9-Aminoacridine - CAS 90-45-9
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
9-Aminoacridine
Catalog Number:
90-45-9
Synonyms:
10-Amino-5-azaanthracene;9AA;9-Acridinamine;9-Amino-acridin;Acridin-9-amine;Aminacrine
CAS Number:
90-45-9
Description:
9-Aminoacridine is a highly fluorescent dye, an acridine analog. It is used clinically as a topical antiseptic and experimentally as a mutagen. It is an intracellular pH indicator and a DNA intercalating agent.
Molecular Weight:
194.23
Molecular Formula:
C13H10N2
Quantity:
Grams to Kilograms
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1=CC=C2C(=C1)C(=C3C=CC=CC3=N2)N
InChI:
InChI=1S/C13H10N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H,(H2,14,15)
InChIKey:
XJGFWWJLMVZSIG-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 90-45-9 9-Aminoacridine

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Reference Reading


1.Chk1 inhibitor synergizes quinacrine mediated apoptosis in breast cancer cells by compromising the base excision repair cascade.
Preet R1, Siddharth S1, Satapathy SR1, Das S1, Nayak A1, Das D1, Wyatt MD2, Kundu CN3. Biochem Pharmacol. 2016 Apr 1;105:23-33. doi: 10.1016/j.bcp.2016.01.017. Epub 2016 Feb 2.
Quinacrine (QC) causes apoptosis in breast cancer cells by induction of DNA damage, arrest of cells in S-phase, and by topoisomerase inhibition. Here, we show that QC-mediated apoptosis is not only due to increased DNA damage but also by compromising cell cycle checkpoints and base excision repair (BER) capacity in breast cancer cells. QC decreased CHK1, CDKs (CDC2, MDM2, CDC6), cyclins (B1, E1) and CDC25-A in a dose dependent manner. The expression of basal ATR remains unaltered but pATR (Ser-428) increased after QC treatment. A CHK1 inhibitor, SB218078, was also tested alone and in combination with QC. Like QC, SB218078 caused apoptosis by DNA damage and S-phase arrest. The combination of QC and SB218078 increased apoptosis by blocking the cell cycle in G2/M, which caused a mitotic catastrophe, and induced DNA damage at a higher level in comparison to individual compound treatments. Both drugs individually or in combination decreased the levels of replication protein A (RPA).
2.Carbon Dots and 9AA as a Binary Matrix for the Detection of Small Molecules by Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry.
Chen Y1, Gao D2,3, Bai H4,5, Liu H4,5, Lin S1, Jiang Y6,4. J Am Soc Mass Spectrom. 2016 Apr 13. [Epub ahead of print]
Application of matrix-assisted laser-desorption/ionization mass spectrometry (MALDI MS) to analyze small molecules have some limitations, due to the inhomogeneous analyte/matrix co-crystallization and interference of matrix-related peaks in low m/z region. In this work, carbon dots (CDs) were for the first time applied as a binary matrix with 9-Aminoacridine (9AA) in MALDI MS for small molecules analysis. By 9AA/CDs assisted desorption/ionization (D/I) process, a wide range of small molecules, including nucleosides, amino acids, oligosaccharides, peptides, and anticancer drugs with a higher sensitivity were demonstrated in the positive ion mode. A detection limit down to 5 fmol was achieved for cytidine. 9AA/CDs matrix also exhibited excellent reproducibility compared with 9AA matrix. Moreover, by exploring the ionization mechanism of the matrix, the influence factors might be attributed to the four parts: (1) the strong UV absorption of 9AA/CDs due to their π-conjugated network; (2) the carboxyl groups modified on the CDs surface act as protonation sites for proton transfer in positive ion mode; (3) the thin layer crystal of 9AA/CDs could reach a high surface temperature more easily and lower transfer energy for LDI MS; (4) CDs could serve as a matrix additive to suppress 9AA ionization.
3.Matrix-assisted laser desorption/ionization mass spectrometry imaging of cell cultures for the lipidomic analysis of potential lipid markers in human breast cancer invasion.
Wang S1,2, Chen X1,2, Luan H3, Gao D1,2, Lin S3, Cai Z3, Liu J4, Liu H1,2, Jiang Y1,5. Rapid Commun Mass Spectrom. 2016 Feb 28;30(4):533-42. doi: 10.1002/rcm.7466.
RATIONALE: Breast cancer is the leading cause of cancer death among women worldwide. Identification of lipid targets that play a role in breast cancer invasion may advance our understanding of the rapid progression of cancer and may lead to the development of new biomarkers for the disease.
4.Synthesis of 9-Aminoacridine Derivatives as Anti-Alzheimer Agents.
Munawar R1, Mushtaq N2, Arif S2, Ahmed A2, Akhtar S2, Ansari S2, Meer S2, Saify ZS3, Arif M2. Am J Alzheimers Dis Other Demen. 2015 Sep 17. pii: 1533317515603115. [Epub ahead of print]
In the present study, some 9-aminoacridine derivatives have been synthesized by condensation of 9-aminoacridine with substituted phenacyl, benzoyl, and benzyl halides (RM1-RM6). Compounds were investigated for acetylcholinesterase and butyrylcholinesterase inhibition potential, considering these enzymes playing a key role in Alzheimer's disease. All derivatives showed better inhibition of enzymes than the standard galantamine, whereas except RM4, all exhibit better results than tacrine, a well-known acridine derivative used for the treatment of Alzheimer's disease.