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Volumn 54, Issue 7, 2011, Pages 2155-2164

Homoisoflavonoids: Natural scaffolds with potent and selective monoamine oxidase-B inhibition properties

Author keywords

[No Author keywords available]

Indexed keywords

3 [4 (DIMETHYLAMINO)BENZYLIDENE]CHROMAN 4 ONE; 3 BENZYL 4H CHROMEN 4 ONE DERIVATIVE; 3 BENZYLCHROMAN 4 ONE DERIVATIVE; 3 BENZYLIDENE 4 CHROMANONE DERIVATIVE; 5,7 DIHYDROXY 3 (4 HYDROXYBENZYLIDENE)CHROMAN 4 ONE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CLORGYLINE; HOMOISOFLAVONOID DERIVATIVE; IPRONIAZID; MOCLOBEMIDE; MOLECULAR SCAFFOLD; MONOAMINE OXIDASE INHIBITOR; SELEGILINE; UNCLASSIFIED DRUG;

EID: 79953769169     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1013709     Document Type: Article
Times cited : (96)

References (60)
  • 1
    • 0034814085 scopus 로고    scopus 로고
    • Interactions of nitrogen-containing xenobiotics with monoamine oxidase (MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors
    • DOI 10.1021/tx010073b
    • Kalgutkar, A. S.; Dalvie, D. K.; Castagnoli, N.; Taylor, T. J. Interactions of nitrogen-containing xenobiotics with monoamine oxidase (MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors Chem. Res. Toxicol. 2001, 14, 1139-1162 (Pubitemid 32911452)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.9 , pp. 1139-1162
    • Kalgutkar, A.S.1    Dalvie, D.K.2    Castagnoli Jr., N.3    Taylor, T.J.4
  • 2
    • 0019811093 scopus 로고
    • The role of phospholipid in the multiple functional forms of brain monoamine oxidase
    • Haung, R. H.; Faulkner, R. The role of phospholipid in the multiple functional forms of brain monoamine oxidase J. Biol. Chem. 1981, 256, 9211-9215 (Pubitemid 12208313)
    • (1981) Journal of Biological Chemistry , vol.256 , Issue.17 , pp. 9211-9215
    • Huang, R.H.1    Faulkner, R.2
  • 5
    • 3242779537 scopus 로고    scopus 로고
    • Regulation of MAO-A and MAO-B gene expression
    • Shih, J. C.; Chen, K. Regulation of MAO-A and MAO-B gene expression Curr. Med. Chem. 2004, 11, 1995-2005 (Pubitemid 38967725)
    • (2004) Current Medicinal Chemistry , vol.11 , Issue.15 , pp. 1995-2005
    • Shih, J.C.1    Chen, K.2
  • 6
    • 0032914318 scopus 로고    scopus 로고
    • Monoamine oxidase: From genes to behavior
    • DOI 10.1146/annurev.neuro.22.1.197
    • Shih, J. C.; Chen, K.; Ridd, M. J. Monoamine oxidase: from genes to behavior Annu. Rev. Neurosci. 1999, 22, 197-217 (Pubitemid 29144886)
    • (1999) Annual Review of Neuroscience , vol.22 , pp. 197-217
    • Shih, J.C.1    Chen, K.2    Ridd, M.J.3
  • 7
    • 0026085336 scopus 로고
    • New directions in monoamine oxidase A and B. Selective inhibitors and substrates
    • Youdim, M. B. H.; Finberg, J. P. M. New directions in monoamine oxidase A and B. Selective inhibitors and substrates Biochem. Pharmacol. 1991, 41 (2) 155-162
    • (1991) Biochem. Pharmacol. , vol.41 , Issue.2 , pp. 155-162
    • Youdim, M.B.H.1    Finberg, J.P.M.2
  • 8
    • 0027339317 scopus 로고
    • Characterization of wild-type and mutant forms of human monoamine oxidase A and B expressed in a mammalian cell line
    • DOI 10.1016/0014-5793(93)81512-X
    • Gottowik, J.; Cesura, A. M.; Malherbe, P.; Lang, G.; Prada, M. D. Characterisation of wild-type and mutant forms of human monoamine oxidase A and B expressed in a mammalian cell line FEBS Lett. 1993, 317, 152-156 (Pubitemid 23043960)
    • (1993) FEBS Letters , vol.317 , Issue.1-2 , pp. 152-156
    • Gottowik, J.1    Cesura, A.M.2    Malherbe, P.3    Lang, G.4    Da Prada, M.5
  • 9
    • 0035971164 scopus 로고    scopus 로고
    • Substrate and inhibitor specificities for human monoamine oxidase A and B are influenced by a single amino acid
    • Geha, R. M.; Rebrin, I.; Chen, K.; Shih, J. C. Substrate and inhibitor specificities for human monoamine oxidase A and B are influenced by a single amino acid J. Biol. Chem. 2001, 276, 9877-9882
    • (2001) J. Biol. Chem. , vol.276 , pp. 9877-9882
    • Geha, R.M.1    Rebrin, I.2    Chen, K.3    Shih, J.C.4
  • 10
    • 0022337937 scopus 로고
    • Distinct monoamine oxidase A and B populations in primate brain
    • Westlund, K. N.; Denney, R. M.; Kochersperger, L. M.; Rose, R. M. Distinct monoamine oxidase A and B populations in primate brain Science 1985, 230, 181-183 (Pubitemid 16228560)
    • (1985) Science , vol.230 , Issue.4722 , pp. 181-183
    • Westlund, K.N.1    Denney, R.M.2    Kochersperger, L.M.3
  • 17
    • 0027175990 scopus 로고
    • 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogues: New reversible, highly potent, and selective monoamine oxidase type B inhibitors
    • DOI 10.1021/jm00061a006
    • Mazouz, F.; Gueddari, S.; Burstein, C.; Mansuy, D.; Milcent, R. 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3 H)-one derivatives and related analogs: new reversible, highly potent, and selective monoamine oxidase type B inhibitors J. Med. Chem. 1993, 36, 1157-1167 (Pubitemid 23159289)
    • (1993) Journal of Medicinal Chemistry , vol.36 , Issue.9 , pp. 1157-1167
    • Mazouz, F.1    Gueddari, S.2    Burstein, C.3    Mansuy, D.4    Milcent, R.5
  • 18
    • 0037549872 scopus 로고    scopus 로고
    • Inhibition of monoamine oxidase type A, but not type B, is an effective means of inducing anticonvulsant activity in the kindling model of epilepsy
    • Löscher, W.; Lehmann, H.; Teschendorf, H. J.; Traut, M.; Gross, G. Inhibition of monoamine oxidase type A, but not type B, is an effective means of inducing anticonvulsant activity in the kindling model of epilepsy J. Pharmacol. Exp. Ther. 1999, 288, 984-992 (Pubitemid 29254135)
    • (1999) Journal of Pharmacology and Experimental Therapeutics , vol.288 , Issue.3 , pp. 984-992
    • Loscher, W.1    Lehmann, H.2    Teschendorf, H.-J.3    Traut, M.4    Gross, G.5
  • 20
    • 0036125677 scopus 로고    scopus 로고
    • Synthesis and biological screening of 2-substituted 5,6-dihydro-5-oxo-4H- 1,3,4-oxadiazine-4-propanenitriles and of their intermediates
    • DOI 10.1002/1522-2675(200202)85:2<559::AID-HLCA559>3.0.CO;2-A
    • Khan, K. M.; Rahat, S.; Choudhary, M. I.; Atta-ur-Rahman; Ghani, U.; Perveen, S.; Khatoon, S.; Dar, A.; Malik, A. Synthesis and biological screening of 2-substituted 5,6-dihydro-5-oxo-4 H -1,3,4-oxadiazine-4-propanenitriles and of their intermediates Helv. Chim. Acta 2002, 85, 559-570 (Pubitemid 34225484)
    • (2002) Helvetica Chimica Acta , vol.85 , Issue.2 , pp. 559-570
    • Khan, K.M.1    Rahat, S.2    Choudhary, M.I.3    Atta-Ur-Rahman4    Ghani, U.5    Perveen, S.6    Khatoon, S.7    Dar, A.8    Malik, A.9
  • 21
    • 17444449069 scopus 로고    scopus 로고
    • 1-N-substituted thiocarbamoyl-3-phenyl-5-thienyl-2-pyrazolines: Synthesis and evaluation as MAO inhibitors
    • DOI 10.1002/ardp.200300732
    • Gokhan, N.; Yesilada, A.; Ucar, G.; Erol, K.; Bilgin, A. A. 1-N-Substituted thiocarbamoyl-3-phenyl-5-thienyl-2-pyrazolines: synthesis and evaluation as MAO inhibitors Arch. Pharm. 2003, 336, 362-371 (Pubitemid 37127992)
    • (2003) Archiv der Pharmazie , vol.336 , Issue.8 , pp. 362-371
    • Gokhan, N.1    Yesilada, A.2    Ucar, G.3    Erol, K.4    Bilgin, A.A.5
  • 23
  • 24
    • 33745126693 scopus 로고    scopus 로고
    • Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of N,N′-bis[2-oxo-2H-benzopyran]-3-carboxamides
    • DOI 10.1016/j.bmcl.2006.04.026, PII S0960894X06004586
    • Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Carradori, S.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F. Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of N, N β-bis[2-oxo-2 H -benzopyran]-3-carboxamides Bioorg. Med. Chem. Lett. 2006, 16, 4135-4140 (Pubitemid 43903192)
    • (2006) Bioorganic and Medicinal Chemistry Letters , vol.16 , Issue.15 , pp. 4135-4140
    • Chimenti, F.1    Secci, D.2    Bolasco, A.3    Chimenti, P.4    Granese, A.5    Carradori, S.6    Befani, O.7    Turini, P.8    Alcaro, S.9    Ortuso, F.10
  • 25
    • 33645870453 scopus 로고    scopus 로고
    • Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC)
    • Vlok, N.; Malan, S. F.; Castagnoli, N.; Bergh, J. J.; Petzer, J. P. Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC) Bioorg. Med. Chem. 2006, 14, 3512-3521
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 3512-3521
    • Vlok, N.1    Malan, S.F.2    Castagnoli, N.3    Bergh, J.J.4    Petzer, J.P.5
  • 28
    • 0025347587 scopus 로고
    • Synthesis and antifungal activity of some 3-benzylidenechroman-4-ones, 3-benzylidenethiochroman-4-ones and 2-benzylidene-1-tetralones
    • Al Nakib, T.; Bezjak, V.; Meegan, M. J.; Chandy, R. Synthesis and antifungal activity of some 3-benzylidenechroman-4-ones, 3- benzylidenethiochroman-4-ones and 2-benzylidene-1-tetralones Eur. J. Med. Chem. 1990, 25, 455-462
    • (1990) Eur. J. Med. Chem. , vol.25 , pp. 455-462
    • Al Nakib, T.1    Bezjak, V.2    Meegan, M.J.3    Chandy, R.4
  • 30
    • 0032588105 scopus 로고    scopus 로고
    • Enantioseparation and anti-rhinovirus activity of 3-benzylchroman-4-ones
    • Quaglia, M. G.; Desideri, N.; Bossu, E.; Sgro, R.; Conti, C. Enantioseparation and anti-rhinovirus activity of 3-benzylchroman-4-ones Chirality 1999, 11 (5/6) 495-500
    • (1999) Chirality , vol.11 , Issue.5-6 , pp. 495-500
    • Quaglia, M.G.1    Desideri, N.2    Bossu, E.3    Sgro, R.4    Conti, C.5
  • 31
    • 33750690473 scopus 로고    scopus 로고
    • Antiviral activity of substituted homoisoflavonoids on enteroviruses
    • DOI 10.1016/j.antiviral.2006.07.003, PII S0166354206002038
    • Tait, S.; Salvati, A. L.; Desideri, N.; Fiore, L. Antiviral activity of substituted homoisoflavonoids on enteroviruses Antiviral Res. 2006, 72 (3) 252-255 (Pubitemid 44708308)
    • (2006) Antiviral Research , vol.72 , Issue.3 , pp. 252-255
    • Tait, S.1    Salvati, A.L.2    Desideri, N.3    Fiore, L.4
  • 32
    • 0024418467 scopus 로고
    • Plant antimutagens, 6. Intricatin and intricatinol, new antimutagenic homoisoflavonoids from Hoffmanosseggia intricata
    • Wall, M. E.; Wani, M. C.; Manikumar, G.; Taylor, H.; McGivney, R. Plant antimutagens, 6. intricatin and intricatinol, new antimutagenic homoisoflavonoids from hoffmanosseggia intricata J. Nat. Prod. 1989, 52, 774-778 (Pubitemid 19218706)
    • (1989) Journal of Natural Products (Lloydia) , vol.52 , Issue.4 , pp. 774-778
    • Wall, M.E.1    Qani, M.C.2    Manikumar, G.3    Taylor, H.4    McGivney, R.5
  • 33
    • 0035996875 scopus 로고    scopus 로고
    • Antimutagenic potential of homoisoflavonoids from Muscari racemosum
    • DOI 10.1016/S0378-8741(02)00135-6, PII S0378874102001356
    • Miadokova, E.; Masterova, I.; Vlckova, V.; Duhova, V.; Toth, J. Antimutagenic potential of homoisoflavonoids from Muscari racemosum J. Ethnopharmacol. 2002, 81, 381-386 (Pubitemid 34786323)
    • (2002) Journal of Ethnopharmacology , vol.81 , Issue.3 , pp. 381-386
    • Miadokova, E.1    Masterova, I.2    Vlckova, V.3    Duhova, V.4    Toth, J.5
  • 34
    • 41249096543 scopus 로고    scopus 로고
    • Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells
    • DOI 10.1016/j.ejmech.2007.06.017, PII S0223523407002590
    • Perjési, P.; Das, U.; De Clercq, E.; Balzarini, J.; Kawase, M.; Sakagami, H.; Stables, J. P.; Lorand, T.; Rozmer, Z.; Dimmock, J. R. Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1- benzopyran-4-ones which display selective toxicity for malignant cells Eur. J. Med. Chem. 2008, 43, 839-845 (Pubitemid 351446154)
    • (2008) European Journal of Medicinal Chemistry , vol.43 , Issue.4 , pp. 839-845
    • Perjesi, P.1    Das, U.2    De Clercq, E.3    Balzarini, J.4    Kawase, M.5    Sakagami, H.6    Stables, J.P.7    Lorand, T.8    Rozmer, Z.9    Dimmock, J.R.10
  • 35
    • 33644785826 scopus 로고    scopus 로고
    • Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids
    • DOI 10.1016/j.bmc.2005.11.031, PII S0968089605011028
    • Siddaiah, V.; Rao, C. V.; Venkateswarlu, S.; Krishnaraju, A. V.; Subbaraju, G. V. Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids Bioorg. Med. Chem. 2006, 14, 2545-2551 (Pubitemid 43343641)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.8 , pp. 2545-2551
    • Siddaiah, V.1    Rao, C.V.2    Venkateswarlu, S.3    Krishnaraju, A.V.4    Subbaraju, G.V.5
  • 36
    • 33846913943 scopus 로고    scopus 로고
    • Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata
    • DOI 10.1016/j.bmcl.2006.12.008, PII S0960894X06013904
    • Siddaiah, V.; Maheswara, M.; Rao, C. V.; Venkateswarlu, S.; Subbaraju, G. V. Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata Bioorg. Med. Chem. Lett. 2007, 17, 1288-1290 (Pubitemid 46240845)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.5 , pp. 1288-1290
    • Siddaiah, V.1    Maheswara, M.2    Venkata Rao, C.3    Venkateswarlu, S.4    Subbaraju, G.V.5
  • 37
    • 0024326068 scopus 로고
    • SYNTHESE ET ACTIVITES ANGIOPROTECTRICE, ANTI-ALLERGIQUE ET ANTIHISTAMINIQUE DE BENZYL-3 CHROMONES (HOMO-ISOFLAVONES)
    • DOI 10.1016/0223-5234(89)90060-3
    • Kirkiacharian, S.; Tongo, H. G.; Bastide, J.; Bastide, P.; Grenie, M. M. Synthèse et activités angioprotectrice, anti-allergique et antihistaminique de benzyl-3 chromones (homo-isoflavones) Eur. J. Med. Chem. 1989, 24, 541-546 (Pubitemid 19285409)
    • (1989) European Journal of Medicinal Chemistry , vol.24 , Issue.5 , pp. 541-546
    • Kirkiacharian, S.1    Tongo, H.G.2    Bastide, J.3    Bastide, P.4    Grenie, M.M.5
  • 42
    • 5844253483 scopus 로고
    • Synthesis of eucomin, 4′demethyleucomin and 5,7-di- O -methyleucomol
    • Krishnamurty, H. G.; Parkash, B.; Seshadri, T. R. Synthesis of eucomin, 4′demethyleucomin and 5,7-di- O -methyleucomol Indian J. Chem. 1974, 12 (6) 554-556
    • (1974) Indian J. Chem. , vol.12 , Issue.6 , pp. 554-556
    • Krishnamurty, H.G.1    Parkash, B.2    Seshadri, T.R.3
  • 43
    • 33646092535 scopus 로고    scopus 로고
    • Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity
    • Yáñez, M.; Fraiz, N.; Cano, E.; Orallo, F. Inhibitory effects of cis- and trans-resveratrol on noradrenaline and 5-hydroxytryptamine uptake and on monoamine oxidase activity Biochem. Biophys. Res. Commun. 2006, 344 (2) 688-695
    • (2006) Biochem. Biophys. Res. Commun. , vol.344 , Issue.2 , pp. 688-695
    • Yáñez, M.1    Fraiz, N.2    Cano, E.3    Orallo, F.4
  • 44
    • 79953777237 scopus 로고    scopus 로고
    • Enzyme Inhibition
    • In; John Wiley & Sons, Inc.: Hoboken, NJ,; Vol., pp 681.
    • Silverman, R. B. Enzyme Inhibition. In Wiley Encyclopedia of Chemical Biology; John Wiley & Sons, Inc.: Hoboken, NJ, 2009; Vol. 1, pp 663-681.
    • (2009) Wiley Encyclopedia of Chemical Biology , vol.1 , pp. 663
    • Silverman, R.B.1
  • 48
    • 76149120388 scopus 로고    scopus 로고
    • AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading
    • Trott, O.; Olson, J. A. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 2010, 31, 455-461
    • (2010) J. Comput. Chem. , vol.31 , pp. 455-461
    • Trott, O.1    Olson, J.A.2
  • 49
    • 70349708583 scopus 로고
    • Oxy-benzyl-chromanone. XI. Miettelung zur brasilin- und haematoxylinfrage
    • Pfeiffer, P.; Breit, E.; Hoyer, H. Oxy-benzyl-chromanone. XI. Miettelung zur brasilin- und haematoxylinfrage J. Prakt. Chem. 1931, 129, 31-54
    • (1931) J. Prakt. Chem. , vol.129 , pp. 31-54
    • Pfeiffer, P.1    Breit, E.2    Hoyer, H.3
  • 50
    • 33646896287 scopus 로고    scopus 로고
    • One-pot synthesis of trans -7-aryl-6 H -6a,7-dihydro[1]benzopyrano[3,4- c ][1,5]benzothiazepines
    • Sathunuru, R.; Koh, B.; Zhang, H.; Biehl, E. One-pot synthesis of trans -7-aryl-6 H -6a,7-dihydro[1]benzopyrano[3,4- c ][1,5]benzothiazepines Heterocycles 2005, 65 (10) 2493-2503
    • (2005) Heterocycles , vol.65 , Issue.10 , pp. 2493-2503
    • Sathunuru, R.1    Koh, B.2    Zhang, H.3    Biehl, E.4
  • 51
    • 37049133975 scopus 로고
    • Stereochemistry of cyclopropyl ketones from the reaction of dimethylsulfoxonium methylide with 3-benzylidene-4-chromanones
    • Bennett, P.; Donnelly, J. A.; Meaney, D. C.; O'Boyle, P. Stereochemistry of cyclopropyl ketones from the reaction of dimethylsulfoxonium methylide with 3-benzylidene-4-chromanones J. Chem. Soc., Perkin Trans. 1 1972, 12, 1554-1559
    • (1972) J. Chem. Soc., Perkin Trans. 1 , vol.12 , pp. 1554-1559
    • Bennett, P.1    Donnelly, J.A.2    Meaney, D.C.3    O'boyle, P.4
  • 53
    • 79953772948 scopus 로고    scopus 로고
    • version 4.1; Schroedinger Inc.: Portland, OR,-2001.
    • Maestro, version 4.1; Schroedinger Inc.: Portland, OR, 1998,-2001.
    • (1998) Maestro
  • 55
    • 0026620007 scopus 로고
    • AMBER*torsional parameters for the peptide backbone
    • DOI 10.1016/0040-4039(93)88034-G
    • McDonald, D. Q.; Still, W. C. AMBER torsional parameters for the peptide backbone Tetrahedron Lett. 1992, 33, 7743-7746 (Pubitemid 23002290)
    • (1992) Tetrahedron Letters , vol.33 , Issue.50 , pp. 7743-7746
    • McDonald, D.Q.1    Still, W.C.2
  • 57
    • 0001308921 scopus 로고
    • A rapid approximation to the solvent accessible surface areas of atoms
    • Hasel, W.; Hendrickson, T. F.; Still, W. C. A rapid approximation to the solvent accessible surface areas of atoms Tetrahedron Comput. Methodol. 1988, 1, 103-116
    • (1988) Tetrahedron Comput. Methodol. , vol.1 , pp. 103-116
    • Hasel, W.1    Hendrickson, T.F.2    Still, W.C.3
  • 60
    • 36148955400 scopus 로고    scopus 로고
    • Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: Safinamide and coumarin analogs
    • DOI 10.1021/jm070677y
    • Binda, C.; Wang, J.; Pisani, L.; Caccia, C.; Carotti, A.; Salvati, P.; Edmondson, D. E.; Mattevi, A. Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: safinamide and coumarin analogs J. Med. Chem. 2007, 50, 5848-5852 (Pubitemid 350106038)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.23 , pp. 5848-5852
    • Binda, C.1    Wang, J.2    Pisani, L.3    Caccia, C.4    Carotti, A.5    Salvati, P.6    Edmondson, D.E.7    Mattevi, A.8


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