Combretastatin A4
Catalog Number: BT-253185
CAS Number: 117048-59-6
Molecular Formula: C₁₈H₂₀O₅
Molecular Weight: 316.3 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Combretastatin A4 (CA4) is a natural compound that belongs to the stilbenoid family. It was first isolated from the bark of the South African tree Combretum caffrum in 1989. Since then, it has been extensively studied for its potential therapeutic applications in various fields, including cancer treatment, cardiovascular diseases, and neurological disorders. This paper aims to provide a comprehensive review of CA4, including its method of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges.
Properties
CAS Number
117048-59-6
Product Name
Combretastatin A4
IUPAC Name
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
Molecular Formula
C₁₈H₂₀O₅
Molecular Weight
316.3 g/mol
InChI
InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
InChI Key
HVXBOLULGPECHP-WAYWQWQTSA-N
SMILES
COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O
Synonyms
1-(3,4,5-trimethoxyphenyl)-2-(3'-hydroxy-4'-methoxyphenyl)ethene
2-methoxy-5-((z)-2-(3,4,5-trimethoxyphenyl)vinyl)phenyl dihydrogen phosphate
3,4,5-trimethoxy-3'-hydroxy-4'-methoxystilbene
CA4DP
combretastatin A-4
combretastatin A-4 disodium phosphate
combretastatin A4
combretastatin A4 phosphate
CRC 87-09
CRC-98-09
deoxycombretastatin A-4
fosbretabulin
isocombretastatin A-4
NSC 817373
NSC-817373
phenol, 2-methoxy-5-((1z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-,1-(dihydrogen phosphate)
phenol, 2-methoxy-5-((z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-, dihydrogen phosphate
2-methoxy-5-((z)-2-(3,4,5-trimethoxyphenyl)vinyl)phenyl dihydrogen phosphate
3,4,5-trimethoxy-3'-hydroxy-4'-methoxystilbene
CA4DP
combretastatin A-4
combretastatin A-4 disodium phosphate
combretastatin A4
combretastatin A4 phosphate
CRC 87-09
CRC-98-09
deoxycombretastatin A-4
fosbretabulin
isocombretastatin A-4
NSC 817373
NSC-817373
phenol, 2-methoxy-5-((1z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-,1-(dihydrogen phosphate)
phenol, 2-methoxy-5-((z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-, dihydrogen phosphate
Canonical SMILES
COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O
Isomeric SMILES
COC1=C(C=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)O
Method of Synthesis or Extraction
Combretastatin A4 can be synthesized using various methods, including chemical synthesis, semi-synthesis, and extraction from natural sources. Chemical synthesis involves the use of organic chemistry techniques to create the compound from scratch. Semi-synthesis involves modifying a natural compound to produce Combretastatin A4. Extraction from natural sources involves isolating the compound from plants or other natural sources.
The efficiency and yield of each method vary depending on the specific technique used. Chemical synthesis and semi-synthesis methods are generally more efficient and yield higher quantities of Combretastatin A4 than extraction from natural sources. However, these methods can be expensive and require specialized equipment and expertise. Extraction from natural sources is a more cost-effective method but yields lower quantities of Combretastatin A4.
Environmental and safety considerations are also important when choosing a method of synthesis or extraction. Chemical synthesis and semi-synthesis methods can produce hazardous waste and require the use of toxic chemicals. Extraction from natural sources can have a lower environmental impact but may require the destruction of natural habitats.
The efficiency and yield of each method vary depending on the specific technique used. Chemical synthesis and semi-synthesis methods are generally more efficient and yield higher quantities of Combretastatin A4 than extraction from natural sources. However, these methods can be expensive and require specialized equipment and expertise. Extraction from natural sources is a more cost-effective method but yields lower quantities of Combretastatin A4.
Environmental and safety considerations are also important when choosing a method of synthesis or extraction. Chemical synthesis and semi-synthesis methods can produce hazardous waste and require the use of toxic chemicals. Extraction from natural sources can have a lower environmental impact but may require the destruction of natural habitats.
Chemical Structure and Biological Activity
The chemical structure of Combretastatin A4 consists of two phenyl rings connected by a double bond and a methoxy group. The compound has been shown to have potent anti-tumor activity by disrupting the microtubule network in cancer cells. Combretastatin A4 binds to the colchicine site on tubulin, preventing the formation of microtubules and leading to cell death.
Biological Effects
Combretastatin A4 has been shown to have a range of biological effects on cell function and signal transduction. In addition to its anti-tumor activity, Combretastatin A4 has been shown to have anti-inflammatory, anti-angiogenic, and anti-thrombotic effects. However, Combretastatin A4 can also have potential toxic effects, including cardiovascular toxicity and neurotoxicity.
Applications
Combretastatin A4 has potential applications in medical research, environmental research, and industrial research. In medical research, Combretastatin A4 has been studied for its role in drug development, including clinical trials for cancer treatment. Combretastatin A4 has also been studied for its potential therapeutic effects in cardiovascular diseases and neurological disorders.
In environmental research, Combretastatin A4 has been studied for its effects on ecosystems and its role in pollution management. Combretastatin A4 has been shown to have potential applications in sustainable agriculture and environmental remediation.
In industrial research, Combretastatin A4 has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations are important when using Combretastatin A4 in industrial settings.
In environmental research, Combretastatin A4 has been studied for its effects on ecosystems and its role in pollution management. Combretastatin A4 has been shown to have potential applications in sustainable agriculture and environmental remediation.
In industrial research, Combretastatin A4 has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations are important when using Combretastatin A4 in industrial settings.
Future Perspectives and Challenges
Current limitations in the use and study of Combretastatin A4 include its potential toxic effects and the need for more research to fully understand its biological effects and mechanisms of action. Possible solutions and improvements include the development of more selective Combretastatin A4 analogs and the use of targeted drug delivery systems.
Future trends and prospects in the application of Combretastatin A4 in scientific research include the development of new therapeutic applications and the use of Combretastatin A4 in combination with other drugs for improved efficacy. However, challenges remain in the development of safe and effective Combretastatin A4-based therapies.
Conclusion:
In conclusion, Combretastatin A4 is a natural compound with potent anti-tumor activity and potential applications in various fields, including medical research, environmental research, and industrial research. The method of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges of Combretastatin A4 have been discussed in this paper. Further research is needed to fully understand the potential of Combretastatin A4 and to develop safe and effective therapies based on this compound.
Future trends and prospects in the application of Combretastatin A4 in scientific research include the development of new therapeutic applications and the use of Combretastatin A4 in combination with other drugs for improved efficacy. However, challenges remain in the development of safe and effective Combretastatin A4-based therapies.
Conclusion:
In conclusion, Combretastatin A4 is a natural compound with potent anti-tumor activity and potential applications in various fields, including medical research, environmental research, and industrial research. The method of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges of Combretastatin A4 have been discussed in this paper. Further research is needed to fully understand the potential of Combretastatin A4 and to develop safe and effective therapies based on this compound.
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