DASB

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DASB
File:DASB.png
File:DASB C-11.png
Systematic (IUPAC) name
3-amino-4-[2-[(di(methyl)amino)methyl]phenyl]sulfanylbenzonitrile
Identifiers
PubChem CID 656408
Chemical data
Formula C16H17N3S
Molar mass 282.392014 g/mol[[Script error: No such module "String".]]
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DASB is a compound that binds to the serotonin transporter. Labeled with carbon-11 — a radioactive isotope — it has been used as a radioligand in neuroimaging with positron emission tomography (PET) since around year 2000.[1] In this context it is regarded as one of the superior radioligands for PET study of the serotonin transporter in the brain,[2] since it has high selectivity for the serotonin transporter.[3]

The DASB image from a human PET scan shows high binding in the midbrain, thalamus and striatum, moderate binding in the medial temporal lobe and anterior cingulate, and low binding in neocortex. The cerebellum is often regarded as a region with no specific serotonin transporter binding and the brain region is used as a reference in some studies.[4]

Since the serotonin transporter is the target of SSRIs used in the treatment of major depression it has been natural to examine DASB binding in depressed patients. Several such research studies have been performed.[5]

There are a number of alternative PET radioligands for imaging the serotonin transporter: [11C]ADAM, [11C]AFM, [11C]DAPA, [11C]McN5652, and [11C]-NS 4194. A related molecule to DASB, that can be labeled with fluorine-18, has also been suggested as a PET radioligand.[6] With single-photon emission computed tomography (SPECT) using the radioisotope iodine-123 there are further radioligands available: [123I]ODAM, [123I]IDAM, [123I]ADAM, and [123I]β-CIT.[2] A few studies have examined the difference in binding between the radioligands in nonhuman primates,[7][8] as well as in pigs.[9]

Other compounds that can be labeled to work as PET radioligands for the study of the serotonin system are, e.g., altanserin and WAY-100635.

Methodological issues

The binding potential of DASB can be estimated with kinetic modeling on a series of brain scans.[10]

A test-retest reproducibility PET study indicates that [11C]DASB can be used to measure the serotonin transporter parameters with high reliability in receptor-rich brain regions.[4]

When the DASB neuroimages are analyzed the kinetic models suggested by Ichise and coworkers[11] can be employed to estimate the binding potential. A test-retest reproducibility experiment has been performed to evaluate this approach.[12]

Studies

Besides the studies listed below a few occupancy studies have been reported.[5]

DASB binding neuroimaging studies (patients compared to healthy control subjects).
What Result Subjects Ref.
5-HTTLPR LALA serotonin transporter genotype Increase in putamen 43/30 [13]
5-HTTLPR LALA serotonin transporter genotype Increase in midbrain 19 [14]
5-HTTLPR LALA serotonin transporter genotype No difference 63 [15]
Age No effect found [16] ([2])
Body mass index Inverse correlation (?)  ? [17]
Seasonality Higher in winter in putamen and caudate 54 [18]
Seasonality Higher in fall and winter 88 [19]
NEO PI-R Neuroticism Positive correlation in thalamus 31 males [20]
Disease
Depressed during major depressive episodes No difference found 20+20 [16]
Depressed with highly negativistic "dysfunctional attitudes" during major depressive episodes Increase in prefrontal cortex, anterior cingulate, thalamus, bilateral caudate, and bilateral putamen 20(?)+20 [16]
Recovered depressed patients No difference found 24+20 males [21]
Unipolar depression Increase in thalamus, insula and striatum 18+34 [22]
Unmedicated unipolar major depression Reduced 5-HTT availability in the thalamus [23]
TCI anxiety in unmedicated unipolar major depression Reduced 5-HTT availability in the thalamus, midbrain and amygdala [23]
Bipolar depression Increase in thalamus, insula and striatum 18+34 [22]
Bipolar depression Decrease in midbrain, amygdala, hippocampus, thalamus, putamen, and anterior cingulate cortex 18+41 [24]
Obsessive compulsive disorder Reduction and correlation with severity in thalamus and midbrain 9+19 [25]
Alcoholism No significant alteration 30 + 18 [26]
Parkinson's disease Reduction in forebrain 5+8 [27]
Non-depressed Parkinson's disease Decreased binding in caudate, midbrain, putamen, orbitofrontal cortex and (non-significantly) dorsolateral prefrontal cortex [28]
Depressed Parkinson's disease patients Increase in prefrontal and dorsolateral cortices 7+7 [29]
Drug/intervention
Abstinent MDMA ('Ecstasy') users Global reduction 23+19 [30]
Former MDMA users and polydrug users No significant difference in brain regions examined 12+9+19 [31]
Reduced synaptic serotonin (by rapid tryptophan depletion) (small reduction in binding potential) 8 [32]
Lowering of brain serotonin (by acute tryptophan depletion) No change observed 25 (14) [33]

References

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  1. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  2. ↑ 2.0 2.1 2.2 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  3. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  4. ↑ 4.0 4.1 W. Gordon Frankle, Mark Slifstein, Roger N. Gunn, Yiyun Huang, Dah-Ren Hwang, E. Ashlie Darr, Rajesh Narendran, Anissa Abi-Dargham and Marc Laruelle (May 1, 2006). "Estimation of Serotonin Transporter Parameters with 11C-DASB in Healthy Humans: Reproducibility and Comparison of Methods". Journal of Nuclear Medicine. 47 (5): 815–826. PMID 16644752. 
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  6. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  7. ↑ Zsolt Szabo, Una D. McCann, Alan A. Wilson, Ursula Scheffel, Taofeek Owonikoko, William B. Mathews, Hayden T. Ravert, John Hilton, Robert F. Dannals,and George A. Ricaurte (May 1, 2002). "Comparison of (+)-11C-McN5652 and 11C-DASB as Serotonin Transporter Radioligands Under Various Experimental Conditions". Journal of Nuclear Medicine. 43 (5): 678–692. PMC 2078607 Freely accessible. PMID 11994534. 
  8. ↑ Yiyun Huang, Dah-Ren Hwang, Raj Narendran, Yasuhiko Sudo, Rano Chatterjee, Sung-A Bae, Osama Mawlawi, Lawrence S. Kegeles, Alan A. Wilson, Hank F. Kung and Marc Laruelle (2002). "Comparative Evaluation in Nonhuman Primates of Five PET Radiotracers for Imaging the Serotonin Transporters: [11C]McN 5652, [11C]ADAM, [11C]DASB, [11C]DAPA, and [11C]AFM". Journal of Cerebral Blood Flow & Metabolism. 22 (11): 1377–1398. doi:10.1097/00004647-200211000-00011. PMID 12439295.  Check date values in: |date= (help)
  9. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  10. ↑ Nathalie Ginovart, Alan A. Wilson, Jeffrey H. Meyer, Doug Hussey and Sylvain Houle (2001). "Positron Emission Tomography Quantification of [11C]-DASB Binding to the Human Serotonin Transporter: Modeling Strategies". Journal of Cerebral Blood Flow & Metabolism. 21: 1342–1353.  Check date values in: |date= (help)
  11. ↑ Masanori Ichise, Jeih-San Liow, Jian-Qiang Lu, Akihiro Takano, Kendra Model, Hiroshi Toyama, Tetsuya Suhara, Kazutoshi Suzuki, Robert B Innis and Richard E Carson (2003). "Linearized Reference Tissue Parametric Imaging Methods: Application to [11C]DASB Positron Emission Tomography Studies of the Serotonin Transporter in Human Brain". Journal of Cerebral Blood Flow & Metabolism. 23 (9): 1096–1112. doi:10.1097/01.WCB.0000085441.37552.CA. PMID 12973026. 
  12. ↑ Jae Seung Kim, Masanori Ichise, Janet Sangare, and Robert B. Innis (2006). "PET Imaging of Serotonin Transporters with [11C]DASB: Test–Retest Reproducibility Using a Multilinear Reference Tissue Parametric Imaging Method". Journal of Nuclear Medicine. 47 (2): 208–214. 
  13. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  14. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  15. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  16. ↑ 16.0 16.1 16.2 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  17. ↑ Ryohei Matsumoto, H. Ito, H. Takahashi, H. Takano and T. Suhara (2008). "Inverse correlation between body mass index and serotonin transporter binding in human brain: A [11C]DASB PET study". NeuroImage. 2, supplement 2: T161. doi:10.1016/j.neuroimage.2008.04.128.  Neuroreceptor Mapping 2008, The Seventh International Symposium on Functional Neuroreceptor Mapping of Living Brain
  18. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  19. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  20. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  21. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  22. ↑ 22.0 22.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  23. ↑ 23.0 23.1 Matthias Reimold, Batra A, Knobel A, Smolka MN, Zimmer A, Mann K, Solbach C, Reischl G, Schwärzler F, Gründer G, Machulla HJ, Bares R, A. Heinz (2008). "Anxiety is associated with reduced central serotonin transporter availability in unmedicated patients with unipolar major depression: a [11C]DASB PET study". Molecular Psychiatry. 13 (6): 606. doi:10.1038/sj.mp.4002149. PMID 18268503. . Electronic publication
  24. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  25. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  26. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  27. ↑ Roger L Albin, Robert A. Koeppe, Nicolaas I. Bohnen, Kristine Wernette, Michael A. Kilbourn and Kirk A. Frey (2008). "Spared caudal brainstem SERT binding in early Parkinson's disease". Journal of Cerebral Blood Flow & Metabolism. 28 (3): 441–444. doi:10.1038/sj.jcbfm.9600599. PMID 18073772. 
  28. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  29. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  30. ↑ Una D McCann, Zsolt Szabo, Esen Seckin, Peter Rosenblatt, William B Mathews, Hayden T Ravert, Robert F Dannals and George A Ricaurte (2005). "Quantitative PET Studies of the Serotonin Transporter in MDMA Users and Controls Using [11C]McN5652 and [11C]DASB". Neuropsychopharmacology. 30 (9): 1741–1750. doi:10.1038/sj.npp.1300736. PMC 2034411 Freely accessible. PMID 15841106.  Check date values in: |date= (help)
  31. ↑ Sudhakar Selvaraj, Rosa Hoshi,Zubin Bhagwagar, Naga Venkatesha Murthy, Rainer Hinz, Philip Cowen, H. Valerie Curran, Paul Grasby (2009). "Brain serotonin transporter binding in former users of MDMA ('ecstasy')". The British Journal of Psychiatry. 194 (4): 355–359. doi:10.1192/bjp.bp.108.050344. PMID 19336788. 
  32. ↑ Peter S. Talbot, W. Gordon Frankle, Dah-Ren Hwang, Yiyun Huang, Raymond F. Suckow, Mark Slifstein, Anissa Abi-Dargham & Marc Laruelle (2004). "Effects of reduced endogenous 5-HT on the in vivo binding of the serotonin transporter radioligand 11C-DASB in healthy humans". Synapse. 55 (3): 164–175. doi:10.1002/syn.20105. PMID 15605360.  Check date values in: |date= (help)
  33. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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