Diallyl trisulfide

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Diallyl trisulfide
Names
Preferred IUPAC name
Di(prop-2-en-1-yl)trisulfane
Other names
Allitridin
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.016.462 Edit this at Wikidata
EC Number
  • 218-107-8
UNII
  • InChI=1S/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2
    Key: UBAXRAHSPKWNCX-UHFFFAOYSA-N
  • InChI=1/C6H10S3/c1-3-5-7-9-8-6-4-2/h3-4H,1-2,5-6H2
    Key: UBAXRAHSPKWNCX-UHFFFAOYAC
  • C=CCSSSCC=C
Properties
C6H10S3
Molar mass 178.33 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diallyl trisulfide (DATS), also known as Allitridin, is an

organosulfur compound with the formula S(SCH2CH=CH2)2. It is one of several compounds produced by hydrolysis of allicin, including diallyl disulfide and diallyl tetrasulfide; DATS is one of the most potent.[1][clarification needed
]

Biological applications

DATS has been shown to selectively kill cancerous cells in the prostate and breast,

caspase-3 activity.[4] These effects appear to contribute to the apoptosis of cancer cells and a decrease in cancer cell proliferation
.

DATS can be metabolized by

ATP-sensitive K+ channel.[5][8] This causes vasodilation and improves hemodynamics.[5]

DATS is a promising treatment for

cardiac arrhythmias through its ability to change the opening of the human ether-à-go-go-related (hERG) channel. hERG is the pore-forming subunit of potassium channels that create delayed rectifier potassium ion currents in many cells, including cardiac myocytes.[9] The delayed rectifier potassium ion current is largely responsible for the repolarization of ventricular cardiac myocytes by permitting potassium efflux. DATS causes a decrease in the steady-state inactivation, alters deactivation, and impairs trafficking of the hERG channel from the endoplasmic reticulum to the plasma membrane of the cell.[10] This decreases the amount of functional potassium ion rectifier channels on the cell membrane and thus, slows depolarization.[10] However, hERG trafficking impairment has also been shown to cause arrhythmias due to the development of long QT syndrome and should be considered in drug development.[10]

References

  1. ISBN 9780854041909.[page needed
    ]
  2. PMID 22981381
    .
  3. PMID 16169930
    .
  4. PMID 18296348
    .
  5. ^
    PMID 17951430
    .
  6. ^
    PMID 22467307
    .
  7. PMID 21126235
    .
  8. PMID 21278703
    .
  9. PMID 22988594
    .
  10. ^
    S2CID 34673800
    .
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