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| Targets |
Glycocyamine-15N,13C2 has no direct pharmacological target as a stable isotope tracer. The unlabeled glycocyamine (guanidinoacetic acid) is a precursor of creatine, synthesized from arginine and glycine via L-arginine:glycine amidinotransferase (AGAT). Glycocyamine activates the Akt/mTOR/S6K signaling pathway through miR-133a-3p and miR-1a-3p, enhancing the expression of myogenic differentiation factors such as MyoD and MyoG. It serves as an effective regulator of energy metabolism and a promoter of myogenic differentiation by increasing muscle creatine concentration and maintaining ATP homeostasis.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
As a stable isotope tracer, Glycocyamine-15N,13C2 is not tested for classical in vitro pharmacological activity. In cell culture studies, it is used to trace glycocyamine metabolism and its conversion to creatine via guanidinoacetate N-methyltransferase (GAMT). The 13C and 15N labels enable precise LC-MS/MS quantification of labeled glycocyamine and its metabolites (creatine and creatinine) in cell lysates, providing insights into creatine biosynthesis and energy metabolism without interfering with normal cellular processes. |
| ln Vivo |
Glycocyamine-15N,13C2 has no independent in vivo pharmacological activity as a therapeutic agent. It is used in animal studies as a stable isotope tracer administered orally or intravenously to investigate creatine biosynthesis, energy homeostasis, and muscle metabolism. The 13C and 15N labels enable tracking of glycocyamine conversion to creatine and creatinine in plasma, muscle, and other tissues, providing information on metabolic flux through the creatine synthesis pathway. Glycocyamine itself is a dietary arginine replacement and supports energy homeostasis.
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| Enzyme Assay |
For in vitro tracer experiments, Glycocyamine-15N,13C2 is dissolved in an appropriate solvent (water, PBS, or cell culture medium) to prepare a stock solution (e.g., 1-10 mM). The tracer is added to cell culture media at a final concentration of 10-500 uM. Cells (e.g., myoblasts, myotubes, hepatocytes) are incubated for 1-72 hours. At each time point, cells are harvested, washed with PBS, and lysed in methanol:water (80:20) containing 0.1% formic acid. After protein precipitation by centrifugation (10,000-15,000 rpm, 10 minutes), the supernatant is analyzed by LC-MS/MS to quantify 13C,15N-labeled glycocyamine, creatine, and creatinine. The dual-labeling enables precise tracking of both carbon and nitrogen atoms through the creatine biosynthesis pathway.
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| Cell Assay |
For cell-based studies, cells (e.g., C2C12 mouse myoblasts, L6 rat myoblasts, primary skeletal muscle cells) are cultured in standard medium (DMEM with 10% FBS, 2 mM glutamine). For myogenic differentiation studies, cells are induced to differentiate by switching to medium containing 2% horse serum. During differentiation, cells are treated with Glycocyamine-15N,13C2 (10-500 uM). After 1-7 days, cells are harvested and lysed. The labeled internal standard is added to lysates at a fixed concentration for quantification of unlabeled metabolites. Following protein precipitation with methanol or acetonitrile and centrifugation, samples are analyzed by LC-MS/MS to quantify 13C,15N-labeled glycocyamine and creatine incorporation. Effects on myogenic differentiation factor expression (MyoD, MyoG) can also be measured by qPCR or Western blot. The dual-labeling enables metabolic flux analysis of creatine biosynthesis.
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| Animal Protocol |
For in vivo tracer studies, Glycocyamine-15N,13C2 is administered to rodents via intravenous injection (tail vein), intraperitoneal injection (50-200 mg/kg), or oral gavage (100-500 mg/kg). Blood samples are collected at multiple time points (0, 15, 30, 60, 120, 240 minutes, 8, 12, 24 hours). At terminal time points, tissues (muscle, liver, kidney, heart, brain) are harvested, snap-frozen in liquid nitrogen, and stored at -80degC. Tissues are homogenized in 0.1% formic acid in methanol or water, centrifuged, and analyzed by LC-MS/MS to quantify 13C,15N-labeled glycocyamine, creatine, and creatinine. For metabolic flux analysis, the rate of conversion of labeled glycocyamine to labeled creatine can be calculated by compartmental modeling of LC-MS/MS data. The 13C and 15N labels enable tracking of both carbon and nitrogen simultaneously.
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| ADME/Pharmacokinetics |
Glycocyamine-15N,13C2 is a stable isotope tracer and follows the same PK properties as unlabeled glycocyamine (guanidinoacetic acid). Glycocyamine is rapidly absorbed from the gastrointestinal tract (oral bioavailability in rodents estimated 30-50%), distributed to muscle and other tissues, and converted to creatine by GAMT (primarily in the liver). The plasma half-life of glycocyamine is approximately 30-60 minutes in rodents. Creatine formed from glycocyamine has a much longer half-life (∼3 hours plasma, days in muscle). The 13C and 15N labels enable precise quantification of these processes without altering pharmacokinetics.
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| Toxicity/Toxicokinetics |
Glycocyamine (guanidinoacetic acid) has low toxicity at nutritional doses. It is a naturally occurring metabolite and a precursor of creatine. The LD50 in rodents is >2,000 mg/kg. At very high doses (>500 mg/kg), glycocyamine may cause gastrointestinal disturbances or mild hepatotoxicity due to increased metabolic demand on methylation pathways (requires S-adenosylmethionine for conversion to creatine). The 13C and 15N-labeled version is chemically identical except for isotopic substitution and exhibits the same safety profile. Standard laboratory safety precautions for handling amino acid derivatives apply. Not intended for human consumption.
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| References |
[1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216.
[2]. Dilger RN, et al. Dietary guanidino acetic acid is an efficacious replacement for arginine for young chicks. Poult Sci. 2013 Jan;92(1):171-7. |
| Additional Infomation |
Glycocyamine-15N,13C2 is not a drug but a stable isotope-labeled research tracer. It has no approved therapeutic status, no clinical trial history as a therapeutic agent, and is not intended for human consumption. This compound is used for research applications including metabolic tracer studies to investigate creatine biosynthesis and energy homeostasis, as an internal standard for LC-MS or GC-MS quantification of glycocyamine, creatine, and creatinine in biological samples, studies of myogenic differentiation and muscle metabolism, and research on creatine deficiency syndromes (e.g., AGAT deficiency, GAMT deficiency, creatine transporter deficiency). Glycocyamine-15N,13C2 is also used in poultry science research as a feed additive tracer for studying glycocyamine as a replacement for dietary arginine. Available with ≥98% purity and high isotopic enrichment (≥99 atom% 13C, ≥98 atom% 15N).
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| Molecular Formula |
C3H7N3O2
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| Molecular Weight |
120.085298776627
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| Exact Mass |
120.057
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| CAS # |
2483829-93-0
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| Related CAS # |
Glycocyamine;352-97-6
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| PubChem CID |
168007042
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| Appearance |
White to off-white solid powder
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| LogP |
-1.6
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
8
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| Complexity |
116
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[13CH2]([13C](=O)O)[15N]=C(N)N
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| InChi Key |
BPMFZUMJYQTVII-LQAOFMTQSA-N
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| InChi Code |
InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)/i1+1,2+1,6+1
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| Chemical Name |
2-(diaminomethylideneamino)acetic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.3271 mL | 41.6354 mL | 83.2709 mL | |
| 5 mM | 1.6654 mL | 8.3271 mL | 16.6542 mL | |
| 10 mM | 0.8327 mL | 4.1635 mL | 8.3271 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.
Calculation results
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.
(2) Be sure to add the solvent(s) in order.
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