SCOPUS 정보 검색 플랫폼

Volumn 370, Issue , 2013, Pages 46-66

Synthesis and biological activity of hydroxylated analogues of KRN7000 (α-galactosylceramide)

(7) Shiozaki, Masao a Tashiro, Takuya a Koshino, Hiroyuki a Shigeura, Tomokuni b Watarai, Hiroshi b Taniguchi, Masaru b Mori, Kenji a

a RIKEN (Japan)

b Institute of Physical and Chemical Research (Japan)

Author keywords

Agelasphins; CD1d; EAE; Glycosylation; iNKT cells; Th1 Th2

Indexed keywords

AGELASPHINS; CD1D; EAE; INKT CELLS; TH1/TH2;

BIOACTIVITY; CELLS; CYTOLOGY; GLYCOSYLATION; HYDROPHILICITY; HYDROXYLATION; PHYSIOLOGY;

T-CELLS;

1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; 2 [2' (HYDROXY)HEXACOSANOYLAMINO] 3,4,5,6 (TETRAHYDROXY)OCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 [2',3' DIHYDROXYHEXACOSANOYLAMINO] 3,4,5 TRIHYDROXYOCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 [2',3' DIHYDROXYHEXACOSANOYLAMINO] 3,4,5,6 TETRAHYDROXYOCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 [2',3',4' TRIHYDROXYHEXACOSANOYLAMINO] 3,4 DIHYDROXYOCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HEXACOSANOYLAMINO 3,4,5 TRIHYDROXYOCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 2 HEXACOSANOYLAMINO 3,4,5,6 TETRAHYDROXYOCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 3,4 DIHYDROXY 2 [2',2' (DIHYDROXY)HEXACOSANOYLAMINO]OCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; 3,4,5 TRI(HYDROXY) 2 [HYDROXYHEXACOSANOYLAMINO]OCTADECYL ALPHA DEXTRO GALACTOPYRANOSIDE; ALPHA GALATOSYLCERAMIDE; GAMMA INTERFERON; IMMUNOSUPPRESSIVE AGENT; INTERLEUKIN 4; SPHINGOSINE; UNCLASSIFIED DRUG;

ALLERGIC ENCEPHALOMYELITIS; ANIMAL EXPERIMENT; ARTICLE; CYTOKINE RELEASE; DRUG SYNTHESIS; FEMALE; GLYCOSYLATION; HYDROPHILICITY; HYDROXYLATION; MOUSE; NATURAL KILLER T CELL; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

ANIMALS; CHEMISTRY TECHNIQUES, SYNTHETIC; FEMALE; GALACTOSYLCERAMIDES; HYDROXYLATION; INTERLEUKIN-4; MICE; NATURAL KILLER T-CELLS; TH1 CELLS; TH2 CELLS;

EID: 84874153830 PISSN: 00086215 EISSN: 1873426X Source Type: Journal
DOI: 10.1016/j.carres.2013.01.010 Document Type: Article

Times cited : (21)

References (33)

1
- 0027177356
- T. Natori, Y. Koezuka, and T. Higa Tetrahedron Lett. 34 1993 5591 5592
- (1993) Tetrahedron Lett. , vol.34 , pp. 5591-5592
- Natori, T.¹ Koezuka, Y.² Higa, T.³

2
- 0027160611
- K. Akimoto, T. Natori, and M. Morita Tetrahedron Lett. 35 1994 5593 5596
- (1994) Tetrahedron Lett. , vol.35 , pp. 5593-5596
- Akimoto, K.¹ Natori, T.² Morita, M.³

3
- 0028204397
- T. Natori, M. Morita, K. Akimoto, and Y. Koezuka Tetrahedron 50 1994 2771 2784
- (1994) Tetrahedron , vol.50 , pp. 2771-2784
- Natori, T.¹ Morita, M.² Akimoto, K.³ Koezuka, Y.⁴

4
- 0029062153
- M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, and H. Fukushima J. Med. Chem. 38 1995 2176 2187
- (1995) J. Med. Chem. , vol.38 , pp. 2176-2187
- Morita, M.¹ Motoki, K.² Akimoto, K.³ Natori, T.⁴ Sakai, T.⁵ Sawa, E.⁶ Yamaji, K.⁷ Koezuka, Y.⁸ Kobayashi, E.⁹ Fukushima, H.¹⁰

5
- 0038228956
- M. Taniguchi, M. Harada, S. Kojo, T. Nakayama, and H. Wakao Annu. Rev. Immunol. 21 2003 483 513
- (2003) Annu. Rev. Immunol. , vol.21 , pp. 483-513
- Taniguchi, M.¹ Harada, M.² Kojo, S.³ Nakayama, T.⁴ Wakao, H.⁵

6
- 0030696696
- T. Kawano, J. Cui, Y. Koezuka, I. Toura, Y. Kaneko, K. Motoki, H. Ueno, R. Nakagawa, H. Sato, E. Kaneko, H. Koseki, and M. Taniguchi Science 278 1997 1626 1629
- (1997) Science , vol.278 , pp. 1626-1629
- Kawano, T.¹ Cui, J.² Koezuka, Y.³ Toura, I.⁴ Kaneko, Y.⁵ Motoki, K.⁶ Ueno, H.⁷ Nakagawa, R.⁸ Sato, H.⁹ Kaneko, E.¹⁰ Koseki, H.¹¹ Taniguchi, M.¹²

7
- 0030826423
- Z. Zeng, A.R. Castano, B.W. Segelke, E.A. Stura, P.A. Peterson, and I.A. Wilson Science 277 1997 339 345
- (1997) Science , vol.277 , pp. 339-345
- Zeng, Z.¹ Castano, A.R.² Segelke, B.W.³ Stura, E.A.⁴ Peterson, P.A.⁵ Wilson, I.A.⁶

8
- 0035807302
- K. Miyamoto, S. Miyake, and T. Yamamura Nature 413 2001 531 534
- (2001) Nature , vol.413 , pp. 531-534
- Miyamoto, K.¹ Miyake, S.² Yamamura, T.³

9
- 3042591658
- T. Yamamura, K. Miyamoto, Z. Illes, E. Paul, M. Araki, and S. Miyake Curr. Top. Med. Chem. 4 2004 561 567
- (2004) Curr. Top. Med. Chem. , vol.4 , pp. 561-567
- Yamamura, T.¹ Miyamoto, K.² Illes, Z.³ Paul, E.⁴ Araki, M.⁵ Miyake, S.⁶

10
- 2942739333
- S. Oki, A. Chiba, T. Yamamura, and S. Miyake J. Clin. Invest. 113 2004 1631 1640
- (2004) J. Clin. Invest. , vol.113 , pp. 1631-1640
- Oki, S.¹ Chiba, A.² Yamamura, T.³ Miyake, S.⁴

11
- 28744438007
- R.M. Ndonye, D.P. Izmirian, M.F. Dunn, K.O.A. Yu, S.A. Porcelli, A. Khurana, M. Kronenberg, S.K. Richardson, and A.R. Howell J. Org. Chem. 70 2005 10260 10270
- (2005) J. Org. Chem. , vol.70 , pp. 10260-10270
- Ndonye, R.M.¹ Izmirian, D.P.² Dunn, M.F.³ Yu, K.O.A.⁴ Porcelli, S.A.⁵ Khurana, A.⁶ Kronenberg, M.⁷ Richardson, S.K.⁸ Howell, A.R.⁹

12
- 15444380934
- K. Murata, T. Toba, K. Nakanishi, B. Takahashi, T. Yamamura, S. Miyake, and H. Annoura J. Org. Chem. 70 2005 2398 2401
- (2005) J. Org. Chem. , vol.70 , pp. 2398-2401
- Murata, K.¹ Toba, T.² Nakanishi, K.³ Takahashi, B.⁴ Yamamura, T.⁵ Miyake, S.⁶ Annoura, H.⁷

13
- 84859918083
- T. Toba, K. Murata, J. Futamura, K. Nakanishi, B. Takahashi, N. Takemoto, M. Tomino, T. Nakatsuka, S. Imajo, M. Goto, T. Yamamura, S. Miyake, and H. Annoura Bioorg. Med. Chem. 20 2012 2850 2859
- (2012) Bioorg. Med. Chem. , vol.20 , pp. 2850-2859
- Toba, T.¹ Murata, K.² Futamura, J.³ Nakanishi, K.⁴ Takahashi, B.⁵ Takemoto, N.⁶ Tomino, M.⁷ Nakatsuka, T.⁸ Imajo, S.⁹ Goto, M.¹⁰ Yamamura, T.¹¹ Miyake, S.¹² Annoura, H.¹³

14
- 34247393287
- T. Toba, K. Murata, K. Nakanishi, B. Takahashi, N. Takemoto, M. Akabane, T. Nakatsuka, S. Imajo, T. Yamamura, S. Miyake, and H. Annoura Bioorg. Med. Chem. Lett. 17 2007 2781 2784
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 2781-2784
- Toba, T.¹ Murata, K.² Nakanishi, K.³ Takahashi, B.⁴ Takemoto, N.⁵ Akabane, M.⁶ Nakatsuka, T.⁷ Imajo, S.⁸ Yamamura, T.⁹ Miyake, S.¹⁰ Annoura, H.¹¹

15
- 84885843404
- T. Tashiro, Y. Hongo, T. Nakagawa, K. Seino, H. Watarai, Y. Ishii, M. Taniguchi, and K. Mori Bioorg. Med. Chem. 16 2008 96 8906
- (2008) Bioorg. Med. Chem. , vol.16 , pp. 96-8906
- Tashiro, T.¹ Hongo, Y.² Nakagawa, T.³ Seino, K.⁴ Watarai, H.⁵ Ishii, Y.⁶ Taniguchi, M.⁷ Mori, K.⁸

16
- 77955653859
- M. Shiozaki, T. Tashiro, H. Koshino, R. Nakagawa, S. Inoue, T. Shigeura, H. Watarai, M. Taniguchi, and K. Mori Carbohydr. Res. 345 2010 1663 1684
- (2010) Carbohydr. Res. , vol.345 , pp. 1663-1684
- Shiozaki, M.¹ Tashiro, T.² Koshino, H.³ Nakagawa, R.⁴ Inoue, S.⁵ Shigeura, T.⁶ Watarai, H.⁷ Taniguchi, M.⁸ Mori, K.⁹

17
- 23944448650
- D.M. Zajonc, C. Cantu III, J. Mattner, D. Zhou, P.B. Savage, A. Bendelac, I.A. Wilson, and L. Tayton Nat. Immunol. 6 2005 810 818
- (2005) Nat. Immunol. , vol.6 , pp. 810-818
- Zajonc, D.M.¹ Cantu Iii, C.² Mattner, J.³ Zhou, D.⁴ Savage, P.B.⁵ Bendelac, A.⁶ Wilson, I.A.⁷ Tayton, L.⁸

18
- 23944479797
- M. Koch, V.S. Stronge, D. Shepherd, S.D. Gadola, B. Mathew, G. Ritter, A.R. Fersht, G.S. Besra, R.R. Schmidt, E.Y. Jones, and V. Cerundolo Nat. Immunol. 6 2005 819 826
- (2005) Nat. Immunol. , vol.6 , pp. 819-826
- Koch, M.¹ Stronge, V.S.² Shepherd, D.³ Gadola, S.D.⁴ Mathew, B.⁵ Ritter, G.⁶ Fersht, A.R.⁷ Besra, G.S.⁸ Schmidt, R.R.⁹ Jones, E.Y.¹⁰ Cerundolo, V.¹¹

19
- 34447131000
- N.A. Borg, K.S. Wun, L. Kjer-Nielsen, M.C.J. Wilce, D.G. Pellicci, R. Koh, G.S. Besra, M. Bharadwaj, D.I. Godfrey, J. McCluskey, and J. Rossjohn Nature 448 2007 44 49
- (2007) Nature , vol.448 , pp. 44-49
- Borg, N.A.¹ Wun, K.S.² Kjer-Nielsen, L.³ Wilce, M.C.J.⁴ Pellicci, D.G.⁵ Koh, R.⁶ Besra, G.S.⁷ Bharadwaj, M.⁸ Godfrey, D.I.⁹ McCluskey, J.¹⁰ Rossjohn, J.¹¹

20
- 68249151165
- D.G. Pellicci, O. Patel, L. Kjer-Nielsen, S.S. Pang, L.C. Sullivan, K. Kyparissoudis, A.G. Brooks, H.H. Reid, S. Gras, I.S. Lucet, R. Koh, M.J. Smyth, T. Mallevaey, J.L. Matsuda, L. Gapin, J. McCluskey, D.I. Godfrey, and J. Rossjohn Immunity 31 2009 47 59
- (2009) Immunity , vol.31 , pp. 47-59
- Pellicci, D.G.¹ Patel, O.² Kjer-Nielsen, L.³ Pang, S.S.⁴ Sullivan, L.C.⁵ Kyparissoudis, K.⁶ Brooks, A.G.⁷ Reid, H.H.⁸ Gras, S.⁹ Lucet, I.S.¹⁰ Koh, R.¹¹ Smyth, M.J.¹² Mallevaey, T.¹³ Matsuda, J.L.¹⁴ Gapin, L.¹⁵ McCluskey, J.¹⁶ Godfrey, D.I.¹⁷ Rossjohn, J.¹⁸

21
- 79952770879
- K.S. Wun, C. Cameron, O. Patel, S.S. Pang, D.G. Pellicci, L.C. Sullivan, S. Keshipeddy, M.H. Young, A.P. Uldrich, M.S. Thakur, S.K. Richardson, A.R. Howell, P.A. Illarionov, A.G. Brooks, G.S. Besra, J. McCluskey, L. Gapin, S.A. Porcelli, D.I. Godfrey, and J. Rossjohn Immunity 34 2011 327 339
- (2011) Immunity , vol.34 , pp. 327-339
- Wun, K.S.¹ Cameron, C.² Patel, O.³ Pang, S.S.⁴ Pellicci, D.G.⁵ Sullivan, L.C.⁶ Keshipeddy, S.⁷ Young, M.H.⁸ Uldrich, A.P.⁹ Thakur, M.S.¹⁰ Richardson, S.K.¹¹ Howell, A.R.¹² Illarionov, P.A.¹³ Brooks, A.G.¹⁴ Besra, G.S.¹⁵ McCluskey, J.¹⁶ Gapin, L.¹⁷ Porcelli, S.A.¹⁸ Godfrey, D.I.¹⁹ Rossjohn, J.²⁰ more..

22
- 0001132410
- R. Eby, S.J. Sondheimer, and C. Schuerch Carbohydr. Res. 73 1979 273 276
- (1979) Carbohydr. Res. , vol.73 , pp. 273-276
- Eby, R.¹ Sondheimer, S.J.² Schuerch, C.³

23
- 34047261471
- C.-W. Chang, Y.-N. Chen, A.K. Adak, K.-H. Lin, D.-L.M. Tzou, and C.-C. Lin Tetrahedron 63 2007 4310 4318
- (2007) Tetrahedron , vol.63 , pp. 4310-4318
- Chang, C.-W.¹ Chen, Y.-N.² Adak, A.K.³ Lin, K.-H.⁴ Tzou, D.-L.M.⁵ Lin, C.-C.⁶

24
- 84874937000
- U.S. Patent, No. 5756,706 (May 26, 1998)
- Mansour, T.; Tse, A. H. L. U.S. Patent, No. 5756,706 (May 26, 1998).
- Mansour, T.¹ Tse, A.H.L.²

25
- 2542433188
- P.H.J. Carlsen, T. Katsuki, V.S. Martin, and K.B. Sharpless J. Org. Chem. 46 1981 3936 3938
- (1981) J. Org. Chem. , vol.46 , pp. 3936-3938
- Carlsen, P.H.J.¹ Katsuki, T.² Martin, V.S.³ Sharpless, K.B.⁴

26
- 52949098710
- T. Tashiro, N. Hongo, R. Nakagawa, K. Seino, H. Watarai, Y. Ishii, M. Taniguchi, and K. Mori Bioorg. Med. Chem. 16 2008 8896 8906
- (2008) Bioorg. Med. Chem. , vol.16 , pp. 8896-8906
- Tashiro, T.¹ Hongo, N.² Nakagawa, R.³ Seino, K.⁴ Watarai, H.⁵ Ishii, Y.⁶ Taniguchi, M.⁷ Mori, K.⁸

27
- 34547907306
- T.M. Rivers, D.H. Spunt, and G.P. Berry J. Exp. Med. 58 1933 39 53
- (1933) J. Exp. Med. , vol.58 , pp. 39-53
- Rivers, T.M.¹ Spunt, D.H.² Berry, G.P.³

28
- 84874929696
- Chapter 15, Unit 15.1
- Miller, S. D.; Carpus, W. J. Curr. Protoc. Immunol. 2007, Chapter 15, Unit 15.1.
- (2007) Curr. Protoc. Immunol.
- Miller, S.D.¹ Carpus, W.J.²

29
- 77950531465
- G. Qian, X. Xia Qin, Y.Q. Zang, B. Ge, T.B. Guo, B. Wan, L. Fang, and J.Z. Zhang Cell Res. 20 2010 480 492
- (2010) Cell Res. , vol.20 , pp. 480-492
- Qian, G.¹ Xia Qin, X.² Zang, Y.Q.³ Ge, B.⁴ Guo, T.B.⁵ Wan, B.⁶ Fang, L.⁷ Zhang, J.Z.⁸

30
- 53149111593
- L.T. Mars, A.-S. Gautron, and J.N. Lucie J. Immunol. 181 2008 2321 2329
- (2008) J. Immunol. , vol.181 , pp. 2321-2329
- Mars, L.T.¹ Gautron, A.-S.² Lucie, J.N.³

31
- 25144519259
- cf.
- cf. S. Marusic, M.W. Leach, J.W. Pelker, M.L. Azoitei, N. Uozumi, J. Cui, M.W.H. Shen, C.M. DeClercq, J.S. Miyashiro, B.A. Carito, P. Thakker, D.L. Simmons, J.P. Leonard, T. Shimizu, and J.D. Clark J. Exp. Med. 202 2005 841 851
- (2005) J. Exp. Med. , vol.202 , pp. 841-851
- Marusic, S.¹ Leach, M.W.² Pelker, J.W.³ Azoitei, M.L.⁴ Uozumi, N.⁵ Cui, J.⁶ Shen, M.W.H.⁷ Declercq, C.M.⁸ Miyashiro, J.S.⁹ Carito, B.A.¹⁰ Thakker, P.¹¹ Simmons, D.L.¹² Leonard, J.P.¹³ Shimizu, T.¹⁴ Clark, J.D.¹⁵

32
- 84874941995
- The IL-4 production in sera after injection of glycolipid ligand is transient (only around 3 h). This is the reason why we compare level of IL-4 with KRN7000 as a positive control in same experimental settings
- The IL-4 production in sera after injection of glycolipid ligand is transient (only around 3 h). This is the reason why we compare level of IL-4 with KRN7000 as a positive control in same experimental settings.

33
- 12144290406
- E. Morgan, R. Varro, H. Sepulveda, J.A. Ember, J. Apgar, J. Wilson, L. Lowe, R. Chen, L. Shivraj, A. Agadir, R. Campos, D. Ernst, and A. Gaur Clin. Immunol. 110 2004 252 266
- (2004) Clin. Immunol. , vol.110 , pp. 252-266
- Morgan, E.¹ Varro, R.² Sepulveda, H.³ Ember, J.A.⁴ Apgar, J.⁵ Wilson, J.⁶ Lowe, L.⁷ Chen, R.⁸ Shivraj, L.⁹ Agadir, A.¹⁰ Campos, R.¹¹ Ernst, D.¹² Gaur, A.¹³

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