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MedKoo Cat#: 591014 | Name: Nonylacridine Orange

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Description:

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

The fluorescent dye 10-N-nonyl acridine orange (NAO) is extensively used for location and quantitative assays of cardiolipin in living cells on the assumption of its high specificity for cardiolipin

Chemical Structure

Nonylacridine Orange

CAS#75168-11-5

Theoretical Analysis

MedKoo Cat#: 591014

Name: Nonylacridine Orange

CAS#: 75168-11-5

Chemical Formula: C26H38BrN3

Exact Mass: 471.2249

Molecular Weight: 471.52

Elemental Analysis: C, 66.09; H, 8.11; Br, 16.91; N, 8.89

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 300.00

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Synonym

10-Nonyl acridine Orange; Acridine Orange 10-nonyl bromide

IUPAC/Chemical Name

Acridinium, 3,6-bis(dimethylamino)-10-nonyl-, bromide (1:1)

InChi Key

DRBHTUDHPPBMCD-UHFFFAOYSA-M

InChi Code

InChI=1S/C26H38N3.BrH/c1-6-7-8-9-10-11-12-17-29-25-19-23(27(2)3)15-13-21(25)18-22-14-16-24(28(4)5)20-26(22)29;/h13-16,18-20H,6-12,17H2,1-5H3;1H/q+1;/p-1

SMILES Code

CCCCCCCCC[N+]1=C2C=C(N(C)C)C=CC2=CC3=C1C=C(N(C)C)C=C3.[Br-]

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

>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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Acridine Orange 10-Nonyl Bromide is a fluorescent probe for cardiolipin (λex: 489 nm, λem: 525 nm).

In vitro activity:

The fluorescent dye, 10 nonyl acridine orange (NAO), has been shown to bind cardiolipin in vitro and is frequently used as a stain in living cells to assay cardiolipin content. Additionally, NAO staining has been used to measure the mitochondrial content of cells as dye binding to mitochondria is reportedly independent of the membrane potential. This study used confocal microscopy to examine the properties of NAO in cortical astrocytes, neonatal cardiomyocytes and in isolated brain mitochondria. This study shows that NAO, a lipophilic cation, stained mitochondria selectively. Reference: J Neurochem. 2002 Jul;82(2):224-33. https://pubmed.ncbi.nlm.nih.gov/12124423/

In vivo activity:

Benomyl also increased oxidative stress in zebrafish, especially in the heart and head, as well as increasing malondialdehyde (MDA) content and decreasing catalase (CAT) and superoxide dismutase (SOD) activities. This indicates that benomyl induced reactive oxygen species (ROS) production and cell membrane peroxidation in vivo. Acridine orange (AO) staining and apoptosis factor detection further indicated that benomyl induced apoptosis in zebrafish. Reference: Environ Sci Pollut Res Int. 2023 Mar;30(12):33090-33100. https://pubmed.ncbi.nlm.nih.gov/36471152/

	Solvent	mg/mL	mM
Solubility
	DMSO	33.3	70.69

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 471.52 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

Formulation protocol:

1. Jacobson J, Duchen MR, Heales SJ. Intracellular distribution of the fluorescent dye nonyl acridine orange responds to the mitochondrial membrane potential: implications for assays of cardiolipin and mitochondrial mass. J Neurochem. 2002 Jul;82(2):224-33. doi: 10.1046/j.1471-4159.2002.00945.x. PMID: 12124423. 2. Ratinaud MH, Leprat P, Julien R. In situ flow cytometric analysis of nonyl acridine orange-stained mitochondria from splenocytes. Cytometry. 1988 May;9(3):206-12. doi: 10.1002/cyto.990090304. PMID: 2454177. 3. Luo Q, Tang S, Xiao X, Wei Y, Cheng B, Huang Y, Zhong K, Tian G, Lu H. Benomyl-induced development and cardiac toxicity in zebrafish embryos. Environ Sci Pollut Res Int. 2023 Mar;30(12):33090-33100. doi: 10.1007/s11356-022-24213-z. Epub 2022 Dec 6. PMID: 36471152. 4. Matsuyama Y, Nakamura T, Yoshida K, Hagi T, Iino T, Asanuma K, Sudo A. Radiodynamic therapy with acridine orange local administration as a new treatment option for primary and secondary bone tumours. Bone Joint Res. 2022 Oct;11(10):715-722. doi: 10.1302/2046-3758.1110.BJR-2022-0105.R2. PMID: 36214462; PMCID: PMC9582865.

In vitro protocol:

In vivo protocol:

1. Luo Q, Tang S, Xiao X, Wei Y, Cheng B, Huang Y, Zhong K, Tian G, Lu H. Benomyl-induced development and cardiac toxicity in zebrafish embryos. Environ Sci Pollut Res Int. 2023 Mar;30(12):33090-33100. doi: 10.1007/s11356-022-24213-z. Epub 2022 Dec 6. PMID: 36471152. 2. Matsuyama Y, Nakamura T, Yoshida K, Hagi T, Iino T, Asanuma K, Sudo A. Radiodynamic therapy with acridine orange local administration as a new treatment option for primary and secondary bone tumours. Bone Joint Res. 2022 Oct;11(10):715-722. doi: 10.1302/2046-3758.1110.BJR-2022-0105.R2. PMID: 36214462; PMCID: PMC9582865.

1: Pogmore AR, Seistrup KH, Strahl H. The Gram-positive model organism Bacillus subtilis does not form microscopically detectable cardiolipin-specific lipid domains. Microbiology. 2018 Apr;164(4):475-482. doi: 10.1099/mic.0.000639. Epub 2018 Mar 5. PubMed PMID: 29504925. 2: Mao G, Qu F, St Croix CM, Tyurina YY, Planas-Iglesias J, Jiang J, Huang Z, Amoscato AA, Tyurin VA, Kapralov AA, Cheikhi A, Maguire J, Klein-Seetharaman J, Bayır H, Kagan VE. Mitochondrial Redox Opto-Lipidomics Reveals Mono-Oxygenated Cardiolipins as Pro-Apoptotic Death Signals. ACS Chem Biol. 2016 Feb 19;11(2):530-40. doi: 10.1021/acschembio.5b00737. Epub 2016 Jan 5. PubMed PMID: 26697918; PubMed Central PMCID: PMC5741079. 3: Collins TJ, Ylanko J, Geng F, Andrews DW. A Versatile Cell Death Screening Assay Using Dye-Stained Cells and Multivariate Image Analysis. Assay Drug Dev Technol. 2015 Nov;13(9):547-57. doi: 10.1089/adt.2015.661. Epub 2015 Sep 30. PubMed PMID: 26422066; PubMed Central PMCID: PMC4652219. 4: Danylovych IuV, Danylovych HV, Kolomiiets' OV, Kosterin SO, Karakhim SO, Chunikhin OIu. [Investigation of nitrosactive compounds influence on polarization of the mitochondrial inner membrane in the rat uterus myocytes using potential sensitive fluorescent probe DiOC6(3)]. Ukr Biochem J. 2014 Jan-Feb;86(1):42-55. Ukrainian. PubMed PMID: 24834717. 5: Van Ruijssevelt L, Smirnov P, Yudina A, Bouchaud V, Voisin P, Moonen C. Observations on the viability of C6-glioma cells after sonoporation with low-intensity ultrasound and microbubbles. IEEE Trans Ultrason Ferroelectr Freq Control. 2013 Jan;60(1):34-45. doi: 10.1109/TUFFC.2013.2535. PubMed PMID: 23287911. 6: Quarato G, Piccoli C, Scrima R, Capitanio N. Functional imaging of membrane potential at the single mitochondrion level: possible application for diagnosis of human diseases. Mitochondrion. 2011 Sep;11(5):764-73. doi: 10.1016/j.mito.2011.06.014. Epub 2011 Jul 6. PubMed PMID: 21762790. 7: Dutot M, Rambaux L, Warnet JM, Rat P. [Oxidative stress modulation using polyphenol-rich blueberries: application on a human retinal cell model]. J Fr Ophtalmol. 2008 Dec;31(10):975-80. French. PubMed PMID: 19107073. 8: Lobasso S, Saponetti MS, Polidoro F, Lopalco P, Urbanija J, Kralj-Iglic V, Corcelli A. Archaebacterial lipid membranes as models to study the interaction of 10-N-nonyl acridine orange with phospholipids. Chem Phys Lipids. 2009 Jan;157(1):12-20. doi: 10.1016/j.chemphyslip.2008.09.002. Epub 2008 Sep 30. PubMed PMID: 18938147. 9: Jones TT, Brewer GJ. Critical age-related loss of cofactors of neuron cytochrome C oxidase reversed by estrogen. Exp Neurol. 2009 Feb;215(2):212-9. doi: 10.1016/j.expneurol.2008.09.011. Epub 2008 Sep 30. PubMed PMID: 18930048; PubMed Central PMCID: PMC3018880. 10: Buratta M, Castigli E, Sciaccaluga M, Pellegrino RM, Spinozzi F, Roberti R, Corazzi L. Loss of cardiolipin in palmitate-treated GL15 glioblastoma cells favors cytochrome c release from mitochondria leading to apoptosis. J Neurochem. 2008 May;105(3):1019-31. doi: 10.1111/j.1471-4159.2007.05209.x. Epub 2007 Dec 24. PubMed PMID: 18182042. 11: Dutot M, Warnet JM, Baudouin C, Rat P. Cytotoxicity of contact lens multipurpose solutions: role of oxidative stress, mitochondrial activity and P2X7 cell death receptor activation. Eur J Pharm Sci. 2008 Feb 5;33(2):138-45. Epub 2007 Nov 6. PubMed PMID: 18065213. 12: Tamietti BF, Machado AH, Maftoum-Costa M, Da Silva NS, Tedesco AC, Pacheco-Soares C. Analysis of mitochondrial activity related to cell death after PDT with AlPCS(4). Photomed Laser Surg. 2007 Jun;25(3):175-9. PubMed PMID: 17603857. 13: Johnson RD, Navratil M, Poe BG, Xiong G, Olson KJ, Ahmadzadeh H, Andreyev D, Duffy CF, Arriaga EA. Analysis of mitochondria isolated from single cells. Anal Bioanal Chem. 2007 Jan;387(1):107-18. Epub 2006 Aug 26. PubMed PMID: 16937092. 14: Wiosetek-Reske AM, Wysocki S, Bak GW. Determination of dipole moment in the ground and excited state by experimental and theoretical methods of N-nonyl acridine orange. Spectrochim Acta A Mol Biomol Spectrosc. 2005 Dec;62(4-5):1172-8. Epub 2005 Jun 9. PubMed PMID: 15950530. 15: Morris RL, Azizuddin K, Lam M, Berlin J, Nieminen AL, Kenney ME, Samia AC, Burda C, Oleinick NL. Fluorescence resonance energy transfer reveals a binding site of a photosensitizer for photodynamic therapy. Cancer Res. 2003 Sep 1;63(17):5194-7. PubMed PMID: 14500343. 16: Shishido S, Koga H, Harada M, Kumemura H, Hanada S, Taniguchi E, Kumashiro R, Ohira H, Sato Y, Namba M, Ueno T, Sata M. Hydrogen peroxide overproduction in megamitochondria of troglitazone-treated human hepatocytes. Hepatology. 2003 Jan;37(1):136-47. PubMed PMID: 12500198. 17: Jacobson J, Duchen MR, Heales SJ. Intracellular distribution of the fluorescent dye nonyl acridine orange responds to the mitochondrial membrane potential: implications for assays of cardiolipin and mitochondrial mass. J Neurochem. 2002 Jul;82(2):224-33. PubMed PMID: 12124423. 18: Piccotti L, Marchetti C, Migliorati G, Roberti R, Corazzi L. Exogenous phospholipids specifically affect transmembrane potential of brain mitochondria and cytochrome C release. J Biol Chem. 2002 Apr 5;277(14):12075-81. Epub 2002 Jan 28. PubMed PMID: 11815626. 19: Mileykovskaya E, Dowhan W, Birke RL, Zheng D, Lutterodt L, Haines TH. Cardiolipin binds nonyl acridine orange by aggregating the dye at exposed hydrophobic domains on bilayer surfaces. FEBS Lett. 2001 Oct 26;507(2):187-90. PubMed PMID: 11684095. 20: Kunz-Schughart LA, Habbersett RC, Freyer JP. Impact of proliferative activity and tumorigenic conversion on mitochondrial function of fibroblasts in 2D and 3D culture. Cell Biol Int. 2001;25(9):919-30. PubMed PMID: 11518499.