Latrunculin B | CAS#76343-94-7 | macrolide

MedKoo Cat#: 598427 | Name: Latrunculin B

Description:

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

Latrunculin B causes concentration-dependent changes in cell shape and actin organization. It sequesters G-actin and prevents F-actin assembly. It binds monomeric actin with 1:1 stoichiometry and can be used to block actin polymerization both in vitro and in cells (Kd = 60 nM).1 The short-term effects of latrunculin B are comparable to those of latrunculin A, although latrunculin B is slightly less potent.2 However, latrunculin B is gradually inactivated by serum so that induced changes are transient in the continued presence of the compound. For this reason, latrunculin B may have fewer unwanted effects than latrunculin A and may be preferred for short-term studies. Latrunculin B is a 14-membered macrolide attached to 2-thiazolidinone moiety; from Red Sea sponge Latrunculia magnifica.

Chemical Structure

Latrunculin B

CAS#76343-94-7

Theoretical Analysis

MedKoo Cat#: 598427

Name: Latrunculin B

CAS#: 76343-94-7

Chemical Formula: C20H29NO5S

Exact Mass: 395.1766

Molecular Weight: 395.51

Elemental Analysis: C, 60.74; H, 7.39; N, 3.54; O, 20.23; S, 8.11

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

Latrunculin B; LAT-B; LATB; LAT B; NSC 339663; NSC-339663; NSC339663;

IUPAC/Chemical Name

(R)-4-((1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl)thiazolidin-2-one

InChi Key

NSHPHXHGRHSMIK-JRIKCGFMSA-N

InChi Code

InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/b5-3-,14-9-/t13-,15-,16-,17+,20-/m1/s1

SMILES Code

O=C1SC[C@@H]([C@]2(O)O[C@]3([H])CC[C@H](C)/C=C\CC/C(C)=C\C(O[C@@](C3)([H])C2)=O)N1

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 395.51 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: 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. 2: 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. 3: Wakatsuki T, Schwab B, Thompson NC, Elson EL. Effects of cytochalasin D and latrunculin B on mechanical properties of cells. J Cell Sci. 2001 Mar;114(Pt 5):1025-36. PubMed PMID: 11181185. 4: 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. 5: Kudrimoti S, Ahmed SA, Daga PR, Wahba AE, Khalifa SI, Doerksen RJ, Hamann MT. Semisynthetic latrunculin B analogs: studies of actin docking support a proposed mechanism for latrunculin bioactivity. Bioorg Med Chem. 2009 Nov 1;17(21):7517-22. doi: 10.1016/j.bmc.2009.09.012. Epub 2009 Sep 16. PubMed PMID: 19800245; PubMed Central PMCID: PMC2782694. 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: Hoye TR, Ayyad SE, Eklov BM, Hashish NE, Shier WT, El-Sayed KA, Hamann MT. Toward computing relative configurations: 16-epi-latrunculin B, a new stereoisomer of the actin polymerization inhibitor latrunculin B. J Am Chem Soc. 2002 Jun 26;124(25):7405-10. PubMed PMID: 12071749. 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: Villanueva MA, Barnay-Verdier S, Priouzeau F, Furla P. Chloroplast and oxygen evolution changes in Symbiodinium sp. as a response to latrunculin and butanedione monoxime treatments under various light conditions. Photosynth Res. 2015 Jun;124(3):305-13. doi: 10.1007/s11120-015-0142-9. Epub 2015 Apr 23. PubMed PMID: 25904178. 10: Moscatelli A, Idilli AI, Rodighiero S, Caccianiga M. Inhibition of actin polymerisation by low concentration Latrunculin B affects endocytosis and alters exocytosis in shank and tip of tobacco pollen tubes. Plant Biol (Stuttg). 2012 Sep;14(5):770-82. doi: 10.1111/j.1438-8677.2011.00547.x. Epub 2012 Jan 30. PubMed PMID: 22288466. 11: Gronewold TM, Sasse F, Lünsdorf H, Reichenbach H. Effects of rhizopodin and latrunculin B on the morphology and on the actin cytoskeleton of mammalian cells. Cell Tissue Res. 1999 Jan;295(1):121-9. PubMed PMID: 9931358. 12: Ethier CR, Read AT, Chan DW. Effects of latrunculin-B on outflow facility and trabecular meshwork structure in human eyes. Invest Ophthalmol Vis Sci. 2006 May;47(5):1991-8. PubMed PMID: 16639007. 13: Xue XH, Guo CQ, Du F, Lu QL, Zhang CM, Ren HY. AtFH8 is involved in root development under effect of low-dose latrunculin B in dividing cells. Mol Plant. 2011 Mar;4(2):264-78. doi: 10.1093/mp/ssq085. Epub 2011 Feb 9. PubMed PMID: 21307369. 14: Peterson JA, Tian B, Geiger B, Kaufman PL. Effect of latrunculin-B on outflow facility in monkeys. Exp Eye Res. 2000 Mar;70(3):307-13. PubMed PMID: 10712817. 15: Blancaflor EB, Hou GC, Mohamalawari DR. The promotive effect of latrunculin B on maize root gravitropism is concentration dependent. Adv Space Res. 2003;31(10):2215-20. PubMed PMID: 14686435. 16: Dowell ML, Lakser OJ, Gerthoffer WT, Fredberg JJ, Stelmack GL, Halayko AJ, Solway J, Mitchell RW. Latrunculin B increases force fluctuation-induced relengthening of ACh-contracted, isotonically shortened canine tracheal smooth muscle. J Appl Physiol (1985). 2005 Feb;98(2):489-97. Epub 2004 Oct 1. PubMed PMID: 15465883. 17: Vondráková Z, Eliášová K, Vágner M. The anti-actin drugs latrunculin and cytochalasin affect the maturation of spruce somatic embryos in different ways. Plant Sci. 2014 May;221-222:90-9. doi: 10.1016/j.plantsci.2014.02.006. Epub 2014 Feb 26. PubMed PMID: 24656339. 18: Sabanay I, Tian B, Gabelt BT, Geiger B, Kaufman PL. Latrunculin B effects on trabecular meshwork and corneal endothelial morphology in monkeys. Exp Eye Res. 2006 Feb;82(2):236-46. Epub 2005 Jul 27. PubMed PMID: 16054137. 19: Okka M, Tian B, Kaufman PL. Effect of low-dose latrunculin B on anterior segment physiologic features in the monkey eye. Arch Ophthalmol. 2004 Oct;122(10):1482-8. PubMed PMID: 15477460. 20: Kurilova LS, Krutetskaia ZI, Lebedev OE. [Effect of latrunculin B, jasplakinolide and brefeldin A on the store-dependent Ca2+ entry in macrophages]. Tsitologiia. 2006;48(10):867-74. Russian. PubMed PMID: 17162846.