DAA1106
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MedKoo CAT#: 531120

CAS#: 220551-92-8

Description: 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

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DAA1106
CAS# 220551-92-8

Theoretical Analysis

MedKoo Cat#: 531120
Name: DAA1106
CAS#: 220551-92-8
Chemical Formula: C23H22FNO4
Exact Mass: 395.15
Molecular Weight: 395.430
Elemental Analysis: C, 69.86; H, 5.61; F, 4.80; N, 3.54; O, 16.18

Price and Availability

Size Price Availability Quantity
100mg USD 350
200mg USD 650
500mg USD 1050
1g USD 1950
2g USD 2850
5g USD 3950
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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:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 56.0 141.62

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.

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. 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: 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.
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.

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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.