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Application Area

H-D-HoArg-OH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

D-Amino Acids

Catalog number

BAT-001563

CAS number

110798-13-5

Molecular Formula

C7H16N4O2

Molecular Weight

188.2

IUPAC Name

(2R)-2-amino-6-(diaminomethylideneamino)hexanoic acid

Synonyms

D-homoarginine; (R)-2-Amino-6-guanidinohexanoic acid

Purity

95%

Density

1.39 g/cm3

Boiling Point

376.3±52.0°C

InChI

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-/m1/s1

InChI Key

QUOGESRFPZDMMT-RXMQYKEDSA-N

Canonical SMILES

C(CCN=C(N)N)CC(C(=O)O)N

One of the key applications of H-D-HoArg-OH (Homoarginine) lies in its potential role within cardiovascular health. Homoarginine has been identified as a biomarker for cardiovascular risk assessment. Studies have demonstrated that elevated levels of homoarginine are associated with better cardiovascular outcomes. This is because Homoarginine can inhibit the activity of arginase, an enzyme that competes with nitric oxide synthase for L-arginine, thus promoting nitric oxide production. As nitric oxide is a crucial molecule for vascular health, aiding in vasodilation and blood pressure regulation, Homoarginine's ability to boost its synthesis can help in preventing cardiovascular diseases and improving overall heart health.

Another significant application of H-D-HoArg-OH is in the field of metabolic disorders, particularly diabetes. Homoarginine is structurally similar to L-arginine, which is involved in the biosynthesis of insulin. Research indicates that Homoarginine levels can influence insulin sensitivity and glucose metabolism, thus playing a role in diabetes management. In diabetic patients, maintaining optimal levels of Homoarginine could potentially improve glycemic control and reduce the risk of complications associated with diabetes. Hence, it could be considered as a therapeutic target or a supplement to support the metabolic health of individuals suffering from diabetes.

H-D-HoArg-OH also finds application in the field of renal health. Kidneys are essential for filtering blood and maintaining homeostasis in the body, and amino acids play significant roles in these processes. Homoarginine has been observed to have nephroprotective effects, potentially by enhancing nitric oxide bioavailability that supports renal function. Research has suggested that higher Homoarginine concentrations might be linked to lower incidences of chronic kidney disease (CKD) and better overall kidney function. This makes Homoarginine a candidate for developing novel therapies aimed at protecting kidney health and mitigating the progression of renal disorders.

Lastly, H-D-HoArg-OH is being investigated for its potential benefits in neurology. The central nervous system heavily relies on the balanced production of nitric oxide for neuronal signaling and brain function. Homoarginine, by influencing nitric oxide synthesis, might have neuroprotective effects. There is ongoing research exploring how Homoarginine supplementation could potentially alleviate symptoms of neurodegenerative diseases such as Alzheimer's and Parkinson's, where nitric oxide dysregulation is often implicated. Enhancing Homoarginine levels could support cognitive function and promote overall brain health, marking a promising avenue for therapeutic intervention in various neurological conditions.

1.A new gonadotropin-releasing hormone (GnRH) superagonist in goldfish: influence of dialkyl-D-homoarginine at position 6 on gonadotropin-II and growth hormone release.

Murthy CK1, Turner RJ, Nestor JJ Jr, Rivier JE, Peter RE. Regul Pept. 1994 Aug 31;53(1):1-15.

The two native forms of gonadotropin-releasing hormones (GnRH) present in goldfish, salmon GnRH (sGnRH) and chicken GnRH-II (cGnRH-II), stimulate gonadotropin-II (GTH-II) and growth hormone (GH) release both in vivo and in vitro. In our previous study using perifused goldfish pituitary fragments, many mammalian GnRH antagonists, especially those with D-Arg6, showed weak to strong stimulation of GTH-II and GH release. In the present study, the dose-related stimulation of GTH-II and GH release by [Ac-D(2)-Nal1, 4Cl-D-Phe2, D-Trp3, D-Arg6, Trp7, D-Ala10] mGnRH (analog J) and [Ac-D(2)-Nal1, 4Cl-D-Phe2, D-Trp3, D-hArg(Et2)6, D-Ala10] mGnRH (analog K) was demonstrated; the stimulatory potency of both analogs was significantly lower than that of native sGnRH. In the presence of analogs J and K, cGnRH-II stimulated GTH-II release was significantly suppressed. Further, GTH-II and GH stimulation by 2 microM of analog K was significantly suppressed by a 'true' GnRH antagonist, [Ac-delta 3-Pro1, 4FD-Phe2, D-Trp3,6] mGnRH (analog E).

2.Solid phase synthesis and some pharmacological properties of 8-D-homoarginine-vasopressin and 1-deamino-8-D-homoarginine-vasopressin.

Gunnar E, Lindeberg G, Melin P, Larsson LE. Int J Pept Protein Res. 1976;8(2):193-8.

Fully protected 8-D-lysine-vasopresin and 1-deamino-8-D-lysine-vasopressin were synthesized by the solid phase method. Selective removal of the lysine protection and reaction with 1-guanyl-3,5-dimethylpyrazole converted D-lysine into D-homoarginine. The title compounds were then obtained by treatment with sodium in liquid ammonia and oxidation in dilute aqueous solution. Although the antidiuretic activities are lower than for the corresponding D-argining derivatives, the even lower pressor effects make the new analogues highly specific antidiuretic agents. The A/P ratios for 8-D-homoarginine-vasopressin and its 1-deamino derivative are 100 and 3,300, respectively.

3.Solid phase synthesis and some hormonal activities of 1-deamino-4-L-valine-8-D-homolysine-and 1-deamino-4-L-valine-8-D-homoarginine-vasopressin.

Lindeberg G, Karlsson SM, Melin P. Int J Pept Protein Res. 1977;10(3):240-4.

1-Deamino-4-L-valine-8-DL-homolysine-vasopressin and protected 1-deamino-4-l-valine-8-D-lysine-vasopressin were synthesized by the solid phase method and were then converted into the title compounds (dVDHLVP and dVDHAVP) by tryptic digestion and epsilon-guanidination, respectively. The new hormone analogues exhibit only moderate antidiuretic potency, dVDHLVP 21 units/mg and dVDHAVP 31 units/mg, but since they are essentially devoid of pressor activity (o.o1 units/mg/ the A/P ratios are very high. In fact, dVDHLVP is the most specific antidiuretic agent in the lysine series known so far.