MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 597348 | Name: Homoarginine
Featured

Description:

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

Homoarginine is an amino acid.

Chemical Structure

Homoarginine
Homoarginine
CAS#156-86-5

Theoretical Analysis

MedKoo Cat#: 597348

Name: Homoarginine

CAS#: 156-86-5

Chemical Formula: C7H16N4O2

Exact Mass: 188.1273

Molecular Weight: 188.23

Elemental Analysis: C, 44.67; H, 8.57; N, 29.77; O, 17.00

Price and Availability

Size Price Availability Quantity
5g USD 300.00 2 Weeks
25g USD 750.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Homoarginine; L-Homoarginine; NSC-27429; NSC27429; NSC 27429;
IUPAC/Chemical Name
N6-carbamimidoyl-L-lysine
InChi Key
QUOGESRFPZDMMT-YFKPBYRVSA-N
InChi Code
InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1
SMILES Code
N[C@@H](CCCCNC(N)=N)C(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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
H-HoArg-OH is a strong inhibitor of human bone and liver alkaline phosphatase.
In vitro activity:
TBD
In vivo activity:
Pathology confirmed the reduction of LV weight after HA (homoarginine) intake by showing a significant decrease in cardiomyocyte cross-sectional area in treated 5/6 Nx (nephrectomy) animals (Table S2, Figure 3). Myocytes from 5/6 Nx animals treated with 400 mg·kg−1·day−1 HA (233 ± 4 μm2) were approximately 12% smaller than myocytes from placebo 5/6 Nx rats (263 ± 4 μm2, P < 0.0001). Sirius red staining revealed a 32% decline in interstitial fibrosis (Table S3, Figure 4) after drug treatment (3.6 ± 0.2%) in comparison to untreated 5/6 Nx controls (5.3 ± 0.5%, P = 0.0041). Hematoxylin and eosin staining showed histological changes in the renal cortex of animals from the 5/6 Nx group in comparison to the unaltered structure in the kidneys of the control group, regardless of HA treatment (Figure 6). Histologic examination of remaining kidneys after 5/6 resection showed minimal segmental glomerular sclerosis and hypertrophy of remnant glomeruli, mesangial matrix accumulation, capillary occlusion, hyalinization, and protein casts in the tubules, similar to previously reported studies. Reference: J Cardiovasc Pharmacol Ther. 2022 Jan-Dec;27:10742484211054620. https://pubmed.ncbi.nlm.nih.gov/34994208/
Solvent mg/mL mM
Solubility
Water 100.0 531.26
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 188.23 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
Formulation protocol:
1. Koch V, Weber C, Riffel JH, Buchner K, Buss SJ, Hein S, Mereles D, Hagenmueller M, Erbel C, März W, Booz C, Albrecht MH, Vogl TJ, Frey N, Hardt SE, Ochs M. Impact of Homoarginine on Myocardial Function and Remodeling in a Rat Model of Chronic Renal Failure. J Cardiovasc Pharmacol Ther. 2022 Jan-Dec;27:10742484211054620. doi: 10.1177/10742484211054620. PMID: 34994208. 2. Wetzel MD, Stanley K, Maity S, Madesh M, Bopassa JC, Awad AS. Homoarginine ameliorates diabetic nephropathy independent of nitric oxide synthase-3. Physiol Rep. 2021 Mar;9(5):e14766. doi: 10.14814/phy2.14766. PMID: 33713581; PMCID: PMC7955794.
In vitro protocol:
TBD
In vivo protocol:
1. Koch V, Weber C, Riffel JH, Buchner K, Buss SJ, Hein S, Mereles D, Hagenmueller M, Erbel C, März W, Booz C, Albrecht MH, Vogl TJ, Frey N, Hardt SE, Ochs M. Impact of Homoarginine on Myocardial Function and Remodeling in a Rat Model of Chronic Renal Failure. J Cardiovasc Pharmacol Ther. 2022 Jan-Dec;27:10742484211054620. doi: 10.1177/10742484211054620. PMID: 34994208. 2. Wetzel MD, Stanley K, Maity S, Madesh M, Bopassa JC, Awad AS. Homoarginine ameliorates diabetic nephropathy independent of nitric oxide synthase-3. Physiol Rep. 2021 Mar;9(5):e14766. doi: 10.14814/phy2.14766. PMID: 33713581; PMCID: PMC7955794.
1: Zinellu A, Paliogiannis P, Carru C, Mangoni AA. Homoarginine and all-cause mortality: A systematic review and meta-analysis. Eur J Clin Invest. 2018 May 28:e12960. doi: 10.1111/eci.12960. [Epub ahead of print] Review. PubMed PMID: 29806958. 2: Dunham NP, Chang WC, Mitchell AJ, Martinie RJ, Zhang B, Bergman JA, Rajakovich LJ, Wang B, Silakov A, Krebs C, Boal AK, Bollinger JM Jr. Two Distinct Mechanisms for C-C Desaturation by Iron(II)- and 2-(Oxo)glutarate-Dependent Oxygenases: Importance of α-Heteroatom Assistance. J Am Chem Soc. 2018 Jun 13;140(23):7116-7126. doi: 10.1021/jacs.8b01933. Epub 2018 Jun 4. PubMed PMID: 29708749; PubMed Central PMCID: PMC5999578. 3: Baldassarri F, Schwedhelm E, Atzler D, Böger RH, Cordts K, Haller B, Pressler A, Müller S, Suchy C, Wachter R, Düngen HD, Hasenfuss G, Pieske B, Halle M, Edelmann F, Duvinage A. Relationship between exercise intervention and NO pathway in patients with heart failure with preserved ejection fraction. Biomarkers. 2018 Apr 12:1-11. doi: 10.1080/1354750X.2018.1460762. [Epub ahead of print] PubMed PMID: 29619838. 4: Da Boit M, Tommasi S, Elliot D, Zinellu A, Sotgia S, Sibson R, Meakin JR, Aspden RM, Carru C, Mangoni AA, Gray SR. Sex Differences in the Associations between L-Arginine Pathway Metabolites, Skeletal Muscle Mass and Function, and their Responses to Resistance Exercise, in Old Age. J Nutr Health Aging. 2018;22(4):534-540. doi: 10.1007/s12603-017-0964-6. PubMed PMID: 29582894. 5: Tommasi S, Elliot DJ, Da Boit M, Gray SR, Lewis BC, Mangoni AA. Homoarginine and inhibition of human arginase activity: kinetic characterization and biological relevance. Sci Rep. 2018 Feb 27;8(1):3697. doi: 10.1038/s41598-018-22099-x. PubMed PMID: 29487337; PubMed Central PMCID: PMC5829263. 6: Konieczna L, Pyszka M, Okońska M, Niedźwiecki M, Bączek T. Bioanalysis of underivatized amino acids in non-invasive exhaled breath condensate samples using liquid chromatography coupled with tandem mass spectrometry. J Chromatogr A. 2018 Mar 23;1542:72-81. doi: 10.1016/j.chroma.2018.02.019. Epub 2018 Feb 12. PubMed PMID: 29477235. 7: Wong A, Bryzek D, Dobosz E, Scavenius C, Svoboda P, Rapala-Kozik M, Lesner A, Frydrych I, Enghild J, Mydel P, Pohl J, Thompson PR, Potempa J, Koziel J. A Novel Biological Role for Peptidyl-Arginine Deiminases: Citrullination of Cathelicidin LL-37 Controls the Immunostimulatory Potential of Cell-Free DNA. J Immunol. 2018 Apr 1;200(7):2327-2340. doi: 10.4049/jimmunol.1701391. Epub 2018 Feb 23. PubMed PMID: 29475987; PubMed Central PMCID: PMC5860981. 8: Mena-Ulecia K, Gonzalez-Norambuena F, Vergara-Jaque A, Poblete H, Tiznado W, Caballero J. Study of the affinity between the protein kinase PKA and homoarginine-containing peptides derived from kemptide: Free energy perturbation (FEP) calculations. J Comput Chem. 2018 Jun 15;39(16):986-992. doi: 10.1002/jcc.25176. Epub 2018 Feb 5. PubMed PMID: 29399821. 9: Schönhoff M, Weineck G, Hoppe J, Hornig S, Cordts K, Atzler D, Gerloff C, Böger R, Neu A, Schwedhelm E, Choe CU. Cognitive performance of 20 healthy humans supplemented with L-homoarginine for 4 weeks. J Clin Neurosci. 2018 Apr;50:237-241. doi: 10.1016/j.jocn.2018.01.035. Epub 2018 Feb 1. PubMed PMID: 29396070. 10: Boyko A, Ksenofontov A, Ryabov S, Baratova L, Graf A, Bunik V. Delayed Influence of Spinal Cord Injury on the Amino Acids of NO(•) Metabolism in Rat Cerebral Cortex Is Attenuated by Thiamine. Front Med (Lausanne). 2018 Jan 15;4:249. doi: 10.3389/fmed.2017.00249. eCollection 2017. PubMed PMID: 29379782; PubMed Central PMCID: PMC5775235. 11: Asakawa D, Takahashi H, Iwamoto S, Tanaka K. De Novo Sequencing of Tryptic Phosphopeptides Using Matrix-Assisted Laser Desorption/Ionization Based Tandem Mass Spectrometry with Hydrogen Atom Attachment. Anal Chem. 2018 Feb 20;90(4):2701-2707. doi: 10.1021/acs.analchem.7b04635. Epub 2018 Feb 6. PubMed PMID: 29359928. 12: Tsikas D, Bollenbach A, Hanff E, Kayacelebi AA. Asymmetric dimethylarginine (ADMA), symmetric dimethylarginine (SDMA) and homoarginine (hArg): the ADMA, SDMA and hArg paradoxes. Cardiovasc Diabetol. 2018 Jan 4;17(1):1. doi: 10.1186/s12933-017-0656-x. PubMed PMID: 29301528; PubMed Central PMCID: PMC5753492. 13: Faller KME, Atzler D, McAndrew DJ, Zervou S, Whittington HJ, Simon JN, Aksentijevic D, Ten Hove M, Choe CU, Isbrandt D, Casadei B, Schneider JE, Neubauer S, Lygate CA. Impaired cardiac contractile function in arginine:glycine amidinotransferase knockout mice devoid of creatine is rescued by homoarginine but not creatine. Cardiovasc Res. 2018 Mar 1;114(3):417-430. doi: 10.1093/cvr/cvx242. PubMed PMID: 29236952; PubMed Central PMCID: PMC5982714. 14: Mann E, Kluesener R, Boschann F, Ruppert J, Armbruster FP, Meinitzer A, Melzer C, Dschietzig TB. Homoarginine Associates with Zonulin and Tryptophan - Findings in a High-Risk Cohort of Patients Carrying an AICD. Clin Lab. 2017 Nov 1;63(11):1911-1918. doi: 10.7754/Clin.Lab.2017.170725. PubMed PMID: 29226642. 15: Kudo T, Nakatani S, Kakizaki M, Arai A, Ishida K, Wada M, Kobata K. Supplemented Chondroitin Sulfate and Hyaluronic Acid Suppress Mineralization of the Chondrogenic Cell Line, ATDC5, via Direct Inhibition of Alkaline Phosphatase. Biol Pharm Bull. 2017;40(12):2075-2080. doi: 10.1248/bpb.b17-00059. PubMed PMID: 29199232. 16: Aula H, Skyttä T, Tuohinen S, Luukkaala T, Hämäläinen M, Virtanen V, Raatikainen P, Moilanen E, Kellokumpu-Lehtinen PL. Adjuvant Breast Cancer Treatments Induce Changes in Homoarginine Level - A Prospective Observational Study. Anticancer Res. 2017 Dec;37(12):6815-6824. PubMed PMID: 29187460. 17: Radhakutty A, Mangelsdorf BL, Drake SM, Rowland A, Smith MD, Mangoni AA, Thompson CH, Burt MG. Opposing effects of rheumatoid arthritis and low dose prednisolone on arginine metabolomics. Atherosclerosis. 2017 Nov;266:190-195. doi: 10.1016/j.atherosclerosis.2017.10.004. Epub 2017 Oct 6. PubMed PMID: 29035782. 18: Ballard KD, Duguid RM, Berry CW, Dey P, Bruno RS, Ward RM, Timmerman KL. Effects of prior aerobic exercise on sitting-induced vascular dysfunction in healthy men. Eur J Appl Physiol. 2017 Dec;117(12):2509-2518. doi: 10.1007/s00421-017-3738-2. Epub 2017 Oct 10. PubMed PMID: 29018989. 19: Raedle-Hurst T, Mueller M, Meinitzer A, Maerz W, Dschietzig T. Homoarginine-A prognostic indicator in adolescents and adults with complex congenital heart disease? PLoS One. 2017 Sep 8;12(9):e0184333. doi: 10.1371/journal.pone.0184333. eCollection 2017. PubMed PMID: 28886170; PubMed Central PMCID: PMC5590899. 20: Olkowicz M, Debski J, Jablonska P, Dadlez M, Smolenski RT. Application of a new procedure for liquid chromatography/mass spectrometry profiling of plasma amino acid-related metabolites and untargeted shotgun proteomics to identify mechanisms and biomarkers of calcific aortic stenosis. J Chromatogr A. 2017 Sep 29;1517:66-78. doi: 10.1016/j.chroma.2017.08.024. Epub 2017 Aug 12. PubMed PMID: 28851525. a