Canavanine sulfate | CAS# 2219-31-0 | Antimutagenic

MedKoo Cat#: 573631 | Name: Canavanine sulfate

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Description:

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

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

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
100mg	USD 250.00	2 Weeks
250mg	USD 450.00	2 Weeks
1g	USD 950.00	2 Weeks

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Related CAS #

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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

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Product Data

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	182.31

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 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.

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:

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.

1: Calabretta LO, Thomas VM, Raines RT. Canavanine versus arginine: Prospects for cell-penetrating peptides. Tetrahedron Lett. 2022 Jun 8;99:153848. doi: 10.1016/j.tetlet.2022.153848. Epub 2022 May 6. PMID: 35873104; PMCID: PMC9302579. 2: Michelangeli C, Vargas RE. L-canavanine influences feed intake, plasma basic amino acid concentrations and kidney arginase activity in chicks. J Nutr. 1994 Jul;124(7):1081-7. doi: 10.1093/jn/124.7.1081. PMID: 8027859. 3: Redman CM, Avellino G, Yu S. Secretion of proalbumin by canavanine-treated Hep-G2 cells. J Biol Chem. 1983 Mar 25;258(6):3446-52. PMID: 6300044. 4: Rosenthal GA, Dahlman DL, Robinson GW. L-Arginine kinase from tobacco hornworm, Manduca sexta (L.). Purification, properties, and interaction with L-canavanine. J Biol Chem. 1977 Jun 10;252(11):3679-83. PMID: 193843. 5: Melangeli C, Rosenthal GA, Dalman DL. The biochemical basis for L-canavanine tolerance by the tobacco budworm Heliothis virescens (Noctuidae). Proc Natl Acad Sci U S A. 1997 Mar 18;94(6):2255-60. doi: 10.1073/pnas.94.6.2255. PMID: 9122181; PMCID: PMC20074. 6: Lee Y, Jun BO, Kim SG, Kwon YM. Purification of ornithine carbamoyltransferase from kidney bean (Phaseolus vulgaris L.) leaves and comparison of the properties of the enzyme from canavanine-containing and -deficient plants. Planta. 1998 Jul;205(3):375-9. doi: 10.1007/s004250050333. PMID: 9640663. 7: Hoshina H, Hortin G, Boime I. Rat pro-opiomelanocortin contains sulfate. Science. 1982 Jul 2;217(4554):63-4. doi: 10.1126/science.6283633. PMID: 6283633. 8: Redman CM, Avellino G. Effects of canavanine on the secretion of plasma proteins by Hep G2 cells. Biochim Biophys Acta. 1985 Nov 20;847(2):198-206. doi: 10.1016/0167-4889(85)90021-7. PMID: 2998480. 9: Malinow MR, Bardana EJ Jr, Pirofsky B, Craig S, McLaughlin P. Systemic lupus erythematosus-like syndrome in monkeys fed alfalfa sprouts: role of a nonprotein amino acid. Science. 1982 Apr 23;216(4544):415-7. doi: 10.1126/science.7071589. PMID: 7071589. 10: Cao Y, Xia R, Chen X, Sun L, Tang X. Breeding and characterization of amino acid-analogue-resistant mutants of Arthrospira platensis. World J Microbiol Biotechnol. 2014 Feb;30(2):423-8. doi: 10.1007/s11274-013-1459-1. Epub 2013 Aug 24. PMID: 23975694. 11: Bolin RW, Cummings DJ. Structural aberrations in T-even bacteriophage. V. Effects of canavanine on the maturation and utilization of specific gene products. J Virol. 1974 Jun;13(6):1378-91. doi: 10.1128/JVI.13.6.1378-1391.1974. PMID: 4833614; PMCID: PMC355458. 12: Soczewka P, Kolakowski D, Smaczynska-de Rooij I, Rzepnikowska W, Ayscough KR, Kaminska J, Zoladek T. Yeast-model-based study identified myosin- and calcium-dependent calmodulin signalling as a potential target for drug intervention in chorea-acanthocytosis. Dis Model Mech. 2019 Jan 28;12(1):dmm036830. doi: 10.1242/dmm.036830. PMID: 30635263; PMCID: PMC6361151. 13: Patil MD, Rathod VP, Bihade UR, Banerjee UC. Purification and characterization of arginine deiminase from Pseudomonas putida: Structural insights of the differential affinities of l-arginine analogues. J Biosci Bioeng. 2019 Feb;127(2):129-137. doi: 10.1016/j.jbiosc.2018.07.021. Epub 2018 Aug 22. PMID: 30143336. 14: Prouty WF, Karnovsky MJ, Goldberg AL. Degradation of abnormal proteins in Escherichia coli. Formation of protein inclusions in cells exposed to amino acid analogs. J Biol Chem. 1975 Feb 10;250(3):1112-22. PMID: 1089651. 15: Schultz JR, Clarke CF. Characterization of Saccharomyces cerevisiae ubiquinone-deficient mutants. Biofactors. 1999;9(2-4):121-9. doi: 10.1002/biof.5520090206. PMID: 10416023. 16: Crine P, Lemieux E. Incorporation of canavanine into rat pars intermedia proteins inhibits the maturation of pro-opiomelanocortin, the common precursor to adrenocorticotropin and beta-lipotropin. J Biol Chem. 1982 Jan 25;257(2):832-8. PMID: 6274867. 17: Drillien R, Lacroute F. Ureidosuccinic acid uptake in yeast and some aspects of its regulation. J Bacteriol. 1972 Jan;109(1):203-8. doi: 10.1128/jb.109.1.203-208.1972. PMID: 4550662; PMCID: PMC247268. 18: Müller AC, Patnala S, Kis O, Bendayan R, Kanfer I. Interactions between phytochemical components of Sutherlandia frutescens and the antiretroviral, atazanavir in vitro: implications for absorption and metabolism. J Pharm Pharm Sci. 2012;15(2):221-33. doi: 10.18433/j3ns3x. PMID: 22579002. 19: Berüter J, Colombo JP, Bachmann C. Purification and properties of arginase from human liver and erythrocytes. Biochem J. 1978 Nov 1;175(2):449-54. doi: 10.1042/bj1750449. PMID: 743206; PMCID: PMC1186090. 20: Zahner H, Schmidtchen D, Mutasa JA. Ivermectin-induced killing of microfilariae in vitro by neutrophils mediated by NO. Exp Parasitol. 1997 Jun;86(2):110-7. doi: 10.1006/expr.1997.4160. PMID: 9207741.