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Introduction

➢The life cycle of Human Immunodeficiency Virus, the pathogen responsible


for HIV AIDS, consists of six steps: infection, reception at the cell,
Synthesis of Matrine Derivatives as possible Figure 1.a. Signals received
integration into the host DNA, production of non-functional polypeptide, by the Mass Spectrometer
cleavage of polypeptide, and rebudding from the cell. HIV Protease Inhibitors over 14 minutes while
testing for the presence of
Matrinamide.
➢Oxymatrine has also been speculated to inhibit the HIV protease enzyme,
making it a possible treatment for HIV-AIDS.
Dr. Walda Powell, Dr. Cassandra Lilly, Dr. Karthik Aghoram
➢Two derivatives of matrinic acid can be synthesized: matrine methyl ester
and matrinamide. They can then be tested on an HIV Protease assay to test
if they inhibit the enzyme.
Shefali Srivastava and Jocelyn Towe Figure 1.b. Amplified signal
➢The objective of this project was to synthesize water soluble derivatives of received by the Mass
Spectrometer at 11.403
matrinic acid and to test them for the inhibition of HIV Protease enzyme.
minute mark confirming the
Method presence of Matrinamide.
Trial 1:

Figure 2. NMR
Spectrum for Matrine
methyl ester.

Multiple attempts were made to synthesize matrinic acid from matrine


Matrine methyl ester and Matrinamide Figure 3. IR Spectrum
using alkaline hydrolysis, and then to use the resulting matrinic acid to
synthesize
e the ester and amide using thionyl chloride and ammonia
were made from Matrine. for Matrinamide.
Non-Cognitive Predictors of Student Success:
A Predictive Validity Comparison Between Domestic and International Students
respectively. However, it was found that due to acidic conditions, matrinic
acid reverted back to matrine, thereby also preventing the synthesis of the
ester and amide.
Trial 2: They were both water soluble. ➢ The water solubility of the ester and amide is convenient as it
Discussion

broadens the applications of these molecules in pharmaceutical


testing and for further testing.

However, they showed no activity for ➢ More research could be done on oxymatrine derivatives instead of
matrine derivatives.

Trial 1 indicated that the synthesis of the matrine ethyl ester via matrinic acid
inhibition of HIV Protease. ➢ The synthesized derivatives are potential activators for the HIV
was time consuming and inefficient. Therefore, the scheme was modified to Protease enzyme and more research is currently being done to
skip the step involving the matrinic acid. Matrine methyl ester was instead confirm this.
synthesized directly from matrine using hydrochloric acid and methanol. The Acknowledgments
ester was then used to make matrinamide by the addition of ammonia and
ethanol over heat. ➢ Chemistry, Physics and Geoscience Department and Biology
Department at Meredith College for providing the instruments and
Methyl matrine ester and matrinamide were then tested for HIV Protease the environment for this project to be successful.
Inhibition using ProteinOne HIV-1 Protease Assay Kit. ➢ Wake Young Women’s Leadership Academy for providing Jocelyn
Towe with the opportunity to contribute to this project.
Results and Verification References
Table 1. Results of HIV Protease Assay testing
➢ The synthesis of the ester and amide was Matrinamide and Matrine methyl ester.

verified using Nuclear Magnetic Resonance • Wang L.; You Y.; Wang S.;Liu B.; Wang J.; Lin X.; Chen.; Liang G.;
Yang H. Synthesis, Characterization and in vitro Anti-tumor
(NMR), Infrared Spectroscopy (IR), and Mass enzyme + enzyme +
enzyme +
substrate + substrate + activities of Matrine derivatives. Bioorganic and Medicinal
Spectrometry (MS). substrate +
buffer
buffer + buffer + Matrine Chemistry Letters. 2012, 22, 4100-4102.
Matrinamide methyl ester
• Zhang B.; Sun Z.; Lv M.; Xu H. Semisynthesis of Matrinic Acid
➢ Both the ester and the amide are water /Alcohol/Ester Derivatives, Their Pesticidal Activities, and
soluble, but impure. 59543 59119 63072
Investigation of Mechanisms of Action against Tetrnychus
cinnabarinus. Journal of Agricultural and Food Chemistry. 2018, 66,
➢ They do not show activity for HIV Protease 12898-12910.
inhibition.