144110-38-3

Basic information

• Product Name: (2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE
• Synonyms: ARPHAMENINE B;ARPHAMENINE B HEMISULFATE MONOHYDRATE;(2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID, HEMISULFATE;(2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE;(2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID (SULFATE FORM);ARPHAMENINE B HEMISULFATE HYDRATE*FROM MICROBIAL SOU;arphamenine B hemisulfate;(2R,5S)-5-Amino-8-guanido-4-oxo-2-p-hydroxyphenylmethyloctanoic acid
• CAS NO: 144110-38-3
• Molecular Formula: C32H52N8O13S
• Molecular Weight: 788.87
• Mol File: 144110-38-3.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• Solubility: ≤0.2mg/ml in DMSO
• CAS DataBase Reference: (2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE(144110-38-3)
• EPA Substance Registry System: (2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE(144110-38-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 144110-38-3(Hazardous Substances Data)

Usage

Description

(2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers at the 2R and 5S positions, and its functional groups include an amino group, a guanidino group, a hydroxyl group, and a carboxylic acid group. (2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE is typically found in the form of a hemisulfate monohydrate, indicating the presence of a sulfate ion and a water molecule in its structure.

Uses

Used in Pharmaceutical Industry:
(2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE is used as a pharmaceutical compound for its potential therapeutic applications. Its unique structure and functional groups may allow it to interact with specific biological targets, such as enzymes or receptors, which could be beneficial in the treatment of various diseases.
Used in Research and Development:
In the field of research and development, (2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE is used as a research tool to study the structure-activity relationships of similar compounds. Its unique properties and reactivity can provide valuable insights into the design and synthesis of new drugs and bioactive molecules.
Used in Enzyme Inhibition Studies:
(2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE can be used as an inhibitor of specific enzymes, such as aminopeptidase B, which is involved in the degradation of peptide substrates. By inhibiting this enzyme, it may help to modulate immune responses and potentially be used in the treatment of immune-related disorders.
Used in Drug Delivery Systems:
Similar to gallotannin, (2R,5S)-5-AMINO-8-GUANIDINO-4-OXO-2-P-HYDROXYPHENYLMETHYLOCTANOIC ACID HEMISULFATE MONOHYDRATE may also be employed in the development of novel drug delivery systems. Its unique structure and functional groups could be utilized to improve the delivery, bioavailability, and therapeutic outcomes of various drugs, particularly in the context of cancer treatment.

Biological Activity

arphamenine b is a specific inhibitor of aminopeptidase b first isolated from bacteria [1]. aminopeptidase b (ap-b) is a zn2+-dependent exopeptidase which selectively removes arg and/or lys residues from the n terminus of several peptide substrates. aminopeptidase b has been involved in processing events occurring either during its intracellular transport along the secretory pathway or at the plasma membrane level [2].

in vitro

arphamenine b inhibited the activity of aminopeptidase enzyme with an ic50 value of 9.0 μm [2]. arphamenine b strongly inhibited transport by the oligopeptide/h+ symporter with the ec50 values of 15 to 67 μm. arphamenine at concentration 100 μm acted as either ineffective or weak inhibitor of membrane-associated hydrolysis [4]. arphamenine selectively suppressed dipeptide hydrolysis [4].

references

[1] umezawa h, aoyagi t, ohuchi s, et al. arphamenines a and b, new inhibitors of aminopeptidase b, produced by bacteria[j]. the journal of antibiotics, 1983, 36(11): 1572-1575.[2] balogh a, cadel s, foulon t, et al. aminopeptidase b: a processing enzyme secreted and associated with the plasma membrane of rat pheochromocytoma (pc12) cells[j]. journal of cell science, 1998, 111(2): 161-169.[3] sajid m, isaac r e, harrow i d. purification and properties of a membrane aminopeptidase from ascaris suum muscle that degrades neuropeptides af1 and af2[j]. molecular and biochemical parasitology, 1997, 89(2): 225-234.[4] daniel h, adibi s a. functional separation of dipeptide transport and hydrolysis in kidney brush border membrane vesicles[j]. the faseb journal, 1994, 8(10): 753-759.