Jasplakinolide | CAS#102396-24-7 | cyclodepsipeptide

MedKoo Cat#: 462155 | Name: Jasplakinolide

Description:

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

Jasplakinolide is a cyclodepsipeptide isolated from marine sponge Jaspis and is active against Candida.

Chemical Structure

Jasplakinolide

CAS#102396-24-7

Theoretical Analysis

MedKoo Cat#: 462155

Name: Jasplakinolide

CAS#: 102396-24-7

Chemical Formula: C36H45BrN4O6

Exact Mass: 708.2522

Molecular Weight: 709.68

Elemental Analysis: C, 60.93; H, 6.39; Br, 11.26; N, 7.89; O, 13.53

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

Jasplakinolide; Jaspamide; NSC 613009

IUPAC/Chemical Name

(4R,5Z,7R,10S,11Z,13R,15Z,17R,19S)-7-((2-bromo-1H-indol-3-yl)methyl)-6,12-dihydroxy-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadeca-5,11,15-triene-2,9-dione

InChi Key

GQWYWHOHRVVHAP-MPNYZYRJSA-N

InChi Code

InChI=1S/C36H45BrN4O6/c1-20-15-21(2)17-23(4)47-32(43)19-30(25-11-13-26(42)14-12-25)40-35(45)31(18-28-27-9-7-8-10-29(27)39-33(28)37)41(6)36(46)24(5)38-34(44)22(3)16-20/h7-15,21-24,30-31,39,42H,16-19H2,1-6H3,(H,38,44)(H,40,45)/b20-15-/t21-,22+,23-,24-,30+,31+/m0/s1

SMILES Code

C/C(C[C@@](/C(O)=N/[C@@](C(N([C@](/C(O)=N/[C@](C1=CC=C(O)C=C1)([H])CC2=O)([H])CC(C3=CC=CC=C3N4)=C4Br)C)=O)([H])C)([H])C)=C([H])/[C@](C[C@](O2)([H])C)([H])C

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 709.68 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: Jasplakinolide reduces actin and tropomyosin dynamics during myofibrillogenesis Jushuo Wang, Yingli Fan, Dipak K. Dube, Jean M. Sanger, Joseph W. Sanger Cytoskeleton (Hoboken) Author manuscript; available in PMC 2015 Sep 12.Published in final edited form as: Cytoskeleton (Hoboken). 2014 Sep; 71(9): 513–529. Published online 2014 Sep 12. doi: 10.1002/cm.21189 PMCID: PMC4194140 2: Actin-Dynamics in Plant Cells: The Function of Actin Perturbing Substances Jasplakinolide, Chondramides, Phalloidin, Cytochalasins, and Latrunculins Andreas Holzinger, Kathrin Blaas Methods Mol Biol. Author manuscript; available in PMC 2016 May 17.Published in final edited form as: Methods Mol Biol. 2016; 1365: 243–261. doi: 10.1007/978-1-4939-3124-8_13 PMCID: PMC4869834 3: Modest Interference with Actin Dynamics in Primary T Cell Activation by Antigen Presenting Cells Preferentially Affects Lamellal Signaling Kole T. Roybal, Emily M. Mace, Danielle J. Clark, Alan D. Leard, Andrew Herman, Paul Verkade, Jordan S. Orange, Christoph Wülfing PLoS One. 2015; 10(8): e0133231. Published online 2015 Aug 3. doi: 10.1371/journal.pone.0133231 PMCID: PMC4523178 4: Jasplakinolide Induces Apoptosis in Various Transformed Cell Lines by a Caspase-3-Like Protease-Dependent Pathway Chikako Odaka, Miranda L. Sanders, Phillip Crews Clin Diagn Lab Immunol. 2000 Nov; 7(6): 947–952. doi: 10.1128/cdli.7.6.947-952.2000 PMCID: PMC95991 5: Actin Stabilization by Jasplakinolide Affects the Function of Bone Marrow-Derived Late Endothelial Progenitor Cells Xiaoyun Zhang, Xiaodong Cui, Lixia Cheng, Xiumei Guan, Hong Li, Xin Li, Min Cheng PLoS One. 2012; 7(11): e50899. Published online 2012 Nov 30. doi: 10.1371/journal.pone.0050899 PMCID: PMC3511387 6: New Structures and Bioactivity Properties of Jasplakinolide (Jaspamide) Analogues from Marine Sponges Sarah J. Robinson, Brandon I. Morinaka, Taro Amagata, Karen Tenney, Walter M. Bray, Nadine C. Gassner, R. Scott Lokey, Phillip Crews J Med Chem. Author manuscript; available in PMC 2011 Feb 25.Published in final edited form as: J Med Chem. 2010 Feb 25; 53(4): 1651–1661. doi: 10.1021/jm9013554 PMCID: PMC2848536 7: New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens Sherif S. Ebada, Werner E. G. Müller, Wenhan Lin, Peter Proksch Mar Drugs. 2019 Feb; 17(2): 100. Published online 2019 Feb 6. doi: 10.3390/md17020100 PMCID: PMC6409940 8: Recruitment Kinetics of Tropomyosin Tpm3.1 to Actin Filament Bundles in the Cytoskeleton Is Independent of Actin Filament Kinetics Mark A. Appaduray, Andrius Masedunskas, Nicole S. Bryce, Christine A. Lucas, Sean C. Warren, Paul Timpson, Jeffrey H. Stear, Peter W. Gunning, Edna C. Hardeman PLoS One. 2016; 11(12): e0168203. Published online 2016 Dec 15. doi: 10.1371/journal.pone.0168203 PMCID: PMC5158027 9: The Biostructural Features of Additional Jasplakinolide (Jaspamide) Analogues Katharine R. Watts, Brandon I. Morinaka, Taro Amagata, Sarah J. Robinson, Karen Tenney, Walter M. Bray, Nadine C. Gassner, R. Scott Lokey, Joseph Media, Frederick A. Valeriote, Phillip Crews J Nat Prod. Author manuscript; available in PMC 2012 Mar 25.Published in final edited form as: J Nat Prod. 2011 Mar 25; 74(3): 341–351. Published online 2011 Jan 11. doi: 10.1021/np100721g PMCID: PMC3070360 10: Jasplakinolide induces primary cilium formation through cell rounding and YAP inactivation Tomoaki Nagai, Kensaku Mizuno PLoS One. 2017; 12(8): e0183030. Published online 2017 Aug 10. doi: 10.1371/journal.pone.0183030 PMCID: PMC5552318