Halomon: Difference between revisions
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'''Halomon''' is a [[halogen|polyhalogenated]] [[monoterpene]] first isolated from the marine [[red algae]] ''Portieria horenmannii''.<ref name=Fuller1>{{cite science | abstract= | author=Fuller, Richard W.; Cardellina, John H., II; Kato, Yoko; Brinen, Linda S.; Clardy, Jon; Snader, Kenneth M.; Boyd, Michael R. | title=A pentahalogenated monoterpene from the red alga Portieria hornemannii produces a novel cytotoxicity profile against a diverse panel of human tumor cell lines | journal=Journal of Medicinal Chemistry |year=1992 | volume=35 | issue=16 | pages=3007-3011 }}</ref><ref name=Fuller2>{{cite science | abstract= | author=Fuller, Richard W.; Cardellina, John H., II; Jurek, Jaroslaw; Scheuer, Paul J.; Alvarado-Lindner, Belinda; McGuire, Mary; Gray, Glenn N.; Steiner, Jorge Rios; Clardy, Jon; et al. | title=Isolation and Structure/Activity Features of Halomon-Related Antitumor Monoterpenes from the Red Alga ''Portieria hornemannii'' | journal=Journal of Medicinal Chemistry |year=1994 | volume=37 | issue=25 | pages=4407-4411 }}</ref> Halomon has attracted research interest because of its promising profile of selective [[cytotoxicity]] that suggests its potential use as an [[chemotherapy|antitumor agent]].<ref name=egorin>{{cite science | abstract= | author=Egorin, Merrill J.; Sentz, Dorothy L.; Rosen, D. Marc; Ballesteros, Michael F.; Kearns, Christine M.; Callery, Patrick S.; Eiseman, Julie L. | title=Plasma pharmacokinetics, bioavailability, and tissue distribution in CD2F1 mice of halomon, an antitumor halogenated monoterpene isolated from the red algae Portieria hornemannii. | journal=Cancer Chemotherapy and Pharmacology |year=1996 | volume=39 | issue=1/2 | pages=51-60 }}</ref> |
'''Halomon''' is a [[halogen|polyhalogenated]] [[monoterpene]] first isolated from the marine [[red algae]] ''Portieria horenmannii''.<ref name=Fuller1>{{cite science | abstract= | author=Fuller, Richard W.; Cardellina, John H., II; Kato, Yoko; Brinen, Linda S.; Clardy, Jon; Snader, Kenneth M.; Boyd, Michael R. | title=A pentahalogenated monoterpene from the red alga Portieria hornemannii produces a novel cytotoxicity profile against a diverse panel of human tumor cell lines | journal=Journal of Medicinal Chemistry |year=1992 | volume=35 | issue=16 | pages=3007-3011 | doi=10.1021/jm00094a012 }}</ref><ref name=Fuller2>{{cite science | abstract= | author=Fuller, Richard W.; Cardellina, John H., II; Jurek, Jaroslaw; Scheuer, Paul J.; Alvarado-Lindner, Belinda; McGuire, Mary; Gray, Glenn N.; Steiner, Jorge Rios; Clardy, Jon; et al. | title=Isolation and Structure/Activity Features of Halomon-Related Antitumor Monoterpenes from the Red Alga ''Portieria hornemannii'' | journal=Journal of Medicinal Chemistry |year=1994 | volume=37 | issue=25 | pages=4407-4411 | doi=10.1021/jm00051a019 }}</ref> Halomon has attracted research interest because of its promising profile of selective [[cytotoxicity]] that suggests its potential use as an [[chemotherapy|antitumor agent]].<ref name=egorin>{{cite science | abstract= | author=Egorin, Merrill J.; Sentz, Dorothy L.; Rosen, D. Marc; Ballesteros, Michael F.; Kearns, Christine M.; Callery, Patrick S.; Eiseman, Julie L. | title=Plasma pharmacokinetics, bioavailability, and tissue distribution in CD2F1 mice of halomon, an antitumor halogenated monoterpene isolated from the red algae Portieria hornemannii. | journal=Cancer Chemotherapy and Pharmacology |year=1996 | volume=39 | issue=1/2 | pages=51-60 | doi=10.1007/s002800050537 }}</ref> |
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Halomon is in a class of chemical compounds known as [[halocarbon]]s, which are often potent [[alkylation|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.<ref name=Fuller1> </ref> |
Halomon is in a class of chemical compounds known as [[halocarbon]]s, which are often potent [[alkylation|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.<ref name=Fuller1> </ref> |
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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.<ref name=Schlama>{{cite science | abstract= | author=Schlama, Thierry; Baati, Rachhid; Gouveneur, Veronique; Valleix, Alain; Flack, John R.; Mioskowski, Charles | title=Total synthesis of (± )-halomon by a Johnson-Claisen rearrangement | journal=Angewandte Chemie, International Edition |year=1998 | volume=37 | issue=15 | pages=2085-2087 }}</ref><ref name=Jung>{{cite science | abstract= | author=Jung, Michael E.; Parker, Michael H. | title=Synthesis of Several Naturally Occurring Polyhalogenated Monoterpenes of the Halomon Class | journal=Journal of Organic Chemistry |year=1997 | volume=62 | issue=21 | pages=7094-7095 }}</ref><ref name=Sotokawa>{{cite science | abstract= | author=Sotokawa, Takayuki; Noda, Takeshi; Pi, Sun; Hirama, Masahiro | title=A three-step synthesis of halomon | journal=Angewandte Chemie |year=2000 | volume=39 | issue=19 | pages=3430-3432 }}</ref> |
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.<ref name=Schlama>{{cite science | abstract= | author=Schlama, Thierry; Baati, Rachhid; Gouveneur, Veronique; Valleix, Alain; Flack, John R.; Mioskowski, Charles | title=Total synthesis of (± )-halomon by a Johnson-Claisen rearrangement | journal=Angewandte Chemie, International Edition |year=1998 | volume=37 | issue=15 | pages=2085-2087 | doi=10.1002/(SICI)1521-3773(19980817)37:15%3C2085::AID-ANIE2085%3E3.0.CO;2-J }}</ref><ref name=Jung>{{cite science | abstract= | author=Jung, Michael E.; Parker, Michael H. | title=Synthesis of Several Naturally Occurring Polyhalogenated Monoterpenes of the Halomon Class | journal=Journal of Organic Chemistry |year=1997 | volume=62 | issue=21 | pages=7094-7095 | doi = 10.1021/jo971371+ }}</ref><ref name=Sotokawa>{{cite science | abstract= | author=Sotokawa, Takayuki; Noda, Takeshi; Pi, Sun; Hirama, Masahiro | title=A three-step synthesis of halomon | journal=Angewandte Chemie |year=2000 | volume=39 | issue=19 | pages=3430-3432 | doi=10.1002/1521-3773(20001002)39:19%3C3430::AID-ANIE3430%3E3.0.CO;2-3 }}</ref> |
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Recent research has shown that halomon and a related halogenated monoterpene are [[enzyme inhibition|inhibitors]] of the enzyme [[DNA methyltransferase]], suggesting a possible [[mechanism of action]] for the pharmacological effects.<ref name=Andrianasolo>{{cite science | abstract= | author=Andrianasolo, Eric H.; France, Dennis; Cornell-Kennon, Susan; Gerwick, William H. | title=DNA Methyl Transferase Inhibiting Halogenated Monoterpenes from the Madagascar Red Marine Alga ''Portieria hornemannii'' | journal=Journal of Natural Products | year=2006 | volume=69 | issue=4 | pages=576-579 }}</ref> |
Recent research has shown that halomon and a related halogenated monoterpene are [[enzyme inhibition|inhibitors]] of the enzyme [[DNA methyltransferase]], suggesting a possible [[mechanism of action]] for the pharmacological effects.<ref name=Andrianasolo>{{cite science | abstract= | author=Andrianasolo, Eric H.; France, Dennis; Cornell-Kennon, Susan; Gerwick, William H. | title=DNA Methyl Transferase Inhibiting Halogenated Monoterpenes from the Madagascar Red Marine Alga ''Portieria hornemannii'' | journal=Journal of Natural Products | year=2006 | volume=69 | issue=4 | pages=576-579 | doi=10.1021/np0503956 }}</ref> |
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==References== |
==References== |
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Revision as of 18:47, 17 September 2006
| Halomon | |
|---|---|
 
| |
| Chemical name | (3S,6R)-6-Bromo-3-(bromomethyl)- 2,3,7-trichloro-7-methyl-1-octene |
| Other names | (-)-Halomon |
| Chemical formula | C10H15Br2Cl3 |
| Molecular mass | 401.39 g/mol |
| CAS number | [142439-86-9] |
| Density | 1.824 g/cm3 |
| Melting point | 56-57 °C |
| SMILES | CC(C)(Cl)[C@H](Br)CC[C@](CBr)(Cl)C(Cl)=C |
| Disclaimer and references | |
Halomon is a polyhalogenated monoterpene first isolated from the marine red algae Portieria horenmannii.[1][2] Halomon has attracted research interest because of its promising profile of selective cytotoxicity that suggests its potential use as an antitumor agent.[3]
Halomon is in a class of chemical compounds known as halocarbons, which are often potent alkylating agents 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.[1]
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.[4][5][6]
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.[7]