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Se-Methylselenocysteine

Alias: Se-Methylselenocysteine Se-MSC MSeCSeMCys SeMSCSe MSC
Cat No.:V7418 Purity: ≥98%
Se-Methylselenocysteine, the precursor of methylselenium, has potent cancer chemopreventive and anti-oxidant effect.
Se-Methylselenocysteine
Se-Methylselenocysteine Chemical Structure CAS No.: 26046-90-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Se-Methylselenocysteine:

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Top Publications Citing lnvivochem Products
Product Description
Se-Methylselenocysteine, the precursor of methylselenium, has potent cancer chemopreventive and anti-oxidant effect. Se-Methylselenocysteine has oral bioactivity and can cause apoptosis.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In SKOV-33 cells, selenium (100–400 μM; 3 days) promotes inertness [1]. Cellular inertness mediated by caspase-3 is induced by 100–400 μM of selenium methyl ester for three days [1]. Examination [1]
ln Vivo
Nude mice given FaDu and A253 head and neck xenografts tumor activity have increased CDDP and cyclophosphamide resistance when treated with selenium selenium (0.2 mg/mouse; face; once daily for 14 days)[2]. For ten months, methyltyrosine (0.75 mg/kg body weight per day) was administered intraperitoneally (IT) to mice suffering from Alzheimer's disease (AD). Reduces oxidative intermediates, neural pathways, and levels of various metal ions. It also inhibits the expression of precursor protein APP and beta-enzyme (BACE1), which lowers the production of amyloid-beta peptide (Aβ), forms fragmented tau hyperphosphorylation, and forms neurofibrillary tangles by promoting protein phosphatase 2A (PP2A) activity (NFT). This protects synaptic proteins and neuronal activity, which in turn improves spatial learning and memory deficits in AD models [3].
Cell Assay
Apoptosis Analysis[1]
Cell Types: SKOV-3 Cell
Tested Concentrations: 100, 200, 400 μM
Incubation Duration: 3 days
Experimental Results: Resulted in a significant increase in the accumulation of Sub-G1 phase, which occurred in a SeMSC concentration and culture time dependence.

Western Blot Analysis[1]
Cell Types: SKOV-3 Cell
Tested Concentrations: 100, 200, 400 μM
Incubation Duration: 3 days
Experimental Results: Resulted in diminished expression of the 32 kDa form of procaspase-3.
Animal Protocol
Animal/Disease Models: Female athymic nude mice (bearing human A253 and FaDu squamous cell carcinoma xenografts) [ 2]
Doses: 0.2mg/only
Route of Administration: po; ]. one time/day for 14 days (7 days before and 7 days after cyclophosphamide or CDDP, 14 days total) Experimental Results:
References

[1]. Se-methylselenocysteine induces apoptosis through caspase activation and Bax cleavage mediated by calpain in SKOV-3 ovarian cancer cells. Cancer Lett. 2002 Aug 8;182(1):83-92.

[2]. 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.

[3]. Se-Methylselenocysteine Ameliorates Neuropathology and Cognitive Deficits by Attenuating Oxidative Stress and Metal Dyshomeostasis in Alzheimer Model Mice. Mol Nutr Food Res. 2018 Jun;62(12):e1800107.

Additional Infomation
Se-methyl-L-selenocysteine is an L-alpha-amino acid compound having methylselanylmethyl as the side-chain. It has a role as an antineoplastic agent. It is a Se-methylselenocysteine, a non-proteinogenic L-alpha-amino acid and a L-selenocysteine derivative. It is a conjugate base of a Se-methyl-L-selenocysteinium. It is a conjugate acid of a Se-methyl-L-selenocysteinate. It is an enantiomer of a Se-methyl-D-selenocysteine. It is a tautomer of a Se-methyl-L-selenocysteine zwitterion.
Methylselenocysteine has been used in trials studying the prevention of Prostate Carcinoma and No Evidence of Disease.
Se-Methylselenocysteine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Se-methylselenocysteine has been reported in Bos taurus, Astragalus bisulcatus, and Euglena gracilis with data available.
Methylselenocysteine is a naturally occurring organoselenium compound found in many plants, including garlic, onions, and broccoli, with potential antioxidant and chemopreventive activities. Se-Methyl-seleno-L-cysteine (MSC) is an amino acid analogue of cysteine in which a methylselenium moiety replaces the sulphur atom of cysteine. This agent acts as an antioxidant when incorporated into glutathione peroxidase and has been shown to exhibit potent chemopreventive activity in animal models.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H9NO2SE
Molecular Weight
182.081
Exact Mass
182.979
CAS #
26046-90-2
Related CAS #
Se-Methylselenocysteine hydrochloride;863394-07-4
PubChem CID
147004
Appearance
White to off-white solid powder
Boiling Point
314.1±37.0 °C at 760 mmHg
Melting Point
177 °C(dec.)
Flash Point
143.7±26.5 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
LogP
-0.89
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
8
Complexity
86.1
Defined Atom Stereocenter Count
1
SMILES
C[Se]C[C@@H](C(=O)O)N
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
Chemical Name
(2R)-2-amino-3-methylselanylpropanoic acid
Synonyms
Se-Methylselenocysteine Se-MSC MSeCSeMCys SeMSCSe MSC
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~83.33 mg/mL (~457.66 mM)
DMSO :< 1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 50 mg/mL (274.60 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.4921 mL 27.4605 mL 54.9209 mL
5 mM 1.0984 mL 5.4921 mL 10.9842 mL
10 mM 0.5492 mL 2.7460 mL 5.4921 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04952129 ACTIVE, NOT RECRUITING Drug: Selenomethionine
Drug: Methylselenocysteine
Colorectal Adenoma University of Auckland, New Zealand 2022-05-06 Phase 1
NCT00489372 COMPLETED Drug: Se-methyl-seleno-L-cysteine
Other: placebo
Other: pharmacological study
Other: laboratory biomarker analysis
Healthy, no Evidence of Disease National Cancer Institute (NCI) 2007-07 Phase 1
NCT01497431 COMPLETED Dietary Supplement: Selenium
Other: Placebo
Other: Laboratory Biomarker Analysis
No Evidence of Disease
Prostate Carcinoma
National Cancer Institute (NCI) 2011-11 Phase 1
NCT01611038 COMPLETED Dietary Supplement: Methylselenocysteine
Dietary Supplement: Placebo
Breast Cancer
Prostate Cancer
Rutgers, The State University of New Jersey 2011-10 Not Applicable
NCT00829205 WITHDRAWN Biological: filgrastim
Biological: rituximab
Dietary Supplement: Se-methyl-seleno-L-cysteine
Lymphoma Cancer Research UK 2009-01 Phase 1
Phase 2
Biological Data
  • Protective effects of MSC on CTX-induced rat bladder toxicity. Photomicrographs show rat bladder with untreated control, MSC alone, CTX alone, or CTX plus MSC. Cyclophosphamide was administered as a single i.v. injection at 150 mg kg−1 (toxic dose) and MSC at 0.75 mg per rat per day by p.o. daily for 14 days before CTX treatment. The bladders were removed at 4 and 24 h after CTX treatment. Conventional formalin-fixed paraffin-embedded sections were stained with haematoxylin and eosin. In order to see large parts of the bladder mucosa, (A, B, and E) are × 100; in order to see more histological details, (C, D, and F) are × 200. (A) Histologic picture of an untreated normal bladder with preserved histological features. (B) No change with MSC alone. Photomicrograph of rat bladder treated with CTX shows an acute mucosal oedema (arrow) at 2 h (C) that progressed to characteristic, severe haemorrhagic cystitis (arrows) at 24 h (D). Se-methylselenocysteine protected from CTX-induced acute mucosal oedema as seen on a long bladder segment with preserved normal histological structure.[2]. Cao S, et al. 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.
  • Se-methylselenocysteine (MSC) protects against myelotoxicity in bone marrow induced by oxaliplatin, histopathological study in Fischer rats. The rats were treated with oxaliplatin at the MTD (15 mg kg−1 i.v. × 1) with or without MSC at 0.75 mg per rat per day by p.o. daily for 21 days, with the first dose having started 14 days before oxaliplatin treatment. The sternums were removed on days 8 and 24 after oxaliplatin treatment and conventional formalin–paraffin sections of the bone marrow from sternum were decalcified and stained with haematoxylin and eosin. Representative photomicrographs of rat bone marrow are shown. All photographs were taken at × 200 magnification. (1) histomorphology of untreated normal bone marrow between bone trabeculae (B). The bone marrow (arrows) is infiltrated with fat .[2]. Cao S, et al. 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.
  • Antitumour activity of CDDP, oxaliplatin, and irinotecan alone and in combination with MSC in rats bearing advanced Ward colorectal carcinoma (A) and CTX and CDDP alone and in combination with MSC in nude mice bearing advanced human A253 and FaDu squamous cell carcinoma xenografts (B). (A) CDDP and oxaliplatin (OXAL) were administered by a single i.v. injection and irinotecan by weekly for 4 weeks. Se-methylselenocysteine at 0.75 mg per rat per day p.o. daily for 21 days, with the first dose having started 14 days before CDDP or oxaliplatin treatment. For irinotecan group (16 rats) , MSC was administered daily for 14 days before and during irinotecan treatment for a total of 35 days. All treatments were initiated 14 days after tumour transplantation when the tumours reached ∼2500–3000 mg. In the oxaliplatin-alone (10 mg kg−1) group, 12 rats were evaluated, and in all other treatment groups, 4 rats were used. (B) ○ Untreated control; ● MSC 0.2 mg per mouse per day × 14; ▴ CTX 100 mg kg−1 or CDDP 8 mg kg−1, i.v. × 1; ▪ CTX 100 mg kg−1 or CDDP 8 mg kg−1 (i.v. × 1) + MSC (0.2 mg per mouse per day × 14). The treatment of CTX and CDDP was initiated on day 0 (7 days after tumour transplantation when the tumours reached ∼200–220 mg) and MSC by p.o. 7 days before and 7 days after CTX or CDDP in a total of 14 days. The mice were humanely killed when tumours reached ∼2000 mg. The numbers in parenthesis indicate the number of rats that achieved CR over the total number of rats treated.[2]. Cao S, et al. 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.
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