J W Daly

Summary

Affiliation: National Institutes of Health
Country: USA

Publications

  1. ncbi request reprint Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, Maryland 20892 0820, USA
    J Nat Prod 68:1556-75. 2005
  2. ncbi request reprint Caffeine analogs: biomedical impact
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892 0820, USA
    Cell Mol Life Sci 64:2153-69. 2007
  3. pmc Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine recepto
    Soushi Kobayashi
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930 0194, Japan
    Beilstein J Org Chem 3:30. 2007
  4. ncbi request reprint Biologically active substances from amphibians: preliminary studies on anurans from twenty-one genera of Thailand
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, DHHS, NIH, Bldg 8, Rm 1A17, Bethesda, MD 20892 USA
    Toxicon 44:805-15. 2004
  5. ncbi request reprint Nicotinic agonists, antagonists, and modulators from natural sources
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892, USA
    Cell Mol Neurobiol 25:513-52. 2005
  6. ncbi request reprint Marine toxins and nonmarine toxins: convergence or symbiotic organisms?
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892 0820, USA
    J Nat Prod 67:1211-5. 2004
  7. pmc Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, MD 20892 0820, USA
    Proc Natl Acad Sci U S A 100:11092-7. 2003
  8. pmc Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    Proc Natl Acad Sci U S A 99:13996-4001. 2002
  9. ncbi request reprint Alkaloids in bufonid toads (melanophryniscus): temporal and geographic determinants for two argentinian species
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institute Health, DHHS, Bethesda, MD 20892 0820, USA
    J Chem Ecol 33:871-87. 2007
  10. doi request reprint Individual and geographic variation of skin alkaloids in three species of Madagascan poison frogs (Mantella)
    John W Daly
    Laboratory of Bioorganic Chemistry, HHS, NIDDK, NIH, Bethesda, MD 20892, USA
    J Chem Ecol 34:252-79. 2008

Collaborators

Detail Information

Publications64

  1. ncbi request reprint Alkaloids from amphibian skin: a tabulation of over eight-hundred compounds
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, Maryland 20892 0820, USA
    J Nat Prod 68:1556-75. 2005
    ....
  2. ncbi request reprint Caffeine analogs: biomedical impact
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892 0820, USA
    Cell Mol Life Sci 64:2153-69. 2007
    ..Adverse effects can include anxiety, hypertension, certain drug interactions, and withdrawal symptoms...
  3. pmc Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine recepto
    Soushi Kobayashi
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930 0194, Japan
    Beilstein J Org Chem 3:30. 2007
    ....
  4. ncbi request reprint Biologically active substances from amphibians: preliminary studies on anurans from twenty-one genera of Thailand
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, DHHS, NIH, Bldg 8, Rm 1A17, Bethesda, MD 20892 USA
    Toxicon 44:805-15. 2004
    ..Trace amounts of pumiliotoxin alkaloids were detected in a ranid frog (Limnonectes kuhli). A further 18 species did not exhibit noxious or toxic properties to a significant extent...
  5. ncbi request reprint Nicotinic agonists, antagonists, and modulators from natural sources
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892, USA
    Cell Mol Neurobiol 25:513-52. 2005
    ..3. Clearly, research on acetylcholine receptors and functions has been dependent on key natural products and the synthetic agents that they inspired...
  6. ncbi request reprint Marine toxins and nonmarine toxins: convergence or symbiotic organisms?
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892 0820, USA
    J Nat Prod 67:1211-5. 2004
    ..The occurrence and possible origin of tetrodotoxin and congeners, including chiriquitoxin, and of the saxitoxin analogue zetekitoxin in amphibians are reviewed...
  7. pmc Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, MD 20892 0820, USA
    Proc Natl Acad Sci U S A 100:11092-7. 2003
    ..Thus, the evolutionary development of a pumiliotoxin 7-hydroxylase would have provided frogs of the genus Dendrobates with a means of enhancing the antipredator potency of ingested PTXs...
  8. pmc Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    Proc Natl Acad Sci U S A 99:13996-4001. 2002
    ....
  9. ncbi request reprint Alkaloids in bufonid toads (melanophryniscus): temporal and geographic determinants for two argentinian species
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institute Health, DHHS, Bethesda, MD 20892 0820, USA
    J Chem Ecol 33:871-87. 2007
    ..Furthermore, alkaloid profiles of M. stelzneri and M. rubriventris strongly differed, probably reflecting differences in the ecosystem and hence in availability of alkaloid-containing arthropods...
  10. doi request reprint Individual and geographic variation of skin alkaloids in three species of Madagascan poison frogs (Mantella)
    John W Daly
    Laboratory of Bioorganic Chemistry, HHS, NIDDK, NIH, Bethesda, MD 20892, USA
    J Chem Ecol 34:252-79. 2008
    ..Alkaloid compositions in mantellid poison frogs are diverse and highly dependent on geographic location that appear to be largely determined by the nature and availability of alkaloid-containing prey items...
  11. ncbi request reprint Ernest Guenther award in chemistry of natural products. Amphibian skin: a remarkable source of biologically active arthropod alkaloids
    John W Daly
    Chief, Section of Pharmacodynamics, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892 0820, USA
    J Med Chem 46:445-52. 2003
  12. ncbi request reprint Stimulation of phosphoinositide breakdown in brain synaptoneurosomes by agents that activate sodium influx: antagonism by tetrodotoxin, saxitoxin, and cadmium
    F Gusovsky
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, Bethesda, Maryland 20892
    Mol Pharmacol 32:479-87. 1987
    ..However, cadmium also may in some way inhibit phosphoinositide breakdown elicited by sodium channel agents at a point subsequent to sodium influx...
  13. ncbi request reprint Voltage-dependent sodium channels in synaptoneurosomes: studies with 22Na+ influx and [3H]saxitoxin and [3H]batrachotoxinin-A 20-alpha-benzoate binding. Effects of proparacaine isothiocyanate
    F Gusovsky
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892
    Brain Res 518:101-6. 1990
    ..The results indicate that virtual elimination of binding sites labeled by [3H]BTX-B in the presence of scorpion venom by PROPRIT has little effect on sodium influx induced by BTX.(ABSTRACT TRUNCATED AT 250 WORDS)..
  14. ncbi request reprint Syntheses and adrenergic activities of ring-fluorinated epinephrines
    A Adejare
    Laboratory of Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, Bethesda, Maryland 20892
    J Med Chem 31:1972-7. 1988
    ..Thus, 2-FEpi is a relatively selective beta-adrenergic ligand, while 6-FEpi is a relatively selective alpha-adrenergic ligand. Fluorine substitution of Epi also can markedly increase potency at either alpha- or beta-adrenergic receptors...
  15. ncbi request reprint 8-Aryl-and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors
    M T Shamim
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, Bethesda, Maryland 20892
    J Med Chem 31:613-7. 1988
    ..8-Piperidinyl and 8-pyrazinyl analogues had very low activities as adenosine receptor antagonists...
  16. ncbi request reprint Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions
    M T Shamim
    Laboratory of Bioorganic Chemistry, National Institutes of Health, Bethesda, Maryland 20892
    J Med Chem 32:1231-7. 1989
    ..Such A2 selectivity is in contrast to the marked A1 selectivity of 8-cycloalkyltheophyllines and 8-cycloalkyl-1,3-dipropulxanthines. The apparent selectivity of certain xanthines is dependent on the assay systems that are compared...
  17. ncbi request reprint Local anesthetics: comparison of effects on batrachotoxin-elicited sodium flux and phosphoinositide breakdown in guinea pig cerebral cortical synaptoneurosomes
    Y Nishizawa
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, Bethesda, Maryland 20892
    Mol Pharmacol 34:707-13. 1988
    ....
  18. ncbi request reprint Adenosine analogs with covalently attached lipids have enhanced potency at A1-adenosine receptors
    K A Jacobson
    Laboratory of Chemistry, NIDDK, Bethesda, MD 20892
    FEBS Lett 225:97-102. 1987
    ..The very high affinity of adenosine-lipid conjugates may be due to stabilization of these adducts in the phospholipid microenvironment of the receptor protein...
  19. ncbi request reprint Structure of alkaloid 275A, a novel 1-azabicyclo[5.3.0]decane from a dendrobatid frog, Dendrobates lehmanni: synthesis of the tetrahydrodiastereomers
    H M Garraffo
    Laboratory of Bioorganic Chemistry, NIDDK, NIH, Bethesda, Maryland 20892 0820, USA
    J Nat Prod 64:421-7. 2001
    ..Alkaloid 1 is often accompanied by other congeners, in particular a 5Z,10Z diastereomer 15, a dihydro analogue 16, and a ketone 17. Such izidines in frogs may arise from dietary ants, as do other classes of izidines...
  20. ncbi request reprint 7-Deaza-2-phenyladenines: structure-activity relationships of potent A1 selective adenosine receptor antagonists
    C E Muller
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892
    J Med Chem 33:2822-8. 1990
    ..Chloro substitution of the 2-phenyl ring appeared to improve the solubility as well as the solubility over A1 affinity ratio of 9-phenyl- and 9-(1-phenylethyl)-substituted 7-deazadenines...
  21. ncbi request reprint Procaine isothiocyanate: an irreversible inhibitor of the specific binding of [3H]batrachotoxinin-A benzoate to sodium channels
    C R Creveling
    Laboratory of Bioorganic, Chemistry National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892
    Neurochem Res 15:441-8. 1990
    ..Protection studies with procaine and other local anesthetics suggest that only the 68 kDa species was related to local anesthetic binding...
  22. ncbi request reprint Imidazodiazepinediones: a new class of adenosine receptor antagonists
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892
    J Med Chem 33:2818-21. 1990
    ..The imidazodiazepinediones had low affinity for brain benzodiazepine sites...
  23. ncbi request reprint Alkaloids from frog skins: selective probes for ion channels and nicotinic receptors
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institutes of Health, Bethesda, MD 20892 0820, USA
    Braz J Med Biol Res 28:1033-42. 1995
    ..The origins of the batrachotoxins, histrionicotoxins, pumiliotoxins and epibatidine are of particular interest in view of their remarkable biological activities...
  24. ncbi request reprint 6beta-Acyloxy(nor)tropanes: affinities for antagonist/agonist binding sites on transfected and native muscarinic receptors
    J W Daly
    National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    J Med Chem 43:2514-22. 2000
    ..The antagonist/agonist binding ratio method is clearly not always reliable for predicting agonist activity at muscarinic receptors...
  25. pmc N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae)
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892 0820, USA
    J Nat Prod 72:1110-4. 2009
    ..The alkaloids in skin extracts of three species of another genus of Amazonian poison frog, Adelphobates, were also characterized, but N-methyldecahydroquinolines were not detected...
  26. ncbi request reprint A stereospecific synthesis of (+/-)-5,8-disubstituted indolizidines and (+/-)-1,4-disubstituted quinolizidines found in poison frog skins
    P Michel
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892 0820, USA
    J Org Chem 65:8908-18. 2000
    ..The structures of the natural alkaloids were thereby established by chiral GC comparison with the exception of indolizidine 209B (I) for which a natural 209B could no longer be detected...
  27. ncbi request reprint Ammonia chemical ionization tandem mass spectrometry in structural determination of alkaloids. II. Tetraponerines from pseudomyrmecine ants
    H M Garraffo
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892-0820, USA
    Rapid Commun Mass Spectrom 15:1409-15. 2001
    ..allaborans) had T-2, T-4 and T-8, while a Chinese ant (T. binghami) had T-5, T-6, T-7 and T-8. Four other ants, T. rufonigra (India), T. penzigi (Africa), T. clypeata (Africa) and T. sp. cf. emeryi (Africa), had no tetraponerines...
  28. ncbi request reprint Effect of fluorine substitution on the adrenergic properties of 3-(tert-butylamino)-1-(3,4-dihydroxyphenoxy)-2-propanol
    A Adejare
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892
    J Med Chem 34:1063-8. 1991
    ....
  29. ncbi request reprint Bioassay-guided isolation of epiquinamide, a novel quinolizidine alkaloid and nicotinic agonist from an Ecuadoran poison frog, Epipedobates tricolor
    Richard W Fitch
    Section on Pharmacodynamics, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, Maryland 20892, USA
    J Nat Prod 66:1345-50. 2003
    ..The off-line screening technique was found to be very sensitive for the detection of compounds active at nicotinic receptors...
  30. pmc Phantasmidine: an epibatidine congener from the ecuadorian poison frog Epipedobates anthonyi
    Richard W Fitch
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892, USA
    J Nat Prod 73:331-7. 2010
    ..After synthesis, this novel rigid agonist may serve as a selective probe for beta4-containing nicotinic receptors and potentially lead to useful pharmaceuticals...
  31. pmc Frog secretions and hunting magic in the upper Amazon: identification of a peptide that interacts with an adenosine receptor
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892
    Proc Natl Acad Sci U S A 89:10960-3. 1992
    ..The vasoactive peptide sauvagine, the opioid peptides, and adenoregulin and related peptides affect behavior in mice and presumably contribute to the behavioral sequelae observed in humans...
  32. ncbi request reprint Multiple effects of caffeine on Ca2+ release and influx in human B lymphocytes
    Y Sei
    Department of Anesthesiology, Uniformed Services University of the Health Sciences, Bethesda, MD 20814 4799, USA
    Cell Calcium 29:149-60. 2001
    ..Our results suggest the need for caution regarding use of caffeine simply as a RYR-activator to study Ca2+ homeostasis in eucaryotic cells...
  33. pmc Indolizidine 239Q and quinolizidine 275I. Major alkaloids in two Argentinian bufonid toads (Melanophryniscus)
    John W Daly
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, MD 20892, USA
    Toxicon 52:858-70. 2008
    ..A third alkaloid, 249F (3), is postulated to be a homopumiliotoxin with an unprecedented conjugated exocyclic diene moiety...
  34. doi request reprint Roughing it: a mantellid poison frog shows greater alkaloid diversity in some disturbed habitats
    Nirina R Andriamaharavo
    Laboratory of Bioorganic Chemistry, NIDDK, NIH, DHHS, Bethesda, Maryland 20892, USA
    J Nat Prod 73:322-30. 2010
    ..This constancy of skin alkaloid composition likely reflects a constancy of dietary prey items consumed by frogs at undisturbed sites...
  35. ncbi request reprint Loperamide: novel effects on capacitative calcium influx
    J W Daly
    Laboratory of Bioorganic Chemistry, National Institutes of Health Bethesda, Maryland 20892, USA
    Cell Mol Life Sci 57:149-57. 2000
    ..The mechanism whereby loperamide enhances levels of intracellular calcium elevated by capacitative calcium influx is, as yet, undefined...
  36. ncbi request reprint Functional characterization of the A2b adenosine receptor in NIH 3T3 fibroblasts
    L E Brackett
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892
    Biochem Pharmacol 47:801-14. 1994
    ..In a series of non-xanthine antagonists, most compounds were equipotent or slightly more potent at the A2a receptor except for alloxazine, which was approximately 9-fold selective for the A2b receptor...
  37. ncbi request reprint Mouse beta-TC6 insulinoma cells: high expression of functional alpha3beta4 nicotinic receptors mediating membrane potential, intracellular calcium, and insulin release
    Masahiro Ohtani
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892 0820, USA
    Mol Pharmacol 69:899-907. 2006
    ..The binding and functional data suggest that the major nicotinic receptor is composed of alpha3 and beta4 subunits. The beta-TC6 cells thus provide a model system for pharmacological study of such nicotinic receptors...
  38. doi request reprint Co-existence of muscarinic and nicotinic receptors and their functional interaction in mouse Beta-TC6 cells
    Masahiro Ohtani
    Chemical Biology, National Institutes of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    Eur J Pharmacol 604:150-7. 2009
    ....
  39. ncbi request reprint Halogenated and isosteric cytisine derivatives with increased affinity and functional activity at nicotinic acetylcholine receptors
    Richard W Fitch
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, MD 20892, USA
    Bioorg Med Chem Lett 15:1221-4. 2005
    ..Caulophylline methiodide was less potent than cytisine, but retained significant activity. Thiocytisine was relatively weak in potency and efficacy, but was significantly selective for the alpha4beta2 subtype...
  40. ncbi request reprint The husbandry and care of dendrobatid frogs
    Mark B St Claire
    Laboratory Animal Science Section and Laboratory of Bioorganic Chemistry, NIDDK, DHHS, NIH, Bethesda, Maryland, USA
    Contemp Top Lab Anim Sci 44:8-14. 2005
    ..A brief summary of dendrobatid research highlights is provided...
  41. ncbi request reprint Phosphorimaging detection and quantitation for isotopic ion flux assays
    Richard W Fitch
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Department of Health and Human Services, Bethesda, MD 20892, USA
    Anal Biochem 342:260-70. 2005
    ..Phosphorimaging detection allows for reliable beta counting of up to 1,200 simultaneous samples with excellent sensitivity and is amenable for application to high-throughput screening...
  42. ncbi request reprint Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase
    Song Ye
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892, USA
    J Med Chem 47:1207-13. 2004
    ..The presence of fluorine on the purine ring increased potency of inhibition, and the most potent compound, beta-2',5'-dideoxy-2-fluoroadenosine (1b), was 3 times more potent than beta-2',5'-dideoxyadenosine...
  43. pmc Membrane potential fluorescence: a rapid and highly sensitive assay for nicotinic receptor channel function
    Richard W Fitch
    Section on Pharmacodynamics, Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    Proc Natl Acad Sci U S A 100:4909-14. 2003
    ..Thus, membrane potential serves as a sensitive measure of nicotinic activity, and the resulting depolarization may be as important as calcium in cell signaling...
  44. ncbi request reprint Reserpine: interactions with batrachotoxin and brevetoxin sites on voltage-dependent sodium channels
    Andrew Flowers
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892, USA
    Cell Mol Neurobiol 22:1-12. 2002
    ..Local anesthetics also may bind to the brevetoxin site...
  45. ncbi request reprint Homoepiboxidines: further potent agonists for nicotinic receptors
    Richard W Fitch
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Kidney and Digestive Diseases, National Institutes of Health, Bethesda, MD 20892, USA
    Bioorg Med Chem 12:179-90. 2004
    ..The time course at such ip doses was significantly longer for homoepiboxidine 3 with marked analgesia still manifest at 30 min post-injection. Epiboxidine and the homoepiboxidines were less toxic than epibatidine...
  46. pmc Melyrid beetles (Choresine): a putative source for the batrachotoxin alkaloids found in poison-dart frogs and toxic passerine birds
    John P Dumbacher
    Smithsonian Conservation Research Center, Front Royal, VA 22630, USA
    Proc Natl Acad Sci U S A 101:15857-60. 2004
    ..The family Melyridae is cosmopolitan, and relatives in Colombian rain forests of South America could be the source of the batrachotoxins found in the highly toxic Phyllobates frogs of that region...
  47. ncbi request reprint Geographic and seasonal variation in alkaloid-based chemical defenses of Dendrobates pumilio from Bocas del Toro, Panama
    Ralph A Saporito
    Department of Biological Sciences, Florida International University, Miami, FL 33199, USA
    J Chem Ecol 32:795-814. 2006
    ..However, a variety of frog skin alkaloids was recently detected in mites, suggesting that mites may also play an important role in chemical defense...
  48. ncbi request reprint Spatial and temporal patterns of alkaloid variation in the poison frog Oophaga pumilio in Costa Rica and Panama over 30 years
    Ralph A Saporito
    Department of Biological Sciences, Florida International University, Miami, FL 33199, USA
    Toxicon 50:757-78. 2007
    ..The results of this study indicate that chemical defense in a dendrobatid poison frog is dependent on geographic location and habitat type, which presumably controls the abundance and nature of alkaloid-containing arthropods...
  49. ncbi request reprint Venom chemistry of the ant Myrmicaria melanogaster from Brunei
    Tappey H Jones
    Department of Chemistry, Virginia Military Institute, Lexington, Virginia 24450, USA
    J Nat Prod 70:160-8. 2007
    ..A biogenetic relationship between the mono- and bicyclic ring systems is proposed...
  50. pmc A common pumiliotoxin from poison frogs exhibits enantioselective toxicity against mosquitoes
    Paul J Weldon
    Conservation and Research Center, Smithsonian Institution, Front Royal, VA 22630, USA
    Proc Natl Acad Sci U S A 103:17818-21. 2006
    ..This value is substantially lower than that estimated for the cutaneous abundance of this compound in some frogs, an observation consistent the function of PTX 251D in anuran chemical defense against ectoparasitic arthropods...
  51. ncbi request reprint Alkaloids of anuran skin: antimicrobial function?
    Cyrus Macfoy
    Biology Department, American Universitym Washington, DC, USA
    Z Naturforsch C 60:932-7. 2005
    ..albicans. The results suggest that certain of the skin alkaloids of poison frogs, in addition to being noxious to predators, may also benefit the frog through protection against skin infections...
  52. ncbi request reprint A revised structure for alkaloid 235C isolated from skin extracts of mantellid (Mantella) frogs of Madagascar
    N Rabe Andriamaharavo
    Laboratoire de Chimie Organique Produits Naturels, Universite d Antananarivo, Antananarivo 1001, Madagascar, School of Chemistry, Queen s University, Belfast BT9 5AG, Northern Ireland, UK
    J Nat Prod 68:1743-8. 2005
    ..A comparison is presented between the mass, infrared, and (1)H NMR spectra of 235C (2) and a synthetic dehydrohomopumiliotoxin (1), initially proposed incorrectly as the structure for 235C...
  53. pmc Formicine ants: An arthropod source for the pumiliotoxin alkaloids of dendrobatid poison frogs
    Ralph A Saporito
    Department of Biological Sciences, Florida International University, Miami, FL 33199, USA
    Proc Natl Acad Sci U S A 101:8045-50. 2004
    ..These findings further support the significance of ant-specialization and alkaloid sequestration in the evolution of bright warning coloration in poison frogs and toads...
  54. doi request reprint N,N-acetals as N-acyliminium ion precursors: synthesis and absolute stereochemistry of epiquinamide
    Marloes A Wijdeven
    Radboud University Nijmegen, Institute for Molecules and Materials, Toernooiveld 1, NL 6525 ED Nijmegen, The Netherlands
    Org Lett 10:4001-3. 2008
    ....
  55. ncbi request reprint Synthesis of alkaloid 223A and a structural revision
    Naoki Toyooka
    Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, 930 0194, Japan
    Org Lett 4:1715-7. 2002
    ..The proposed structure for natural 223A (A, absolute configuration unknown) was revised to B, and the relative stereostructure was determined to be 5R*,6R*,8R*,9S* by the present synthesis...
  56. ncbi request reprint Imidazo[2,1-i]purin-5-ones and related tricyclic water-soluble purine derivatives: potent A(2A)- and A(3)-adenosine receptor antagonists
    Christa E Muller
    Pharmaceutical Institute Poppelsdorf, University of Bonn, Bonn, Germany
    J Med Chem 45:3440-50. 2002
    ..The most potent A(3) antagonist of the present series was (R)-4-methyl-8-ethyl-2-phenyl-imidazo[2,1-i]purin-5-one (R-24) exhibiting a K(i) value of 2.3 nM and high selectivity for A(3) receptors vs all other AR subtypes...
  57. ncbi request reprint 1,8-disubstituted xanthine derivatives: synthesis of potent A2B-selective adenosine receptor antagonists
    Alaa M Hayallah
    University of Bonn, Pharmaceutical Institute Poppelsdorf, Bonn, Germany
    J Med Chem 45:1500-10. 2002
    ..30-fold selectivity versus rat A1, and greater than 400-fold selectivity versus human A2A and A3 ARs. The new potent, selective, water-soluble A2B antagonists may be useful research tools for investigating A2B receptor function...
  58. ncbi request reprint Patients with malignant hyperthermia demonstrate an altered calcium control mechanism in B lymphocytes
    Yoshitatsu Sei
    Uniformed Services University of the Health Sciences, Bethesda, Maryland 20814 4799, USA
    Anesthesiology 97:1052-8. 2002
    ..Because human B lymphocytes express the RYR1, it is hypothesized that Ca2+ homeostasis in B lymphocytes is altered in MHS individuals...
  59. ncbi request reprint Dihydropyridines as inhibitors of capacitative calcium entry in leukemic HL-60 cells
    Jacquie L Harper
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, Bldg 8, Rm 1A17, National Institutes of Health, Bethesda, MD 20892, USA
    Biochem Pharmacol 65:329-38. 2003
    ..N-Methylnitrendipine (IC(50) 2.6 microM, MRS 1844) and N-propargylnifrendipine (IC(50) 1.7 microM, MRS 1845) represent possible lead compounds for the development of selective SOC channel inhibitors...
  60. pmc Oribatid mites as a major dietary source for alkaloids in poison frogs
    Ralph A Saporito
    Department of Biological Sciences, Florida International University, Miami, FL 33199, USA
    Proc Natl Acad Sci U S A 104:8885-90. 2007
    ..pumilio, as well as in the diets of other poison frogs. The results of this study indicate that mites are a significant arthropod repository of a variety of alkaloids and represent a major dietary source of alkaloids in poison frogs...
  61. ncbi request reprint Caffeine analogs: effects on ryanodine-sensitive calcium-release channels and GABAA receptors
    Dan Shi
    Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland, USA
    Cell Mol Neurobiol 23:331-47. 2003
    ..6. Structure-activity relationships for xanthines do differ for calcium-release channels and and for different sites on GABAA receptors, but no highly selective lead compounds were identified...
  62. ncbi request reprint Factors associated with frequent admissions to an acute geriatric psychiatric inpatient unit
    Benjamin K P Woo
    Senior Behavioral Health Program, University of California, San Diego, CA 92103 8631, USA
    J Geriatr Psychiatry Neurol 19:226-30. 2006
    ....
  63. pmc The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: a potent sodium-channel blocker
    Mari Yotsu-Yamashita
    Graduate School of Agricultural Science, Tohoku University, Sendai 981 8555, Japan
    Proc Natl Acad Sci U S A 101:4346-51. 2004
    ..The IC50 values were 280 pM for human heart channels, 6.1 pM for rat brain IIa channels, and 65 pM for rat skeletal muscle channels, thus being roughly 580-, 160-, and 63-fold more potent at these channels than saxitoxin...
  64. ncbi request reprint Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors
    Naoki Toyooka
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama 930 0194, Japan
    Bioorg Med Chem Lett 17:5872-5. 2007
    ..Thus, based on these studies, it would appear that C4 substituents greater in length than the allyl of 1-epi-207I reduce alpha7-potency without affecting alpha4beta2-potency...