DAA1106 | CAS#220551-92-8 | PBR ligand

MedKoo Cat#: 531120 | Name: DAA1106

Description:

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

DAA1106 is a potent and selective ligand for peripheral benzodiazepine receptor (PBR), as a potent and selective agonist at the peripheral benzodiazepine receptor.

Chemical Structure

DAA1106

CAS#220551-92-8

Theoretical Analysis

MedKoo Cat#: 531120

Name: DAA1106

CAS#: 220551-92-8

Chemical Formula: C23H22FNO4

Exact Mass: 395.1533

Molecular Weight: 395.43

Elemental Analysis: C, 69.86; H, 5.61; F, 4.80; N, 3.54; O, 16.18

Price and Availability

Size	Price	Availability
100mg	USD 650.00	2 Weeks
200mg	USD 1,050.00	2 Weeks
500mg	USD 2,150.00	2 Weeks
1g	USD 3,450.00	2 Weeks

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Synonym

DAA1106; DAA-1106; DAA 1106

IUPAC/Chemical Name

N-[(2,5-dimethoxyphenyl)methyl]-N-(5-fluoro-2-phenoxyphenyl)acetamide

InChi Key

DCRZYADKQRHHSF-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H22FNO4/c1-16(26)25(15-17-13-20(27-2)10-12-22(17)28-3)21-14-18(24)9-11-23(21)29-19-7-5-4-6-8-19/h4-14H,15H2,1-3H3

SMILES Code

CC(N(CC1=CC(OC)=CC=C1OC)C2=CC(F)=CC=C2OC3=CC=CC=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

>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:

DAA1106 is a potent and selective ligand for peripheral benzodiazepine receptor (PBR) and is a potent and selective agonist at the peripheral benzodiazepine receptor.

In vitro activity:

This study wanted to determine the relative contributions of astrocytes and activated brain macrophages to [3H]DAA1106 binding. Since macrophages are the predominant infected cells in the brain in lentiviral encephailitis (Ellis et al., 2007), the association between infected macrophages and [3H]DAA1106 binding in the brain was also determined. Immunostaining for astrocytes (GFAP), activated brain macrophages (CD68) and the SIV envelope protein gp110 with [3H]DAA1106 autoradiography were combined on on frozen brain sections obtained from the frontal cortex of SIVE macaques. [3H]DAA1106 binding overlapped with CD68 labeled activated macrophages (Figure 4A) and SIV-infected macrophages (Figure 4C), but not with GFAP labeled astrocytes (Figure 4B). Similar results including colocalization of HIV infected cells with [3H]DAA1106 autoradiography were seen in HIVE brain tissues (Figure 4D). Next, it was tested whether [3H]DAA1106 binding in homogenized brain tissue correlated with the abundance of astrocytes or activated macrophages or SIV-infected macrophages labeled with GFAP, CD68 and SIV gp110 respectively. Each cell-type was quantified using confocal microscopy and correlated with [3H]DAA1106 Bmax values obtained from the same brain regions in the same macaques. [3H]DAA1106 binding correlated significantly with the abundance of SIV-infected macrophages (r=0.9646; p=0.0084) and activated macrophages (r=0.8308; p=0.0160) but weakly with the abundance of GFAP-stained astrocytes (r=0.6755; p=0.0958) (Table 2). Reference: Neurobiol Dis. 2008 Feb; 29(2): 232–241. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2258458/

In vivo activity:

DAA1106 (N-(2,5-Dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)acetamide), is a potent and selective ligand for peripheral benzodiazepine receptors (PBR) in mitochondrial fractions of rat (K(i)=0.043 nM) and monkey (K(i)=0.188 nM) brains. After iv injection of [(11)C]DAA1106 into mice, high accumulations of radioactivity were found in the olfactory bulb and cerebellum, the high PBR density regions in the brain. Coinjection of [(11)C]DAA1106 with unlabeled DAA1106 and PBR-selective PK11195 displayed a significant reduction of radioactivity, suggesting a high specific binding of [(11)C]DAA1106 to PBR. Although this tracer was rapidly metabolized in the plasma, only [(11)C]DAA1106 was detected in the brain tissues, suggesting the specific binding in the brain due to the tracer itself. These findings revealed that [(11)C]DAA1106 is a potential and selective positron emitting radioligand for PBR. Reference: Nucl Med Biol. 2003 Jul;30(5):513-9. https://pubmed.ncbi.nlm.nih.gov/12831989/

	Solvent	mg/mL	mM
Solubility
	DMSO	56.0	141.62

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 395.43 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. Venneti S, Wagner AK, Wang G, Slagel SL, Chen X, Lopresti BJ, Mathis CA, Wiley CA. The high affinity peripheral benzodiazepine receptor ligand DAA1106 binds specifically to microglia in a rat model of traumatic brain injury: implications for PET imaging. Exp Neurol. 2007 Sep;207(1):118-27. doi: 10.1016/j.expneurol.2007.06.003. Epub 2007 Jun 19. PMID: 17658516; PMCID: PMC2042945. 2. Venneti S, Wang G, Wiley CA. The high affinity peripheral benzodiazepine receptor ligand DAA1106 binds to activated and infected brain macrophages in areas of synaptic degeneration: implications for PET imaging of neuroinflammation in lentiviral encephalitis. Neurobiol Dis. 2008 Feb;29(2):232-41. doi: 10.1016/j.nbd.2007.08.016. Epub 2007 Sep 7. PMID: 17920902; PMCID: PMC2258458. 3. Zhang MR, Kida T, Noguchi J, Furutsuka K, Maeda J, Suhara T, Suzuki K. [(11)C]DAA1106: radiosynthesis and in vivo binding to peripheral benzodiazepine receptors in mouse brain. Nucl Med Biol. 2003 Jul;30(5):513-9. doi: 10.1016/s0969-8051(03)00016-7. PMID: 12831989.

In vitro protocol:

In vivo protocol:

1. Zhang MR, Kida T, Noguchi J, Furutsuka K, Maeda J, Suhara T, Suzuki K. [(11)C]DAA1106: radiosynthesis and in vivo binding to peripheral benzodiazepine receptors in mouse brain. Nucl Med Biol. 2003 Jul;30(5):513-9. doi: 10.1016/s0969-8051(03)00016-7. PMID: 12831989.

1: Kim T, Pae AN. Translocator protein (TSPO) ligands for the diagnosis or treatment of neurodegenerative diseases: a patent review (2010-2015; part 1). Expert Opin Ther Pat. 2016 Nov;26(11):1325-1351. PubMed PMID: 27607364. 2: Shi H, Braun A, Wang L, Liang SH, Vasdev N, Ritter T. Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides. Angew Chem Int Ed Engl. 2016 Aug 26;55(36):10786-90. doi: 10.1002/anie.201604106. PubMed PMID: 27491349. 3: Zischler J, Krapf P, Richarz R, Zlatopolskiy BD, Neumaier B. Automated synthesis of 4-[(18)F]fluoroanisole, [(18)F]DAA1106 and 4-[(18)F]FPhe using Cu-mediated radiofluorination under "minimalist" conditions. Appl Radiat Isot. 2016 Sep;115:133-7. doi: 10.1016/j.apradiso.2016.04.030. PubMed PMID: 27372807. 4: Preshlock S, Calderwood S, Verhoog S, Tredwell M, Huiban M, Hienzsch A, Gruber S, Wilson TC, Taylor NJ, Cailly T, Schedler M, Collier TL, Passchier J, Smits R, Mollitor J, Hoepping A, Mueller M, Genicot C, Mercier J, Gouverneur V. Enhanced copper-mediated (18)F-fluorination of aryl boronic esters provides eight radiotracers for PET applications. Chem Commun (Camb). 2016 Jun 28;52(54):8361-4. doi: 10.1039/c6cc03295h. PubMed PMID: 27241832. 5: Zlatopolskiy BD, Zischler J, Krapf P, Zarrad F, Urusova EA, Kordys E, Endepols H, Neumaier B. Copper-mediated aromatic radiofluorination revisited: efficient production of PET tracers on a preparative scale. Chemistry. 2015 Apr 7;21(15):5972-9. doi: 10.1002/chem.201405586. PubMed PMID: 25708748. 6: Brody AL, Okita K, Shieh J, Liang L, Hubert R, Mamoun M, Farahi J, Mandelkern MA. Radiation dosimetry and biodistribution of the translocator protein radiotracer [(11)C]DAA1106 determined with PET/CT in healthy human volunteers. Nucl Med Biol. 2014 Nov-Dec;41(10):871-5. doi: 10.1016/j.nucmedbio.2014.07.004. PubMed PMID: 25156039; PubMed Central PMCID: PMC4192057. 7: Tredwell M, Preshlock SM, Taylor NJ, Gruber S, Huiban M, Passchier J, Mercier J, Génicot C, Gouverneur V. A general copper-mediated nucleophilic 18F fluorination of arenes. Angew Chem Int Ed Engl. 2014 Jul 21;53(30):7751-5. doi: 10.1002/anie.201404436. PubMed PMID: 24916101. 8: Tegler G, Estrada S, Hall H, Wanhainen A, Björck M, Sörensen J, Antoni G. Autoradiography screening of potential positron emission tomography tracers for asymptomatic abdominal aortic aneurysms. Ups J Med Sci. 2014 Aug;119(3):229-35. doi: 10.3109/03009734.2014.894157. PubMed PMID: 24555564; PubMed Central PMCID: PMC4116762. 9: Chopra A. N-(6-[(18)F]Fluoro-4-phenoxypyridin-3-yl)-N-(2-methoxybenzyl)acetamide. 2013 Mar 26 [updated 2013 Apr 25]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK133225/ PubMed PMID: 23638491. 10: Yasuno F, Kosaka J, Ota M, Higuchi M, Ito H, Fujimura Y, Nozaki S, Takahashi S, Mizukami K, Asada T, Suhara T. Increased binding of peripheral benzodiazepine receptor in mild cognitive impairment-dementia converters measured by positron emission tomography with [¹¹C]DAA1106. Psychiatry Res. 2012 Jul 30;203(1):67-74. doi: 10.1016/j.pscychresns.2011.08.013. PubMed PMID: 22892349. 11: Wang M, Gao M, Zheng QH. Fully automated synthesis of PET TSPO radioligands [11C]DAA1106 and [18F]FEDAA1106. Appl Radiat Isot. 2012 Jun;70(6):965-73. doi: 10.1016/j.apradiso.2012.03.011. PubMed PMID: 22469868. 12: Leung K. N-Acetyl-N-(2-[(11)C]methoxybenzyl)-2-phenoxy-5-pyridinamine. 2007 Jun 12 [updated 2011 Aug 25]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23547/ PubMed PMID: 20641745. 13: Maeda J, Zhang MR, Okauchi T, Ji B, Ono M, Hattori S, Kumata K, Iwata N, Saido TC, Trojanowski JQ, Lee VM, Staufenbiel M, Tomiyama T, Mori H, Fukumura T, Suhara T, Higuchi M. In vivo positron emission tomographic imaging of glial responses to amyloid-beta and tau pathologies in mouse models of Alzheimer's disease and related disorders. J Neurosci. 2011 Mar 23;31(12):4720-30. doi: 10.1523/JNEUROSCI.3076-10.2011. PubMed PMID: 21430171; PubMed Central PMCID: PMC3251921. 14: Owen DR, Gunn RN, Rabiner EA, Bennacef I, Fujita M, Kreisl WC, Innis RB, Pike VW, Reynolds R, Matthews PM, Parker CA. Mixed-affinity binding in humans with 18-kDa translocator protein ligands. J Nucl Med. 2011 Jan;52(1):24-32. doi: 10.2967/jnumed.110.079459. PubMed PMID: 21149489; PubMed Central PMCID: PMC3161826. 15: Leung K. N-Benzyl-N-methyl-2-[7,8-dihydro-7-(2-[(18)F]fluoroethyl)-8-oxo-2-phenyl-9H-purin -9-yl]acetamide. 2010 May 6 [updated 2010 Aug 19]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK45545/ PubMed PMID: 20734501. 16: Leung K. N-Benzyl-N-ethyl-2-[7,8-dihydro-7-(2-[(18)F]fluoroethyl)-8-oxo-2-phenyl-9H-purin- 9-yl]acetamide. 2010 May 6 [updated 2010 Aug 19]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK45546/ PubMed PMID: 20734500. 17: Leung K. N-Acetyl-N-(2-[(18)F]fluoroethoxybenzyl)-2-phenoxy-5-pyridinamine . 2008 Aug 12 [updated 2008 Aug 22]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23694/ PubMed PMID: 20641889. 18: Leung K. [(11)C]N-Methyl-N-phenyl-[2-(4-chlorophenyl)-6,8-dichloroimidazo[1,2-a]pyridin-3- yl]acetamide. 2008 Oct 8 [updated 2008 Dec 2]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23620/ PubMed PMID: 20641816. 19: Yanamoto K, Zhang MR. N-Benzyl-N-ethyl -2-(7-[(11)C]-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide. 2007 Dec 4 [updated 2007 Dec 31]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23484/ PubMed PMID: 20641683. 20: Leung K. 3-Fluoromethyl-N-[(11)C]methyl-4-phenyl-N-(phenylmethyl)quinoline-2-carboxamide . 2007 Aug 9 [updated 2007 Sep 17]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23422/ PubMed PMID: 20641622.