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
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
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 Target | Pharmacology | Condition | Potency |
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Target ID: P11412 Gene ID: 855480.0 Gene Symbol: ZWF1 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/422557 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Secondary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Photoactivation of the nematicidal compound alpha-terthienyl from roots of marigolds (Tagetes species). A possible singlet oxygen role. | 1979 Mar 25 |
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Characterization of cutaneous phototoxicity induced by topical alpha-terthienyl and ultraviolet A radiation. | 1986 Sep |
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Isolation of the insecticidal components of Tagetes minuta (Compositae) against mosquito larvae and adults. | 1995 Sep |
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Pharmacokinetics, metabolism and toxicity of the plant-derived photoxin alpha-terthienyl. | 1995 Sep |
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Novel protein kinase C inhibitors: alpha-terthiophene derivatives. | 1998 Oct 6 |
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Photodynamic inactivation of oropharyngeal Candida strains. | 2014 Sep 25 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3734487
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/422557
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.
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EPA PESTICIDE CODE |
74751
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m10587
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1081-34-1
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C019101
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DTXSID2041206
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Terthiophene
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SUBSTANCE RECORD