ALLYL DISULFIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10S2
Molecular Weight	146.274
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C=CCSSCC=C

InChI

InChIKey=PFRGXCVKLLPLIP-UHFFFAOYSA-N

InChI=1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2

HIDE SMILES / InChI

Molecular Formula	C6H10S2
Molecular Weight	146.274
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122 | https://www.ncbi.nlm.nih.gov/pubmed/29329251 | https://www.ncbi.nlm.nih.gov/pubmed/28847761

Diallyl disulfide (DADS) or allyl disulfide is the main organosulfur ingredient in garlic, with known antioxidant and anti-inflammatory activities. It has been shown to have multi-targeted antitumor activities in a variety of cancer cells Experiments in vitro have revealed, that diallyl disulfide inhibits the metastasis of type Ⅱ esophageal-gastric junction adenocarcinoma cells via NF-κB and PI3K/AKT signaling pathways. At the same time, was shown the drug suppresses cell stemness, proliferation, metastasis and glucose metabolism in breast cancer stem cells partly through the inhibition of CD44/PKM2/AMPK. Besides diallyl disulfide can be a promising agent for the treatment of emphysema, this was discovered in experiments on rats. And also drug shows protective effects against acetaminophen (AAP)-induced acute hepatotoxicity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
PI3K-Akt signaling pathway 24 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122	Inhibitor 8146
CD44 antigen 1 Target ID: P16070\|\|\|Q13419\|\|\|Q13980\|\|\|Q86Z27\|\|\|Q9UCB0 Gene ID: 960.0 Gene Symbol: CD44 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Inhibitor 8146
Pyruvate kinase PKM 1 Target ID: P14618\|\|\|Q96E76 Gene ID: 5315.0 Gene Symbol: PKM Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Inhibitor 8146
AMPK signaling pathway 4 Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Inhibitor 8146

Conditions

Condition	Modality	Highest Phase	Product
Esophageal-gastric junction adenocarcinoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122	Primary	Basic research	Unknown Approved Use Unknown
Emphysema 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29329251	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 426 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Primary	Preclinical	Unknown Approved Use Unknown
Acetaminophen-induced hepatotoxicity 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28847761	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Hepatic metabolism of diallyl disulphide in rat and man.	2003 Dec	14742141
A comparative study of allitin and garlic on lipid turnover in a teleost, Anabas testudineus (Bloch).	2003 Mar	15267155
Photocontact allergy to diallyl disulfide.	2003 Sep	14744409
Chemoprotective effect of diallyl trisulfide from garlic against carbon tetrachloride-induced acute liver injury of rats.	2004	15630193
Anticarcinogenic properties of garlic: a review.	2004	15615431
Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells.	2004	15523159
Conjugated docosahexaenoic acid suppresses KPL-1 human breast cancer cell growth in vitro and in vivo: potential mechanisms of action.	2004	15217495
Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3.	2004	15203378
Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice.	2004 Aug	15301936
[The experimental study of garlicin in treating Pneumocystis carinii pneumonia in rats].	2004 Dec	15830863
Repetitive treatments of colon HT-29 cells with diallyl disulfide induce a prolonged hyperacetylation of histone H3 K14.	2004 Dec	15659844
Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells.	2004 Dec	15500931
Garlic metabolites fail to inhibit the activation of the transcription factor NF-kappaB and subsequent expression of the adhesion molecule E-selectin in human endothelial cells.	2004 Feb	14991270
[Diallyl disulfide-induced G2/M arrest of human gastric cancer MGC803 cells involves activation of p38 MAP kinase pathways].	2004 Feb	14960237
Mechanism and kinetics of synthesis of allicin.	2004 Jan	14964414
Influence of organosulphur compounds from garlic on the secretion of matrix metalloproteinases and their inhibitor TIMP-1 by cultured HUVEC cells.	2004 Jul	15499972
Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell lines.	2004 Jul	14976134
Enhancement of diallyl disulfide-induced apoptosis by inhibitors of MAPKs in human HepG2 hepatoma cells.	2004 Jul 15	15194004
Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-Jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2.	2004 Jul 22	15184882
Biological activity of volatile di-n-propyl disulfide from seeds of neem, Azadirachta indica (Meliaceae), to two species of stored grain pests, Sitophilus oryzae (L.) and Tribolium castaneum (Herbst).	2004 Jun	15279303
[Preventive effect and clinical significance of garlicin injection on mechanical ventilator-associated low respiratory tract deep-seated fungal infection].	2004 Jun	15250201
Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.	2004 Jun 2	15161248
Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake.	2004 Mar 1	14980597
[The initiation of G2/M checkpoint by diallyl disulfide requires the activation of p38 MAP kinase in HL-60 cells].	2004 May	15182534
The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride.	2004 May	15046820
Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation.	2004 May 14	15139418
Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes.	2004 Nov	15604822
Use of gloves in protection from diallyl disulphide allergy.	2004 Nov	15527433
Diallyl disulfide, a chemopreventive agent in garlic, induces multidrug resistance-associated protein 2 expression.	2004 Nov 12	15474518
Induction of detoxifying enzymes by garlic organosulfur compounds through transcription factor Nrf2: effect of chemical structure and stress signals.	2004 Nov 15	15477009
Signal transduction pathways leading to cell cycle arrest and apoptosis induction in cancer cells by Allium vegetable-derived organosulfur compounds: a review.	2004 Nov 2	15476856
Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells.	2004 Oct	15304301
Antioxidant effects of sulfur-containing amino acids.	2004 Oct 31	15515186
Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis.	2004 Sep	15234078
Garlic's ability to prevent in vitro Cu2+-induced lipoprotein oxidation in human serum is preserved in heated garlic: effect unrelated to Cu2+-chelation.	2004 Sep 1	15341661
Diallyl disulfide-induced G2/M arrest of human gastric cancer MGC803 cells involves activation of p38 MAP kinase pathways.	2004 Sep 15	15309729
Diallyldisulfide-induced calcium response of HL-60 human promyelocytes.	2004 Sep-Oct	15587801
Inhibition by allyl sulfides and crushed garlic of O6-methylguanine formation in liver DNA of dimethylnitrosamine-treated rats.	2005	15749632
Differential effects of organosulfur compounds from garlic oil on nitric oxide and prostaglandin E2 in stimulated macrophages.	2005 Apr	15811776
Growth suppressing effect of garlic compound diallyl disulfide on prostate cancer cell line (PC-3) in vitro.	2005 Apr	15802821
Analytical method for appreciation of garlic therapeutic potential and for validation of a new formulation.	2005 Apr 29	15862674
Modulation of cytokine secretion by garlic oil derivatives is associated with suppressed nitric oxide production in stimulated macrophages.	2005 Apr 6	15796590
Protective effect of diallyl disulfide on oxidative stress-injured neuronally differentiated PC12 cells.	2005 Feb 18	15710234
Diallyl disulfide inhibits N-acetyltransferase activity and gene expression in human esophagus epidermoid carcinoma CE 81T/VGH cells.	2005 Jul	15833378
Differential effects of diallyl disulfide on neuronal cells depend on its concentration.	2005 Jul 1	15863251
A case-control study in Shanghai of fruit and vegetable intake and endometrial cancer.	2005 Jun 6	15886701
Garlic-fingered chefs.	2005 Mar	15811038
Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability.	2005 Mar 23	15769123
Allyl disulfide as donor and cyanide as acceptor of sulfane sulfur in the mouse tissues.	2005 Mar-Apr	15886420
Garlic arrests MDA-MB-435 cancer cells in mitosis, phosphorylates the proapoptotic BH3-only protein BimEL and induces apoptosis.	2005 May 9	15827557

Patents

Sample Use Guides

In Vivo Use Guide

Rat emphysema model: the rat emphysema model was established by intraperitoneal injection of cigarette smoke extract (CSE). Each rat in the CSE group was intraperitoneally injected with 1mL CSE-PBS solution on days 1, 8, and 15. Rats in the diallyl disulfide (DADS) and budesonide groups were intraperitoneally injected with 1 mL of CSE on Days 1, 8, and 15 along with the daily injection of DADS or budesonide. The doss of test groups were as follows: 100 and 10 mg/kg/day for DADS and budesonide, respectively.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Diallyl disulfide (DADS) inhibited cell viability of OE19 cells with low cytotoxicity to healthy hepatocytes, L02 cells, in vitro. Non-toxic doses of DADS were ≤10 µg/ml for a 24-h treatment. These non-toxic doses of DADS were found to block the metastasis of OE19 cells by suppressing MMPs, increasing u-PA and TIMPs, as well as altering the balance of MMPs/TIMPs, which at least in part resulted from the suppression of NF-κB and PI3K/AKT signaling pathways.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 23:13:49 UTC 2022` Edited by `admin` on `Fri Dec 16 23:13:49 UTC 2022`
Record UNII	5HI47O6OA7
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ALLYL DISULFIDE

Systematic Name

English

ALLYL DISULPHIDE

Systematic Name

English

NSC-29228

Code

English

ALLYL DISULFIDE [FHFI]

Common Name

English

DIALLYL DISULPHIDE

Systematic Name

English

2-PROPENYL DISULFIDE

Systematic Name

English

FEMA NO. 2028

Code

English

DIALLYL DISULFIDE [HSDB]

Common Name

English

ALLYL DISULFIDE [USP-RS]

Common Name

English

DIALLYL DISULFIDE

Systematic Name

English

DIALLYLDISULFIDE

Systematic Name

English

2-PROPENYL DISULPHIDE

Systematic Name

English

DISULFIDE, DI-2-PROPENYL

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

129087