Latrunculins A | CAS#122876-48-6 | marine toxin

MedKoo Cat#: 598436 | Name: Latrunculins A

Description:

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

Latrunculins A is a novel marine toxin that disrupt microfilament organization in cultured cells.

Chemical Structure

Latrunculins A

CAS#122876-48-6

Theoretical Analysis

MedKoo Cat#: 598436

Name: Latrunculins A

CAS#: 122876-48-6

Chemical Formula: C22H31NO6S

Exact Mass: 437.1872

Molecular Weight: 437.55

Elemental Analysis: C, 60.39; H, 7.14; N, 3.20; O, 21.94; S, 7.33

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

Latrunculins A;

IUPAC/Chemical Name

(4S)-4-((1R,5Z,7S,9S,12Z,16R,18S)-18-hydroxy-4,12-dimethyl-14-oxo-8,15,19-trioxatricyclo[14.3.1.07,9]icosa-5,12-dien-18-yl)thiazolidin-2-one

InChi Key

MSHYYZSYRGWFES-DQVGGNGZSA-N

InChi Code

InChI=1S/C22H31NO6S/c1-13-3-6-15-10-16(11-22(26,29-15)19-12-30-21(25)23-19)27-20(24)9-14(2)5-8-18-17(28-18)7-4-13/h4,7,9,13,15-19,26H,3,5-6,8,10-12H2,1-2H3,(H,23,25)/b7-4-,14-9-/t13?,15-,16-,17+,18+,19-,22+/m1/s1

SMILES Code

O=C1SC[C@H]([C@]2(O)C[C@]3([H])OC(/C=C(C)\CC[C@]4([H])O[C@@]4([H])/C=C\C(C)CC[C@@](C3)([H])O2)=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 437.55 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.

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: Helal MA, Khalifa S, Ahmed S. Differential binding of latrunculins to G-actin: a molecular dynamics study. J Chem Inf Model. 2013 Sep 23;53(9):2369-75. doi: 10.1021/ci400317j. Epub 2013 Aug 29. PubMed PMID: 23988111. 2: 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. 3: Johnson S, Rahmani R, Drew DR, Williams MJ, Wilkinson M, Tan YH, Huang JX, Tonkin CJ, Beeson JG, Baum J, Smith BJ, Baell JB. Truncated Latrunculins as Actin Inhibitors Targeting Plasmodium falciparum Motility and Host Cell Invasion. J Med Chem. 2016 Dec 22;59(24):10994-11005. doi: 10.1021/acs.jmedchem.6b01109. Epub 2016 Dec 2. PubMed PMID: 28002959. 4: Khalifa S, Ahmed S, Mesbah M, Youssef D, Hamann M. Quantitative determination of latrunculins A and B in the Red Sea sponge Negombata magnifica by high performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 17;832(1):47-51. Epub 2006 Jan 18. PubMed PMID: 16431167. 5: Spector I, Shochet NR, Kashman Y, Groweiss A. Latrunculins: novel marine toxins that disrupt microfilament organization in cultured cells. Science. 1983 Feb 4;219(4584):493-5. PubMed PMID: 6681676. 6: Holzinger A, Blaas K. Actin-Dynamics in Plant Cells: The Function of Actin-Perturbing Substances: Jasplakinolide, Chondramides, Phalloidin, Cytochalasins, and Latrunculins. Methods Mol Biol. 2016;1365:243-61. doi: 10.1007/978-1-4939-3124-8_13. PubMed PMID: 26498789; PubMed Central PMCID: PMC4869834. 7: Foissner I, Wasteneys GO. Wide-ranging effects of eight cytochalasins and latrunculin A and B on intracellular motility and actin filament reorganization in characean internodal cells. Plant Cell Physiol. 2007 Apr;48(4):585-97. Epub 2007 Feb 27. PubMed PMID: 17327257. 8: Peterson JA, Tian B, McLaren JW, Hubbard WC, Geiger B, Kaufman PL. Latrunculins' effects on intraocular pressure, aqueous humor flow, and corneal endothelium. Invest Ophthalmol Vis Sci. 2000 Jun;41(7):1749-58. PubMed PMID: 10845595. 9: El Sayed KA, Youssef DT, Marchetti D. Bioactive natural and semisynthetic latrunculins. J Nat Prod. 2006 Feb;69(2):219-23. PubMed PMID: 16499319. 10: Williams BD, Smith AB 3rd. Total synthesis of (+)-18-epi-latrunculol A: development of a synthetic route. J Org Chem. 2014 Oct 3;79(19):9284-96. doi: 10.1021/jo501733m. Epub 2014 Sep 22. PubMed PMID: 25243951; PubMed Central PMCID: PMC4184459. 11: Khanfar MA, Youssef DT, El Sayed KA. Semisynthetic latrunculin derivatives as inhibitors of metastatic breast cancer: biological evaluations, preliminary structure-activity relationship and molecular modeling studies. ChemMedChem. 2010 Feb 1;5(2):274-85. doi: 10.1002/cmdc.200900430. PubMed PMID: 20043312; PubMed Central PMCID: PMC3529144. 12: Spector I, Shochet NR, Blasberger D, Kashman Y. Latrunculins--novel marine macrolides that disrupt microfilament organization and affect cell growth: I. Comparison with cytochalasin D. Cell Motil Cytoskeleton. 1989;13(3):127-44. PubMed PMID: 2776221. 13: Khanfar MA, Youssef DT, El Sayed KA. 3D-QSAR studies of latrunculin-based actin polymerization inhibitors using CoMFA and CoMSIA approaches. Eur J Med Chem. 2010 Sep;45(9):3662-8. doi: 10.1016/j.ejmech.2010.05.012. Epub 2010 May 12. PubMed PMID: 20684858; PubMed Central PMCID: PMC2918725. 14: Ebrahim HY, El Sayed KA. Discovery of Novel Antiangiogenic Marine Natural Product Scaffolds. Mar Drugs. 2016 Mar 11;14(3). pii: E57. doi: 10.3390/md14030057. PubMed PMID: 26978377; PubMed Central PMCID: PMC4820311. 15: Poulsen NC, Spector I, Spurck TP, Schultz TF, Wetherbee R. Diatom gliding is the result of an actin-myosin motility system. Cell Motil Cytoskeleton. 1999;44(1):23-33. PubMed PMID: 10470016. 16: Ahmed SA, Odde S, Daga PR, Bowling JJ, Mesbah MK, Youssef DT, Khalifa SI, Doerksen RJ, Hamann MT. Latrunculin with a highly oxidized thiazolidinone ring: structure assignment and actin docking. Org Lett. 2007 Nov 8;9(23):4773-6. Epub 2007 Oct 12. PubMed PMID: 17929935; PubMed Central PMCID: PMC2529398. 17: Spector I, Braet F, Shochet NR, Bubb MR. New anti-actin drugs in the study of the organization and function of the actin cytoskeleton. Microsc Res Tech. 1999 Oct 1;47(1):18-37. PubMed PMID: 10506759. 18: Johnson TA, Sohn J, Inman WD, Estee SA, Loveridge ST, Vervoort HC, Tenney K, Liu J, Ang KK, Ratnam J, Bray WM, Gassner NC, Shen YY, Lokey RS, McKerrow JH, Boundy-Mills K, Nukanto A, Kanti A, Julistiono H, Kardono LB, Bjeldanes LF, Crews P. Natural product libraries to accelerate the high-throughput discovery of therapeutic leads. J Nat Prod. 2011 Dec 27;74(12):2545-55. doi: 10.1021/np200673b. Epub 2011 Nov 30. PubMed PMID: 22129061; PubMed Central PMCID: PMC3246535. 19: Eid ES, Abo-Elmatty DM, Hanora A, Mesbah NM, Abou-El-Ela SH. Molecular and protein characterization of two species of the latrunculin-producing sponge Negombata from the Red Sea. J Pharm Biomed Anal. 2011 Dec 15;56(5):911-5. doi: 10.1016/j.jpba.2011.07.037. Epub 2011 Jul 30. PubMed PMID: 21852057. 20: 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.