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Volumn 42, Issue 24, 1999, Pages 4961-4969

Structure-activity relationship studies of novel heteroretinoids: Induction of apoptosis in the HL-60 cell line by a novel isoxazole-containing heteroretinoid

Author keywords

[No Author keywords available]

Indexed keywords

ALITRETINOIN; ISOTRETINOIN; ISOXAZOLE DERIVATIVE; RETINOIC ACID; RETINOIC ACID RECEPTOR; RETINOID DERIVATIVE; RETINOID X RECEPTOR;

EID: 0033518207     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm991059n     Document Type: Article
Times cited : (53)

References (33)
  • 1
    • 0015383455 scopus 로고
    • Apoptosis: A basic biological phenomenon with wide-ranging implications in tissue kinetics
    • Kerr, J. F. R.; Wyllie, A. H.; Currie, A. R. Apoptosis: a basic biological phenomenon with wide-ranging implications in tissue kinetics. Br. J. Cancer 1972, 26, 239-257.
    • (1972) Br. J. Cancer , vol.26 , pp. 239-257
    • Kerr, J.F.R.1    Wyllie, A.H.2    Currie, A.R.3
  • 2
    • 0028890119 scopus 로고
    • Apoptosis and cancer: The failure of controls on cell death and cell survival
    • Martin, S. J.; Green, D. R. Apoptosis and cancer: the failure of controls on cell death and cell survival. Crit. Rev. Oncol. / Hematol. 1995, 18, 137-153.
    • (1995) Crit. Rev. Oncol. / Hematol. , vol.18 , pp. 137-153
    • Martin, S.J.1    Green, D.R.2
  • 3
    • 0028025563 scopus 로고
    • Apoptosis in cancer therapy: Crossing the threshold
    • Fisher, D. E. Apoptosis in cancer therapy: crossing the threshold. Cell 1994, 78, 539-542.
    • (1994) Cell , vol.78 , pp. 539-542
    • Fisher, D.E.1
  • 4
    • 0028242277 scopus 로고
    • Clinical implications of basic research cancer therapy meets p53
    • Kinzler, K. W.; Bogelstein, B. Clinical implications of basic research cancer therapy meets p53. N. Engl. J. Med. 1994, 331, 49-50.
    • (1994) N. Engl. J. Med. , vol.331 , pp. 49-50
    • Kinzler, K.W.1    Bogelstein, B.2
  • 5
    • 0029935682 scopus 로고    scopus 로고
    • Involvement of the CD95 (APO-1/Fas) receptor/ligand system in drug-induced apoptosis in leukemia cells
    • Friesen, C.; Herr, I.; Krammer, P. H.; Debatin, K.-M. Involvement of the CD95 (APO-1/Fas) receptor/ligand system in drug-induced apoptosis in leukemia cells. Nat. Med. 1996, 5, 574-577.
    • (1996) Nat. Med. , vol.5 , pp. 574-577
    • Friesen, C.1    Herr, I.2    Krammer, P.H.3    Debatin, K.-M.4
  • 8
    • 0027276857 scopus 로고
    • 9-cis-retinoic acid inhibits activation-driven T-cell apoptosis: Implications for retinoid X receptor involvement in thymocyte development
    • Yang, Y.; Vacchio, M.; Ashwell, J. D. 9-cis-Retinoic acid inhibits activation-driven T-cell apoptosis: Implications for retinoid X receptor involvement in thymocyte development. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6170-6174.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 6170-6174
    • Yang, Y.1    Vacchio, M.2    Ashwell, J.D.3
  • 11
    • 0031566154 scopus 로고    scopus 로고
    • Possible involvement of Bcl-2 pathway in retinoid X receptor alpha-induced apoptosis of HL-60 cells
    • Agarwal, N.; Mehta, K. Possible involvement of Bcl-2 pathway in retinoid X receptor alpha-induced apoptosis of HL-60 cells. Biochem. Biophys. Res. Commun. 1997, 230, 251-253.
    • (1997) Biochem. Biophys. Res. Commun. , vol.230 , pp. 251-253
    • Agarwal, N.1    Mehta, K.2
  • 12
    • 18844469945 scopus 로고    scopus 로고
    • A novel retinoic acid receptor (RAR)-selective antagonist inhibits differentiation and apoptosis of HL-60 cells: Implications of RAR alpha-mediated signals in myeloid leukemic cells
    • Ueno, H.; Kizaki, M.; Matsushita, H.; Muto, A.; Yamato, K.; Nishihara, T.; Yoshimura, H.; Koeffler, H. P.; Ikeda, Y. A novel retinoic acid receptor (RAR)-selective antagonist inhibits differentiation and apoptosis of HL-60 cells: implications of RAR alpha-mediated signals in myeloid leukemic cells. Leuk. Res. 1998, 22, 517-525.
    • (1998) Leuk. Res. , vol.22 , pp. 517-525
    • Ueno, H.1    Kizaki, M.2    Matsushita, H.3    Muto, A.4    Yamato, K.5    Nishihara, T.6    Yoshimura, H.7    Koeffler, H.P.8    Ikeda, Y.9
  • 13
    • 0030869788 scopus 로고    scopus 로고
    • Induction of apoptosis without differentiation by retinoic acid in PLB-985 cells requires the activation of both RAR and RXR
    • Monczak, Y.; Trudel, M.; Lamph, W. W.; Miller W. H., Jr. Induction of apoptosis without differentiation by retinoic acid in PLB-985 cells requires the activation of both RAR and RXR. Blood 1997, 90, 3345-3355.
    • (1997) Blood , vol.90 , pp. 3345-3355
    • Monczak, Y.1    Trudel, M.2    Lamph, W.W.3    Miller W.H., Jr.4
  • 15
    • 0027762643 scopus 로고
    • Clinical aspects of topical retinoids
    • Biro, D. E.; Shalita, A. R. Clinical aspects of topical retinoids. Skin Pharmacol. 1993, 6 (Suppl. 1), 24-34.
    • (1993) Skin Pharmacol. , vol.6 , Issue.1 SUPPL. , pp. 24-34
    • Biro, D.E.1    Shalita, A.R.2
  • 16
    • 0028012324 scopus 로고
    • Isotretinoin therapy in acne vulgaris, a 10 year retrospective study in singapore
    • Shahidallah, M.; Tham, S. N.; Goh, C. L. Isotretinoin therapy in acne vulgaris, a 10 year retrospective study in Singapore. Int. J. Dermatol. 1994, 33, 60-63.
    • (1994) Int. J. Dermatol. , vol.33 , pp. 60-63
    • Shahidallah, M.1    Tham, S.N.2    Goh, C.L.3
  • 22
    • 0030727160 scopus 로고    scopus 로고
    • Retinoic acid conjugates as potential antitumor agents. Synthesis and biological activity of conjugates with ARA-A, ARA-C, the 3(2H)furanone and aniline mustard moieties
    • Manfredini, S.; Simoni, D.; Ferroni, R.; Bazzanini, R.; Vertuani, S.; Hates, S.; De Clercq, E.; Balzarini, J. Retinoic acid conjugates as potential antitumor agents. Synthesis and biological activity of conjugates with ARA-A, ARA-C, the 3(2H)furanone and aniline mustard moieties. J. Med. Chem. 1997, 40, 3581-3857.
    • (1997) J. Med. Chem. , vol.40 , pp. 3581-3857
    • Manfredini, S.1    Simoni, D.2    Ferroni, R.3    Bazzanini, R.4    Vertuani, S.5    Hates, S.6    De Clercq, E.7    Balzarini, J.8
  • 23
    • 0032417646 scopus 로고    scopus 로고
    • Retinoids as potential chemotherapeutic agents. Synthesis, cytostatic and differentiating activities of new heterocyclic analogues of retinoic acid
    • Manfredini, S.; Simoni, D.; Caminiti, G.; Vertuani, S.; Invidiata, F. P.; Moscato, B.; Hates, S.; De Clercq, E.; Balzarini, J. Retinoids as potential chemotherapeutic agents. Synthesis, cytostatic and differentiating activities of new heterocyclic analogues of retinoic acid. Med. Chem. Res. 1998, 8:6, 291-304.
    • (1998) Med. Chem. Res. , vol.8 , Issue.6 , pp. 291-304
    • Manfredini, S.1    Simoni, D.2    Caminiti, G.3    Vertuani, S.4    Invidiata, F.P.5    Moscato, B.6    Hates, S.7    De Clercq, E.8    Balzarini, J.9
  • 24
    • 0026697933 scopus 로고
    • New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents
    • Lepage, F.; Tombret, F.; Cuvier, G.; Marivain, A.; Gllardin, J. M. New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents. Eur. J. Med. Chem. 1992, 27, 581-593.
    • (1992) Eur. J. Med. Chem. , vol.27 , pp. 581-593
    • Lepage, F.1    Tombret, F.2    Cuvier, G.3    Marivain, A.4    Gllardin, J.M.5
  • 25
    • 33845550921 scopus 로고
    • Methods for the stereoselective cis cyanohydroxylation and carboxylation of olefins
    • Kozikowski, A. P.; Adamczyk, M. Methods for the stereoselective cis cyanohydroxylation and carboxylation of olefins. J. Org. Chem. 1983, 48, 366-372.
    • (1983) J. Org. Chem. , vol.48 , pp. 366-372
    • Kozikowski, A.P.1    Adamczyk, M.2
  • 28
    • 0021925201 scopus 로고
    • Synthesis and characterization of selected heteroretinoids. Pharmacological activity as assessed in vitamin A deficient hamster tracheal organ cultures. Single-crystal X-ray diffraction analysis of 4,4-dimethylthiochroman-6-yl methyl ketone 1,1-dioxide and ethyl (E)-p-[2-(4,4-dimethylthiochroman-6-yl)propenyl]benzoate
    • Waugh, K. M.; Berlin, K. D.; Ford, W. T.; Holt, E. M.; Carrol, J. P.; Schomber, P. R.; Thompson, M. D.; Schiff, L. J. Synthesis and characterization of selected heteroretinoids. Pharmacological activity as assessed in Vitamin A deficient hamster tracheal organ cultures. Single-crystal X-ray diffraction analysis of 4,4-dimethylthiochroman-6-yl methyl ketone 1,1-dioxide and ethyl (E)-p-[2-(4,4-dimethylthiochroman-6-yl)propenyl]benzoate. J. Med. Chem. 1985, 28, 116-124.
    • (1985) J. Med. Chem. , vol.28 , pp. 116-124
    • Waugh, K.M.1    Berlin, K.D.2    Ford, W.T.3    Holt, E.M.4    Carrol, J.P.5    Schomber, P.R.6    Thompson, M.D.7    Schiff, L.J.8
  • 29
    • 0025139398 scopus 로고
    • HL-60 cells induced to differentiate towards neutrophils subsequently die via apoptosis
    • Martin, S. J.; Bradley, J. G.; Cotter, T. J. HL-60 cells induced to differentiate towards neutrophils subsequently die via apoptosis. Clin. Exp. Immunol. 1990, 79, 448-453.
    • (1990) Clin. Exp. Immunol. , vol.79 , pp. 448-453
    • Martin, S.J.1    Bradley, J.G.2    Cotter, T.J.3
  • 30
    • 0344769634 scopus 로고    scopus 로고
    • note
    • 31 Our data show that the cytotoxic activity of 14b (Figure 3a) is correlated prevalently with its ability to induce apoptosis in HL-60 cells (Figure 3b).
  • 31
    • 0031443822 scopus 로고    scopus 로고
    • Apoptosis and necrosis in toxicology: A continuum or distinct modes of cell death?
    • Raffray, M.; Cohen, G. M. Apoptosis and necrosis in toxicology: a continuum or distinct modes of cell death? Pharmacol. Ther. 1997, 75, 153-177.
    • (1997) Pharmacol. Ther. , vol.75 , pp. 153-177
    • Raffray, M.1    Cohen, G.M.2
  • 32
    • 0344769635 scopus 로고    scopus 로고
    • Data not shown
    • Data not shown.
  • 33
    • 0028848443 scopus 로고
    • Differential RXR & RAR activity of stilbene retinoid analogues bearing thiazole and imidazole carboxylic acids
    • and references therein
    • Beard, R. L.; Colon, D. F.; Klein, E. S.; Vorse, K. A.; Chandraratna, R. A. S. Differential RXR & RAR activity of stilbene retinoid analogues bearing thiazole and imidazole carboxylic acids. Bioorg. Med. Chem. Lett. 1995, 5, 2729-2734 and references therein.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2729-2734
    • Beard, R.L.1    Colon, D.F.2    Klein, E.S.3    Vorse, K.A.4    Chandraratna, R.A.S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.