Molecular structure of Jasplakinolide, CAS Number: 102396-24-7
Jasplakinolide (CAS 102396-24-7)
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Alternate Names:
Jasplakinolide also known as Jaspamide; (3S,6R,9R,13S,15R,16E,19S)-3,5,13,15,17,19-Hexamethyl-6-[(2-bromo-1H-indole-3-yl)methyl]-9-(4-hydroxyphenyl)-12-oxa-2,5,8-triazacyclononadeca-16-ene-1,4,7,11-tetraone; cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-8S-hydroxy-2S,4E,6R-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
Application:
Jasplakinolide is a cell permeable compound which stabilizes pre-formed actin filaments and inhibits their disassembly
CAS Number:
102396-24-7
Purity:
≥97%
Molecular Weight:
709.67
Molecular Formula:
C36H45BrN4O6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Jasplakinolide is a naturally occurring macrocyclic peptide which induces the polymerization of actin into filaments (F-actin). Jasplakinolide is demonstrated to bind to F-actin competitively with Phalloidin (sc-202763), an irreversible stabilizer of F-actin, to stabilize the filaments and to promote filamentous assembly of actin. Actin filaments form the structural foundation of the cytoskeleton and native regulation of actin polymerization/depolymerization is for mechanical processes in the cell. Antiproliferative and cytotoxic effects are produced by Jasplakinolide, attributed to prevention of F-actin depolymerization and to induced overpolymerization of monomeric actin. Jasplakinolide was shown to enhance the interleukin-2 apoptotic signal in CTLL-20 interleukin-2-dependent T cells, suggesting a participation of the actin cytoskeleton in the transduction of proliferative signals to cells. Jasplakinolide prevents activation of store-mediated Ca2+ entry into human platelets, also through its effect on the actin cytoskeleton.
Jasplakinolide (CAS 102396-24-7) References
- The anti-proliferative agent jasplakinolide rearranges the actin cytoskeleton of plant cells. | Sawitzky, H., et al. 1999. Eur J Cell Biol. 78: 424-33. PMID: 10430024
- Role of actin-filament disassembly in lamellipodium protrusion in motile cells revealed using the drug jasplakinolide. | Cramer, LP. 1999. Curr Biol. 9: 1095-105. PMID: 10531004
- Effects of jasplakinolide on the kinetics of actin polymerization. An explanation for certain in vivo observations. | Bubb, MR., et al. 2000. J Biol Chem. 275: 5163-70. PMID: 10671562
- A role for the actin cytoskeleton in the initiation and maintenance of store-mediated calcium entry in human platelets. Evidence for conformational coupling. | Rosado, JA., et al. 2000. J Biol Chem. 275: 7527-33. PMID: 10713057
- In vitro screening of crude extracts and pure metabolites obtained from marine invertebrates for the treatment of breast cancer. | Stingl, J., et al. 1992. Cancer Chemother Pharmacol. 30: 401-6. PMID: 1505079
- A simple model for the cooperative stabilisation of actin filaments by phalloidin and jasplakinolide. | Visegrády, B., et al. 2005. FEBS Lett. 579: 6-10. PMID: 15620683
- Dynamics of an F-actin aggresome generated by the actin-stabilizing toxin jasplakinolide. | Lázaro-Diéguez, F., et al. 2008. J Cell Sci. 121: 1415-25. PMID: 18398002
- New class of antifungal agents: jasplakinolide, a cyclodepsipeptide from the marine sponge, Jaspis species. | Scott, VR., et al. 1988. Antimicrob Agents Chemother. 32: 1154-7. PMID: 3190203
- Growth modulation and differentiation of acute myeloid leukemia cells by jaspamide. | Fabian, I., et al. 1995. Exp Hematol. 23: 583-7. PMID: 7601248
- Jasplakinolide's inhibition of the growth of prostate carcinoma cells in vitro with disruption of the actin cytoskeleton. | Senderowicz, AM., et al. 1995. J Natl Cancer Inst. 87: 46-51. PMID: 7666463
- Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin. | Bubb, MR., et al. 1994. J Biol Chem. 269: 14869-71. PMID: 8195116
- Jasplakinolide: interaction with radiation and hyperthermia in human prostate carcinoma and Lewis lung carcinoma. | Takeuchi, H., et al. 1998. Cancer Chemother Pharmacol. 42: 491-6. PMID: 9788576
- Actin stabilization by jasplakinolide enhances apoptosis induced by cytokine deprivation. | Posey, SC. and Bierer, BE. 1999. J Biol Chem. 274: 4259-65. PMID: 9933626
Inhibitor of:
α-actinin-3, α-centractin, αPIX, β-centractin, β1-Syntrophin, ζ2-COP, 3110003A17Rik, 4921517D21Rik, 4930403N07Rik, 4930488E11Rik, 4932418E24Rik, 6230427J02Rik, 6720456B07Rik, 7420426K07Rik, Abi-1, ABLIM1, ABLIM2, ACT, ACTA1, ACTBL1, ACTC1, ACTG1, ACTL10, ACTL7A, ACTL7B, ACTL8, ACTR10, Adducin β, adseverin, AFAP-1L2, ANK-1, Ankyrin B, Annexin VIII, AP-1μ2, AP-3μ2, Arp-T2, Arp2, ArpM1, Astrotactin, Astrotactin 2, BAIAP2L2, beta-Actin, BPAG1, C11orf56, C20orf134, Caldesmon, Calpactin, Calponin 2, Calponin 3, CAP1, CAPS-1, CAPS1, CapZ-α, CapZ-α2, CapZ-α3, CARMIL, CCDC158, Ccdc163, CCDC53, CLEC-2I, CLP36, COBLL1, Cofilin 2, Complexin-2, Coronin 2B, Coronin 6, CTTNBP2NL, Cypher, Cytokeratin 2E, Cytokeratin 75, Cytospin-A, Dab2, DENND1C, Desmuslin, DIAPH3, EG238829, EHBP1, EHBP1L1, ENTHD1, EPB41L5, Epiplakin (EPPK), epsin, Espin, EXDL3, FAM160A2, FAM21A, FAM39E, FBF1, FBLIM1, FBP21, FGD1, Filamin 1, Flightless I, FLJ23152, FMNL3, FNBP1L, Formin 2, FSIP2, Gas2L2, GCC1, Gelsolin, Gm1568, Gm498, GOLGA6L1, golgin 160, GS28, HIP-55, hnRNP F, HPV16 E4, I-Plastin, IPP, IRSp53, KBTBD7, Keratin 24, Keratin 83, KIAA0754, KIAA1033, KIAA1407, KLHDC7B, KRTAP10-1, KRTAP10-7, L-Plastin, Lad, Lamellipodin, Laminin-5, Leiomodin 3, Leiomodin1, LRCH3, LRRC16B, LRRC9, LSP1, LURAP1, LUZP1, LUZP2, Mex3d, MICAL1, MIZIP, MORN1, MORN3, Munc13-4, Muscle Actin, Muskelin, MYBPH, Myelin P2, MYH13, MYH14, MYH6, MYH7, MYH8, Myo2p, MyoD, Myoferlin, myopalladin, Myosin Ic, Myosin If, Myosin IIIa, Myosin Va, Myosin Vb, Myosin Vc, Myosin VIIB, Myosin X, Myosin XVI, Myosin-13, Myotilin, MYPT1, NACAD, NCKAP5L, Nebulin, neuroligin X, Neuron navigator 2, NHS, NHSL1, NO145, Obscurin, OBSL1, Olfr1076, Olfr73, Otoferlin, OTTMUSG00000005737, PACSIN2, pantophysin, PARV (parvin), Parvin beta, PCDH1_Pcdh1, PDCL3, periaxin, PHACTR2, PHACTR4, Phakinin, plakophilin 4, POF1B, POM121L2, POP1, Profilin, Profilin-4, ProSAPiP1, PSD, PSG20, R-PE, Rab 3 GAP p150, Rab 4B, RBM28, REEP3, Rho F, Riboflavin Kinase, RIM-BP2, RNF4, Rootletin, RUFY1, SCAMP3, SCFD2, SCRN3, Sec1, Sec15B, SEC22A, Sec24B, Sec3, Septin 10, Septin 11, Septin 2, Septin 5, Septin 6, SHD1, shootin1, SHROOM1, SHROOM4, SIPA1L, Slac2-a, SMAP1L, Smooth Muscle Actin, SNAPC 50, SNX5, SPACA1, SPECC1, spectrin α, spectrin β III, Spir-1, Sso1, Sso2, SUN1, SUN3, Supervillin, SYAP1, Synaptopodin, Synaptotagmin IX, Synaptotagmin XI, Synaptotagmin XVI, Syne-1, Syne-3, Syne-4, Syntaxin 12, Syntaxin 4, Syntaxin 8, T-Plastin, t-SNARE 1, Tβ-15a, TCTA, Tektin 3, TIP20, Titin, TMED3, TMED9, Tmsb15b1, TRAPPC2L, tropomodulin, Tropomyosin, Tropomyosin β, Tropomyosin 4, Tuba, Unc18-3, UNC45B, v-SNARE Vti1a, Veli1, Villin, VWA3B, Whirlin, Xinα, YIF1A, YIF1B, YIPF3, YJEFN3, and zygin 1.Activator of:
α-actinin-4, α-parvin, β-parvin, γ2-COP, 2310002L09Rik, 2310044H10Rik, 4.1R, 4921517D21Rik, 4930488E11Rik, 4930502E18Rik, 4930504O13Rik, 4930511I11Rik, 4931429I11Rik, 6330403A02Rik, 6720456B07Rik, 7420426K07Rik, Abi-3, ABLIM1, ABLIM3, Abp1, ACTA1, ACTBL1, ACTG2, ACTL10, ACTL7A, ACTL8, ACTR10, ADAM12, adseverin, AFAP-110, AFAP-1L1, AGAP1, AIP5, AJAP1, Ajuba, Amphiphysin I, Ankyrin B, AP-2μ1, AP-2σ1, ARHGAP17, ARHGAP18, ARHGAP29, ARHGAP30, ARHGAP36, ARHGAP42, ARHGEF9, ARL4D, ARL8B, Arp-T1, Arp3, Arp3β, Arp3C, Arp7, ARPC5L, Asef, AVL9, BAIAP3, Basal bodies, BC055107, BIG2, BIG3, BIN3, C11orf56, C19orf21, C20orf134, cadherin-20, Cappuccino, CapZ-α1, CapZ-α2, CapZ-α3, CapZ-β, CD3-ζ, CD58, CD72, Cdc42EP2, CDCrel-1, CED-2, CED-5, Centaurin α1, centlein, CEP152, Clathrin LCA, CLCP1, Clostridium difficile Toxin A, Cofilin 1, COPB, COPZ1, Cordon-bleu, Coronin 1B, Coronin 1C, Coronin 2A, Coronin 6, Coronin 7, Cortactin, COTL1, CR16, CYFIP1, CYFIP2, Cylicin-2, D6Wsu116e, DAAM1, DAAM2, DDEF1, DDEFL1, Desmin, DIAPH3, DOCK 11, Dynactin 2, Dynactin 3, DYSFIP1, ECT2L, EG432995, EHD2, EPHEXIN, EPLIN, Eps8, epsin, ESPNL, EVL, Exo84, FAM18A, FAM190A, FAM21A, FAM38B, FAM39E, Fascin 2, FCHO1, FCHO2, FCHSD1, FCHSD2, FGD2, FGD5, FGD6, FGF-11, FHOD1, FHOD3, Fibulin-7, Filamin β, Filamin 2, FLJ10357, FMNL1, FMNL2, FNBP2, FNBP3, FNBP4, FNDC1, Frabin, FRMD3, Gas2, GBF1, Gm498, Gm732, Gm996, GMF-β, GMF-γ, GOLGA6A-D, GRF-1, Hairy, HepaCAM, HRF, HSPC300, IBA2, INF2, IQGAP2, IQGAP3, Junctophilin-4, Kaptin, KIF3B, KLHDC8A, KRAP, L-Selectin, Lamellipodin, Las17, Leiomodin 1, Leiomodin1, LIMK-1, LIN-2, Liprin β2, LLGL2, LOC339809, LOC344065, LOC391356, MACF1, MAL2, MEIG1, MICAL3, MICALCL, MOB1B, Moesin, MRCKα, MRCKβ, MRTF-B, MSE55, MYH9, Myocardin, Myosin Ia, Myosin IIIb, Myosin IXa, Myosin VI, Myosin VIIa, Myosin XVIIIb, Myosin-13, Myosin-XIX, Myosin-XVA, MYPT3, N-WASP, NCKAP5L, Nebulette, NECAP 2, NEURL1B, NHS, NTF2, Nup133, Nup50, OBCAM, p21-ARC, p34-ARC, p41-ARCb, PACSIN1, palladin, pan-Cytokeratin, Paralemmin 3, PHLDB1, Pinch-1, PLEKHG1, PLEKHG6, plexin-A2, POF1B, POSH, prefoldin 5, prefoldin 6, Profilin-2, Profilin-3, Profilin-4, Rab 2A, Rab 2B, Rab 3A, Rab 4A, Rab 5A, Rab11-FIP1, RBM22, RBM33, REPS1, Rho GDIγ, Rho H, Rho J, rhophilin-2, RLTPR, RPL24, RPRC1, SCRN1, SCRN2, Sec24C, Sec4, Sec6, Sept14, Septin 1, Septin 12, Septin 7, Septin 8, Shrm, Slac2-b, Slac2-c, SNX9, SPATA13, spectrin α I, Spir-2, SRGAP1, Stereocilin, STON1, STON2, Swiprosin-2, SYDE1, SYDE2, Syne-2, SYNPO2L, Syntabulin, Syntaxin 19, Syntaxin 2, Syntaxin 7, T-Plastin, Tβ-10, TC10, TESK1, TI-VAMP, TMCC1, TMEM191B, TMEM191C, TMEM207, TMEM211, TMEM229A, TMEM64, TMEM74, Tmsbl1, Tns, transgelin-2, transgelin-3, Trav13d-3, Trav13n-1, Trav14n-3, Trav16dv11, Trav4n-3, Trav5n-4, Trav6d-5, Trav7d-2, Trav8d-1, Trav9n-3, TRBV3, tropomodulin, tropomodulin 1, tropomodulin 2, tropomodulin 3, tropomodulin 4, Tropomyosin, Tropomyosin α, TRS85, Twinfilin-1, Twinfilin-2, Unc18-2, Vac17p, VAM1, VAMP-5, VgI-4, vinculin, WAVE1, WAVE2, WDR1, WIP, WIRE, Xinβ, XPLN, and YIPF6.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Jasplakinolide, 50 µg | sc-202191 | 50 µg | $184.00 | |||
Jasplakinolide, 100 µg | sc-202191A | 100 µg | $305.00 |