Vapreotide CAS 103222-11-3

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Vapreotide , chemical name D-Phenylalanyl-L-cysteinyl-L-phenylalanyl-D-tryptophyl-L-lysyl-L-threoninol acetate salt hydrate (C57H70N12O9S2 · C2H4O2 · xH2O), CAS 103222-11-3. It contains multiple amino acid residues and one acetate molecule, and may exist in the form of hydrates. Its relative molecular weight is 1257.5 Da. It is a white or almost white solid powder, sometimes also in a light yellow color tone. The pH value has a significant impact on its chemical properties and biological activity. It has high solubility in water, methanol, and ethanol, while its solubility is relatively low in organic solvents such as chloroform, benzene, and dichloromethane. It is stable under acidic conditions (pH<3), but slowly decomposes under alkaline conditions (pH>10). It is a somatostatin analogue used to treat neuroendocrine tumors and other endocrine disorders.

This method relates to a method for preparing Vapreotide belonging to the field of chemical synthesis. Vasopril is a physiologically active pentapeptide compound that can be used to treat intestinal diseases such as ulcerative colitis and Crohn's disease. This article provides a method for preparing vaccinin, which is simple to operate, has low raw material input, low cost, and high yield, and has good economic and practical value.

A method for preparing vaccinin, comprising the following steps:

(1) React Rink Amide resin with HMPTA to obtain HMPTA treated Rink Amide resin;

(2) React the HMPTA treated Rink Amide resin obtained in step (1) with a tetrafluoroborate solution containing aminophenylacetylene to obtain a solid-phase synthesis intermediate;

(3) Perform an oxidation reaction on the solid-phase synthesis intermediate obtained in step (2) to obtain the oxidized solid-phase synthesis intermediate;

(4) Perform a cleavage reaction on the oxidized solid-phase synthesis intermediate obtained in step (3) to obtain the crude product of valproide;

(5) Perform deprotection, desalination, and decolorization treatment on the crude product obtained in step (4) to obtain the target product Vapreotide.

In step (1), the reaction conditions between the Rink Amide resin and HMPTA are as follows: treated with piperidine in an aqueous DMF solution. By the action of piperidine, the tertiary amine groups of Rink Amide resin are converted into HMPTA treated tertiary amine groups, thereby enhancing its reactivity and stability.

In step (2), the reaction conditions between the tetrafluoroborate solution containing aminophenylacetylene and HMPTA treated Rink Amide resin are as follows: the reaction is carried out in a mixed solution of methanol, acetonitrile, and water. In this step, the tetrafluoroborate of aminophenylacetylene is condensed with the carboxyl group of Rink Amide resin to connect aminophenylacetylene to the resin, forming a solid-phase synthesis intermediate.

In step (3), the oxidation reaction conditions are as follows: the reaction is carried out in a mixed solution of methanol, acetonitrile, and water. In this step, the imine groups in the solid-phase synthesis intermediate are oxidized into carbon carbon double bonds by using iodine and sodium hydroxide as oxidants to obtain the oxidized solid-phase synthesis intermediate. The specific chemical equation is as follows:

Rink-NH-CH═CH-CO^- + I₂ + NaOH → Rink-NH-CH═CH-COOH + NaI + H₂O

In step (4), the cracking reaction conditions are as follows: the reaction is carried out in a mixed solution of methanol, acetonitrile, and water. In this step, the oxidized solid-phase synthesis intermediate is cleaved from the resin by using methanol and acetonitrile as solvents to obtain the crude product of valproide. The specific chemical equation is as follows:

Rink-NH-CH═CH-COOH → Rink + NH-CH═CH-COOH

In step (5), the deprotection, desalination, and decolorization treatments are as follows: using trifluoroacetic acid to remove the Boc protective group on the amino group; Remove ion impurities from the reaction solution using ion exchange resin; Use activated carbon for decolorization. Through these processing steps, a high-purity target product, vaccinin, can be obtained. The specific chemical equation is as follows:

Unprotection:

Rink-NH-CH₂C(CH₃)₃+CF₃COOH → Rink-NH-CH₂CH=CHCOOH+CH₃COOH+CO₂+H₂O

Desalination and decolorization: It does not involve chemical equations, but through the action of ion exchange resin and activated carbon, ion impurities and color impurities in the reaction solution can be removed, improving the purity and appearance quality of the product.

This method has the following advantages: simple operation, low raw material input, low cost, and high yield. By adopting the method of iodine oxidation of linear valproide resin in the solid phase, the operational difficulties caused by traditional liquid-phase oxidation are avoided, and the oxidation yield is increased by 10% -20%. The total yield of this method can reach 68%, with a crude peptide purity of 85%.

Vapreotide is a drug with multiple chemical uses, and its chemical structure and biological activity make it widely applicable in clinical treatment. In addition to being used for the treatment of esophageal variceal bleeding in patients with liver cirrhosis, valproide also has the following common chemical uses:

Application in digestive system diseases

 

Treatment of acute pancreatitis
The pathogenesis of acute pancreatitis is secondary pancreatic self digestion due to abnormal activation of digestive enzymes. Somatostatin analogs are the strongest pancreatic exocrine inhibitors, and as somatostatin analogs, vasopressin may reduce or completely inhibit postprandial pancreatic and gastrointestinal hormone secretion, alleviate pancreatic burden, and reduce the risk of pancreatic injury (necrosis), making it one of the potential drugs for treating acute pancreatitis.
Treating gastrointestinal and pancreatic fistulas
Somatostatin and its analogues can inhibit the release and secretion of various gastrointestinal hormones, prolong the passage time of food in the intestine, and enhance water and electrolyte absorption. Vaptin may reduce the inflammatory response around the fistula opening through this mechanism, making it possible for the fistula to self heal and be used for the treatment of gastrointestinal and pancreatic fistulas.

Application in endocrine diseases

 

Treating acromegaly
Acromegaly is an endocrine and metabolic disorder caused by excessive secretion of growth hormone (GH) by the pituitary gland, resulting in abnormal enlargement of body size and internal organs, accompanied by corresponding physiological dysfunction. GH adenomas mainly express SSTR2 and SSTR5, and vasopressin has a high affinity for these two subtypes. When patients are not suitable for surgery, valproide may be one of the preferred therapeutic drugs, as it can induce tumor shrinkage and restore normal levels of IGF-I and GH in patients.
Treatment of diabetes retinopathy
Photocoagulation is the first choice for the treatment of diabetes retinopathy (DR), but intravitreal injection of somatostatin analog is a promising treatment option for the control of proliferative DR and frequent diabetes macular edema (DME). The human retina, especially the pigment epithelium, has abundant SST and SSTR. Patients with proliferative DR and DME have lower levels of intravitreal SST, which is associated with ischemia induced angiogenesis in the pathogenesis of DR and blood-brain barrier disruption involved in DME pathogenesis. Vaptin may exert neuroregulatory and anti angiogenic effects on the retina, preventing bleeding and proliferation, and protecting the integrity of the blood retinal barrier.

Application in pain treatment

 

SST acts on peripheral SSTR to suppress the body's perception of nociceptive stimuli. The analgesic effect of SST may be achieved through the inhibition of capsaicin gated ion channels, and vasopressin can be used for pain relief when opioid drugs are ineffective. Various clinical studies have confirmed that systemic, intrathecal, epidural, and intracranial administration of SST or octreotide leads to inhibition of several types of pain, including cancer-related pain, bone pain, arthritis pain, visceral pain, and migraine.

Regulating immune function
Somatostatin and its analogues can regulate the immune function of the body. Vaptin may enhance the body's immune surveillance and clearance capabilities by affecting the activity and function of immune cells, helping the body recognize and clear tumor cells.

The mechanism of anti tumor activity of varpropide

 

Directly inhibit tumor cell proliferation
Vaptin binds to SSTR, binds to adenylate cyclase and inhibits its activity, reducing the cAMP content that promotes cell proliferation in tumor cells, thereby inhibiting tumor cell proliferation. At the same time, it can activate protein phosphatase, inhibit DNA and protein synthesis, interfere with the cell cycle, and cause tumor cells to stagnate at specific stages of the cell cycle, unable to continue proliferation.
Inhibit tumor angiogenesis
The growth and metastasis of tumors depend on the formation of new blood vessels. Vaptin has inhibitory effects on various factors that generate tumor blood vessels, such as vascular endothelial growth factor, insulin-like factor, etc. It can inhibit the release and activity of these factors, thereby reducing the generation of tumor blood vessels, cutting off the nutritional supply of tumors, and inhibiting tumor growth and metastasis.

Vapreotide is a synthetic cyclic octapeptide compound with the chemical name D-phenylalanine-cysteine-tyrosine-D-tryptophan-lysine-valine-cysteine-tryptamide [2-7] disulfide monosuccinate. Its molecular formula is C₅₇H₇₀N₁₂O₉S₂ and its molecular weight is approximately 1131.37. This compound forms a stable cyclic structure through disulfide bonds, endowing it with unique chemical properties and biological activities.

In terms of physical properties, Vapreotide is a white to off-white solid with a high density (predicted value approximately 1.40 g/cm³), a melting point range of 176-180℃, and a predicted boiling point of up to 1540.9℃. These characteristics indicate strong intermolecular forces and high structural stability of the molecule. In terms of water solubility, Vapreotide exhibits good solubility, with a water solution concentration of up to 60 mg/mL (53.03 mM), which provides the necessary conditions for its absorption and distribution in the body.

In terms of chemical stability, the cyclic structure connects the cysteine residues (Cys2-Cys7) through disulfide bonds, forming a rigid spatial conformation that effectively resists enzymatic hydrolysis and chemical degradation. This stability enables it to maintain its active conformation in both in vitro and in vivo experiments, prolonging its action time. The storage conditions are strict, requiring storage at -20℃ or below in a dark, dry, and sealed environment to prevent molecular structure disruption due to temperature fluctuations or humidity effects.

In terms of biological activity, Vapreotide, as a synthetic analogue of somatostatin, exerts direct and indirect biological effects by binding with high affinity to the SSTR2 and SSTR5 subtypes of somatostatin receptors. Its mechanism of action includes inhibiting the release of vasoactive peptides and reducing portal venous pressure. It has demonstrated significant efficacy in treating acute esophageal variceal bleeding and preventing recurrence of bleeding after endoscopic treatment. Clinical trials have confirmed that the rapid-release formulation Sanvar IR can be used for early hemostatic intervention and to prevent bleeding recurrence within 5 days after surgery.

In terms of application fields, the chemical properties of Vapreotide make it an ideal tool for life science research. In pharmacological experiments, it is used as a model peptide to study receptor-mediated signaling pathways and cellular response processes; in molecular mechanism analysis, its controllable cellular-level activity helps to explore the molecular basis of disease occurrence and development. Moreover, Vapreotide can be combined with fluorescent probes or chemical markers to provide visualization and quantitative analysis methods for in vitro experiments, further expanding its application scope in the field of scientific research.

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