US EPA

7419686 

Journal Article 

Anti-cancer activity of carbamate derivatives of melampomagnolide B 

Janganati, V; Penthala, NR; Madadi, NR; Chen, Z; Crooks, PA; , 

2014 

Yes 

Bioorganic & Medicinal Chemistry Letters
ISSN: 0960-894X
EISSN: 1464-3405 

PERGAMON-ELSEVIER SCIENCE LTD 

OXFORD 

24 

15 

3499-3502 

English 

24928404 

10.1016/j.bmcl.2014.05.059 

WOS:000339228700056 

https://linkinghub.elsevier.com/retrieve/pii/S0960894X14005599
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Melampomagnolide B (MMB) is a natural sesquiterpene structurally related to parthenolide (PTL). We have shown that MMB exhibits anti-leukemic properties similar to PTL. Unlike PTL, the presence of a primary hydroxyl group in the MMB molecule allows the opportunity for examining the biological activity of a variety of conjugated analogs of MMB. We have now synthesized a series of carbamate analogs of MMB and evaluated these derivatives for anti-cancer activity against a panel of sixty human cancer cell lines. Analogs 6a and 6e exhibited promising anti-leukemic activity against human leukemia cell line CCRF-CEM with GI50 values of 680 and 620 nM, respectively. Analog 6a also showed GI50 values of 1.98 and 1.38 μM respectively, against RPMI-8226 and SR leukemia cell lines and GI50 values of 460 and 570 nM against MDA-MB-435 melanoma and MDA-MB-468 breast cancer cell lines, respectively. Analog 6e had GI50 values of 650 and 900 nM against HOP-92 non-small cell lung and RXF 393 renal cancer cell lines. 

Anti-cancer activity; Carbamates; Heterocyclic amines; Melampomagnolide B; Parthenolide; antileukemic agent; antineoplastic agent; carbamic acid derivative; melampomagnolide b; reactive oxygen metabolite; unclassified drug; [1alpha methyl 8 methylene 9 oxo 1alpha,2,3,6,7, 7alpha,8,9,10alpha,10beta decahydrooxirenol(2',3':9,10)cyclodecal[1,2 b]furan 5 yl]methyl (3 morpholinopropyl)carbamate; [1alpha methyl 8 methylene 9 oxo 1alpha,2,3,6,7, 7alpha,8,9,10alpha,10beta decahydrooxirenol(2',3':9,10)cyclodecal[1,2 b]furan 5 yl]methyl [3 (1h imidazol 1 yl)propyl]carbamate; [1alpha methyl 8 methylene 9 oxo 1alpha,2,3,6,7, 7alpha,8,9,10alpha,10beta decahydrooxirenol(2',3':9,10)cyclodecal[1,2 b]furan 5 yl]methyl [5 (methylthio) 1h 1,2,4 triazol 3 yl]carbamate; [1alpha methyl 8 methylene 9 oxo 1alpha,2,3,6,7, 7alpha,8,9,10alpha,10beta decahydrooxirenol[2',3':9,10]cyclodecal[1,2 b]furan 5 yl]methyl 4,4 difluoropiperidine 1 carboxylate; [1alpha methyl 8 methylene 9 oxo 1alpha,2,3,6,7, 7alpha,8,9,10alpha,10beta decahydrooxirenol[2',3':9,10]cyclodecal[1,2 b]furan 5 yl]methyl [2 (pyridin 2 yl)ethyl]carbamate; [1alpha methyl 8 methylene 9 oxo 1alpha,2,3,6,7, 7alpha,8,9,10alpha,10beta decahydrooxirenol[2',3':9,10]cyclodecal[1,2 b]furan 5 yl]methyl [2 (pyrrolidin 1 yl)ethyl]carbamate; [1alpha methyl 8 methylene 9 oxo 1alpha,2,3,6,7, 7alpha,8,9,10alpha,10beta decahydrooxirenol[2',3':9,10]cyclodecal[1,2 b]furan 5 yl]methyl [2 morpholino ethyl]carbamate; antineoplastic agent; carbamic acid derivative; melampomagnolide B; sesquiterpene; antineoplastic agent; carbamic acid derivative; hydroxyl group; melampomagnolide b; parthenolide; antineoplastic activity; apoptosis; article; breast cancer; breast cancer cell line; cancer cell; cancer inhibition; carbon nuclear magnetic resonance; central nervous system tumor; colon cancer; controlled study; drug half life; drug synthesis; human; human cell; kidney cancer; leukemia; leukemia cell line; lung cancer; lung cancer cell line; lung non small cell cancer; melanoma; Michael addition; nuclear magnetic resonance; ovary cancer; oxidative stress; prostate cancer; renal cancer cell line; structure activity relation; cell proliferation; chemical structure; chemistry; dose response; drug effects; drug screening; synthesis; Tanacetum parthenium; tumor cell line; Article; biological activity; cancer cell line; non small cell lung cancer; Antineoplastic Agents, Phytogenic; Carbamates; Cell Line, Tumor; Cell Proliferation; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Sesquiterpenes; Structure-Activity Relationship; Tanacetum parthenium