Halomon
Encyclopedia
Halomon is a polyhalogenated
monoterpene
first isolated from the marine red algae
Portieria hornemannii
. Halomon has attracted research interest because of its promising profile of selective cytotoxicity
that suggests its potential use as an antitumor agent
.
Halomon is in a class of chemical compounds known as halocarbon
s, which are often potent alkylating agent
s which may be toxic to individual cells or to living organisms. The red algae that naturally produce halomon and other related compounds probably do so as a poisonous defense against fish or other marine life that may see it as a potential source of food. Halomon, however, is a selective toxin; studies at the National Cancer Institute
have indicated that it is more toxic to certain types of tumor cells than to other cells.
The natural algal source of halomon is difficult to locate, identify, and collect and the concentration of halomon in the alga is low. Therefore, obtaining a sufficient amount of halomon to conduct preclinical research has been difficult. Consequently, there has been active interest in developing synthetic methods in the laboratory for the preparation of halomon and related compounds.
Recent research has shown that halomon and a related halogenated monoterpene are inhibitors of the enzyme DNA methyltransferase
, suggesting a possible mechanism of action
for the pharmacological effects.
Halogen
The halogens or halogen elements are a series of nonmetal elements from Group 17 IUPAC Style of the periodic table, comprising fluorine , chlorine , bromine , iodine , and astatine...
monoterpene
Monoterpene
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear or contain rings...
first isolated from the marine red algae
Red algae
The red algae are one of the oldest groups of eukaryotic algae, and also one of the largest, with about 5,000–6,000 species of mostly multicellular, marine algae, including many notable seaweeds...
Portieria hornemannii
Portieria hornemannii
Portieria hornemannii is a species of red algae in the family Rhizophyllidaceae. The chemical halomon was discovered in this species.-External links:* at AlgaeBase...
. Halomon has attracted research interest because of its promising profile of selective cytotoxicity
Cytotoxicity
Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are a chemical substance, an immune cell or some types of venom .-Cell physiology:...
that suggests its potential use as an antitumor agent
Chemotherapy
Chemotherapy is the treatment of cancer with an antineoplastic drug or with a combination of such drugs into a standardized treatment regimen....
.
Halomon is in a class of chemical compounds known as halocarbon
Halocarbon
Halocarbon compounds are chemicals in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms resulting in the formation of organofluorine compounds, organochlorine compounds, organobromine compounds, and organoiodine compounds...
s, which are often potent alkylating agent
Alkylation
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene . Alkylating agents are widely used in chemistry because the alkyl group is probably the most common group encountered in...
s which may be toxic to individual cells or to living organisms. The red algae that naturally produce halomon and other related compounds probably do so as a poisonous defense against fish or other marine life that may see it as a potential source of food. Halomon, however, is a selective toxin; studies at the National Cancer Institute
National Cancer Institute
The National Cancer Institute is part of the National Institutes of Health , which is one of 11 agencies that are part of the U.S. Department of Health and Human Services. The NCI coordinates the U.S...
have indicated that it is more toxic to certain types of tumor cells than to other cells.
The natural algal source of halomon is difficult to locate, identify, and collect and the concentration of halomon in the alga is low. Therefore, obtaining a sufficient amount of halomon to conduct preclinical research has been difficult. Consequently, there has been active interest in developing synthetic methods in the laboratory for the preparation of halomon and related compounds.
Recent research has shown that halomon and a related halogenated monoterpene are inhibitors of the enzyme DNA methyltransferase
DNA methyltransferase
In biochemistry, the DNA methyltransferase family of enzymescatalyze the transfer of a methyl group to DNA. DNA methylation serves a wide variety of biological functions...
, suggesting a possible mechanism of action
Mechanism of action
In pharmacology, the term mechanism of action refers to the specific biochemical interaction through which a drug substance produces its pharmacological effect...
for the pharmacological effects.