S-Adenosyl-L-homocysteine is an organosulfur compound, an S-adenosyl derivative of L-homocysteine. It has multiple functions, including acting as a cofactor, an inhibitor of EC 2.1.1.79 (cyclopropane-fatty acyl-phospholipid synthase), an inhibitor of EC 2.1.1.72 [site-specific DNA methyltransferase (adenine-specific)], a basic metabolite, and an epitope. It belongs to the adenosine class, organosulfur class, homocysteine derivative class, and homocysteine class. It is the conjugate acid of S-adenosyl-L-homocysteine and also the zwitterion tautomer of S-adenosyl-L-homocysteine. 5'-S-(3-amino-3-carboxypropyl)-5'-thioadenosine is generated from S-adenosylmethionine via transmethylation. S-adenosylhomocysteine is a metabolite present in or produced by Escherichia coli (K12 strain, MG1655 strain).
S-Adenosyl-L-homocysteine has been reported to exist in Daphnia frenulum, Drosophila melanogaster, and other organisms with relevant data.
S-Adenosylhomocysteine is an amino acid derivative and an intermediate in the synthesis of cysteine and adenosine. S-Adenosylhomocysteine (SAH) is formed after S-adenosylmethionine (SAM)-dependent methylation (homocysteine-methionine cycle) in biomolecules such as DNA, RNA, and proteins. Subsequently, it is hydrolyzed by S-adenosylhomocysteine hydrolases to produce adenosine and homocysteine. Because SAH regulates the methylation-dependent reaction, SAH levels and the SAH/SAM ratio can be used to assess the methylation status of macromolecules.
S-Adenosylhomocysteine (AdoHcy) is a direct precursor to all homocysteine in the body. This reaction is catalyzed by S-adenosylhomocysteine hydrolases and is reversible, with the equilibrium favoring the formation of AdoHcy. In vivo, the action of adenosine deaminase drives the reaction toward homocysteine production. This enzyme converts adenosine, the second product of the S-adenosine homocysteine hydrolase reaction, into inosine. Except for the methyl transfer of betaine and methylcobalamin in the methionine synthase reaction, all methylation reactions using S-adenosine methionine (AdoMet) as a methyl donor produce AdoHcy. Methylation plays a crucial role in the epigenetic regulation of protein expression through DNA and histone methylation. The inhibition of these AdoMet-mediated processes by AdoHcy has been shown to be a mechanism of metabolic alteration. Because the conversion of AdoHcy to homocysteine is reversible and the equilibrium favors AdoHcy production, elevated plasma homocysteine levels are usually accompanied by elevated AdoHcy levels. Many neurodegenerative diseases, such as dementia, depression, or Parkinson's disease, have reported transmethylation pathway disorders characterized by abnormalities in S-adenosine methionine, S-adenosine homocysteine, or their ratios. (A3511, A3512). 5'-S-(3-amino-3-carboxypropyl)-5'-thioadenosine. Formed by transmethylation of S-adenosylmethionine.

C14H20N6O5S

384.41

384.121

979-92-0

439155

White to off-white solid powder

1.9±0.1 g/cm3

787.5±70.0 °C at 760 mmHg

209 - 211 °C

430.0±35.7 °C

0.0±2.9 mmHg at 25°C

1.839

0.15

5

11

7

26

504

5

O[C@@H]1[C@H](O)[C@@H](CSCC[C@H](N)C(=O)O)O[C@H]1N1C=NC2C(=NC=NC1=2)N

ZJUKTBDSGOFHSH-WFMPWKQPSA-N

InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1

(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]butanoic acid

S-Adenosylhomocysteine; S-Adenosyl-L-homocysteine

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

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

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.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*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).

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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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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).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)