Dendroamides, New Cyclic Hexapeptides from a Blue-Green Alga. Multidrug-Resistance Reversing Activity of Dendroamide A

Ogino, Junichi; Moore, Richard E.; Patterson, Gregory M. L.; Smith, Charles D.

doi:10.1021/np960178s

Cited by 142 publications

(96 citation statements)

References 35 publications

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“…MeOH was removed from the combined extract by evaporation under reduced pressure and and the mixture was then dried by lyophilization. The resulting oil from the 80% MeOH fraction was redissolved in 80% MeOH, and the compounds were isolated using multiple C 18 RP-HPLC runs (Phenomenex Gemini C 18 (8.6,3.7,1.6) 5,7,8,8',9 4,8,8' 7 30.3,CH 1.95,m 5,6,8,8' 8,8' 8 17.8,CH3 0.67,d (6.9) 6,7,8' 8' 15.8,CH3 0.53,d (6.9) 6,7,8 NH (2) 2.86, dd (13.6, 6.0) 5,6,8,9/9' 5,6,8,9/9' 8 135.4,qC 9/9' 129.0,CH 7.01,d (7.4) 7,9/9',11 3,6,7b,OH 10/10' 127.4,CH 6.94,dd (7.4,7. Note the observed long-range J coupling between H-2 and H-6 in both balgacyc...…”

Section: Methodsmentioning

confidence: 99%

“…6 Another seemingly unrelated activity is related to multidrug-resistance reversing activity, which has been reported for several members of this family. 7 Most interestingly, Gerwick and coworkers reported significant antimalarial activity for the venturamides. 8 Independently, we have determined antimalarial activity for the aerucyclamides 9 that displayed improved activity when compared to the earlier study.…”

Section: Introductionmentioning

confidence: 99%

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Balgacyclamides, Antiplasmodial Heterocyclic Peptides from Microcystis aeruguinosa EAWAG 251

et al. 2014

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The isolation and structural characterization of three new heterocyclic and macrocyclic peptides, balgacyclamides A-C, from Microcystis aeruginosa EAWAG 251 are reported. The constitutions were determined by 2D-NMR methods and mass spectrometry, and the configurations were assigned after ozonolysis and hydrolysis by HPLC-MS methods using Marfey's method as well as GC-MS using authentic standards. Balgacyclamides A and B were active against Plasmodium falciparum K1 in the low micromolar range, while displaying low toxicity to rat myoblasts. The isolation and structural characterization of three new heterocyclic and macrocyclic peptides, balgacyclamides A-C from Microcystis aeruginosa EAWAG 251 is reported. The constitution was determined by 2D-NMR methods and mass spectrometry and the configuration was assigned by HPLC-MS methods using Marfey's method as well as GC-MS using authentic standards. Balgacyclamides A and B were active against Plasmodium falciparum K1 in the low micromolar range, while displaying low toxicity to rat myoblasts.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Balgacyclamides, Antiplasmodial Heterocyclic Peptides from Microcystis aeruguinosa EAWAG 251

et al. 2014

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“…57 The natural product was isolated in 1996 on the basis of displaying multidrug-resistance (MDR) reversing activity in tumor cells. 58 MDR refers to a situation whereby cancer cells develop resistance to drugs while undergoing chemotherapy and its development has been a major hurdle to successful cancer chemotherapy.…”

Section: Application Of the Hendrickson Reagent In Total Synthesis Ofmentioning

confidence: 99%

The Hendrickson ‘POP’ reagent and analogues thereof: synthesis, structure, and application in organic synthesis

Moussa¹

2012

Arkivoc

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This comprehensive review discusses the synthesis, structure, and application of the Hendrickson 'POP' reagent and its analogues in organic synthesis. Specifically, the review describes applications of the preceding dehydrating agents in functional group interconversions, heterocycle synthesis, and total synthesis of natural products. Many examples are provided from the literature to show the scope and selectivity (regio and chemo) in these transformations.

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“…The natural products dendroamide A and patellamides B, C and D are the main representatives of this group (Fig. 2) (Fu et al, 1998;Ogino et al, 1996;Williams and Jacobs, 1993). These molecules typically have a smaller ring size than cycloporin A derivatives (hexa-or octapeptides) and exhibit thiazole, thiazoline, oxazole or oxazoline structural units.…”

Section: Body Task 1 Synthesize Potential Inhibitor Compounds Using mentioning

confidence: 99%

Discovery of Potent Inhibitors for Breast Cancer Multidrug Resistance

Chang¹,

Finn²,

Urbatsch³

2006

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Public reporting burden for this collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing this collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing this burden to Department of Defense, Washington Headquarters Services, Directorate for Information 5e. TASK NUMBER 5f. WORK UNIT NUMBER PERFORMING ORGANIZATION NAME(S) AND ADDRESS(ES) 8. PERFORMING ORGANIZATION REPORT NUMBERThe Scripps Research Institute La Jolla, CA 92037 SPONSORING / MONITORING AGENCY NAME(S) AND ADDRESS(ES) 10. SPONSOR/MONITOR'S ACRONYM(S) U.S. Army Medical Research and Materiel CommandFort Detrick, Maryland 21702-5012 SPONSOR/MONITOR'S REPORT NUMBER(S) DISTRIBUTION / AVAILABILITY STATEMENTApproved for Public Release; Distribution Unlimited SUPPLEMENTARY NOTESOriginal contains colored plates: ALL DTIC reproductions will be in black and white. ABSTRACTThe development of MDR in metastatic breast cancer is the primary cause of failure in the current chemotherapy treatment regimens. Although the precise nature of this clinical phenomenon is unclear and is likely due to several factors, the majority of breast tumors, like several other cancers, acquire resistance by multidrug efflux pumps. Several inhibitors (like Novartis compound PSC833) have already been discovered targeting both human MDR transporters. These MDR reversing agents however have been lacking in their potencies and their mechanism of action has been unknown. We have applied a highly integrated and innovative approach for the discovery of potent MDR inhibitors of breast cancer MDR by combining the most cutting-edge methods in chemical synthesis, drug discovery, and molecular structure. We have implemented click chemistry to produce a library of inhibitors, (2) developed functional assays, and (3) determined the structure of a close ortholog of hMDR1 with these anti-cancer compounds. 4 SUBJECT TERMS IntroductionThe development of MDR in metastatic breast cancer is the primary cause of failure in the current chemotherapy treatment regimens. Although the precise nature of this clinical phenomenon is unclear and is likely due to several factors, the majority of breast tumors, like several other cancers, acquire resistance by multidrug efflux pumps. Several inhibitors (like Novartis compound PSC833) have already been discovered targeting both human MDR transporters. These MDR reversing agents however have been lacking in their potencies and their mechanism of action has been unknown. We have applied a highly integrated and innovative approach for the discovery of potent MDR inhibitors of breast cancer MDR by combining the most cutting-edge methods in chemical synthesis, drug discovery, and molecular structure. We have implemented a new style of chemistry called click chemistry to produce a library of inhibitors, (2) dev...

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Dendroamides, New Cyclic Hexapeptides from a Blue-Green Alga. Multidrug-Resistance Reversing Activity of Dendroamide A

Cited by 142 publications

References 35 publications

Balgacyclamides, Antiplasmodial Heterocyclic Peptides from Microcystis aeruguinosa EAWAG 251

Balgacyclamides, Antiplasmodial Heterocyclic Peptides from Microcystis aeruguinosa EAWAG 251

The Hendrickson ‘POP’ reagent and analogues thereof: synthesis, structure, and application in organic synthesis

Discovery of Potent Inhibitors for Breast Cancer Multidrug Resistance

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