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MedKoo Cat#: 527712 | Name: Se-Methylselenocysteine
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Description:

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

Se-Methylselenocysteine, also known as MSeC and SeMCys, is a drug potentially for the treatment of solid tumours. Se-methylselenocysteine offers selective protection against organ-specific toxicity induced by clinically active agents and enhances further antitumour activity, resulting in improved therapeutic index. Se-methylselenocysteine exerts pro-apoptosis effects through increasing Cx43 expression, which in turn down-regulates Bcl-2 and up-regulates bad expression.

Chemical Structure

Se-Methylselenocysteine
Se-Methylselenocysteine
CAS#26046-90-2

Theoretical Analysis

MedKoo Cat#: 527712

Name: Se-Methylselenocysteine

CAS#: 26046-90-2

Chemical Formula: C4H9NO2Se

Exact Mass: 182.9799

Molecular Weight: 182.08

Elemental Analysis: C, 26.39; H, 4.98; N, 7.69; O, 17.57; Se, 43.37

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 650.00 2 Weeks
1g USD 1,250.00 2 Weeks
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Synonym
Se-Methylselenocysteine; MSeC; Se-MSC; SeMCys; Se MSC; SeMSC;
IUPAC/Chemical Name
(R)-2-amino-3-(methylselanyl)propanoic acid
InChi Key
XDSSPSLGNGIIHP-VKHMYHEASA-N
InChi Code
InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
SMILES Code
N[C@@H](C[Se]C)C(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 water
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Se-methylselenocysteine prevents tert-butyl hydroperoxide-induced increases in malondialdehyde (MDA) levels and glutathione reductase and glutathione peroxidase (GPX) activity, as well as decreases in glutathione (GSH) levels, in HepG2 cells. It also has an additive effect on irinotecan-induced tumor growth reduction in a FaDu mouse xenograft model.
In vitro activity:
This study investigated the cytotoxic effects of Se-methylselenocysteine in vitro. There were no signs of general toxicity of Se-methylselenocysteine-polyglycerol dendrimer (SeMeCys-DPGLy) against CHO-K1 cells detectable when cell viability was greater than 98%. Additionally, SeMeCys-DPGLy reduced head and neck squamous cell carcinoma cell viability and proliferation at higher doses and long incubation times. Reference: J Biomater Sci Polym Ed. 2022 Apr;33(5):651-667. https://pubmed.ncbi.nlm.nih.gov/34809530/
In vivo activity:
This study determined that Se-methylselenocysteine improved cognitive deficits by attenuating synaptic and metabolic abnormalities associated with Alzheimer’s disease in mice. There were differentially expressed proteins related to metabolism, synapses, and antioxidant proteins in diseased mice compared to wild type. Se-Methylselenocysteine treatment reversed 138 proteins in the diseased group, suggesting its influence on key factors in Alzheimer's disease pathology. Reference: ACS Chem Neurosci. 2021 Apr 7;12(7):1112-1132. https://pubmed.ncbi.nlm.nih.gov/33689275/
Solvent mg/mL mM
Solubility
Water 83.3 457.66
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 182.08 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:
1. Gonçalves Correa ND, Silva FD, Vieira DP, Soares CRJ, de Queiroz AAA. In vitro cytotoxic data on Se-methylselenocysteine conjugated to dendritic poly(glycerol) against human squamous carcinoma cells. J Biomater Sci Polym Ed. 2022 Apr;33(5):651-667. doi: 10.1080/09205063.2021.2008788. Epub 2021 Dec 19. PMID: 34809530. 2. Selvam AK, Jawad R, Gramignoli R, Achour A, Salter H, Björnstedt M. A Novel mRNA-Mediated and MicroRNA-Guided Approach to Specifically Eradicate Drug-Resistant Hepatocellular Carcinoma Cell Lines by Se-Methylselenocysteine. Antioxidants (Basel). 2021 Jul 7;10(7):1094. doi: 10.3390/antiox10071094. PMID: 34356326; PMCID: PMC8301172. 3. Ma J, Huang J, Sun J, Zhou Y, Ji X, Guo D, Liu C, Li J, Zhang J, Song H. L-Se-methylselenocysteine sensitizes lung carcinoma to chemotherapy. Cell Prolif. 2021 May;54(5):e13038. doi: 10.1111/cpr.13038. Epub 2021 Apr 1. PMID: 33793020; PMCID: PMC8088472. 4. Du X, Shi Q, Zhao Y, Xie Y, Li X, Liu Q, Iqbal J, Zhang H, Liu X, Shen L. Se-Methylselenocysteine (SMC) Improves Cognitive Deficits by Attenuating Synaptic and Metabolic Abnormalities in Alzheimer's Mice Model: A Proteomic Study. ACS Chem Neurosci. 2021 Apr 7;12(7):1112-1132. doi: 10.1021/acschemneuro.0c00549. Epub 2021 Mar 9. PMID: 33689275.
In vitro protocol:
1. Gonçalves Correa ND, Silva FD, Vieira DP, Soares CRJ, de Queiroz AAA. In vitro cytotoxic data on Se-methylselenocysteine conjugated to dendritic poly(glycerol) against human squamous carcinoma cells. J Biomater Sci Polym Ed. 2022 Apr;33(5):651-667. doi: 10.1080/09205063.2021.2008788. Epub 2021 Dec 19. PMID: 34809530. 2. Selvam AK, Jawad R, Gramignoli R, Achour A, Salter H, Björnstedt M. A Novel mRNA-Mediated and MicroRNA-Guided Approach to Specifically Eradicate Drug-Resistant Hepatocellular Carcinoma Cell Lines by Se-Methylselenocysteine. Antioxidants (Basel). 2021 Jul 7;10(7):1094. doi: 10.3390/antiox10071094. PMID: 34356326; PMCID: PMC8301172.
In vivo protocol:
1. Ma J, Huang J, Sun J, Zhou Y, Ji X, Guo D, Liu C, Li J, Zhang J, Song H. L-Se-methylselenocysteine sensitizes lung carcinoma to chemotherapy. Cell Prolif. 2021 May;54(5):e13038. doi: 10.1111/cpr.13038. Epub 2021 Apr 1. PMID: 33793020; PMCID: PMC8088472. 2. Du X, Shi Q, Zhao Y, Xie Y, Li X, Liu Q, Iqbal J, Zhang H, Liu X, Shen L. Se-Methylselenocysteine (SMC) Improves Cognitive Deficits by Attenuating Synaptic and Metabolic Abnormalities in Alzheimer's Mice Model: A Proteomic Study. ACS Chem Neurosci. 2021 Apr 7;12(7):1112-1132. doi: 10.1021/acschemneuro.0c00549. Epub 2021 Mar 9. PMID: 33689275.
1: Yao Z, Zhang Y, Li H, Deng Z, Zhang X. Synergistic effect of Se-methylselenocysteine and vitamin E in ameliorating the acute ethanol-induced oxidative damage in rat. J Trace Elem Med Biol. 2015 Jan;29:182-7. doi: 10.1016/j.jtemb.2014.08.004. PubMed PMID: 25213679. 2: Yang H, Jia X. Safety evaluation of Se-methylselenocysteine as nutritional selenium supplement: acute toxicity, genotoxicity and subchronic toxicity. Regul Toxicol Pharmacol. 2014 Dec;70(3):720-7. doi: 10.1016/j.yrtph.2014.10.014. PubMed PMID: 25444999. 3: Avila FW, Yang Y, Faquin V, Ramos SJ, Guilherme LR, Thannhauser TW, Li L. Impact of selenium supply on Se-methylselenocysteine and glucosinolate accumulation in selenium-biofortified Brassica sprouts. Food Chem. 2014 Dec 15;165:578-86. doi: 10.1016/j.foodchem.2014.05.134. PubMed PMID: 25038715. 4: Cao S, Durrani FA, Tóth K, Rustum YM. Se-methylselenocysteine offers selective protection against toxicity and potentiates the antitumour activity of anticancer drugs in preclinical animal models. Br J Cancer. 2014 Apr 2;110(7):1733-43. doi: 10.1038/bjc.2014.85. PubMed PMID: 24619073; PubMed Central PMCID: PMC3974093. 5: Sánchez-Martínez M, Pérez-Corona T, Martínez-Villaluenga C, Frías J, Peñas E, Porres JM, Urbano G, Cámara C, Madrid Y. Synthesis of [(77)Se]-methylselenocysteine when preparing sauerkraut in the presence of [(77)Se]-selenite. Metabolic transformation of [ (77)Se]-methylselenocysteine in Wistar rats determined by LC-IDA-ICP-MS. Anal Bioanal Chem. 2014 Dec;406(30):7949-58. doi: 10.1007/s00216-014-8224-7. PubMed PMID: 25311192. 6: Davis TZ, Stegelmeier BL, Green BT, Welch KD, Hall JO. Evaluation of the respiratory elimination kinetics of selenate and Se-methylselenocysteine after oral administration in lambs. Res Vet Sci. 2013 Dec;95(3):1163-8. doi: 10.1016/j.rvsc.2013.09.015. PubMed PMID: 24210249. 7: Huang G, Yong BC, Xu MH, Li JC, Guo HH, Shen JN. Analysis of Selenium Levels in Osteosarcoma Patients and the Effects of Se-Methylselenocysteine on Osteosarcoma Cells In Vitro. Nutr Cancer. 2015;67(5):847-56. doi: 10.1080/01635581.2015.1042548. PubMed PMID: 26121331. 8: Wang C, Zeng Z, Liu Q, Zhang R, Ni J. Se-methylselenocysteine inhibits apoptosis induced by clusterin knockdown in neuroblastoma N2a and SH-SY5Y cell lines. Int J Mol Sci. 2014 Nov 18;15(11):21331-47. doi: 10.3390/ijms151121331. PubMed PMID: 25411798; PubMed Central PMCID: PMC4264228. 9: Lu Z, Qi L, Li GX, Bo XJ, Liu GD, Wang JM. Se-methylselenocysteine suppresses the growth of prostate cancer cell DU145 through connexin 43-induced apoptosis. J Cancer Res Ther. 2015 Oct-Dec;11(4):840-5. doi: 10.4103/0973-1482.139265. PubMed PMID: 26881528. 10: Coyne CP, Jones T, Bear R. Simultaneous Dual Selective Targeted Delivery of Two Covalent Gemcitabine Immunochemotherapeutics and Complementary Anti-Neoplastic Potency of [Se]-Methylselenocysteine. J Cancer Ther. 2015 Jan;6(1):62-89. PubMed PMID: 25821636; PubMed Central PMCID: PMC4376018. 11: Ávila FW, Faquin V, Yang Y, Ramos SJ, Guilherme LR, Thannhauser TW, Li L. Assessment of the anticancer compounds Se-methylselenocysteine and glucosinolates in Se-biofortified broccoli (Brassica oleracea L. var. italica) sprouts and florets. J Agric Food Chem. 2013 Jul 3;61(26):6216-23. doi: 10.1021/jf4016834. PubMed PMID: 23763668. 12: Shin HS, Yang WJ, Choi EM. The preventive effect of Se-methylselenocysteine on γ-radiation-induced oxidative stress in rat lungs. J Trace Elem Med Biol. 2013 Apr;27(2):154-9. doi: 10.1016/j.jtemb.2012.09.003. PubMed PMID: 23176811. 13: Chintala S, Tóth K, Cao S, Durrani FA, Vaughan MM, Jensen RL, Rustum YM. Se-methylselenocysteine sensitizes hypoxic tumor cells to irinotecan by targeting hypoxia-inducible factor 1alpha. Cancer Chemother Pharmacol. 2010 Oct;66(5):899-911. doi: 10.1007/s00280-009-1238-8. PubMed PMID: 20066420; PubMed Central PMCID: PMC2916970. 14: Lee JT, Lee TJ, Park JW, Kwon TK. Se-methylselenocysteine sensitized TRAIL-mediated apoptosis via down-regulation of Bcl-2 expression. Int J Oncol. 2009 May;34(5):1455-60. PubMed PMID: 19360359. 15: Tsuji Y, Suzuki N, T Suzuki K, Ogra Y. Selenium metabolism in rats with long-term ingestion of Se-methylselenocysteine using enriched stable isotopes. J Toxicol Sci. 2009 Apr;34(2):191-200. PubMed PMID: 19336976. 16: Suzuki KT, Tsuji Y, Ohta Y, Suzuki N. Preferential organ distribution of methylselenol source Se-methylselenocysteine relative to methylseleninic acid. Toxicol Appl Pharmacol. 2008 Feb 15;227(1):76-83. PubMed PMID: 18035386. 17: Zhang J, Wang X, Xu T. Elemental selenium at nano size (Nano-Se) as a potential chemopreventive agent with reduced risk of selenium toxicity: comparison with se-methylselenocysteine in mice. Toxicol Sci. 2008 Jan;101(1):22-31. PubMed PMID: 17728283. 18: Hurst R, Elliott RM, Goldson AJ, Fairweather-Tait SJ. Se-methylselenocysteine alters collagen gene and protein expression in human prostate cells. Cancer Lett. 2008 Sep 28;269(1):117-26. doi: 10.1016/j.canlet.2008.04.025. PubMed PMID: 18514395. 19: Johnson WD, Morrissey RL, Kapetanovic I, Crowell JA, McCormick DL. Subchronic oral toxicity studies of Se-methylselenocysteine, an organoselenium compound for breast cancer prevention. Food Chem Toxicol. 2008 Mar;46(3):1068-78. PubMed PMID: 18082924; PubMed Central PMCID: PMC2279231. 20: Wang J, Jiao NL, Zheng J. [Effects of Se-methylselenocysteine on biological behavior of and matrix metalloproteinase-2 expression in human breast cancer MDA-MB-231 cells]. Ai Zheng. 2008 Feb;27(2):119-25. Chinese. PubMed PMID: 18279606.