DASB

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DASB
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PubChem CID
E number{{#property:P628}}
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FormulaC16H17N3S
Molar mass282.392014 g/mol

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

References

  1. ↑ S. Houle, N. Ginovart, D. Hussey, J.H. Meyer, A.A. Wilson (2000). "Imaging the serotonin transporter with positron emission tomography: initial human studies with [11C]DAPP and [11C]DASB". European Journal of Nuclear Medicine and Molecular Imaging. 27 (11): 1719. doi:10.1007/s002590000365. Unknown parameter |month= ignored (help)
  2. ↑ 2.0 2.1 2.2 Peter Brust, Swen Hess and Ulrich Müller and Zsolt Szabo (2006). "Neuroimaging of the Serotonin Transporter — Possibilities and Pitfalls" (PDF). Current Psychiatry Reviews. 2 (1): 111&ndash, 149. doi:10.2174/157340006775101508. Unknown parameter |month= ignored (help)
  3. ↑ Alan A. Wilson, Nathalie Ginovart, Doug Hussey, Jeff Meyer & Sylvain Houle (2002). "In vitro and in vivo characterisation of [11C]-DASB: a probe for in vivo measurements of the serotonin transporter by positron emission tomography". Nuclear Medicine and Biology. 29 (5): 509&ndash, 515. doi:10.1016/S0969-8051(02)00316-5. PMID 12088720. Unknown parameter |month= ignored (help)
  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 (2006). "Estimation of Serotonin Transporter Parameters with 11C-DASB in Healthy Humans: Reproducibility and Comparison of Methods". Journal of Nuclear Medicine. 47 (5): 815&ndash, 826. PMID 16644752. Unknown parameter |day= ignored (help); Unknown parameter |month= ignored (help)
  5. ↑ 5.0 5.1 Jeffrey H. Meyer (2007). "Imaging the serotonin transporter during major depressive disorder and antidepressant treatment". Journal of Psychiatry & Neuroscience. 32 (2): 86–82. PMID 17353938. Unknown parameter |month= ignored (help)
  6. ↑ Sudha Garg, Shankar R. Thopate, Richard C. Minton, Kimberly W. Black, Andrew J. H. Lynch, and Pradeep K. Garg (2007). "3-Amino-4-(2-((4-[18F]fluorobenzyl)methylamino)methylphenylsulfanyl)benzonitrile, an F-18 fluorobenzyl analogue of DASB: synthesis, in vitro binding, and in vivo biodistribution studies". Bioconjug Chem. 18 (5): 1612&ndash, 1618. doi:10.1021/bc070112g S1043-1802(07)00112-7 Check |doi= value (help). PMID 17705553. Unknown parameter |month= ignored (help); Check date values in: |year= (help)
  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 (2002). "Comparison of (+)-11C-McN5652 and 11C-DASB as Serotonin Transporter Radioligands Under Various Experimental Conditions". Journal of Nuclear Medicine. 43 (5): 678&ndash, 692. PMID 11994534. Unknown parameter |day= ignored (help); Unknown parameter |month= ignored (help)
  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: 1377–1398. doi:10.1097/00004647-200211000-00011. Check date values in: |year= (help)
  9. ↑ Svend B. Jensen, Donald F. Smith, Dirk Bender, Steen Jakobsen, Dan Peters, Elsebet Ø. Nielsen, Gunnar M. Olsen, Jørgen Scheel-Krüger, Alan Wilson, Paul Cumming (2003). "[11C]-NS 4194 versus [11C]-DASB for PET imaging of serotonin transporters in living porcine brain". Synapse. 49 (3): 170&ndash, 177. doi:10.1002/syn.10222. Unknown parameter |month= ignored (help); Check date values in: |year= (help)
  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&ndash, 1353. Check date values in: |year= (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: 1096&ndash, 1112. doi:10.1097/01.WCB.0000085441.37552.CA.
  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. ↑ Nicole Praschak-Rieder, J. Kennedy, A. Wilson, D. Hussey, A. Boovariwala, M. Willeit, N. Ginovart, S. Tharmalingam, M. Masellis, S. Houle & Jeffrey H. Meyer (2007). "Novel 5-HTTLPR allele associates with higher serotonin transporter binding in putamen: a [11C] DASB positron emission tomography study". Biological Psychiatry. 62 (4): 327&ndash, 331. doi:10.1016/j.biopsych.2006.09.022. PMID 17210141. Unknown parameter |month= ignored (help)
  14. ↑ M. Reimold, M. N. Smolka, G. Schumann, A. Zimmer, J. Wrase, K. Mann, X.-Z. Hu, D. Goldman, G. Reischl, C. Solbach, H.-J. Machulla, R. Bares1 and A. Heinz (2007). "Midbrain serotonin transporter binding potential measured with [11C]DASB is affected by serotonin transporter genotype". Journal of Neural Transmission. 114 (5): 635. doi:10.1007/s00702-006-0609-0. Unknown parameter |month= ignored (help); Check date values in: |year= (help)
  15. ↑ 15.0 15.1 15.2 Jeffrey H. Meyer, Sylvain Houle, Sandra Sagrati, Anna Carella, Doug F. Hussey, Nathalie Ginovart, Verdell Goulding, James Kennedy, Alan A. Wilson (2004). "Brain Serotonin Transporter Binding Potential Measured With Carbon 11–Labeled DASB Positron Emission Tomography. Effects of Major Depressive Episodes and Severity of Dysfunctional Attitudes". Archives of General Psychiatry. 61 (12): 1271. doi:10.1001/archpsyc.61.12.1271. PMID 15583118. Unknown parameter |month= ignored (help); Check date values in: |year= (help)
  16. ↑ 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
  17. ↑ Jan Kalbitzer, David Erritzoe, Klaus K. Holst, Finn Å. Nielsen, Lisbeth Marner, Szabolcs Lehel, Tine Arentzen, Terry L. Jernigan, & Gitte M. Knudsen (10 September 2008). "Seasonal changes in brain serotonin transporter binding in short 5-HTTLPR-allele carriers but not in long-allele homozygotes". Nature Precedings.
  18. ↑ Nicole Praschak-Rieder, Matthaeus Willeit, Alan A. Wilson, Sylvain Houle & Jeffrey H. Meyer (2008). "Seasonal variation in human brain serotonin transporter binding". Archives of general psychiatry. 65 (9): 1072–1078. doi:10.1001/archpsyc.65.9.1072. PMID 18762593. Unknown parameter |month= ignored (help)
  19. ↑ Akihiro Takano, Ryosuke Arakawaa, Mika Hayashia, Hidehiko Takahashia, Hiroshi Itoa & Tetsuya Suhara (2007). "Relationship between neuroticism personality trait and serotonin transporter binding". Biological Psychiatry. 62 (6): 588&ndash, 592. doi:10.1016/j.biopsych.2006.11.007. PMID 17336939. Unknown parameter |month= ignored (help); Check date values in: |year= (help)
  20. ↑ Zubin Bhagwagar, Naga Murthy, Sudhakar Selvaraj, Rainer Hinz, Matthew Taylor, Sabrina Fancy, Paul Grasby, and Philip Cowen (2007). "5-HTT Binding in Recovered Depressed Patients and Healthy Volunteers: A Positron Emission Tomography Study With [11C]DASB". The American Journal of Psychiatry. 164: 1858&ndash, 1865. doi:10.1176/appi.ajp.2007.06111933. Unknown parameter |month= ignored (help)
  21. ↑ 21.0 21.1 Dara M. Cannon, Masanori Ichise, Denise Rollis, Jacqueline M. Klaver, Shilpa K. Gandhi, Dennis S. Charney, Husseini K. Manji and Wayne C. Drevets (2007). "Elevated serotonin transporter binding in major depressive disorder assessed using positron emission tomography and [11C]DASB; comparison with bipolar disorder". Biological Psychiatry. 62 (8): 870&ndash, 877. doi:10.1016/j.biopsych.2007.03.016. PMID 17678634. Unknown parameter |month= ignored (help)
  22. ↑ 22.0 22.1 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: 606. doi:10.1038/sj.mp.4002149. PMID 18268503.. Electronic publication
  23. ↑ Maria A. Oquendo; Ramin S. Hastings; Yung-yu Huang; Norman Simpson; R. Todd Ogden; Xian-zhang Hu; David Goldman; Victoria Arango; Ronald L. Van Heertum; J. John Mann; Ramin V. Parsey (2007). "Brain Serotonin Transporter Binding in Depressed Patients With Bipolar Disorder Using Positron Emission Tomography". Archives of General Psychiatry. 64 (2): 201&ndash, 208. doi:10.1001/archpsyc.64.2.201. PMID 17283287. Unknown parameter |month= ignored (help)
  24. ↑ M. Reimold, M. N. Smolka, A. Zimmer, A. Batra, A. Knobel, C. Solbach, A. Mundt, H. U. Smoltczyk, D. Goldman, K. Mann, G. Reischl, H.-J. Machulla, R. Bares and A. Heinz (2007). "Reduced availability of serotonin transporters in obsessive-compulsive disorder correlates with symptom severity - a [11C]DASB PET study". Journal of Neural Transmission. 114 (12): 1603&ndash, 1609. doi:10.1007/s00702-007-0785-6. Unknown parameter |month= ignored (help); Check date values in: |year= (help)
  25. ↑ Amira K. Brown, David T. George, Masahiro Fujita, Jeih-San Liow, Masanori Ichise, Joseph Hibbeln, Subroto Ghose, Janet Sangare, Daniel Hommer & Robert B. Innis (2007). "PET [11C]DASB imaging of serotonin transporters in patients with alcoholism". Alcohol Clin Exp Res. 31 (1): 28&ndash, 32. doi:10.1111/j.1530-0277.2006.00261.x. PMID 17207098. Unknown parameter |month= ignored (help); line feed character in |author= at position 145 (help)
  26. ↑ 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: 441–444. doi:10.1038/sj.jcbfm.9600599.
  27. ↑ M. Guttman, I. Boileau, J. Warsh, J. A. Saint-Cyr, N. Ginovart, T. McCluskey, S. Houle, A. Wilson, E. Mundo, P. Rusjan, J. Meyer & S. J. Kish (2007). "Brain serotonin transporter binding in non-depressed patients with Parkinson's disease". European Journal of Neurology. 14 (5): 523–528. doi:10.1111/j.1468-1331.2007.01727.x. PMID 17437611. Unknown parameter |month= ignored (help)
  28. ↑ Isabelle Boileau, Jerry J. Warsh, Mark Guttman, Jean A. Saint-Cyr, Tina McCluskey, Pablo Rusjan, Sylvain Houle, Alan A. Wilson, Jeffrey H. Meyer, Stephen J. Kish (2008). "Elevated serotonin transporter binding in depressed patients with Parkinson's disease: A preliminary PET study with [(11)C]DASB". Movement Disorders. 23: 1776. doi:10.1002/mds.22212. PMID 18661545. Unknown parameter |month= ignored (help)
  29. ↑ 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: 1741–1750. doi:10.1038/sj.npp.1300736. Check date values in: |year= (help)
  30. ↑ 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: 355–359. doi:10.1192/bjp.bp.108.050344.
  31. ↑ 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&ndash, 175. doi:10.1002/syn.20105. Check date values in: |year= (help)
  32. ↑ Nicole Praschak-Riedera, Alan A. Wilson, Douglas Hussey, Anna Carella, Corie Wei, Nathalie Ginovart, Markus J. Schwarz, Johanna Zach, Sylvain Houle and Jeffrey H. Meyer (2005). "Effects of Tryptophan Depletion on the Serotonin Transporter in Healthy Humans". Biological Psychiatry. 58 (10): 825&ndash, 830. doi:10.1016/j.biopsych.2005.04.038. Unknown parameter |month= ignored (help)


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