Ziconotide CAS 107452-89-1

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Ziconotide acetate is a peptide drug composed of D-phenylalanine β- Ala, Gly, L-ornithine, L-tryptophan, and Cys, a total of six amino acids, were synthesized by solid-phase peptide synthesis method, and then modified, cut, purified, and freeze-dried to produce. Its molecular formula is C50H64N10O12S2, molecular weight is 1033.25, CAS 107452-89-1. It is a white or almost white loose block or powder. Stable under acidic to neutral conditions, but may be unstable under alkaline conditions. Easy to dissolve in water and methanol, slightly soluble in ethanol, almost insoluble in ether or chloroform. Commonly used in the fields of biochemistry and medicine. It is an antibacterial drug that has inhibitory effects on various bacteria. In addition, it can also be used for in vivo structural and functional research, pharmacological research, and other aspects.

The chemical laboratory synthesis method of acetic acid zeconomide usually involves multiple steps, including amino acid condensation, modification, cleavage, and purification. Due to the complex chemical reactions and precise experimental conditions involved in peptide synthesis, it is necessary to have certain organic synthesis experience and professional skills. The following is a possible chemical laboratory synthesis method for Ziconotide Acetate:

1. Materials and reagents

Amino acids: D-phenylalanine β- Ala, Gly, L-ornithine, L-tryptophan, and Cys (or their thiol derivatives).

Reagents: Acetic anhydride, DCC, NMM, TFA, HPLC grade methanol and acetonitrile, TLC silica gel plate, column chromatography silica gel, activated carbon.

Equipment: rotary evaporator, column chromatography system, dialysis bag, high-performance liquid chromatography.

2. Synthesis steps

(1) Synthesis of peptide chains: D-phenylalanine β- Ala, Gly, L-ornithine, L-tryptophan, and Cys are sequentially connected to form peptide chains. The classic solid-phase peptide synthesis method (SPPS) can be used to protect the amino groups of amino acids with 9-fluororenylmethoxycarbonyl (Fmoc) protecting groups, and then connect them to the solid-phase carrier. Subsequently, other amino acid residues were sequentially added to each amino group, and Fmoc protective groups were removed using deprotection reagents such as piperidine.

(2) Cutting and purification: After completing peptide chain synthesis, the peptide is cut off from the solid-phase carrier using a cutting reagent (such as TFA) and purified. Purification methods can include gel filtration chromatography (GFC), reverse phase high-performance liquid chromatography (RP-HPLC), or capillary electrophoresis.

(3) Modification and deprotection: Modify the peptide chain as needed, such as adding ester groups or conducting other chemical reactions. After modification, use appropriate deprotection reagents to remove residual chemical protective groups and obtain the free form of ziconotid acetate.

(4) Analysis and quality control: Through various analytical methods such as mass spectrometry (MS), nuclear magnetic resonance (NMR), and high-performance liquid chromatography (HPLC), characterize and analyze the synthesized ziconomide acetate to ensure that its structure, purity, and quality meet the requirements.

(5) Crystallization and storage: Crystallize the synthesized zecanopeptide acetate to improve its stability and purity. After crystallization, store the crystals under appropriate conditions to maintain their stability and purity.

In the synthesis process of Ziconotide Acetate, the reaction of Ziconotid Acetate with Acetic Anhydride to obtain Ziconotid Acetate is a key step. Here are the detailed steps and corresponding chemical equations.

The reaction equation between Ziconotid and Acetic Anhydride:

(CNH₂N+2O₂NH₂+(n+1) CH₃COOH → CnH₂N+2O₂NCH₃COOH+(n+1) H₂O)

Among them, (CNH2N+2O2NH2) represents ziconotid.

The reaction equation for removing excess acetic anhydride:

(CNH₂n+2O₂NCH₃COOH+H₂O → CnH₂N+2O₂NH₂+CH₃COOH)

This reaction is a hydrolysis reaction, which promotes hydrolysis by adjusting the pH value through hydrochloric acid or sodium hydroxide solution.

1. Experimental equipment and reagents

Equipment: Magnetic stirrer, condenser tube, drip funnel, round bottom flask, rotary evaporator.

Reagents: Acetic Anhydride, Anhydrous Pyridine, Toluene, Hydrochloric Acid, Sodium Hydroxide.

2. Experimental steps

(1) Add ziconotid and an appropriate amount of anhydrous pyridine to a round bottomed flask containing a magnetic stirrer, and stir evenly.

(2) Slowly add acetic anhydride to the reaction mixture while controlling the temperature below 30 ℃.

(3) Continuously stir with magnetic force during the reaction process and closely observe the progress of the reaction. When the reaction mixture becomes viscous, the temperature can be appropriately increased to promote the reaction.

(4) After the reaction is complete, pour the reaction mixture into the ice water mixture to terminate the reaction.

(5) Remove the solvent and excess acetic anhydride through a rotary evaporator to obtain the crude product.

(6) Purify the crude product by column chromatography to further purify ziconol acetate.

(7) Purity was detected by high-performance liquid chromatography to collect the target product.

The molecular structure analysis of acetidide can be carried out from the following aspects:
1. Basic structural analysis

Ziconotide acetate is a peptide drug composed of multiple amino acids connected by peptide bonds. Based on the known molecular formula and molecular weight, the basic structure of ziconotide acetate can be analyzed.
Amino acid sequence analysis: Based on molecular formula and molecular weight, the amino acid sequence of acetic acid zeconomide can be inferred. Due to the presence of D-phenylalanine, Ziconotid acetate β- Ala, Gly, L-ornithine, L-tryptophan, and Cys are composed of six amino acids, so the connection order and mode of each amino acid can be calculated.
Spatial structure analysis: Ziconotid acetate has a specific spatial structure, which is closely related to its pharmacological effects and biological activities. X-ray crystallography, nuclear magnetic resonance (NMR), and other techniques can be used to analyze the spatial structure of ziconotid acetate. Through these techniques, the three-dimensional conformation of acetic acid zeconomide at the atomic level can be obtained, and its biological activity can be studied.
2. Stereochemical analysis
Stereochemical analysis is the science of studying the three-dimensional structure of molecules. Stereochemical analysis helps to understand the biological activity and pharmacological mechanism of action of zeconomide acetate in its molecular structure analysis. For example, the analysis of amino acid configuration (D-type or L-type) can affect the activity of drugs.

Ziconotide,Also known as Prialt or intrathecal Ziconotide (ITZ), it is an efficient and highly selective N-type calcium channel antagonist derived from Conus magus toxin. It exhibits great potential in chronic pain management by specifically acting on these channels, effectively reducing synaptic transmission. The following is a detailed analysis of its development prospects:

Market potential

With the continuous development of pain management, patients' demand for efficient and low side effect analgesic drugs is increasing. As a new and efficient analgesic drug, this compound has enormous market potential. The following is a detailed analysis of its market potential:

• Increased patient demand: With the aging population and the continuous increase in the number of chronic pain patients, the demand for highly effective analgesics is also continuing to grow. As an analgesic drug with a unique mechanism of action, it can meet the needs of this group of patients and therefore has broad market prospects.
• Widely used in clinical practice: it can not only be used to alleviate chronic pain such as neuropathic pain and cancer pain, but also for other types of pain management. This wide range of applications makes it more competitive in the market.
• Policy support: Governments around the world are continuously increasing their support for the field of pain management and have introduced a series of relevant policies to promote its development. This provides strong policy support for the development and promotion of such analgesic drugs.
• Research and development progress: With the in-depth study of its mechanism of action, its research and development progress is also constantly advancing. In the future, it is expected to make breakthroughs in treating more types of pain, thereby further expanding its market space.

Research progress and future research directions

In recent years, there has been continuous scientific research progress on this substance, laying a solid foundation for its future development prospects. The following is a detailed analysis of its scientific research progress and future research directions:

• In depth study on the mechanism of action: Researchers have conducted in-depth research on the binding mechanism between ziconomide and N-type calcium channels, revealing its unique analgesic mechanism. This not only helps us better understand its analgesic effect, but also provides a theoretical basis for its future drug development.
• Exploration of new indications: In addition to chronic pain management, researchers are also exploring the application of this substance in other indications. For example, studies have shown that it may have potential effects such as antiepileptic and antidepressant effects. The exploration of these new indications will further expand its application scope.
• Optimization of drug delivery system: In order to improve the analgesic effect and patient compliance of this compound, researchers are studying how to optimize its drug delivery system. For example, by developing new drug delivery devices or improving existing drug delivery methods, it can more accurately target the painful area, thereby enhancing its analgesic effect.
• Combination therapy research: In order to improve the analgesic effect and reduce side effects, researchers are exploring the combination therapy of this substance with other drugs. By reasonable drug combinations and dosage adjustments, its analgesic effect can be further improved and the risk of side effects can be reduced.

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