Canavanine sulfate
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MedKoo CAT#: 573631

CAS#: 2219-31-0

Description: Canavanine sulfate is a biochemical with antimutagenic activity. This product has been shown to potentiate the cytotoxicity of doxorubicin and cisplatin in arginine deprived human cancer cells


Chemical Structure

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Canavanine sulfate
CAS# 2219-31-0

Theoretical Analysis

MedKoo Cat#: 573631
Name: Canavanine sulfate
CAS#: 2219-31-0
Chemical Formula: C5H14N4O7S
Exact Mass: 274.0583
Molecular Weight: 274.25
Elemental Analysis: C, 21.90; H, 5.15; N, 20.43; O, 40.84; S, 11.69

Price and Availability

Size Price Availability Quantity
100.0mg USD 225.0 2 Weeks
250.0mg USD 345.0 2 Weeks
1.0g USD 645.0 2 Weeks
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Synonym: AI3-52581, Canavanine sulfate, L-Canavanine sulfate

IUPAC/Chemical Name: L-Homoserine, O-((aminoiminomethyl)amino)-, sulfate (1:1)

InChi Key: MVIPJKVMOKFIEV-DFWYDOINSA-N

InChi Code: 1S/C5H12N4O3.H2O4S/c6-3(4(10)11)1-2-12-9-5(7)8;1-5(2,3)4/h3H,1-2,6H2,(H,10,11)(H4,7,8,9);(H2,1,2,3,4)/t3-;/m0./s1

SMILES Code: N[C@@H](CCONC(=N)N)C(=O)O.OS(=O)(=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: >3 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

Product Data:

Biological target: L-Canavanine sulfate is a selective inhibitor of inducible NO synthase.
In vitro activity: L-Canavanine sulfate (L-CAV) causes only a limited degree of cytotoxicity in HeLa, Hep G2, and SK-HEP-1 cells when given alone in arginine-rich media with IC50 values ranging from 5 to 10 mM. In HaCaT keratinocyte cell line, IC50 of L-Canavanine sulfate exceeds the concentration of 10 mM, indicating low cytotoxicity in normal cells in vitro. In arginine-free media, IC50 of L-Canavanine sulfate in HeLa, Hep G2, and SK-HEP-1 cells are 0.21±0.04; 0.64±0.16; and 1.18±0.14 mM, respectively. L-Canavanine sulfate, which is hardly toxic alone, potentiates the cytotoxicity of vinblastine (VIN) and paclitaxel (PTX) in HeLa and hepatocellular carcinoma cells. Reference: Phytomedicine. 2015 Dec 15;22(14):1232-7. https://linkinghub.elsevier.com/retrieve/pii/S0944-7113(15)00319-0
In vivo activity: In order to determine if this effect also obtains at more moderate dietary protein concentrations, 30 female BALB/c mice were fed a basal diet with 14% protein (15.7% dry matter basis) and another 30 were fed the same diet plus 1% canavanine. Neither mean (Control 873.2 d, Canavanine 870.0 d; SEM = 34.2 d; P = 0.949 from ANOVA) nor median (Control 902 d, Canavanine 884.5 d; P = 0.9058 from Mann-Whitney) lifespans differed between groups.Although mean antinuclear antibody (ANA) titers did not differ between control and canavanine-treated mice at 833 days of age (19.84 vs 20.39 respectively; SEM = 2.64; P = 0.889 from ANOVA), one canavanine-treated mouse displayed an outlying ANA value of 50 (next lower value = 30) denoting possible early sign of incipient autoimmune disease in that individual. There may be an interaction between dietary protein level and canavanine with respect to lifespan in mice. Reference: Nutr Metab (Lond). 2005 Feb 25;2(1):7. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/15733319/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 182.31

Preparing Stock Solutions

The following data is based on the product molecular weight 274.25 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
In vitro protocol: 1. Nurcahyanti AD, Wink M. Cytotoxic potentiation of vinblastine and paclitaxel by L-canavanine in human cervical cancer and hepatocellular carcinoma cells. Phytomedicine. 2015 Dec 15;22(14):1232-7. doi: 10.1016/j.phymed.2015.10.007. Epub 2015 Oct 30. PMID: 26655405.
In vivo protocol: 1. Brown DL. Canavanine-induced longevity in mice may require diets with greater than 15.7% protein. Nutr Metab (Lond). 2005 Feb 25;2(1):7. doi: 10.1186/1743-7075-2-7. PMID: 15733319; PMCID: PMC554090. 2. Teale DM, Atkinson AM. L-canavanine restores blood pressure in a rat model of endotoxic shock. Eur J Pharmacol. 1994 Dec 12;271(1):87-92. doi: 10.1016/0014-2999(94)90268-2. PMID: 7535234.

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1: Ntuli SSBN, Gelderblom WCA, Katerere DR. The mutagenic and antimutagenic activity of Sutherlandia frutescens extracts and marker compounds. BMC Complement Altern Med. 2018 Mar 15;18(1):93. doi: 10.1186/s12906-018-2159-z. PubMed PMID: 29544492; PubMed Central PMCID: PMC5856389.

2: Krasuska U, Andrzejczak O, Staszek P, Bogatek R, Gniazdowska A. Canavanine Alters ROS/RNS Level and Leads to Post-translational Modification of Proteins in Roots of Tomato Seedlings. Front Plant Sci. 2016 Jun 14;7:840. doi: 10.3389/fpls.2016.00840. eCollection 2016. PubMed PMID: 27379131; PubMed Central PMCID: PMC4905978.

3: Nurcahyanti AD, Wink M. L-Canavanine potentiates the cytotoxicity of doxorubicin and cisplatin in arginine deprived human cancer cells. PeerJ. 2016 Jan 7;4:e1542. doi: 10.7717/peerj.1542. eCollection 2016. PubMed PMID: 26839743; PubMed Central PMCID: PMC4734457.

4: Nurcahyanti AD, Wink M. Cytotoxic potentiation of vinblastine and paclitaxel by L-canavanine in human cervical cancer and hepatocellular carcinoma cells. Phytomedicine. 2015 Dec 15;22(14):1232-7. doi: 10.1016/j.phymed.2015.10.007. Epub 2015 Oct 30. PubMed PMID: 26655405.