Symadex free base | C-1311 | XLS-002 | 138154-39-9

MedKoo Cat#: 201510 | Name: Symadex free base

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Description:

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

Symadex, also known as imidazoacridone; XLS-002 and C-1311, is a member of the novel imidazoacridinone family of anticancer agents. Imidazoacridone has shown activity in experimental tumour models both in vitro and in nude mice. C-1311 at the EC(99) dose delayed progression of cells through the S phase which was followed by G2 arrest. C-1311 does not induce rapid apoptosis in HT-29 cells, instead drug exposure leads to prolonged G2 arrest followed by G2 to M transit and cell death during mitosis in the process of mitotic catastrophe.

Chemical Structure

Symadex free base

CAS#138154-39-9 (free base)

Theoretical Analysis

MedKoo Cat#: 201510

Name: Symadex free base

CAS#: 138154-39-9 (free base)

Chemical Formula: C20H22N4O2

Exact Mass: 350.1743

Molecular Weight: 350.42

Elemental Analysis: C, 68.55; H, 6.33; N, 15.99; O, 9.13

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 385.00	2 Weeks

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Related CAS #

138154-55-9 (HCl) 138154-39-9 (free base)

Synonym

C-1311, C1311; C 1311; XLS-002; XLS 002; XLS002; Imidacrine; SYMADEX.

IUPAC/Chemical Name

5-((2-(diethylamino)ethyl)amino)-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one

InChi Key

CUNDRHORZHFPLY-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H22N4O2/c1-3-23(4-2)10-9-21-15-6-7-16-19-18(15)20(26)14-11-13(25)5-8-17(14)24(19)12-22-16/h5-8,11-12,21,25H,3-4,9-10H2,1-2H3

SMILES Code

O=C1C2=C(C=CC(O)=C2)N(C=N3)C4=C3C=CC(NCCN(CC)CC)=C14

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 (5mg/mL)

Shelf Life

>5 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

Related CAS# 138154-55-9 (Imidazoacridone hydrochloride) 138154-39-9 (Imidazoacridone free base)

Certificate of Analysis

View CoA: current batch, Lot#S9G06M17

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 350.42 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: Laskowski T, Kosno M, Andrałojć W, Frackowiak JE, Borzyszkowska-Bukowska J, Szczeblewski P, Radoń N, Świerżewska M, Woźny A, Paluszkiewicz E, Mazerska Z. The interactions of monomeric acridines and unsymmetrical bisacridines (UAs) with DNA duplexes: an insight provided by NMR and MD studies. Sci Rep. 2023 Mar 1;13(1):3431. doi: 10.1038/s41598-023-30587-y. PMID: 36859494; PMCID: PMC9977845. 2: Mlejnek P, Havlasek J, Pastvova N, Dolezel P, Dostalova K. Lysosomal sequestration of weak base drugs, lysosomal biogenesis, and cell cycle alteration. Biomed Pharmacother. 2022 Sep;153:113328. doi: 10.1016/j.biopha.2022.113328. Epub 2022 Jul 1. PMID: 35785701. 3: Niemira M, Borowa-Mazgaj B, Bader SB, Moszyńska A, Ratajewski M, Karaś K, Kwaśniewski M, Krętowski A, Mazerska Z, Hammond EM, Skwarska A. Anticancer Imidazoacridinone C-1311 is Effective in Androgen-Dependent and Androgen- Independent Prostate Cancer Cells. Biomedicines. 2020 Aug 19;8(9):292. doi: 10.3390/biomedicines8090292. PMID: 32825120; PMCID: PMC7555468. 4: Skwarska A, Ramachandran S, Dobrynin G, Leszczynska KB, Hammond EM. The imidazoacridinone C-1311 induces p53-dependent senescence or p53-independent apoptosis and sensitizes cancer cells to radiation. Oncotarget. 2017 May 9;8(19):31187-31198. doi: 10.18632/oncotarget.16102. PMID: 28415717; PMCID: PMC5458200. 5: Laskowski T, Czub J, Sowiński P, Mazerski J. Intercalation complex of imidazoacridinone C-1311, a potential anticancer drug, with DNA helix d(CGATCG)2: stereostructural studies by 2D NMR spectroscopy. J Biomol Struct Dyn. 2016;34(3):653-63. doi: 10.1080/07391102.2015.1049552. Epub 2015 Nov 26. PMID: 26211888. 6: Isambert N, Campone M, Bourbouloux E, Drouin M, Major A, Yin W, Loadman P, Capizzi R, Grieshaber C, Fumoleau P. Evaluation of the safety of C-1311 (SYMADEX) administered in a phase 1 dose escalation trial as a weekly infusion for 3 consecutive weeks in patients with advanced solid tumours. Eur J Cancer. 2010 Mar;46(4):729-34. doi: 10.1016/j.ejca.2009.12.005. Epub 2009 Dec 22. PMID: 20031390. 7: Bram EE, Adar Y, Mesika N, Sabisz M, Skladanowski A, Assaraf YG. Structural determinants of imidazoacridinones facilitating antitumor activity are crucial for substrate recognition by ABCG2. Mol Pharmacol. 2009 May;75(5):1149-59. doi: 10.1124/mol.109.054791. Epub 2009 Feb 27. PMID: 19251825. 8: Alami N, Paterson J, Belanger S, Juste S, Grieshaber CK, Leyland-Jones B. Comparative cytotoxicity of C-1311 in colon cancer in vitro and in vivo using the hollow fiber assay. J Chemother. 2007 Oct;19(5):546-53. doi: 10.1179/joc.2007.19.5.546. PMID: 18073154. 9: Hyzy M, Bozko P, Konopa J, Skladanowski A. Antitumour imidazoacridone C-1311 induces cell death by mitotic catastrophe in human colon carcinoma cells. Biochem Pharmacol. 2005 Mar 1;69(5):801-9. doi: 10.1016/j.bcp.2004.11.028. Epub 2005 Jan 18. PMID: 15710357.