Decynium-22

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Decynium-22
The chemical structure of decynium-22
Names
IUPAC name
1-Ethyl-2-[(1-ethyl-2(1H)-quinolinylidene)methyl]quinolinium iodide
Other names
Decynium-22, Pseudocyanine iodide, Pseudoisocyanine iodide
Identifiers
977-96-8
ChemSpider 4588533
EC Number 213-556-6
Jmol 3D model Interactive image
PubChem 5484462
  • InChI=1S/C23H23N2.HI/c1-3-24-20(15-13-18-9-5-7-11-22(18)24)17-21-16-14-19-10-6-8-12-23(19)25(21)4-2;/h5-17H,3-4H2,1-2H3;1H/q+1;/p-1
    Key: GMYRVMSXMHEDTL-UHFFFAOYSA-M
  • InChI=1/C23H23N2.HI/c1-3-24-20(15-13-18-9-5-7-11-22(18)24)17-21-16-14-19-10-6-8-12-23(19)25(21)4-2;/h5-17H,3-4H2,1-2H3;1H/q+1;/p-1
    Key: GMYRVMSXMHEDTL-REWHXWOFAU
  • CCN1C(=CC2=[N+](C3=CC=CC=C3C=C2)CC)C=CC4=CC=CC=C41.[I-]
Properties
C23H23IN2
Molar mass 454.36 g·mol−1
Appearance Powder, or a dark red solid
Melting point 273 °C (523 °F; 546 K)
Solubility in DMSO Soluble to 10 mM
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Decynium-22 is a cation derivative of quinoline, and a potent inhibitor of the plasma membrane monoamine transporter (PMAT),[1] as well as all members of the organic cation transporter (OCT) family in both human and rat cells.[2] However, it has little effect on high affinity monoamine transporters such as the dopamine transporter and norepinephrine transporter.[3]

Transporter inhibition

Decynium has been shown to have a very high affinity to organic cation transporters in a variety of species, including human,[4][5] rat,[6] and pig.[7] Decynium-22 has been shown to block the uptake of 1-methyl-4-phenylpyridinium (MPP) via the OCT3 transporter in rat astrocytes.[8]

Fluorescence

Decynium-22 emits a low fluorescence yield (around 0.001), and in its monomeric form is a weakly fluorescent. However, aggregated decynium-22 emits a strong superradiant emission with a maximum near 570-580 nm.[9][10] 480 nm light falls near a short wavelength peak of the excitation spectrum of these aggregates. Decynium-22 fluorescence caused by aggregation can be observed in astrocytes.[3]

Schizophrenia and depression

Decynium-22 has recently been investigated for its role in increasing extracellular serotonin in the brain in neuropharmacology research. The transportation of the neurotransmitter serotonin is often disrupted in psychiatric disorders characterized by social impairment, such as schizophrenia and depression. Serotonin is primarily taken up by the 5-HT transporter (SERT), although it is also taken up by auxiliary transporters, known as "uptake 2", which include OCT and PMAT.

The most commonly prescribed antidepressant drugs are the selective serotonin reuptake inhibitors (SSRIs), which act by blocking the high affinity SERT. A proposed explanation for the limited efficacy of SSRIs is the presence of the low affinity transporters OCT and PMAT, which limit the ability of SSRIs to increase extracellular serotonin. Decynium-22 blocked serotonin uptake via these auxiliary transporters, and when used in conjunction with SSRIs, decynium-22 enhanced the effects of SSRIs to inhibit serotonin clearance.[11] A similar effect was seen in SERT knock-out mice, which resulted in an improvement of social behavior.[12] When OCT3 was knocked out in mice, however, decynium-22 was ineffectual, indicating that the anti-depressant effects of decynium-22 are dependent upon its blockage of the OCT3.[11]

References

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  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
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  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Stiel H, Daehne S, Teuchner K. J-aggregates of pseudoisocyanine in solution: New data from nonlinear spectroscopy. J Lumines. 1988;39:351–357.
  10. ↑ Struganova IA. Dynamics of formation of 1,1′-diethyl-2,2′-cyanine iodide J-aggregates in solution. J Physical Chem A. 2000;104:9670–9674.
  11. ↑ 11.0 11.1 Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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