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Volumn 52, Issue 4, 2009, Pages 1005-1017

Total synthesis of photoactivatable or fluorescent anandamide probes: Novel bioactive compounds with angiogenic activity

Author keywords

[No Author keywords available]

Indexed keywords

7,10,13,16 DOCOSATETRAENOYLETHANOLAMIDE; ANANDAMIDE; CANNABINOID RECEPTOR; COPPER; HOMO GAMA LINOLENOYLETHANOLAMIDE; MATRIX METALLOPROTEINASE; UNCLASSIFIED DRUG; VIRODHAMINE;

EID: 64349118888     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8011382     Document Type: Article
Times cited : (14)

References (63)
  • 1
    • 34548500793 scopus 로고    scopus 로고
    • Discovery and isolation of anandamide and other endocannabinoids
    • Hanus, L. O. Discovery and isolation of anandamide and other endocannabinoids. Chem. Biodiversity 2007, 4, 1828-1841.
    • (2007) Chem. Biodiversity , vol.4 , pp. 1828-1841
    • Hanus, L.O.1
  • 4
    • 55249114431 scopus 로고    scopus 로고
    • The elmiric acids: Biologically active anandamide analogs
    • doi:10.1016/j.neuropharm.2007.11. 011
    • (b) Burstein, S. The elmiric acids: biologically active anandamide analogs. Neuropharmacology 2007, doi:10.1016/j.neuropharm.2007.11. 011.
    • (2007) Neuropharmacology
    • Burstein, S.1
  • 8
    • 64349093859 scopus 로고    scopus 로고
    • Mechoulam, R. Cannabinoids as Therapeutics; Mechoulam, R., Ed.; Milestones in Drug Therapy; Birkhauser Publisher: Basel, Switzerland, 2005.
    • Mechoulam, R. Cannabinoids as Therapeutics; Mechoulam, R., Ed.; Milestones in Drug Therapy; Birkhauser Publisher: Basel, Switzerland, 2005.
  • 9
    • 64349094708 scopus 로고    scopus 로고
    • Anandamide, an endogenous ligand of cannabinoids receptors, inhibits human breast cancer cell proliferation through a lipid rafts mediated mechanism
    • Grimaldi, C.; Bibulco, M. Anandamide, an endogenous ligand of cannabinoids receptors, inhibits human breast cancer cell proliferation through a lipid rafts mediated mechanism. Pharmacologyonline 2007, 1, 1-45.
    • (2007) Pharmacologyonline , vol.1 , pp. 1-45
    • Grimaldi, C.1    Bibulco, M.2
  • 10
    • 33947128224 scopus 로고    scopus 로고
    • Endocannabinoids and the regulation of their levels in health and disease
    • Di Marzo, V.; Petrosino, S. Endocannabinoids and the regulation of their levels in health and disease. Curr. Opin. Lipidol. 2007, 18, 129-140.
    • (2007) Curr. Opin. Lipidol , vol.18 , pp. 129-140
    • Di Marzo, V.1    Petrosino, S.2
  • 12
    • 9944235039 scopus 로고    scopus 로고
    • Binding affinity and agonist activity of putative endogenous cannabinoids at the human neocortical CB1 receptor
    • (a) Steffens, M.; Zentner, J.; Honegger, J.; Feuerstein, T. J. Binding affinity and agonist activity of putative endogenous cannabinoids at the human neocortical CB1 receptor. Biochem. Pharmacol. 2005, 69, 169-178.
    • (2005) Biochem. Pharmacol , vol.69 , pp. 169-178
    • Steffens, M.1    Zentner, J.2    Honegger, J.3    Feuerstein, T.J.4
  • 14
    • 34247603124 scopus 로고    scopus 로고
    • Endocannabinoids and their receptors: Physiology, pathology and pharmacology
    • Fride, E.; Gobshtis, N. Endocannabinoids and their receptors: physiology, pathology and pharmacology. Immunol., Endocr. Metab. Agents Med. Chem. 2007, 7, 157-173.
    • (2007) Immunol., Endocr. Metab. Agents Med. Chem , vol.7 , pp. 157-173
    • Fride, E.1    Gobshtis, N.2
  • 15
    • 64349097613 scopus 로고    scopus 로고
    • A full issue of the British Journal of Pharmacology (2008, 153 (2)) is dedicated to reviews and topics on the CB2 receptor, stemming from a meeting CB2 Receptors: New Vistas that was held in Canada in June 2007.
    • A full issue of the British Journal of Pharmacology (2008, 153 (2)) is dedicated to reviews and topics on the CB2 receptor, stemming from a meeting "CB2 Receptors: New Vistas" that was held in Canada in June 2007.
  • 17
    • 34250818776 scopus 로고    scopus 로고
    • Coevolution between cannabinoid receptors and endocannabinoid ligands
    • (b) McPartland, J. M.; Norris, R. W.; Kilpatrick, C. W. Coevolution between cannabinoid receptors and endocannabinoid ligands. Gene 2007, 397, 126-135.
    • (2007) Gene , vol.397 , pp. 126-135
    • McPartland, J.M.1    Norris, R.W.2    Kilpatrick, C.W.3
  • 18
    • 28944453205 scopus 로고    scopus 로고
    • Cannabinoid signalling
    • Demuth, D. G.; Molleman, A. Cannabinoid signalling. Life Sci. 2006, 78, 549-563.
    • (2006) Life Sci , vol.78 , pp. 549-563
    • Demuth, D.G.1    Molleman, A.2
  • 21
    • 35648960873 scopus 로고    scopus 로고
    • The complications of promiscuity: Endocannabinoid action and metabolism
    • Alexander, S. P.; Kendall, D. A. The complications of promiscuity: endocannabinoid action and metabolism. Br. J. Pharmacol. 2007, 152, 602-623.
    • (2007) Br. J. Pharmacol , vol.152 , pp. 602-623
    • Alexander, S.P.1    Kendall, D.A.2
  • 22
    • 35649011495 scopus 로고    scopus 로고
    • The contribution of cyclooxygenase-2 to endocannabinoid metabolism and action
    • Fowler, C. J. The contribution of cyclooxygenase-2 to endocannabinoid metabolism and action. Br. J. Pharmacol. 2007, 152, 594-601.
    • (2007) Br. J. Pharmacol , vol.152 , pp. 594-601
    • Fowler, C.J.1
  • 23
    • 35748973885 scopus 로고    scopus 로고
    • Novel cannabinoid receptors
    • Brown, A. J. Novel cannabinoid receptors. Br. J. Pharmacol. 2007, 152, 567-575.
    • (2007) Br. J. Pharmacol , vol.152 , pp. 567-575
    • Brown, A.J.1
  • 24
    • 64349092189 scopus 로고    scopus 로고
    • Di Marzo, V.; De Petrocellis, L. Non-CB1 Non CB2 Receptors for Endocannabinoids. In Endocannabinoids: The Brain and Body's Marijuana and Beyond; Onaivi, E. S., Sugiura, T., Di Marzo, V., Eds.; Taylor & Francis: Boca Raton, FL, 2006; 15, pp 1-174.
    • Di Marzo, V.; De Petrocellis, L. Non-CB1 Non CB2 Receptors for Endocannabinoids. In Endocannabinoids: The Brain and Body's Marijuana and Beyond; Onaivi, E. S., Sugiura, T., Di Marzo, V., Eds.; Taylor & Francis: Boca Raton, FL, 2006; Vol. 15, pp 1-174.
  • 26
    • 2342587090 scopus 로고    scopus 로고
    • Novel pharmacological targets for cannabinoids
    • Pertwee, R. G. Novel pharmacological targets for cannabinoids. Curr. Neuropharmacol. 2004, 2, 9-29.
    • (2004) Curr. Neuropharmacol , vol.2 , pp. 9-29
    • Pertwee, R.G.1
  • 27
  • 29
    • 64349102847 scopus 로고    scopus 로고
    • Anandamide Mediated Angiogenesis: Interplay between CB1 Receptor and Non CB1/CB2 Anandamide Receptor
    • Burlington, VT, International Cannabinoid Research Society
    • Perry, S. N.; Johnson, I. J.; Mukhopadhyay, S. Anandamide Mediated Angiogenesis: Interplay between CB1 Receptor and Non CB1/CB2 Anandamide Receptor. Proceedings ofthe 16th Annual Symposium ofCannabinoids, Burlington, VT, 2006; International Cannabinoid Research Society, 2006; p 61.
    • (2006) Proceedings ofthe 16th Annual Symposium ofCannabinoids , pp. 61
    • Perry, S.N.1    Johnson, I.J.2    Mukhopadhyay, S.3
  • 30
    • 64349106443 scopus 로고    scopus 로고
    • CB1 Receptor and Non-CB1/CB2 Annadmaide Receptor Mediated Differential S-Ni- trosylation of MMP: A Novel Angiogenic Switch for the Regulation of Angiogenesis
    • Burlington, VT, International Cannabinoid Research Society
    • Hilderbrandt, S.; Johnson, I. J.; Mukhopadhyay, S. CB1 Receptor and Non-CB1/CB2 Annadmaide Receptor Mediated Differential S-Ni- trosylation of MMP: A Novel Angiogenic Switch for the Regulation of Angiogenesis (2008). Proceedings of the 18th Annual Symposium of Cannbinoids, Burlington, VT, 2008; International Cannabinoid Research Society, 2008; p 17.
    • (2008) Proceedings of the 18th Annual Symposium of Cannbinoids , pp. 17
    • Hilderbrandt, S.1    Johnson, I.J.2    Mukhopadhyay, S.3
  • 31
    • 34248574537 scopus 로고    scopus 로고
    • Anandamide-mediated CB1/CB2 cannabinoid receptor-independent nitric oxide production in rabbit aortic endothelial cells
    • McCollum, L.; Howlett; Mukhopadhyay, S. Anandamide-mediated CB1/CB2 cannabinoid receptor-independent nitric oxide production in rabbit aortic endothelial cells. J. Pharmacol. Exp. Ther. 2007, 321, 930-937.
    • (2007) J. Pharmacol. Exp. Ther , vol.321 , pp. 930-937
    • McCollum, L.1    Howlett2    Mukhopadhyay, S.3
  • 32
    • 0242637558 scopus 로고    scopus 로고
    • Fluorescent ligands, antibodies, and proteins for the study of receptors
    • Daly, C. J.; McGrath, J. C. Fluorescent ligands, antibodies, and proteins for the study of receptors. Pharmacol. Ther. 2003, 100, 101-118.
    • (2003) Pharmacol. Ther , vol.100 , pp. 101-118
    • Daly, C.J.1    McGrath, J.C.2
  • 33
    • 33846889729 scopus 로고    scopus 로고
    • Photoaffinity labeling and its application in structural biology
    • Vodovozova, E. L. Photoaffinity labeling and its application in structural biology. Biochemistry (Moscow) 2007, 72, 1-20.
    • (2007) Biochemistry (Moscow) , vol.72 , pp. 1-20
    • Vodovozova, E.L.1
  • 34
    • 24044531286 scopus 로고    scopus 로고
    • Organic azides: An exploding diversity of a unique class of compounds
    • (a) Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Organic azides: an exploding diversity of a unique class of compounds. Angew. Chem., Int. Ed. 2005, 44, 5188-240.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 5188-5240
    • Brase, S.1    Gil, C.2    Knepper, K.3    Zimmermann, V.4
  • 35
    • 85028579626 scopus 로고    scopus 로고
    • Photochemical Reactivity of Azides
    • 2nd ed, Horspool, W. M, Lenci, F, Eds, CRC Press:Boca Raton, FL, Chapter 44
    • (b) Bucher, G. Photochemical Reactivity of Azides. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press:Boca Raton, FL, 2004; Chapter 44.
    • (2004) CRC Handbook of Organic Photochemistry and Photobiology
    • Bucher, G.1
  • 36
    • 26244461164 scopus 로고    scopus 로고
    • Development and application of diazirines in biological and synthetic macromolecular systems
    • (c) Blencowe, A.; Hayes, W. Development and application of diazirines in biological and synthetic macromolecular systems. Soft Matter 2005, 1, 178-205.
    • (2005) Soft Matter , vol.1 , pp. 178-205
    • Blencowe, A.1    Hayes, W.2
  • 37
    • 32544459067 scopus 로고    scopus 로고
    • Photochemical fishing approaches for identifying target proteins and elucidating the structure of a ligand-binding region using carbene-generating photoreactive probes
    • (d) Sadakane, Y.; Hatanaka, Y. Photochemical fishing approaches for identifying target proteins and elucidating the structure of a ligand-binding region using carbene-generating photoreactive probes. Anal. Sci. 2006, 22, 209-218.
    • (2006) Anal. Sci , vol.22 , pp. 209-218
    • Sadakane, Y.1    Hatanaka, Y.2
  • 38
    • 0028246688 scopus 로고    scopus 로고
    • Abadji, V.; Lin, S.; Taha, G.; Griffin, G.; Stevenson, L. A.; Pertwee, R. G.; Makriyannis, A. (R)-Methanandamide: a chiral novel ananda- mide possessing higher potency and metabolic stability. J. Med. Chem. 1994, 37, 1889-1893.
    • (a) Abadji, V.; Lin, S.; Taha, G.; Griffin, G.; Stevenson, L. A.; Pertwee, R. G.; Makriyannis, A. (R)-Methanandamide: a chiral novel ananda- mide possessing higher potency and metabolic stability. J. Med. Chem. 1994, 37, 1889-1893.
  • 39
    • 33748457916 scopus 로고    scopus 로고
    • Non-cannabinoid CB1, non-cannabinoid CB2 antinociceptive effects of several novel compounds in the PPQ stretch test in mice
    • (b) Haller, V. L.; Cichewicz, D. L.; Welch, S. P. Non-cannabinoid CB1, non-cannabinoid CB2 antinociceptive effects of several novel compounds in the PPQ stretch test in mice. Eur. J. Pharmacol. 2006, 546, 60-68.
    • (2006) Eur. J. Pharmacol , vol.546 , pp. 60-68
    • Haller, V.L.1    Cichewicz, D.L.2    Welch, S.P.3
  • 40
    • 64349094099 scopus 로고    scopus 로고
    • It must be realized that we are not looking for a specific ligand for CB1 or CB2 receptors but for a mimic of eCBs, mainly anandamide, to search for novel putative receptors. However, very little is known about these targeted new receptors. It is therefore rather difficult to anticipate what structural requirements would be needed for a synthetic ligand.
    • It must be realized that we are not looking for a specific ligand for CB1 or CB2 receptors but for a mimic of eCBs, mainly anandamide, to search for novel putative receptors. However, very little is known about these targeted new receptors. It is therefore rather difficult to anticipate what structural requirements would be needed for a synthetic ligand.
  • 41
  • 42
    • 2942631046 scopus 로고    scopus 로고
    • A synthetic route to anandamide analogues carrying a substituent at the terminal carbon and an acetylene group in the end pentyl chain
    • Altundas, R.; Mahadevan, A.; Razdan, R. K. A synthetic route to anandamide analogues carrying a substituent at the terminal carbon and an acetylene group in the end pentyl chain. Tetrahedron Lett. 2004, 45, 5449-5451.
    • (2004) Tetrahedron Lett , vol.45 , pp. 5449-5451
    • Altundas, R.1    Mahadevan, A.2    Razdan, R.K.3
  • 43
    • 26444528969 scopus 로고    scopus 로고
    • High affinity electrophilic and photoactivatable covalent endocannabinoid probes for the CB1 receptor
    • Li, C.; Xu, W.; Vadivel, S. K.; Fan, P.; Makriyannis, A. High affinity electrophilic and photoactivatable covalent endocannabinoid probes for the CB1 receptor. J. Med. Chem. 2005, 48, 6423-6429.
    • (2005) J. Med. Chem , vol.48 , pp. 6423-6429
    • Li, C.1    Xu, W.2    Vadivel, S.K.3    Fan, P.4    Makriyannis, A.5
  • 44
    • 0034680724 scopus 로고    scopus 로고
    • The synthesis of N-vanillyl-arachidonoyl-amide (arvanil) and its analogs: An improved procedure for the synthesis of the key synthon methyl 14-hydroxy-(all-cis)-5.8.11-tetradecatrienoate
    • Dasse, O.; Mahadevan, A.; Han, L.; Martin, B. R.; Marzo, V. D.; Razdan, R. K. The synthesis of N-vanillyl-arachidonoyl-amide (arvanil) and its analogs: an improved procedure for the synthesis of the key synthon methyl 14-hydroxy-(all-cis)-5.8.11-tetradecatrienoate. Tetrahedron 2000, 56, 9195-9202.
    • (2000) Tetrahedron , vol.56 , pp. 9195-9202
    • Dasse, O.1    Mahadevan, A.2    Han, L.3    Martin, B.R.4    Marzo, V.D.5    Razdan, R.K.6
  • 45
    • 0042334839 scopus 로고    scopus 로고
    • 3 promoted coupling reactions for the preparation of skipped diynes
    • 3 promoted coupling reactions for the preparation of skipped diynes. Tetrahedron 2003, 59, 7787-7790.
    • (2003) Tetrahedron , vol.59 , pp. 7787-7790
    • Caruso, T.1    Spinella, A.2
  • 46
    • 0028850528 scopus 로고    scopus 로고
    • Leonard, N. J.; Neelima. 1,1,1,3,3,3-Hexafluoro-2-propanol for the removal of the 4,4′-dimethoxytrityl protecting group from the 5′- hydroxyl of acid-sensitive nucleosides and nucleotides. Tetrahedron Lett. 1995, 36, 7833-7336.
    • Leonard, N. J.; Neelima. 1,1,1,3,3,3-Hexafluoro-2-propanol for the removal of the 4,4′-dimethoxytrityl protecting group from the 5′- hydroxyl of acid-sensitive nucleosides and nucleotides. Tetrahedron Lett. 1995, 36, 7833-7336.
  • 47
  • 48
    • 64349097920 scopus 로고    scopus 로고
    • In our first attempts, there were both side products with over-reduced double bond(s) and compounds with not-yet-reduced alkyne(s) and they migrated with the same Rf hampered by the presence of amine and boron and/or nickel derivatives salts in the ethanolic reaction mixture, Thus, unfortunately, development and completion of the hydrogenation reaction could not be monitored by hydrogen absorption measurement or TLC. We had to use a trial and error approach to find the level of poisoning of the catalyst and reaction time
    • f (hampered by the presence of amine and boron and/or nickel derivatives salts in the ethanolic reaction mixture). Thus, unfortunately, development and completion of the hydrogenation reaction could not be monitored by hydrogen volume absorption measurement or TLC. We had to use a trial and error approach to find the level of poisoning of the catalyst and reaction time.
  • 49
    • 25444455673 scopus 로고    scopus 로고
    • A linpchin approach to unsaturatted fatty acids 11,12-epoxyeicosatrienoic acid and 11S,12S-dihydroxyeicosa-trienoic acid ethyl esters
    • Taber, D. F.; Zhang, Z. J. A linpchin approach to unsaturatted fatty acids 11,12-epoxyeicosatrienoic acid and 11S,12S-dihydroxyeicosa-trienoic acid ethyl esters. Org. Chem. 2005, 70, 8093-8095.
    • (2005) Org. Chem , vol.70 , pp. 8093-8095
    • Taber, D.F.1    Zhang, Z.J.2
  • 50
    • 0011383755 scopus 로고
    • Utilisation du chloro-4 butène-2 ol-1 en synthèse organiqueaction sur les composé organomanesiens.
    • (a) Colonge, J.; Poilane, G. Utilisation du chloro-4 butène-2 ol-1 en synthèse organiqueaction sur les composé organomanesiens. Bull. Soc. Chim. Fr. 1955, 953, 955.
    • (1955) Bull. Soc. Chim. Fr , vol.953 , pp. 955
    • Colonge, J.1    Poilane, G.2
  • 51
    • 0027400864 scopus 로고
    • A mild and convenient Barbier-type allylation od aldehyddes to homoallylic alcohol via iodide ion promoted stannylation of allylic bromides and chlorides with tin(II) chloride
    • (b) Imai, T.; Nishida, S. A mild and convenient Barbier-type allylation od aldehyddes to homoallylic alcohol via iodide ion promoted stannylation of allylic bromides and chlorides with tin(II) chloride. Synthesis 1993, 4, 395-399.
    • (1993) Synthesis , vol.4 , pp. 395-399
    • Imai, T.1    Nishida, S.2
  • 52
    • 64349119637 scopus 로고    scopus 로고
    • We were mostly preoccupied with double selectivity versus monose- lectivity on the dichloride 22
    • We were mostly preoccupied with double selectivity versus monose- lectivity on the dichloride 22.
  • 53
    • 0001127824 scopus 로고    scopus 로고
    • First total synthesis of (-)-aplyolide A
    • Hansen, T. V.; Stenstrom, Y. First total synthesis of (-)-aplyolide A. Tetrahedron: Asymmetry 2001, 12, 1407-1417.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 1407-1417
    • Hansen, T.V.1    Stenstrom, Y.2
  • 54
    • 0000179776 scopus 로고
    • Total synthesis of 7,7-, 10,10-, and 13,13-difluoroarachidonic acids
    • (a) Kwok, P.-Y.; Muellner, F. W.; Chen, C.-K.; Fried, J. Total synthesis of 7,7-, 10,10-, and 13,13-difluoroarachidonic acids. J. Am. Chem. Soc. 1987, 109, 3684-3692.
    • (1987) J. Am. Chem. Soc , vol.109 , pp. 3684-3692
    • Kwok, P.-Y.1    Muellner, F.W.2    Chen, C.-K.3    Fried, J.4
  • 55
    • 0017812207 scopus 로고
    • Douglas Fir Tusock Moth pheromone: Identification of a diene analogue of the principal attractant and synthesis of stereochemically defined 1,6-, 2,6- and 3,6-heneicosadien-11-ones
    • (b) Smith, L. M.; Smith, R. G.; Loehr, T. M.; Daves, G. D. Douglas Fir Tusock Moth pheromone: identification of a diene analogue of the principal attractant and synthesis of stereochemically defined 1,6-, 2,6- and 3,6-heneicosadien-11-ones. J. Org. Chem. 1978, 43, 2361-2366.
    • (1978) J. Org. Chem , vol.43 , pp. 2361-2366
    • Smith, L.M.1    Smith, R.G.2    Loehr, T.M.3    Daves, G.D.4
  • 56
    • 0011028736 scopus 로고
    • Receptor-selective fluorescent probes for use in neuroscience
    • Blackburn, C.; Neumeyer, J. L. Receptor-selective fluorescent probes for use in neuroscience. Med. Chem. Res. 1992, 2, 257-275.
    • (1992) Med. Chem. Res , vol.2 , pp. 257-275
    • Blackburn, C.1    Neumeyer, J.L.2
  • 57
    • 0032871199 scopus 로고    scopus 로고
    • Synthesis of an artificial glycoconjugate polymer carrying Pk antigenic trisaccharide and its potent neutralization activity against Shiga-like toxin
    • Dohi, H.; Nishida, Y.; Mizuno, M.; Shinkai, M.; Kobayashi, T.; Takeda, T.; Uzawa, H.; Kobayashi, K. Synthesis of an artificial glycoconjugate polymer carrying Pk antigenic trisaccharide and its potent neutralization activity against Shiga-like toxin. Bioorg. Med. Chem. 1999, 7, 2053-2062.
    • (1999) Bioorg. Med. Chem , vol.7 , pp. 2053-2062
    • Dohi, H.1    Nishida, Y.2    Mizuno, M.3    Shinkai, M.4    Kobayashi, T.5    Takeda, T.6    Uzawa, H.7    Kobayashi, K.8
  • 58
    • 0028293533 scopus 로고
    • Synthesis of a radioactive photoaffinity arachidonic acid analog
    • Perrier, H.; Prasit, P.; Wang, Z. Synthesis of a radioactive photoaffinity arachidonic acid analog. Tetrahedron Lett. 1994, 35, 1501-1502.
    • (1994) Tetrahedron Lett , vol.35 , pp. 1501-1502
    • Perrier, H.1    Prasit, P.2    Wang, Z.3
  • 59
    • 64349104824 scopus 로고
    • Substituted Diaziridines and Diazirines
    • U.S. Patent 3,525,736, American Cyanamid Compagny
    • (a) Church, R. F. R.; Conn, R.; Weiss, M. J. Substituted Diaziridines and Diazirines. U.S. Patent 3,525,736 1970; American Cyanamid Compagny.
    • (1970)
    • Church, R.F.R.1    Conn, R.2    Weiss, M.J.3
  • 60
    • 0000330501 scopus 로고    scopus 로고
    • Church, R. F. R.; Weiss, M. J. Diazirines. II. Synthesis and properties of small functionalized diazirine molecules. Some observations on the reaction of a diaziridine with the iodine- iodide ion system. J. Org. Chem. 1970, 35 (8), 2465-2471.
    • (b) Church, R. F. R.; Weiss, M. J. Diazirines. II. Synthesis and properties of small functionalized diazirine molecules. Some observations on the reaction of a diaziridine with the iodine- iodide ion system. J. Org. Chem. 1970, 35 (8), 2465-2471.
  • 61
    • 64349100728 scopus 로고    scopus 로고
    • These experiments were run by Pr. Vincenzo DiMarzo team (Napoli) with the same conditions as the ones reported in our preliminary paper see ref 34
    • These experiments were run by Pr. Vincenzo DiMarzo team (Napoli) with the same conditions as the ones reported in our preliminary paper (see ref 34).
  • 62
    • 0026470956 scopus 로고
    • Interaction of endothelial cells with a laminin A chain peptide (SIKVAV) in vitro and induction of angiogenic behavior in vivo
    • Grant, D. S.; Kinsella, J. L.; Fridman, R.; Auerbach, R.; Piasecki, B. A.; Yamada, Y.; Zain, M.; Kleinman, H. K. Interaction of endothelial cells with a laminin A chain peptide (SIKVAV) in vitro and induction of angiogenic behavior in vivo. J. Cell Physiol. 1992, 153, 614-625.
    • (1992) J. Cell Physiol , vol.153 , pp. 614-625
    • Grant, D.S.1    Kinsella, J.L.2    Fridman, R.3    Auerbach, R.4    Piasecki, B.A.5    Yamada, Y.6    Zain, M.7    Kleinman, H.K.8
  • 63
    • 0029127230 scopus 로고
    • Polverini. Angiogenesis mediated by soluble forms of E-selectin and vascular cell adhesionmolecule-1
    • Koch, A. E.; Halloran, M. M.; Haskell, C. J.; Shah; Polverini. Angiogenesis mediated by soluble forms of E-selectin and vascular cell adhesionmolecule-1. Nature 1995, 376, 517-519.
    • (1995) Nature , vol.376 , pp. 517-519
    • Koch, A.E.1    Halloran, M.M.2    Haskell, C.J.3    Shah4


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