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MedKoo Cat#: 206923 | Name: SHetA2

Description:

WARNING: This product is for research use only, not for human or veterinary use.

SHetA2 is discontinued now.

Chemical Structure

SHetA2
SHetA2
CAS#361483-66-1

Theoretical Analysis

MedKoo Cat#: 206923

Name: SHetA2

CAS#: 361483-66-1

Chemical Formula: C20H23N3O2S2

Exact Mass: 401.1232

Molecular Weight: 401.54

Elemental Analysis: C, 59.82; H, 5.77; N, 10.46; O, 7.97; S, 15.97

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
SHetA2; SHetA-2; SHetA 2; NSC721689; NSC 721689; NSC-721689.
IUPAC/Chemical Name
1-(4-nitrophenyl)-3-(2,2,4,4-tetramethylthiochroman-6-yl)thiourea
InChi Key
FWWKIYPMUZVMQG-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H23N3O2S2/c1-19(2)12-20(3,4)27-17-10-7-14(11-16(17)19)22-18(26)21-13-5-8-15(9-6-13)23(24)25/h5-11H,12H2,1-4H3,(H2,21,22,26)
SMILES Code
S=C(NC1=CC2=C(C=C1)SC(C)(C)CC2(C)C)NC3=CC=C(C=C3)[N+]([O-])=O
Appearance
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

Preparing Stock Solutions

The following data is based on the product molecular weight 401.54 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
1: Mahjabeen S, Hatipoglu MK, Chandra V, Benbrook DM, Garcia-Contreras L. Optimization of a Vaginal Suppository Formulation to Deliver SHetA2 as a Novel Treatment for Cervical Dysplasia. J Pharm Sci. 2017 Oct 5. pii: S0022-3549(17)30675-5. doi: 10.1016/j.xphs.2017.09.018. [Epub ahead of print] PubMed PMID: 28989018. 2: Fallatah MM, Liu S, Sevigny MB, Zou H, Louie MC. Novel flexible heteroarotinoid, SL-1-18, promotes ERα degradation to inhibit breast cancer cell growth. Cancer Lett. 2017 Nov 1;408:82-91. doi: 10.1016/j.canlet.2017.08.026. Epub 2017 Aug 25. PubMed PMID: 28844711. 3: Gnanasekaran KK, Benbrook DM, Nammalwar B, Thavathiru E, Bunce RA, Berlin KD. Synthesis and evaluation of second generation Flex-Het scaffolds against the human ovarian cancer A2780 cell line. Eur J Med Chem. 2015;96:209-17. doi: 10.1016/j.ejmech.2015.03.070. Epub 2015 Apr 4. PubMed PMID: 25880346. 4: Liu S, Louie MC, Rajagopalan V, Zhou G, Ponce E, Nguyen T, Green L. Synthesis and evaluation of the diarylthiourea analogs as novel anti-cancer agents. Bioorg Med Chem Lett. 2015 Mar 15;25(6):1301-5. doi: 10.1016/j.bmcl.2015.01.042. Epub 2015 Jan 30. PubMed PMID: 25701251. 5: Benbrook DM, Nammalwar B, Long A, Matsumoto H, Singh A, Bunce RA, Berlin KD. SHetA2 interference with mortalin binding to p66shc and p53 identified using drug-conjugated magnetic microspheres. Invest New Drugs. 2014 Jun;32(3):412-23. doi: 10.1007/s10637-013-0041-x. Epub 2013 Nov 20. PubMed PMID: 24254390; PubMed Central PMCID: PMC4045313. 6: Benbrook DM, Guruswamy S, Wang Y, Sun Z, Mohammed A, Zhang Y, Li Q, Rao CV. Chemoprevention of colon and small intestinal tumorigenesis in APC(min/+) mice by SHetA2 (NSC721689) without toxicity. Cancer Prev Res (Phila). 2013 Sep;6(9):908-16. doi: 10.1158/1940-6207.CAPR-13-0171. Epub 2013 Jul 12. PubMed PMID: 23852423; PubMed Central PMCID: PMC3769959. 7: Kabirov KK, Kapetanovic IM, Benbrook DM, Dinger N, Mankovskaya I, Zakharov A, Detrisac C, Pereira M, Martín-Jiménez T, Onua E, Banerjee A, van Breemen RB, Nikolić D, Chen L, Lyubimov AV. Oral toxicity and pharmacokinetic studies of SHetA2, a new chemopreventive agent, in rats and dogs. Drug Chem Toxicol. 2013 Jul;36(3):284-95. doi: 10.3109/01480545.2012.710632. Epub 2012 Sep 5. PubMed PMID: 22947079. 8: Doppalapudi RS, Riccio ES, Davis Z, Menda S, Wang A, Du N, Green C, Kopelovich L, Rao CV, Benbrook DM, Kapetanovic IM. Genotoxicity of the cancer chemopreventive drug candidates CP-31398, SHetA2, and phospho-ibuprofen. Mutat Res. 2012 Jul 4;746(1):78-88. doi: 10.1016/j.mrgentox.2012.03.009. Epub 2012 Apr 10. PubMed PMID: 22498038; PubMed Central PMCID: PMC3375211. 9: Dawson MI, Fontana JA. The peptidomimetic, 1-adamantyl-substituted, and flex-het classes of retinoid-derived molecules: structure-activity relationships and retinoid receptor-independent anticancer activities. Mini Rev Med Chem. 2010 Jun;10(6):455-91. Review. PubMed PMID: 20370709. 10: Chengedza S, Benbrook DM. NF-kappaB is involved in SHetA2 circumvention of TNF-alpha resistance, but not induction of intrinsic apoptosis. Anticancer Drugs. 2010 Mar;21(3):297-305. doi: 10.1097/CAD.0b013e3283350e43. PubMed PMID: 20032777; PubMed Central PMCID: PMC2902153. 11: Moxley KM, Chengedza S, Benbrook DM. Induction of death receptor ligand-mediated apoptosis in epithelial ovarian carcinoma: The search for sensitizing agents. Gynecol Oncol. 2009 Dec;115(3):438-42. doi: 10.1016/j.ygyno.2009.09.007. Epub 2009 Oct 4. Erratum in: Gynecol Oncol. 2010 Jun;117(3):510. Benbrook, Doris Mangiaracina [added]. PubMed PMID: 19804900; PubMed Central PMCID: PMC2783732. 12: Masamha CP, Benbrook DM. Cyclin D1 degradation is sufficient to induce G1 cell cycle arrest despite constitutive expression of cyclin E2 in ovarian cancer cells. Cancer Res. 2009 Aug 15;69(16):6565-72. doi: 10.1158/0008-5472.CAN-09-0913. Epub 2009 Jul 28. PubMed PMID: 19638577. 13: Liu T, Masamha CP, Chengedza S, Berlin KD, Lightfoot S, He F, Benbrook DM. Development of flexible-heteroarotinoids for kidney cancer. Mol Cancer Ther. 2009 May;8(5):1227-38. doi: 10.1158/1535-7163.MCT-08-1069. Epub 2009 May 5. PubMed PMID: 19417155; PubMed Central PMCID: PMC2888972. 14: Lin Y, Liu X, Yue P, Benbrook DM, Berlin KD, Khuri FR, Sun SY. Involvement of c-FLIP and survivin down-regulation in flexible heteroarotinoid-induced apoptosis and enhancement of TRAIL-initiated apoptosis in lung cancer cells. Mol Cancer Ther. 2008 Nov;7(11):3556-65. doi: 10.1158/1535-7163.MCT-08-0648. PubMed PMID: 19001438. 15: Liu Z, Zhang Y, Hua YF, Covey JM, Benbrook DM, Chan KK. Metabolism of a sulfur-containing heteroarotionoid antitumor agent, SHetA2, using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008 Nov;22(21):3371-81. doi: 10.1002/rcm.3744. PubMed PMID: 18837006. 16: Myers T, Chengedza S, Lightfoot S, Pan Y, Dedmond D, Cole L, Tang Y, Benbrook DM. Flexible heteroarotinoid (Flex-Het) SHetA2 inhibits angiogenesis in vitro and in vivo. Invest New Drugs. 2009 Aug;27(4):304-18. doi: 10.1007/s10637-008-9175-7. Epub 2008 Sep 18. PubMed PMID: 18802666; PubMed Central PMCID: PMC2701494. 17: Lin YD, Chen S, Yue P, Zou W, Benbrook DM, Liu S, Le TC, Berlin KD, Khuri FR, Sun SY. CAAT/enhancer binding protein homologous protein-dependent death receptor 5 induction is a major component of SHetA2-induced apoptosis in lung cancer cells. Cancer Res. 2008 Jul 1;68(13):5335-44. doi: 10.1158/0008-5472.CAN-07-6209. PubMed PMID: 18593935. 18: Benbrook DM, Lightfoot S, Ranger-Moore J, Liu T, Chengedza S, Berry WL, Dozmorov I. Gene expression analysis of biological systems driving an organotypic model of endometrial carcinogenesis and chemoprevention. Gene Regul Syst Bio. 2008;2:21-42. PubMed PMID: 19784388; PubMed Central PMCID: PMC2733085. 19: Le TC, Berlin KD, Benson SD, Eastman MA, Bell-Eunice G, Nelson AC, Benbrook DM. Heteroarotinoids with anti-cancer activity against ovarian cancer cells. Open Med Chem J. 2007 Oct 24;1:11-23. doi: 10.2174/1874104500701010011. PubMed PMID: 19662136; PubMed Central PMCID: PMC2709466. 20: Zhang Y, Hua Y, Benbrook DM, Covey JM, Dai G, Liu Z, Chan KK. High performance liquid chromatographic analysis and preclinical pharmacokinetics of the heteroarotinoid antitumor agent, SHetA2. Cancer Chemother Pharmacol. 2006 Nov;58(5):561-9. Epub 2006 Mar 14. PubMed PMID: 16534614.