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Indolequinones
Indolequinones are molecules which are based upon an indole but have two additional ketone groups (quinone) attached to the ring structure. This simple indolequinone indole-5,6-quinone is produced during the ripening of some fruit. Other examples of indolequinones and the related mitosenes include natural compound mitomycin The mitomycins are a family of aziridine-containing natural products isolated from ''Streptomyces caespitosus'' or ''Streptomyces lavendulae.'' They include mitomycin A, mitomycin B, and mitomycin C. When the name mitomycin occurs alone, it usually ... and the related chemotherapeutic agent apaziquone. External links * {{heterocyclic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mitomycin
The mitomycins are a family of aziridine-containing natural products isolated from ''Streptomyces caespitosus'' or ''Streptomyces lavendulae.'' They include mitomycin A, mitomycin B, and mitomycin C. When the name mitomycin occurs alone, it usually refers to mitomycin C, its international nonproprietary name. Mitomycin C is used as a medicine for treating various disorders associated with the growth and spread of cells. Biosynthesis In general, the biosynthesis of all mitomycins proceeds via combination of 3-amino-5-hydroxybenzoic acid (AHBA), D-glucosamine, and carbamoyl phosphate, to form the mitosane core, followed by specific tailoring steps. The key intermediate, AHBA, is a common precursor to other anticancer drugs, such as rifamycin and ansamycin. Specifically, the biosynthesis begins with the addition of phosphoenolpyruvate (PEP) to erythrose-4-phosphate (E4P) with a yet undiscovered enzyme, which is then ammoniated to give 4-amino-3-deoxy-D-arabino heptulosonic acid- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Apaziquone
Apaziquone (tentative trade name EOquin) is an indolequinone that is a bioreductive prodrug similar to the older chemotherapeutic agent mitomycin C. In hypoxic cells, such as those on the inner surface of the urinary bladder, apaziquone is converted to active metabolites by intracellular reductases. The active metabolites alkylate DNA and lead to apoptosis. This activity is preferentially expressed in neoplastic cells. After administration of apaziquone directly into the urinary bladder (intravesically), the drug and its active metabolite were not detected in plasma, and there were no systemic side effects. Apaziquone has been applied in clinical studies sponsored by Spectrum Pharmaceuticals and Allergan for the treatment of superficial (non-muscle invasive) bladder cancer. Approximately 70% of all newly diagnosed patients with bladder cancer have non-muscle invasive bladder cancer and over one million patients in the United States and Europe are affected by the disease. The U.S ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indole
Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence. The amino acid tryptophan is an indole derivative and the precursor of the neurotransmitter serotonin. General properties and occurrence Indole is a solid at room temperature. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many perfumes. It also occurs in coal tar. The corresponding substituent is called indolyl. Indole undergoes electrophilic substitution, mainly at position 3 (see diagra ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considere ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Quinone
The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully Conjugated system, conjugated cyclic diketone, dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone" (thus the name of the class). Other important examples are 1,2-benzoquinone (''ortho''-quinone), 1,4-naphthoquinone and anthraquinone, 9,10-anthraquinone. The name is derived from that of quinic acid (with the suffix "-one" indicating a ketone), since it is one of the compounds obtained upon oxidation of quinic acid. Quinic acid, like quinine is obtained from cinchona bark, called wikt:quinaquina, quinaquina in the indigenous languages of Peruvian tribes. Properties Quinones are oxidized derivatives of aromatic compounds and are often re ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Indole-5,6-quinone
Indole-5,6-quinone is an indolequinone, a chemical compound found in the oxidative browning reaction of fruits like bananas where it is mediated by the tyrosinase type polyphenol oxidase from tyrosine and catecholamine A catecholamine (; abbreviated CA) is a monoamine neurotransmitter, an organic compound that has a catechol (benzene with two hydroxyl side groups next to each other) and a side-chain amine. Catechol can be either a free molecule or a su ...s leading to the formation of catechol melanin. Like many quinones it can undergo redox reactions via the corresponding 5,6-dihydroxyindole. See also * Dopachrome References Indolequinones {{heterocyclic-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mitosene
The mitosenes are a class of organic chemicals based on a quinone-containing three-ring structure related to the two-ring core of the indolequinones. They are derived from the mitomycins by reduction and are the active alkylating agents responsible for the antitumor Cancer can be treated by surgery, chemotherapy, radiation therapy, hormonal therapy, targeted therapy (including immunotherapy such as monoclonal antibody therapy) and synthetic lethality, most commonly as a series of separate treatments (e.g. ... activity of the mitomycins. References {{organic-chem-stub Quinones DNA replication inhibitors Enones ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Mitomycin
The mitomycins are a family of aziridine-containing natural products isolated from ''Streptomyces caespitosus'' or ''Streptomyces lavendulae.'' They include mitomycin A, mitomycin B, and mitomycin C. When the name mitomycin occurs alone, it usually refers to mitomycin C, its international nonproprietary name. Mitomycin C is used as a medicine for treating various disorders associated with the growth and spread of cells. Biosynthesis In general, the biosynthesis of all mitomycins proceeds via combination of 3-amino-5-hydroxybenzoic acid (AHBA), D-glucosamine, and carbamoyl phosphate, to form the mitosane core, followed by specific tailoring steps. The key intermediate, AHBA, is a common precursor to other anticancer drugs, such as rifamycin and ansamycin. Specifically, the biosynthesis begins with the addition of phosphoenolpyruvate (PEP) to erythrose-4-phosphate (E4P) with a yet undiscovered enzyme, which is then ammoniated to give 4-amino-3-deoxy-D-arabino heptulosonic acid- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Apaziquone
Apaziquone (tentative trade name EOquin) is an indolequinone that is a bioreductive prodrug similar to the older chemotherapeutic agent mitomycin C. In hypoxic cells, such as those on the inner surface of the urinary bladder, apaziquone is converted to active metabolites by intracellular reductases. The active metabolites alkylate DNA and lead to apoptosis. This activity is preferentially expressed in neoplastic cells. After administration of apaziquone directly into the urinary bladder (intravesically), the drug and its active metabolite were not detected in plasma, and there were no systemic side effects. Apaziquone has been applied in clinical studies sponsored by Spectrum Pharmaceuticals and Allergan for the treatment of superficial (non-muscle invasive) bladder cancer. Approximately 70% of all newly diagnosed patients with bladder cancer have non-muscle invasive bladder cancer and over one million patients in the United States and Europe are affected by the disease. The U.S ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
