Jasplakinolide

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

MedKoo CAT#: 462155

CAS#: 102396-24-7

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


Chemical Structure

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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: 709.682
Elemental Analysis: C, 60.93; H, 6.39; Br, 11.26; N, 7.89; O, 13.53

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

Preparing Stock Solutions

The following data is based on the product molecular weight 709.682 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

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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