ADT-OH
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MedKoo CAT#: 530463

CAS#: 18274-81-2

Description: ADT-OH is a derivative of anethole dithiolethione (ADT) and synthetic hydrogen sulfide (H2S) donor. In the in vitro glucose-oxygen deprivation (OGD) model, ADT-OH markedly attenuated tPA-enhanced Akt activation and VEGF expression in brain microvascular endothelial cells. Finally, ADT-OH improved functional outcomes in mice subjected to MCAO and tPA infusion. H2S donors reduced tPA-induced cerebral hemorrhage by possibly inhibiting the Akt-VEGF-MMP9 cascade. Administration of H2S donors has potential as a novel modality to improve the safety of tPA following stroke.

Chemical Structure

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ADT-OH
CAS# 18274-81-2
Instruction

Theoretical Analysis

MedKoo Cat#: 530463
Name: ADT-OH
CAS#: 18274-81-2
Chemical Formula: C9H6OS3
Exact Mass: 225.96
Molecular Weight: 226.326
Elemental Analysis: C, 47.76; H, 2.67; O, 7.07; S, 42.50

Price and Availability

Size Price Availability Quantity
100mg USD 750
200mg USD 1250
500mg USD 2150
1g USD 2950
2g USD 4250
5g USD 6950
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Synonym: ADT-OH; Desmethylanethol trithione; ACS1.

IUPAC/Chemical Name: 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione

InChi Key: IWBBKLMHAILHAR-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H6OS3/c10-7-3-1-6(2-4-7)8-5-9(11)13-12-8/h1-5,10H

SMILES Code: S=C1SSC(C2=CC=C(O)C=C2)=C1

Appearance: Yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 226.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Cai FF, Xu HR, Yu SH, Li P, Lu YY, Chen J, Bi ZQ, Sun HS, Cheng J, Zhuang HQ, Hua ZC. ADT-OH inhibits malignant melanoma metastasis in mice via suppressing CSE/CBS and FAK/Paxillin signaling pathway. Acta Pharmacol Sin. 2022 Jul;43(7):1829-1842. doi: 10.1038/s41401-021-00799-x. Epub 2021 Nov 18. PMID: 34795411; PMCID: PMC9253130.


2: Cai F, Xu H, Cao N, Zhang X, Liu J, Lu Y, Chen J, Yang Y, Cheng J, Hua ZC, Zhuang H. ADT-OH, a hydrogen sulfide-releasing donor, induces apoptosis and inhibits the development of melanoma in vivo by upregulating FADD. Cell Death Dis. 2020 Jan 16;11(1):33. doi: 10.1038/s41419-020-2222-9. PMID: 31949127; PMCID: PMC6965651.


3: Wei SW, Zou MM, Huan J, Li D, Zhang PF, Lu MH, Xiong J, Ma YX. Role of the hydrogen sulfide-releasing donor ADT-OH in the regulation of mammal neural precursor cells. J Cell Physiol. 2022 Jul;237(7):2877-2887. doi: 10.1002/jcp.30726. Epub 2022 Mar 27. PMID: 35342944.


4: Marwah MK, Shokr H, Sanchez-Aranguren L, Badhan RKS, Wang K, Ahmad S. Transdermal Delivery of a Hydrogen Sulphide Donor, ADT-OH Using Aqueous Gel Formulations for the Treatment of Impaired Vascular Function: an Ex Vivo Study. Pharm Res. 2022 Feb;39(2):341-352. doi: 10.1007/s11095-021-03164-z. Epub 2022 Jan 27. PMID: 35088236; PMCID: PMC8881439.


5: Duan SF, Zhang MM, Zhang X, Liu W, Zhang SH, Yang B, Dong Q, Han JG, Yu HL, Li T, Ji XY, Wu DD, Zhang XJ. HA-ADT suppresses esophageal squamous cell carcinoma progression via apoptosis promotion and autophagy inhibition. Exp Cell Res. 2022 Nov 1;420(1):113341. doi: 10.1016/j.yexcr.2022.113341. Epub 2022 Sep 6. PMID: 36075445.


6: Ou X, Xia T, Yang C, Yu C, Zhang S, Huang R, Chen C, Zhou C. Novel H2S donor proglumide-ADT-OH protects HUVECs from ox-LDL-induced injury through NF-κB and JAK/SATA pathway. Open Med (Wars). 2021 Sep 8;16(1):1318-1327. doi: 10.1515/med-2021-0287. PMID: 34568579; PMCID: PMC8428624.


7: Hasegawa U, Tateishi N, Uyama H, van der Vlies AJ. Hydrolysis-Sensitive Dithiolethione Prodrug Micelles. Macromol Biosci. 2015 Nov;15(11):1512-22. doi: 10.1002/mabi.201500156. Epub 2015 Jun 23. PMID: 26102371.


8: Hammers MD, Singh L, Montoya LA, Moghaddam AD, Pluth MD. Synthesis of Amino- ADT Provides Access to Hydrolytically Stable Amide-Coupled Hydrogen Sulfide Releasing Drug Targets. Synlett. 2016;27(9):1349-1353. doi: 10.1055/s-0035-1560603. PMID: 27397970; PMCID: PMC4936786.


9: Dong Q, Yang B, Han JG, Zhang MM, Liu W, Zhang X, Yu HL, Liu ZG, Zhang SH, Li T, Wu DD, Ji XY, Duan SF. A novel hydrogen sulfide-releasing donor, HA-ADT, suppresses the growth of human breast cancer cells through inhibiting the PI3K/AKT/mTOR and Ras/Raf/MEK/ERK signaling pathways. Cancer Lett. 2019 Jul 28;455:60-72. doi: 10.1016/j.canlet.2019.04.031. Epub 2019 Apr 28. PMID: 31042588.


10: Hasegawa U, Tateishi N, Uyama H, van der Vlies AJ. Back Cover: Macromol. Biosci. 11/2015. Macromol Biosci. 2015 Nov;15(11):1626. doi: 10.1002/mabi.201570042. PMID: 26502003.


11: Wen S, Cao C, Ge J, Yang W, Wang Y, Mou Y. Research Progress of H2S Donors Conjugate Drugs Based on ADTOH. Molecules. 2022 Dec 31;28(1):331. doi: 10.3390/molecules28010331. PMID: 36615525; PMCID: PMC9822322.


12: Hasegawa U, van der Vlies AJ. Design and synthesis of polymeric hydrogen sulfide donors. Bioconjug Chem. 2014 Jul 16;25(7):1290-300. doi: 10.1021/bc500150s. Epub 2014 Jul 1. PMID: 24942989.


13: Jia J, Xiao Y, Wang W, Qing L, Xu Y, Song H, Zhen X, Ao G, Alkayed NJ, Cheng J. Differential mechanisms underlying neuroprotection of hydrogen sulfide donors against oxidative stress. Neurochem Int. 2013 Jun;62(8):1072-8. doi: 10.1016/j.neuint.2013.04.001. Epub 2013 Apr 12. PMID: 23587562; PMCID: PMC4040256.


14: Zhou X, Cao Y, Ao G, Hu L, Liu H, Wu J, Wang X, Jin M, Zheng S, Zhen X, Alkayed NJ, Jia J, Cheng J. CaMKKβ-dependent activation of AMP-activated protein kinase is critical to suppressive effects of hydrogen sulfide on neuroinflammation. Antioxid Redox Signal. 2014 Oct 20;21(12):1741-58. doi: 10.1089/ars.2013.5587. Epub 2014 Mar 13. PMID: 24624937; PMCID: PMC5695757.


15: Liu H, Wang Y, Xiao Y, Hua Z, Cheng J, Jia J. Hydrogen Sulfide Attenuates Tissue Plasminogen Activator-Induced Cerebral Hemorrhage Following Experimental Stroke. Transl Stroke Res. 2016 Jun;7(3):209-19. doi: 10.1007/s12975-016-0459-5. Epub 2016 Mar 28. PMID: 27018013.


16: Chen ZZ, Xie YD, Shao LH, Wang QT, Xu YH, Bian XL. 5-(4-Hydroxyphenyl)-3H-1,2-dithiole-3-thione-based fibrates as potential hypolipidemic and hepatoprotective agents. Bioorg Med Chem Lett. 2018 Dec 15;28(23-24):3787-3792. doi: 10.1016/j.bmcl.2018.10.003. Epub 2018 Oct 3. PMID: 30337230.


17: Li H, Mu J, Sun J, Xu S, Liu W, Xu F, Li Z, Xu J, Hua H, Li D. Hydrogen sulfide releasing oridonin derivatives induce apoptosis through extrinsic and intrinsic pathways. Eur J Med Chem. 2020 Feb 1;187:111978. doi: 10.1016/j.ejmech.2019.111978. Epub 2019 Dec 19. PMID: 31877536.


18: Duan SF, Zhang MM, Dong Q, Yang B, Liu W, Zhang X, Yu HL, Zhang SH, Khan NH, Wu DD, Zhang XJ, Cen J. A Water-Soluble Hydrogen Sulfide Donor Suppresses the Growth of Hepatocellular Carcinoma via Inhibiting the AKT/GSK-3β/β-Catenin and TGF-β/Smad2/3 Signaling Pathways. J Oncol. 2023 Mar 7;2023:8456852. doi: 10.1155/2023/8456852. PMID: 36925651; PMCID: PMC10014162.


19: Song H, Sun Y, Xu G, Hou B, Ao G. Synthesis and biological evaluation of novel hydrogen sulfide releasing glycyrrhetic acid derivatives. J Enzyme Inhib Med Chem. 2016 Dec;31(6):1457-63. doi: 10.3109/14756366.2016.1144596. Epub 2016 Feb 21. PMID: 26899462.


20: da Costa Marques LA, Teixeira SA, de Jesus FN, Wood ME, Torregrossa R, Whiteman M, Costa SKP, Muscará MN. Vasorelaxant Activity of AP39, a Mitochondria-Targeted H2S Donor, on Mouse Mesenteric Artery Rings In Vitro. Biomolecules. 2022 Feb 9;12(2):280. doi: 10.3390/biom12020280. PMID: 35204781; PMCID: PMC8961640.