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7724-76-7, Isopentenyladenosine ,Riboprine, CAS:7724-76-7

7724-76-7, Isopentenyladenosine ,
Riboprine,
CAS:7724-76-7
C15H21N5O4 / 335.36
MFCD00005741

 利波腺苷, Isopentenyladenosine ,Riboprine

6-(3,3-Dimethylallylamino)-9-(b-D-ribofuranosyl)purine

6-(3,3-Dimethylallylamino)-9-(b-D-ribofuranosyl)purine is an energy metabolism agent that mimics cytokinin, a plant hormone. It has been shown to affect the angiogenic process and induce apoptosis in HL60 cells through the pro-apoptotic protein Bax. 6-(3,3-Dimethylallylamino)-9-(b-D-ribofuranosyl)purine has also been used as a model system to study the structure of dna, which is important for understanding how it replicates. 6-(3,3-Dimethylallylamino)-9-(b-D-ribofuranosyl)purine is structurally similar to adenosine and binds to the A3 receptor with high affinity. This drug is active as an analogue of adenosine and may be useful for treating diseases such as heart disease or diabetes.

Riboprine is a molecule of great scientific interest due to its potential as an anticancer and immunomodulatory agent. It is a purine nucleoside analogue that has recently been explored for its potential applications in immunodeficiencies and cancer chemotherapy. In this paper, we will explore riboprine's definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background

Riboprine, a modified nucleoside with the structure of 6-(1'-beta-D-ribofuranosyl)-purine, was first synthesized in the early 1960s by the chemist George Hitchings, who shared the Nobel Prize in Physiology or Medicine for his work in this field. Riboprine is a drug that is closely related to inosine, but with the distinguishing factor of a ribose sugar instead of a deoxyribose sugar. The molecule is metabolized to the active metabolite of ribonucleotide reductase, an enzyme that catalyzes the first step in the formation of DNA. Riboprine's close structural similarity to inosine has led to its exploration in the field of anticancer research and immunodeficiencies.

Synthesis and Characterization

Riboprine is synthesized from 6-chloropurine. The chloro group is displaced by ribose under acidic conditions, and the product is crystallized using a method described by Hitchings and his colleagues. Characterization of the molecule is conducted using a variety of techniques including ultraviolet-visible (UV-VIS) spectrophotometry, nuclear magnetic resonance (NMR), and high-performance liquid chromatography (HPLC). These techniques are useful to determine the purity and composition of the synthesized product.

Analytical Methods

The analytical methods used to study riboprine include NMR, HPLC, and mass spectrometry. NMR spectroscopy is highly effective in determining the chemical structure of riboprine since it provides excellent spectral resolution. HPLC is commonly used to separate and quantify the amount of riboprine in a sample. Furthermore, mass spectrometry can also be used as a powerful tool to study the pharmacokinetics of the molecule in vivo.

Biological Properties

Riboprine has shown to be useful in combating cancers, such as breast cancer, ovarian carcinoma, leukemia, and prostate cancer. This chemical agent is effective against tumor cells due to its ability to undergo phosphorylation by tumor cells. In addition, riboprine has been explored for its effects on the immune system. Studies have shown that riboprine modulates the immune response by increasing antibody production and enhancing the phagocytic activity of macrophages.

Toxicity and Safety in Scientific Experiments

Riboprine's low toxicity profile has made it an attractive candidate for the treatment of different diseases, but data on its safety profile is limited. In in vivo studies, riboprine at high doses has caused weight loss and changes in behavior. However, the toxicity was not life-threatening, and there was no indication of gross organ damage.

Applications in Scientific Experiments

Riboprine has been explored for its potential use as an antitumor agent and is undergoing clinical trials for use in breast cancer treatment. Riboprine also has potential as an immunomodulatory agent, and it can enhance phagocytic activity of macrophages, which can help to improve immune function. The molecule has potential applications as an antiviral agent in diseases such as human immunodeficiency virus (HIV) and hepatitis B virus (HBV).

Current State of Research

Currently, research on riboprine has focused on developing novel formulations of riboprine to increase its efficacy and reduce toxicity. Studies have been conducted to explore the pharmacokinetics and pharmacodynamics of riboprine through in vitro and in vivo models.

Potential Implications in Various Fields of Research and Industry

Riboprine has a wide range of implications in the fields of cancer research, immunodeficiencies, and antiviral therapies. It can also be explored as a potential platform for drug delivery systems, and as a potential candidate for developing biomaterials for wound healing and other regenerative medicine applications.

Limitations

The limited toxicity data available requires appropriate precautions when conducting experiments with riboprine. Additional studies are necessary to assess the safety and efficacy of riboprine.

Future Directions

There is a need for further development of innovative formulations of riboprine to enhance its efficacy and reduce toxicity. In addition, the potential applications of riboprine as an antiviral agent require more research to be done. Other future directions include exploring riboprine's potential as an immunological adjuvant and as a systemic therapeutic for the treatment of immune system-related diseases, such as inflammatory bowel diseases, rheumatoid arthritis, and lupus. Ultimately, further studies of riboprine are needed to broaden our understanding of the chemical, biological, and pharmacological properties of this molecule.

CAS Number7724-76-7
Product NameRiboprine
IUPAC Name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
Molecular FormulaC15H21N5O4
Molecular Weight335.36 g/mol
InChIInChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
InChI KeyUSVMJSALORZVDV-SDBHATRESA-N
SMILESCC(=CCNC1=NC=NC2=C1N=CN2C3C(C(C(O3)CO)O)O)C
SynonymsN-(3-Methyl-2-butenyl)-adenosine; 6-(3-Methyl-2-butenylamino)-9-β-D-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)-9-β-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)-β,D-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)purine riboside; 6-(γ,γ-Dime
Canonical SMILESCC(=CCNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O)C
Isomeric SMILESCC(=CCNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)C


CAS No: 7724-76-7 Synonyms: N6-(3,3-Dimethylallylamino)purine ribosideN6-(2-Isopentenyl)adenosine MDL No: MFCD00005741 Chemical Formula: C15H21N5O4 Molecular Weight: 335.36


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