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MedKoo Cat#: 533788 | Name: Naphthyridine-azaquinolone
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Description:

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

Naphthyridine-azaquinolone, also known as Npt-Azq, is a novel repeat-structure-specific DNA ligand, specifically binding slipped-CAG DNA intermediates of expansion mutations. Npt-Azq binds the G-A region of the mismatch, which causes significant changes in the structure of the DNA, which in turn causes changes in the electrochemical properties of DNA/Npt-Azq films. For a 20-mer DNA containing an A-A mismatch, the electron-transfer resistance (RCT) of the system is significantly different in the presence of bound Npt-Azq, presumably due to the structural differences in the two films. Npt-Azq does not bind to matched DNA, and thus, the presence of Npt-Azq does not affect the electrochemical properties of such films.

Chemical Structure

Naphthyridine-azaquinolone
Naphthyridine-azaquinolone
CAS#500722-22-5

Theoretical Analysis

MedKoo Cat#: 533788

Name: Naphthyridine-azaquinolone

CAS#: 500722-22-5

Chemical Formula: C24H25N7O3

Exact Mass: 459.2019

Molecular Weight: 459.51

Elemental Analysis: C, 62.73; H, 5.48; N, 21.34; O, 10.45

Price and Availability

Size Price Availability Quantity
10mg USD 850.00 2 months
25mg USD 1,650.00 2 months
50mg USD 2,950.00 2 months
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Related CAS #
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Synonym
Naphthyridine-azaquinolone; Npt-Azq;
IUPAC/Chemical Name
3-[[3-[(7-Methyl-1,8-naphthyridin-2-yl)amino]-3-oxopropyl]amino]-N-[(7-oxo-8H-1,8-naphthyridin-2-yl)methyl]propanamide
InChi Key
BWINWCKASXYPFA-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H25N7O3/c1-15-2-3-16-5-8-19(30-23(16)27-15)29-22(34)11-13-25-12-10-20(32)26-14-18-7-4-17-6-9-21(33)31-24(17)28-18/h2-9,25H,10-14H2,1H3,(H,26,32)(H,28,31,33)(H,27,29,30,34)
SMILES Code
O=C(NCC1=NC2=C(C=CC(N2)=O)C=C1)CCNCCC(NC3=NC4=NC(C)=CC=C4C=C3)=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 459.51 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.

Recalculate based on batch purity %
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: Murakami E, Nakamori M, Nakatani K, Shibata T, Tainaka K. Intracerebral Distribution of CAG Repeat-Binding Small Molecule Visualized by Whole-Brain Imaging. Bioconjug Chem. 2023 Dec 20;34(12):2187-2193. doi: 10.1021/acs.bioconjchem.3c00470. Epub 2023 Nov 10. PMID: 37948852. 2: Ahamad S, Bhat SA. The Emerging Landscape of Small-Molecule Therapeutics for the Treatment of Huntington's Disease. J Med Chem. 2022 Dec 22;65(24):15993-16032. doi: 10.1021/acs.jmedchem.2c00799. Epub 2022 Dec 9. PMID: 36490325. 3: Hasuike Y, Tanaka H, Gall-Duncan T, Mehkary M, Nakatani K, Pearson CE, Tsuji S, Mochizuki H, Nakamori M. CAG repeat-binding small molecule improves motor coordination impairment in a mouse model of Dentatorubral-pallidoluysian atrophy. Neurobiol Dis. 2022 Feb;163:105604. doi: 10.1016/j.nbd.2021.105604. Epub 2021 Dec 28. PMID: 34968706. 4: Deshmukh AL, Caron MC, Mohiuddin M, Lanni S, Panigrahi GB, Khan M, Engchuan W, Shum N, Faruqui A, Wang P, Yuen RKC, Nakamori M, Nakatani K, Masson JY, Pearson CE. FAN1 exo- not endo-nuclease pausing on disease-associated slipped- DNA repeats: A mechanism of repeat instability. Cell Rep. 2021 Dec 7;37(10):110078. doi: 10.1016/j.celrep.2021.110078. PMID: 34879276. 5: Dohno C , Hagihara M , Binti Mohd Zaifuddin N , Nihei M , Saito K , Nakatani K . Small molecule-induced trinucleotide repeat contractions during in vitro DNA synthesis. Chem Commun (Camb). 2021 Apr 4;57(26):3235-3238. doi: 10.1039/d1cc00349f. Epub 2021 Mar 1. PMID: 33646236. 6: Nakamori M, Mochizuki H. Targeting Expanded Repeats by Small Molecules in Repeat Expansion Disorders. Mov Disord. 2021 Feb;36(2):298-305. doi: 10.1002/mds.28397. Epub 2020 Dec 7. PMID: 33284473. 7: Wright GEB, Black HF, Collins JA, Gall-Duncan T, Caron NS, Pearson CE, Hayden MR. Interrupting sequence variants and age of onset in Huntington's disease: clinical implications and emerging therapies. Lancet Neurol. 2020 Nov;19(11):930-939. doi: 10.1016/S1474-4422(20)30343-4. PMID: 33098802. 8: Costa MDC. Recent therapeutic prospects for Machado-Joseph disease. Curr Opin Neurol. 2020 Aug;33(4):519-526. doi: 10.1097/WCO.0000000000000832. PMID: 32657894. 9: Nakamori M, Panigrahi GB, Lanni S, Gall-Duncan T, Hayakawa H, Tanaka H, Luo J, Otabe T, Li J, Sakata A, Caron MC, Joshi N, Prasolava T, Chiang K, Masson JY, Wold MS, Wang X, Lee MYWT, Huddleston J, Munson KM, Davidson S, Layeghifard M, Edward LM, Gallon R, Santibanez-Koref M, Murata A, Takahashi MP, Eichler EE, Shlien A, Nakatani K, Mochizuki H, Pearson CE. A slipped-CAG DNA-binding small molecule induces trinucleotide-repeat contractions in vivo. Nat Genet. 2020 Feb;52(2):146-159. doi: 10.1038/s41588-019-0575-8. Epub 2020 Feb 14. PMID: 32060489; PMCID: PMC7043212. 10: Li J, Sakata A, He H, Bai LP, Murata A, Dohno C, Nakatani K. Naphthyridine- Benzoazaquinolone: Evaluation of a Tricyclic System for the Binding to (CAG)n Repeat DNA and RNA. Chem Asian J. 2016 Jul 5;11(13):1971-81. doi: 10.1002/asia.201600527. Epub 2016 Jun 14. PMID: 27146450. 11: Kobori A, Nakatani K. Dimer of 2,7-diamino-1,8-naphthyridine for the detection of mismatches formed by pyrimidine nucleotide bases. Bioorg Med Chem. 2008 Dec 15;16(24):10338-44. doi: 10.1016/j.bmc.2008.10.035. Epub 2008 Oct 17. PMID: 18996698. 12: Nakatani K, He H, Uno SN, Yamamoto T, Dohno C. Synthesis of dimeric 2-amino-1,8-naphthyridine and related DNA-binding molecules. Curr Protoc Nucleic Acid Chem. 2008 Mar;Chapter 8:Unit 8.6. doi: 10.1002/0471142700.nc0806s32. PMID: 18428804. 13: Goto Y, Suda H, Kobori A, Nakatani K. Analysis of mismatched DNA by mismatch binding ligand (MBL)-Sepharose affinity chromatography. Anal Bioanal Chem. 2007 Jul;388(5-6):1165-73. doi: 10.1007/s00216-007-1323-y. Epub 2007 May 31. PMID: 17541568. 14: Li X, Song H, Nakatani K, Kraatz HB. Exploiting small molecule binding to DNA for the detection of single-nucleotide mismatches and their base environment. Anal Chem. 2007 Mar 15;79(6):2552-5. doi: 10.1021/ac0615504. Epub 2007 Feb 6. PMID: 17279726. 15: Hagihara M, Nakatani K. Inhibition of DNA replication by a d(CAG) repeat binding ligand. Nucleic Acids Symp Ser (Oxf). 2006;(50):147-8. doi: 10.1093/nass/nrl073. PMID: 17150860. 16: Nakatani K, Hagihara S, Goto Y, Kobori A, Hagihara M, Hayashi G, Kyo M, Nomura M, Mishima M, Kojima C. Solution structure of a small-molecular ligand complexed with CAG trinucleotide repeat DNA. Nucleic Acids Symp Ser (Oxf). 2005;(49):49-50. doi: 10.1093/nass/49.1.49. PMID: 17150627. 17: Hagihara S, Kumasawa H, Goto Y, Hayashi G, Kobori A, Saito I, Nakatani K. Detection of guanine-adenine mismatches by surface plasmon resonance sensor carrying naphthyridine-azaquinolone hybrid on the surface. Nucleic Acids Res. 2004 Jan 9;32(1):278-86. doi: 10.1093/nar/gkh171. PMID: 14715926; PMCID: PMC373281.