NM, Murphy CJ, Russell P. Substratum compliance regulates human trabecular meshwork cell behaviors and response to latrunculin B. Invest Ophthalmol Vis Sci. 2011 Dec 2;52(13):9298-303. doi: 10.1167/iovs.11-7857. PubMed PMID: 22064990; PubMed Central PMCID: PMC3250097. 9: Thomasy SM, Wood JA, Kass PH, Murphy CJ, Russell P. Substratum stiffness and latrunculin B regulate matrix gene and protein expression in human trabecular meshwork cells. Invest Ophthalmol Vis Sci. 2012 Feb 23;53(2):952-8. doi: 10.1167/iovs.11-8526. Print 2012 Feb. PubMed PMID: 22247475; PubMed Central PMCID: PMC3317432. 10: Thomasy SM, Morgan JT, Wood JA, Murphy CJ, Russell P. Substratum stiffness and latrunculin B modulate the gene expression of the mechanotransducers YAP and TAZ in human trabecular meshwork cells. Exp Eye Res. 2013 Aug;113:66-73. doi: 10.1016/j.exer.2013.05.014. Epub 2013 May 29. PubMed PMID: 23727052; PubMed Central PMCID: PMC3737383. 11: Oguri S, Matsuo J, Hayashi Y, Nakamura S, Hanawa T, Fukumoto T, Mizutani Y, Yao T, Akizawa K, Suzuki H, Shimizu C, Matsuno K, Kamiya S, Yamaguchi H. Ciliates promote the transfer of the gene encoding the extended-spectrum β-lactamase CTX-M-27 between Escherichia coli strains. J Antimicrob Chemother. 2011 Mar;66(3):527-30. doi: 10.1093/jac/dkq487. Epub 2010 Dec 21. PubMed PMID: 21177671. 12: Soudani N, Ghantous CM, Farhat Z, Shebaby WN, Zibara K, Zeidan A. Calcineurin/NFAT Activation-Dependence of Leptin Synthesis and Vascular Growth in Response to Mechanical Stretch. Front Physiol. 2016 Sep 29;7:433. eCollection 2016. PubMed PMID: 27746739; PubMed Central PMCID: PMC5040753. 13: Murphy KC, Morgan JT, Wood JA, Sadeli A, Murphy CJ, Russell P. The formation of cortical actin arrays in human trabecular meshwork cells in response to cytoskeletal disruption. Exp Cell Res. 2014 Oct 15;328(1):164-171. doi: 10.1016/j.yexcr.2014.06.014. Epub 2014 Jun 30. PubMed PMID: 24992043; PubMed Central PMCID: PMC4178168. 14: Keller H, Zadeh AD, Eggli P. Localised depletion of polymerised actin at the front of Walker carcinosarcoma cells increases the speed of locomotion. Cell Motil Cytoskeleton. 2002 Nov;53(3):189-202. PubMed PMID: 12211101. 15: Ko MK, Kim EK, Gonzalez JM Jr, Tan JC. Dose- and time-dependent effects of actomyosin inhibition on live mouse outflow resistance and aqueous drainage tissues. Sci Rep. 2016 Feb 17;6:21492. doi: 10.1038/srep21492. PubMed PMID: 26884319; PubMed Central PMCID: PMC4756686. 16: Smyth JW, Vogan JM, Buch PJ, Zhang SS, Fong TS, Hong TT, Shaw RM. Actin cytoskeleton rest stops regulate anterograde traffic of connexin 43 vesicles to the plasma membrane. Circ Res. 2012 Mar 30;110(7):978-89. doi: 10.1161/CIRCRESAHA.111.257964. Epub 2012 Feb 9. PubMed PMID: 22328533; PubMed Central PMCID: PMC3621031. 17: Bozavikov P, Rajshankar D, Lee W, McCulloch CA. Particle size influences fibronectin internalization and degradation by fibroblasts. Exp Cell Res. 2014 Oct 15;328(1):172-85. doi: 10.1016/j.yexcr.2014.06.018. Epub 2014 Jul 1. PubMed PMID: 24995996. 18: Rounds CM, Hepler PK, Winship LJ. The apical actin fringe contributes to localized cell wall deposition and polarized growth in the lily pollen tube. Plant Physiol. 2014 Sep;166(1):139-51. doi: 10.1104/pp.114.242974. Epub 2014 Jul 18. PubMed PMID: 25037212; PubMed Central PMCID: PMC4149702. 19: Chia JX, Efimova N, Svitkina TM. Neurite outgrowth is driven by actin polymerization even in the presence of actin polymerization inhibitors. Mol Biol Cell. 2016 Sep 28. pii: mbc.E16-04-0253. [Epub ahead of print] PubMed PMID: 27682586; PubMed Central PMCID: PMC5170553. 20: Wang X, Tanaka M, Krstin S, Peixoto HS, Moura CCM, Wink M. Cytoskeletal interference - A new mode of action for the anticancer drugs camptothecin and topotecan. Eur J Pharmacol. 2016 Oct 15;789:265-274. doi: 10.1016/j.ejphar.2016.07.044. Epub 2016 Jul 27. PubMed PMID: 27474470.