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MedKoo Cat#: 592045 | Name: Methoxy-X04
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Description:

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

Methoxy-X04 beta-amyloid plaques are used in fluorescence microscopy.

Chemical Structure

Methoxy-X04
Methoxy-X04
CAS# 863918-78-9

Theoretical Analysis

MedKoo Cat#: 592045

Name: Methoxy-X04

CAS#: 863918-78-9

Chemical Formula: C23H20O3

Exact Mass: 344.1412

Molecular Weight: 344.41

Elemental Analysis: C, 80.21; H, 5.85; O, 13.94

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 weeks
10mg USD 550.00 2 weeks
25mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Methoxy-X04
IUPAC/Chemical Name
2,5-Bis(2-(4-hydroxyphenyl)vinyl)anisole
InChi Key
FGYNZFHVGOFCMD-KHVHPYDTSA-N
InChi Code
InChI=1S/C23H20O3/c1-26-23-16-19(3-2-17-6-12-21(24)13-7-17)5-11-20(23)10-4-18-8-14-22(25)15-9-18/h2-16,24-25H,1H3/b3-2+,10-4+
SMILES Code
COC1=CC(/C=C/C2=CC=C(O)C=C2)=CC=C1/C=C/C3=CC=C(O)C=C3
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methoxy-X04 is a fluorescent dye that crosses the blood-brain barrier and selectively binds to beta-pleated sheets found in dense core amyloid Aβ plaques.
In vitro activity:
Methoxy-X04 is a derivative of Congo red and Chrysamine-G that contains no acid groups and is therefore smaller and much more lipophilic than Congo red or Chrysamine-G. Methoxy-X04 retains in vitro binding affinity for amyloid beta (Abeta) fibrils (Ki = 26.8 nM) very similar to that of Chrysamine-G (Ki = 25.3 nM). Reference: J Neuropathol Exp Neurol. 2002 Sep;61(9):797-805. https://pubmed.ncbi.nlm.nih.gov/12230326/
In vivo activity:
This study isolated amyloid plaque-containing (using labelling with methoxy-XO4, XO4+) and non-containing (XO4-) microglia from an AD mouse model. XO4+ microglial transcriptomes demonstrated dysregulated expression of genes associated with late onset AD. This study further showed that the transcriptional program associated with XO4+ microglia from mice is present in a subset of human microglia isolated from brains of individuals with AD. Reference: Nat Commun. 2021 May 21;12(1):3015. https://pubmed.ncbi.nlm.nih.gov/34021136/
Solvent mg/mL mM comments
Solubility
DMF 30.0 87.11
DMSO 29.8 86.56
DMSO:PBS (pH 7.2) (1:2) 0.3 0.96
Ethanol 6.0 17.26
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 344.41 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
Formulation protocol:
1. Klunk WE, Bacskai BJ, Mathis CA, Kajdasz ST, McLellan ME, Frosch MP, Debnath ML, Holt DP, Wang Y, Hyman BT. Imaging Abeta plaques in living transgenic mice with multiphoton microscopy and methoxy-X04, a systemically administered Congo red derivative. J Neuropathol Exp Neurol. 2002 Sep;61(9):797-805. doi: 10.1093/jnen/61.9.797. PMID: 12230326. 2. Grubman A, Choo XY, Chew G, Ouyang JF, Sun G, Croft NP, Rossello FJ, Simmons R, Buckberry S, Landin DV, Pflueger J, Vandekolk TH, Abay Z, Zhou Y, Liu X, Chen J, Larcombe M, Haynes JM, McLean C, Williams S, Chai SY, Wilson T, Lister R, Pouton CW, Purcell AW, Rackham OJL, Petretto E, Polo JM. Transcriptional signature in microglia associated with Aβ plaque phagocytosis. Nat Commun. 2021 May 21;12(1):3015. doi: 10.1038/s41467-021-23111-1. PMID: 34021136; PMCID: PMC8140091. 3. Bisht K, El Hajj H, Savage JC, Sánchez MG, Tremblay MÈ. Correlative Light and Electron Microscopy to Study Microglial Interactions with β-Amyloid Plaques. J Vis Exp. 2016 Jun 1;(112):54060. doi: 10.3791/54060. PMID: 27286292; PMCID: PMC4927759.
In vitro protocol:
1. Klunk WE, Bacskai BJ, Mathis CA, Kajdasz ST, McLellan ME, Frosch MP, Debnath ML, Holt DP, Wang Y, Hyman BT. Imaging Abeta plaques in living transgenic mice with multiphoton microscopy and methoxy-X04, a systemically administered Congo red derivative. J Neuropathol Exp Neurol. 2002 Sep;61(9):797-805. doi: 10.1093/jnen/61.9.797. PMID: 12230326.
In vivo protocol:
1. Grubman A, Choo XY, Chew G, Ouyang JF, Sun G, Croft NP, Rossello FJ, Simmons R, Buckberry S, Landin DV, Pflueger J, Vandekolk TH, Abay Z, Zhou Y, Liu X, Chen J, Larcombe M, Haynes JM, McLean C, Williams S, Chai SY, Wilson T, Lister R, Pouton CW, Purcell AW, Rackham OJL, Petretto E, Polo JM. Transcriptional signature in microglia associated with Aβ plaque phagocytosis. Nat Commun. 2021 May 21;12(1):3015. doi: 10.1038/s41467-021-23111-1. PMID: 34021136; PMCID: PMC8140091. 2. Bisht K, El Hajj H, Savage JC, Sánchez MG, Tremblay MÈ. Correlative Light and Electron Microscopy to Study Microglial Interactions with β-Amyloid Plaques. J Vis Exp. 2016 Jun 1;(112):54060. doi: 10.3791/54060. PMID: 27286292; PMCID: PMC4927759.
1: Furcila D, DeFelipe J, Alonso-Nanclares L. A Study of Amyloid-β and Phosphotau in Plaques and Neurons in the Hippocampus of Alzheimer's Disease Patients. J Alzheimers Dis. 2018;64(2):417-435. doi: 10.3233/JAD-180173. PubMed PMID: 29914033. 2: Jährling N, Becker K, Saghafi S, Dodt HU. Light-Sheet Fluorescence Microscopy: Chemical Clearing and Labeling Protocols for Ultramicroscopy. Methods Mol Biol. 2017;1563:33-49. doi: 10.1007/978-1-4939-6810-7_3. PubMed PMID: 28324600. 3: Nabuurs RJ, Kapoerchan VV, Metaxas A, Hafith S, de Backer M, Welling MM, Jiskoot W, van den Nieuwendijk AM, Windhorst AD, Overkleeft HS, van Buchem MA, Overhand M, van der Weerd L. Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds. Bioorg Med Chem. 2016 Dec 1;24(23):6139-6148. doi: 10.1016/j.bmc.2016.05.022. Epub 2016 May 18. PubMed PMID: 27838168. 4: Bisht K, El Hajj H, Savage JC, Sánchez MG, Tremblay MÈ. Correlative Light and Electron Microscopy to Study Microglial Interactions with β-Amyloid Plaques. J Vis Exp. 2016 Jun 1;(112). doi: 10.3791/54060. PubMed PMID: 27286292; PubMed Central PMCID: PMC4927759. 5: Brendel M, Probst F, Jaworska A, Overhoff F, Korzhova V, Albert NL, Beck R, Lindner S, Gildehaus FJ, Baumann K, Bartenstein P, Kleinberger G, Haass C, Herms J, Rominger A. Glial Activation and Glucose Metabolism in a Transgenic Amyloid Mouse Model: A Triple-Tracer PET Study. J Nucl Med. 2016 Jun;57(6):954-60. doi: 10.2967/jnumed.115.167858. Epub 2016 Feb 18. PubMed PMID: 26912428. 6: Jährling N, Becker K, Wegenast-Braun BM, Grathwohl SA, Jucker M, Dodt HU. Cerebral β-Amyloidosis in Mice Investigated by Ultramicroscopy. PLoS One. 2015 May 27;10(5):e0125418. doi: 10.1371/journal.pone.0125418. eCollection 2015. PubMed PMID: 26017149; PubMed Central PMCID: PMC4446269. 7: Brendel M, Jaworska A, Grießinger E, Rötzer C, Burgold S, Gildehaus FJ, Carlsen J, Cumming P, Baumann K, Haass C, Steiner H, Bartenstein P, Herms J, Rominger A. Cross-sectional comparison of small animal [18F]-florbetaben amyloid-PET between transgenic AD mouse models. PLoS One. 2015 Feb 23;10(2):e0116678. doi: 10.1371/journal.pone.0116678. eCollection 2015. PubMed PMID: 25706990; PubMed Central PMCID: PMC4338066. 8: Burgess A, Nhan T, Moffatt C, Klibanov AL, Hynynen K. Analysis of focused ultrasound-induced blood-brain barrier permeability in a mouse model of Alzheimer's disease using two-photon microscopy. J Control Release. 2014 Oct 28;192:243-8. doi: 10.1016/j.jconrel.2014.07.051. Epub 2014 Aug 6. PubMed PMID: 25107692. 9: Boländer A, Kieser D, Scholz C, Heyny-von Haußen R, Mall G, Goetschy V, Czech C, Schmidt B. Synthesis of methoxy-X04 derivatives and their evaluation in Alzheimer's disease pathology. Neurodegener Dis. 2014;13(4):209-13. doi: 10.1159/000351436. Epub 2013 Sep 25. PubMed PMID: 24080522. 10: Bertoncini CW, Celej MS. Small molecule fluorescent probes for the detection of amyloid self-assembly in vitro and in vivo. Curr Protein Pept Sci. 2011 May;12(3):205-20. Review. PubMed PMID: 21348839. 11: Burgold S, Bittner T, Dorostkar MM, Kieser D, Fuhrmann M, Mitteregger G, Kretzschmar H, Schmidt B, Herms J. In vivo multiphoton imaging reveals gradual growth of newborn amyloid plaques over weeks. Acta Neuropathol. 2011 Mar;121(3):327-35. doi: 10.1007/s00401-010-0787-6. Epub 2010 Dec 7. PubMed PMID: 21136067; PubMed Central PMCID: PMC3038220. 12: Cohen AD, Ikonomovic MD, Abrahamson EE, Paljug WR, Dekosky ST, Lefterov IM, Koldamova RP, Shao L, Debnath ML, Mason NS, Mathis CA, Klunk WE. Anti-Amyloid Effects of Small Molecule Aβ-Binding Agents in PS1/APP Mice. Lett Drug Des Discov. 2009 Sep;6(6):437. PubMed PMID: 20119496; PubMed Central PMCID: PMC2812908. 13: Garcia-Alloza M, Prada C, Lattarulo C, Fine S, Borrelli LA, Betensky R, Greenberg SM, Frosch MP, Bacskai BJ. Matrix metalloproteinase inhibition reduces oxidative stress associated with cerebral amyloid angiopathy in vivo in transgenic mice. J Neurochem. 2009 Jun;109(6):1636-47. doi: 10.1111/j.1471-4159.2009.06096.x. Epub 2009 Apr 8. PubMed PMID: 19457117; PubMed Central PMCID: PMC3281746. 14: Koenigsknecht-Talboo J, Meyer-Luehmann M, Parsadanian M, Garcia-Alloza M, Finn MB, Hyman BT, Bacskai BJ, Holtzman DM. Rapid microglial response around amyloid pathology after systemic anti-Abeta antibody administration in PDAPP mice. J Neurosci. 2008 Dec 24;28(52):14156-64. doi: 10.1523/JNEUROSCI.4147-08.2008. PubMed PMID: 19109498; PubMed Central PMCID: PMC2743894. 15: Hyman B. In reply to Zou et al. "New amyloid plaques or a game of hide-and-seek?". Int J Biol Sci. 2008 Aug 8;4(4):245. PubMed PMID: 18726000; PubMed Central PMCID: PMC2519177. 16: Zou K, Maeda T, Michikawa M, Komano H. New amyloid plaques or a game of hide-and-seek? Int J Biol Sci. 2008 Jul 9;4(4):200-1. PubMed PMID: 18690290; PubMed Central PMCID: PMC2491729. 17: Robbins EM, Betensky RA, Domnitz SB, Purcell SM, Garcia-Alloza M, Greenberg C, Rebeck GW, Hyman BT, Greenberg SM, Frosch MP, Bacskai BJ. Kinetics of cerebral amyloid angiopathy progression in a transgenic mouse model of Alzheimer disease. J Neurosci. 2006 Jan 11;26(2):365-71. PubMed PMID: 16407531. 18: Brendza RP, Bacskai BJ, Cirrito JR, Simmons KA, Skoch JM, Klunk WE, Mathis CA, Bales KR, Paul SM, Hyman BT, Holtzman DM. Anti-Abeta antibody treatment promotes the rapid recovery of amyloid-associated neuritic dystrophy in PDAPP transgenic mice. J Clin Invest. 2005 Feb;115(2):428-33. PubMed PMID: 15668737; PubMed Central PMCID: PMC544607. 19: Sadowski M, Pankiewicz J, Scholtzova H, Tsai J, Li Y, Carp RI, Meeker HC, Gambetti P, Debnath M, Mathis CA, Shao L, Gan WB, Klunk WE, Wisniewski T. Targeting prion amyloid deposits in vivo. J Neuropathol Exp Neurol. 2004 Jul;63(7):775-84. PubMed PMID: 15290902. 20: Klunk WE, Bacskai BJ, Mathis CA, Kajdasz ST, McLellan ME, Frosch MP, Debnath ML, Holt DP, Wang Y, Hyman BT. Imaging Abeta plaques in living transgenic mice with multiphoton microscopy and methoxy-X04, a systemically administered Congo red derivative. J Neuropathol Exp Neurol. 2002 Sep;61(9):797-805. PubMed PMID: 12230326.