Thioflavin

Source: Wikipedia, the free encyclopedia.
Thioflavin T
Names
Preferred IUPAC name
2-[4-(Dimethylamino)phenyl]-3,6-dimethyl-1,3-benzothiazol-3-ium chloride
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.017.482 Edit this at Wikidata
UNII
  • InChI=1S/C17H19N2S.ClH/c1-12-5-10-15-16(11-12)20-17(19(15)4)13-6-8-14(9-7-13)18(2)3;/h5-11H,1-4H3;1H/q+1;/p-1 checkY
    Key: JADVWWSKYZXRGX-UHFFFAOYSA-M checkY
  • InChI=1/C17H19N2S.ClH/c1-12-5-10-15-16(11-12)20-17(19(15)4)13-6-8-14(9-7-13)18(2)3;/h5-11H,1-4H3;1H/q+1;/p-1
    Key: JADVWWSKYZXRGX-REWHXWOFAC
  • [Cl-].s2c1cc(ccc1[n+](c2c3ccc(N(C)C)cc3)C)C
Properties
C17H19ClN2S
Molar mass 318.86 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Thioflavins are

neurodegenerative diseases
.

Thioflavin T

Thioflavin T (Basic Yellow 1, Methylene yellow, CI 49005, or ThT) is a

plaques composed of amyloid beta found in the brains of Alzheimer's disease patients).[1]

When it binds to

red shift of its emission spectrum.[5][6] Additional studies also consider fluorescence changes as result of the interaction with double stranded DNA.[7] This change in fluorescent behavior can be caused by many factors that affect the excited state charge distribution of thioflavin T, including binding to a rigid, highly-ordered nanopocket, and specific chemical interactions between thioflavin T and the nanopocket.[8][9]

Prior to binding to an amyloid fibril, thioflavin T emits weakly around 427 nm. Quenching effects of the nearby excitation peak at 450 nm is suspected to play a role in minimizing emissions.

When excited at 450 nm, thioflavin T produces a strong fluorescence signal at approximately 482 nm upon binding to amyloids. Thioflavin T molecule consists of a benzylamine and a benzothiazole ring connected through a carbon-carbon bond. These two rings can rotate freely when the molecule is in solution. The free rotation of these rings results in quenching of any excited state generated by photon excitation. However, when thioflavin T binds to amyloid fibrils, the two rotational planes of the two rings become immobilized and therefore, this molecule can maintain its excited state.[1]

Thioflavin T fluorescence is often used as a diagnostic of amyloid structure, but it is not perfectly specific for amyloid. Depending on the particular protein and experimental conditions, thioflavin T may

false negative
results.

lysosomes
which accumulate in the human brain during normal aging.

In adult C. elegans, exposure to thioflavin T results "in a profoundly extended lifespan and slowed aging" at some levels, but decreased lifespan at higher levels.[12]

Thioflavin S

Thioflavin S is a homogenous mixture of compounds that results from the methylation of dehydrothiotoluidine with

Congo red
.

See also

References

  1. ^
    PMID 20399286
    .
  2. PMID 28393556
    .
  3. PMID 26503040
    .
  4. ^ "Thioflavin T". National Center for Biotechnology Information. PubChem.
  5. ^ a b c H. LeVine III, Methods in Enzymology. 309, 274 (1999)
  6. PMID 19693614
    .
  7. doi:10.1016/s1010-6030(03)00320-4
    .
  8. ^
    PMID 20826442
    .
  9. doi:10.1002/qua.25349
    .
  10. PMID 8453378
    .
  11. PMID 21291268
    .
  12. PMID 21451522
    .
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