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Details

Stereochemistry ACHIRAL
Molecular Formula C12H8S3
Molecular Weight 248.387
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-TERTHIENYL

SMILES

S1C=CC=C1C2=CC=C(S2)C3=CC=CS3

InChI

InChIKey=KXSFECAJUBPPFE-UHFFFAOYSA-N
InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H

HIDE SMILES / InChI

Description

Alpha-Terthienyl is a pigment in African marigolds (Tagetes spp.) and exhibits antifungal, insecticidal, and nematicidal properties related to its ability to sensitize the formation of singlet oxygen. Terthiophene is the compound responsible for the insecticidal activity of Tagetes minuta. Alpha-Terthienyl is also used as building block in the production of organic semiconductors.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
To investigate cutaneous UV phototoxicity 1% alpha-Terthienyl in 3% Azone gel was topically applied to mature female white guinea pigs. Investigators noted enhanced cutaneous phototoxicity with multiple applications; 3 per 24 hour period vs 1 per 24 hour period. The optimal interval between single drug application and irradiation was between 1-6 h to achieve maximum photosensitization. Clinical changes included mild erythema and inhibition of hair regrowth during the first 72 h after irradiation, with increasing erythema and edema progressing to erosion and crusting at 1 week. Clinical changes remained localized to the a-T -treated sites. Histopathologic changes at 72 h after irradiation paralleled macroscopic changes with crusting, subepidermal and intraepidermal edema and vesiculation, the presence of "sunburn" cells in the epidermis, and epidermal erosion ranging to complete epidermal degeneration.
Route of Administration: Topical
In Vitro Use Guide
32 microM alpha-Terthienyl was added to an emulsion of 1 micro-g/mL of glucose-6-phosphate dehydrogenase, from yeast, in a buffer of 0.1 M triethanolamine buffer, pH 7.6, and 1 g liter-’ of Tween 2O. Photooxidation was induced with UV radiation. Periodically 50 micro-L was extracted and assayed for glucose-6-phosphate dehydrogenase activity. Photoactivated alpha-terthienyl reduced glucose-6-phosphatase dehydrogenase by 76 and 97% after 36 and 90 minutes respectively.