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α-Galactosylceramide

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In combination with a peptide antigen, α-GalCer is able to stimulate a strong immune response against the epitope. The CD1d:glycolipid:TCR interaction activates the iNKT cell which can then activate the dendritic cell. This causes the release of a range of cytokines and licenses the dendritic cell to
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InChI=1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1
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Morita, Masahiro; Motoki, Kazuhiro; Akimoto, Kohji; Natori, Takenori; Sakai, Teruyuki; Sawa, Eiji; Yamaji, Kazuo; Koezuka, Yasuhiko; Kobayashi, Eiichi (1995-06-01). "Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice".
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activate a peptide-specific T cell response. This adjuvant acts through this cellular interaction, rather than through classic pattern recognition receptor pathways.
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Cerundolo, Vincenzo; Silk, Jonathan D.; Masri, S. Hajar; Salio, Mariolina (January 2009). "Harnessing invariant NKT cells in vaccination strategies".
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of the iNKT cell is able to bind the CD1d:glycolipid complex leading to iNKT cell activation in both mice and humans.
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derived from structure-activity relationship studies of galactosylceramides isolated from the marine
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CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N(CO1((((O1)CO)O)O)O)((CCCCCCCCCCCCCC)O)O
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Except where otherwise noted, data are given for materials in their
146: 122: 112: 529:"Going both ways: Immune regulation via CD1d-dependent NKT cells" 447: 237: 373:189–190 °C (372–374 °F; 462–463 K) 199: 98: 8: 252: 26: 560: 219: 471: 298: 273: 248: 280:Key: VQFKFAKEUMHBLV-BYSUZVQFSA-N 174: 154: 7: 190: 442:α-GalCer is a potent activator of 68:-oxy}octadecan-2-yl]hexacosanamide 25: 533:Journal of Clinical Investigation 334: 328: 33: 383:(at 25 °C , 100 kPa). 482:Journal of Medicinal Chemistry 337: 322: 1: 438:Immunostimulatory properties 662: 586:Nature Reviews Immunology 377: 309: 289: 264: 82: 74: 59: 46: 41: 32: 18:Alpha-Galactosylceramide 450:antigen. The invariant 422:. α-GalCer is a strong 61:Systematic IUPAC name 28:α-Galactosylceramide 545:10.1172/jci200423594 525:Kronenberg, Mitchell 399:α-Galactosylceramide 494:10.1021/jm00012a018 355: g·mol 136:Beilstein Reference 29: 523:Godfrey, Dale I.; 419:Agelas mauritianus 387:Infobox references 27: 539:(10): 1379–1388. 488:(12): 2176–2187. 458:Adjuvant activity 430:activity in many 426:and shows potent 409:) is a synthetic 395:Chemical compound 393: 392: 233:CompTox Dashboard 124:Interactive image 77:α-GalCer, KRN7000 16:(Redirected from 653: 626: 625: 581: 575: 574: 564: 520: 514: 513: 476: 354: 339: 336: 330: 324: 317:Chemical formula 257: 256: 241: 239: 223: 203: 192: 178: 158: 126: 102: 37: 30: 21: 661: 660: 656: 655: 654: 652: 651: 650: 631: 630: 629: 598:10.1038/nri2451 583: 582: 578: 522: 521: 517: 478: 477: 473: 469: 460: 452:T cell receptor 440: 424:immunostimulant 396: 389: 384: 352: 342: 333: 327: 319: 305: 302: 297: 296: 285: 282: 281: 278: 272: 271: 260: 242: 235: 226: 206: 193: 181: 161: 138: 129: 116: 105: 92: 78: 70: 69: 55: 54:-hexacosanamide 23: 22: 15: 12: 11: 5: 659: 657: 649: 648: 643: 633: 632: 628: 627: 576: 527:(2004-11-15). 515: 470: 468: 465: 459: 456: 446:, and a model 439: 436: 394: 391: 390: 385: 381:standard state 378: 375: 374: 371: 365: 364: 361: 357: 356: 350: 344: 343: 340: 331: 325: 320: 315: 312: 311: 307: 306: 304: 303: 300: 292: 291: 290: 287: 286: 284: 283: 279: 276: 275: 267: 266: 265: 262: 261: 259: 258: 250:DTXSID40935847 245: 243: 231: 228: 227: 225: 224: 216: 214: 208: 207: 205: 204: 196: 194: 186: 183: 182: 180: 179: 171: 169: 163: 162: 160: 159: 151: 149: 143: 142: 139: 134: 131: 130: 128: 127: 119: 117: 110: 107: 106: 104: 103: 95: 93: 88: 85: 84: 80: 79: 76: 72: 71: 64: 63: 57: 56: 50: 44: 43: 39: 38: 24: 14: 13: 10: 9: 6: 4: 3: 2: 658: 647: 644: 642: 639: 638: 636: 623: 619: 615: 611: 607: 603: 599: 595: 591: 587: 580: 577: 572: 568: 563: 558: 554: 550: 546: 542: 538: 534: 530: 526: 519: 516: 511: 507: 503: 499: 495: 491: 487: 483: 475: 472: 466: 464: 457: 455: 453: 449: 445: 437: 435: 433: 429: 425: 421: 420: 416: 412: 408: 404: 400: 388: 382: 376: 372: 370: 369:Melting point 367: 366: 363:White powder 362: 359: 358: 351: 349: 346: 345: 321: 318: 314: 313: 308: 299: 295: 288: 274: 270: 263: 255: 251: 247: 246: 244: 234: 230: 229: 222: 218: 217: 215: 213: 210: 209: 202: 198: 197: 195: 189: 185: 184: 177: 173: 172: 170: 168: 165: 164: 157: 153: 152: 150: 148: 145: 144: 140: 137: 133: 132: 125: 121: 120: 118: 114: 109: 108: 101: 97: 96: 94: 91: 87: 86: 81: 73: 67: 62: 58: 53: 49: 45: 40: 36: 31: 19: 592:(1): 28–38. 589: 585: 579: 536: 532: 518: 485: 481: 474: 461: 441: 431: 417: 406: 402: 398: 397: 176:ChEMBL384200 156:CHEBI:466659 83:Identifiers 75:Other names 65: 51: 428:anti-tumour 360:Appearance 310:Properties 100:158021-47-7 641:Immunology 635:Categories 467:References 444:iNKT cells 411:glycolipid 348:Molar mass 221:WX671898JF 111:3D model ( 90:CAS Number 48:IUPAC name 606:1474-1741 553:0021-9738 502:0022-2623 622:38675164 614:19079136 571:15545985 434:models. 403:α-GalCer 141:7326597 510:7783149 432:in vivo 407:KRN7000 353:858.340 201:2826713 188:PubChem 646:Lipids 620:  612:  604:  569:  562:525753 559:  551:  508:  500:  415:sponge 294:SMILES 167:ChEMBL 42:Names 618:S2CID 269:InChI 147:ChEBI 113:JSmol 610:PMID 602:ISSN 567:PMID 549:ISSN 506:PMID 498:ISSN 448:CD1d 212:UNII 594:doi 557:PMC 541:doi 537:114 490:doi 238:EPA 191:CID 637:: 616:. 608:. 600:. 588:. 565:. 555:. 547:. 535:. 531:. 504:. 496:. 486:38 484:. 405:, 332:99 326:50 624:. 596:: 590:9 573:. 543:: 512:. 492:: 401:( 341:9 338:O 335:N 329:H 323:C 240:) 236:( 115:) 66:N 52:N 20:)

Index

Alpha-Galactosylceramide
alpha-galactosylceramide
IUPAC name
Systematic IUPAC name
CAS Number
158021-47-7
JSmol
Interactive image
Beilstein Reference
ChEBI
CHEBI:466659
ChEMBL
ChEMBL384200
PubChem
2826713
UNII
WX671898JF
CompTox Dashboard
DTXSID40935847
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Melting point
standard state
Infobox references
glycolipid
sponge
Agelas mauritianus

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