Fascaplysin chloride | SC 622398 | CAS# 114719-57-2

MedKoo Cat#: 329606 | Name: Fascaplysin chloride

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Description:

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

Fascaplysin is an inhibitor of cyclin D kinase 4/ cyclin D1 (IC50 = 0.35 μM). Fascaplysin induces caspase mediated crosstalk between apoptosis and autophagy through the inhibition of PI3K/AKT/mTOR signaling cascade in human leukemia HL-60 cells.

Chemical Structure

Fascaplysin chloride

CAS#114719-57-2

Theoretical Analysis

MedKoo Cat#: 329606

Name: Fascaplysin chloride

CAS#: 114719-57-2

Chemical Formula: C18H11ClN2O

Exact Mass: 0.0000

Molecular Weight: 306.75

Elemental Analysis: C, 70.48; H, 3.61; Cl, 11.56; N, 9.13; O, 5.22

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks

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Related CAS #

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Synonym

Fascaplisine; Fascaplysin chloride; Fascaplysine chloride; NSC 622398; NSC622398; NSC-622398.

IUPAC/Chemical Name

12,13-dihydro-13-oxo-pyrido[1,2-a:3,4-b']diindol-5-ium, monochloride

InChi Key

PWUOOJVYZQILBG-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H10N2O.ClH/c21-18-13-6-2-4-8-15(13)20-10-9-12-11-5-1-3-7-14(11)19-16(12)17(18)20;/h1-10H;1H

SMILES Code

O=C1C2=C3NC4=C(C=CC=C4)C3=CC=[N+]2C5=C1C=CC=C5.[Cl-]

Appearance

Solid powder

Purity

>95% (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

>2 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 306.75 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: Mischitelli M, Jemaà M, Almasry M, Faggio C, Lang F. Triggering of Suicidal Erythrocyte Death by Fascaplysin. Cell Physiol Biochem. 2016;39(4):1638-47. doi: 10.1159/000447865. PubMed PMID: 27626793. 2: Manda S, Sharma S, Wani A, Joshi P, Kumar V, Guru SK, Bharate SS, Bhushan S, Vishwakarma RA, Kumar A, Bharate SB. Discovery of a marine-derived bis-indole alkaloid fascaplysin, as a new class of potent P-glycoprotein inducer and establishment of its structure-activity relationship. Eur J Med Chem. 2016 Jan 1;107:1-11. doi: 10.1016/j.ejmech.2015.10.049. PubMed PMID: 26560048. 3: Ampofo E, Später T, Müller I, Eichler H, Menger MD, Laschke MW. The Marine-Derived Kinase Inhibitor Fascaplysin Exerts Anti-Thrombotic Activity. Mar Drugs. 2015 Nov 9;13(11):6774-91. doi: 10.3390/md13116774. PubMed PMID: 26569265; PubMed Central PMCID: PMC4663553. 4: Mahgoub T, Eustace AJ, Collins DM, Walsh N, O'Donovan N, Crown J. Kinase inhibitor screening identifies CDK4 as a potential therapeutic target for melanoma. Int J Oncol. 2015 Sep;47(3):900-8. doi: 10.3892/ijo.2015.3097. PubMed PMID: 26201960; PubMed Central PMCID: PMC4532220. 5: Kumar S, Guru SK, Pathania AS, Manda S, Kumar A, Bharate SB, Vishwakarma RA, Malik F, Bhushan S. Fascaplysin induces caspase mediated crosstalk between apoptosis and autophagy through the inhibition of PI3K/AKT/mTOR signaling cascade in human leukemia HL-60 cells. J Cell Biochem. 2015 Jun;116(6):985-97. doi: 10.1002/jcb.25053. PubMed PMID: 25561006. 6: Mahale S, Bharate SB, Manda S, Joshi P, Bharate SS, Jenkins PR, Vishwakarma RA, Chaudhuri B. Biphenyl-4-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-methylamide (CA224), a nonplanar analogue of fascaplysin, inhibits Cdk4 and tubulin polymerization: evaluation of in vitro and in vivo anticancer activity. J Med Chem. 2014 Nov 26;57(22):9658-72. doi: 10.1021/jm5014743. PubMed PMID: 25368960. 7: Hamilton G. Cytotoxic effects of fascaplysin against small cell lung cancer cell lines. Mar Drugs. 2014 Mar 7;12(3):1377-89. doi: 10.3390/md12031377. PubMed PMID: 24608973; PubMed Central PMCID: PMC3967216. 8: Zhu YP, Liu MC, Cai Q, Jia FC, Wu AX. A cascade coupling strategy for one-pot total synthesis of β-carboline and isoquinoline-containing natural products and derivatives. Chemistry. 2013 Jul 29;19(31):10132-7. doi: 10.1002/chem.201301734. PubMed PMID: 23788489. 9: Bharate SB, Sawant SD, Singh PP, Vishwakarma RA. Kinase inhibitors of marine origin. Chem Rev. 2013 Aug 14;113(8):6761-815. doi: 10.1021/cr300410v. Review. PubMed PMID: 23679846. 10: Bharate SB, Manda S, Mupparapu N, Battini N, Vishwakarma RA. Chemistry and biology of fascaplysin, a potent marine-derived CDK-4 inhibitor. Mini Rev Med Chem. 2012 Jun;12(7):650-64. Review. PubMed PMID: 22512549. 11: Shafiq MI, Steinbrecher T, Schmid R. Fascaplysin as a specific inhibitor for CDK4: insights from molecular modelling. PLoS One. 2012;7(8):e42612. doi: 10.1371/journal.pone.0042612. PubMed PMID: 22905154; PubMed Central PMCID: PMC3419161. 12: Lu Z, Ding Y, Li XC, Djigbenou DR, Grimberg BT, Ferreira D, Ireland CM, Van Wagoner RM. 3-bromohomofascaplysin A, a fascaplysin analogue from a Fijian Didemnum sp. ascidian. Bioorg Med Chem. 2011 Nov 15;19(22):6604-7. doi: 10.1016/j.bmc.2011.05.046. PubMed PMID: 21696970; PubMed Central PMCID: PMC3205246. 13: Yan X, Chen H, Lu X, Wang F, Xu W, Jin H, Zhu P. Fascaplysin exert anti-tumor effects through apoptotic and anti-angiogenesis pathways in sarcoma mice model. Eur J Pharm Sci. 2011 Jul 17;43(4):251-9. doi: 10.1016/j.ejps.2011.04.018. PubMed PMID: 21569843. 14: Zheng YL, Lu XL, Lin J, Chen HM, Yan XJ, Wang F, Xu WF. Direct effects of fascaplysin on human umbilical vein endothelial cells attributing the anti-angiogenesis activity. Biomed Pharmacother. 2010 Oct;64(8):527-33. doi: 10.1016/j.biopha.2009.04.046. PubMed PMID: 19932581. 15: Waldmann H, Eberhardt L, Wittstein K, Kumar K. Silver catalyzed cascade synthesis of alkaloid ring systems: concise total synthesis of fascaplysin, homofascaplysin C and analogues. Chem Commun (Camb). 2010 Jul 7;46(25):4622-4. doi: 10.1039/c001350a. PubMed PMID: 20386812. 16: Lu XL, Zheng YL, Chen HM, Yan XJ, Wang F, Xu WF. [Anti-proliferation of human cervical cancer HeLa cell line by fascaplysin through apoptosis induction]. Yao Xue Xue Bao. 2009 Sep;44(9):980-6. Chinese. PubMed PMID: 20055172. 17: Aubry C, Wilson AJ, Emmerson D, Murphy E, Chan YY, Dickens MP, García MD, Jenkins PR, Mahale S, Chaudhuri B. Fascaplysin-inspired diindolyls as selective inhibitors of CDK4/cyclin D1. Bioorg Med Chem. 2009 Aug 15;17(16):6073-84. doi: 10.1016/j.bmc.2009.06.070. PubMed PMID: 19632122. 18: Liu N, Fang H, Li Y, Xu W. Recent research in selective cyclin-dependent kinase 4 inhibitors for anti-cancer treatment. Curr Med Chem. 2009;16(36):4869-88. Review. PubMed PMID: 19929781. 19: Lin J, Yan XJ, Chen HM. Fascaplysin, a selective CDK4 inhibitor, exhibit anti-angiogenic activity in vitro and in vivo. Cancer Chemother Pharmacol. 2007 Mar;59(4):439-45. PubMed PMID: 16816972. 20: García MD, Wilson AJ, Emmerson DP, Jenkins PR, Mahale S, Chaudhuri B. Synthesis, crystal structure and biological activity of beta-carboline based selective CDK4-cyclin D1 inhibitors. Org Biomol Chem. 2006 Dec 21;4(24):4478-84. PubMed PMID: 17268643.