Ascididemin | CAS#114622-04-7 | bioactive chemical

MedKoo Cat#: 598604 | Name: Ascididemin

Description:

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

Ascididemin can be viewed as a fused phenanthroline with quinoline; from the Mediterranean ascidian Cystodytes dellechiajei.

Chemical Structure

Ascididemin

CAS#114622-04-7

Theoretical Analysis

MedKoo Cat#: 598604

Name: Ascididemin

CAS#: 114622-04-7

Chemical Formula: C18H9N3O

Exact Mass: 283.0746

Molecular Weight: 283.29

Elemental Analysis: C, 76.32; H, 3.20; N, 14.83; O, 5.65

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

Ascididemin; Leptoclinidinone; NSC 675670; NSC-675670; NSC675670; CRL 8274; CRL-8274; CRL8274.

IUPAC/Chemical Name

9H-quinolino[4,3,2-de][1,10]phenanthrolin-9-one

InChi Key

BTAIBIXHXSXUFN-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H9N3O/c22-18-12-5-3-8-19-15(12)16-14-11(7-9-20-16)10-4-1-2-6-13(10)21-17(14)18/h1-9H

SMILES Code

O=C(C1=C2N=CC=C1)C3=NC4=CC=CC=C4C5=CC=NC2=C53

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 283.29 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: Yin H, Shan N, Wang S, Yao ZJ. Total synthesis of ascididemin-type alkaloids using alkyne building blocks. J Org Chem. 2014 Oct 17;79(20):9748-53. doi: 10.1021/jo501927e. Epub 2014 Sep 30. PubMed PMID: 25238030. 2: Morvan D. Functional metabolomics uncovers metabolic alterations associated to severe oxidative stress in MCF7 breast cancer cells exposed to ascididemin. Mar Drugs. 2013 Oct 11;11(10):3846-60. doi: 10.3390/md11103846. PubMed PMID: 24152560; PubMed Central PMCID: PMC3826138. 3: Petersen IN, Crestey F, Kristensen JL. Total synthesis of ascididemin via anionic cascade ring closure. Chem Commun (Camb). 2012 Sep 18;48(72):9092-4. doi: 10.1039/c2cc34725c. Epub 2012 Aug 3. PubMed PMID: 22864261. 4: Guittat L, De Cian A, Rosu F, Gabelica V, De Pauw E, Delfourne E, Mergny JL. Ascididemin and meridine stabilise G-quadruplexes and inhibit telomerase in vitro. Biochim Biophys Acta. 2005 Aug 5;1724(3):375-84. PubMed PMID: 15950388. 5: Matsumoto SS, Biggs J, Copp BR, Holden JA, Barrows LR. Mechanism of ascididemin-induced cytotoxicity. Chem Res Toxicol. 2003 Feb;16(2):113-22. PubMed PMID: 12588181. 6: Dirsch VM, Kirschke SO, Estermeier M, Steffan B, Vollmar AM. Apoptosis signaling triggered by the marine alkaloid ascididemin is routed via caspase-2 and JNK to mitochondria. Oncogene. 2004 Feb 26;23(8):1586-93. PubMed PMID: 14716300. 7: Sharma V, Sharma PC, Kumar V. A mini review on pyridoacridines: Prospective lead compounds in medicinal chemistry. J Adv Res. 2015 Jan;6(1):63-71. doi: 10.1016/j.jare.2014.11.002. Epub 2014 Nov 15. Review. PubMed PMID: 25685544; PubMed Central PMCID: PMC4293674. 8: Delfourne E, Darro F, Portefaix P, Galaup C, Bayssade S, Bouteillé A, Le Corre L, Bastide J, Collignon F, Lesur B, Frydman A, Kiss R. Synthesis and in vitro antitumor activity of novel ring D analogues of the marine pyridoacridine ascididemin: structure-activity relationship. J Med Chem. 2002 Aug 15;45(17):3765-71. PubMed PMID: 12166949. 9: Dassonneville L, Wattez N, Baldeyrou B, Mahieu C, Lansiaux A, Banaigs B, Bonnard I, Bailly C. Inhibition of topoisomerase II by the marine alkaloid ascididemin and induction of apoptosis in leukemia cells. Biochem Pharmacol. 2000 Aug 15;60(4):527-37. PubMed PMID: 10874127. 10: Delfourne E, Kiss R, Le Corre L, Dujols F, Bastide J, Collignon F, Lesur B, Frydman A, Darro F. Synthesis and in vitro antitumor activity of ring C and D-substituted phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine. Bioorg Med Chem. 2004 Aug 1;12(15):3987-94. PubMed PMID: 15246075. 11: Delfourne E, Kiss R, Le Corre L, Dujols F, Bastide J, Collignon F, Lesur B, Frydman A, Darro F. Synthesis and in vitro antitumor activity of phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine: structure-activity relationship. J Med Chem. 2003 Jul 31;46(16):3536-45. PubMed PMID: 12877592. 12: Debnath B, Gayen S, Bhattacharya S, Samanta S, Jha T. QSAR study on some pyridoacridine ascididemin analogues as anti-tumor agents. Bioorg Med Chem. 2003 Dec 1;11(24):5493-9. PubMed PMID: 14642593. 13: Delfourne E, Kiss R, Le Corre L, Merza J, Bastide J, Frydman A, Darro F. Synthesis and in vitro antitumor activity of an isomer of the marine pyridoacridine alkaloid ascididemin and related compounds. Bioorg Med Chem. 2003 Oct 1;11(20):4351-6. PubMed PMID: 13129571. 14: Bonnard I, Bontemps N, Lahmy S, Banaigs B, Combaut G, Francisco C, Colson P, Houssier C, Waring MJ, Bailly C. Binding to DNA and cytotoxic evaluation of ascididemin, the major alkaloid from the Mediterranean ascidian Cystodytes dellechiajei. Anticancer Drug Des. 1995 Jun;10(4):333-46. PubMed PMID: 7786398. 15: Marshall KM, Barrows LR. Biological activities of pyridoacridines. Nat Prod Rep. 2004 Dec;21(6):731-51. Epub 2004 Oct 29. Review. PubMed PMID: 15565252. 16: Copp BR, Kayser O, Brun R, Kiderlen AF. Antiparasitic activity of marine pyridoacridone alkaloids related to the ascididemins. Planta Med. 2003 Jun;69(6):527-31. PubMed PMID: 12865971. 17: Raeder S, Bracher F. A novel approach to the pyridoacridine ring system: synthesis of the topoisomerase inhibitor 13-deazaascididemin. Arch Pharm (Weinheim). 2012 Oct;345(10):822-6. doi: 10.1002/ardp.201200019. Epub 2012 Jul 4. PubMed PMID: 22760790. 18: von Schwarzenberg K, Vollmar AM. Targeting apoptosis pathways by natural compounds in cancer: marine compounds as lead structures and chemical tools for cancer therapy. Cancer Lett. 2013 May 28;332(2):295-303. doi: 10.1016/j.canlet.2010.07.004. Epub 2010 Jul 31. Review. PubMed PMID: 20673697. 19: Nilar N, Sidebottom PJ, Carté BK, Butler MS. Three new pyridoacridine type alkaloids from a singaporean ascidian. J Nat Prod. 2002 Aug;65(8):1198-200. PubMed PMID: 12193032. 20: Delfourne E, Bastide J. Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents. Med Res Rev. 2003 Mar;23(2):234-52. Review. PubMed PMID: 12500290.