Knowledge (XXG)

Fura-2-acetoxymethyl ester

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346:. When added to cells, Fura-2AM crosses cell membranes and once inside the cell, the acetoxymethyl groups are removed by cellular esterases. Removal of the acetoxymethyl esters regenerates "Fura-2", the pentacarboxylate calcium indicator. Measurement of Ca-induced fluorescence at both 340 nm and 380 nm allows for calculation of calcium concentrations based 340/380 ratios. The use of the ratio automatically cancels out certain variables such as local differences in fura-2 concentration or cell thickness that would otherwise lead to artifacts when attempting to image calcium concentrations in cells. 175: 415: 295: 24: 96: 198:
InChI=1S/C44H47N3O24/c1-25-7-8-32(46(16-39(53)65-20-60-26(2)48)17-40(54)66-21-61-27(3)49)35(11-25)58-9-10-59-36-12-31-13-37(43-45-15-38(71-43)44(57)69-24-64-30(6)52)70-34(31)14-33(36)47(18-41(55)67-22-62-28(4)50)19-42(56)68-23-63-29(5)51/h7-8,11-15H,9-10,16-24H2,1-6H3
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InChI=1/C44H47N3O24/c1-25-7-8-32(46(16-39(53)65-20-60-26(2)48)17-40(54)66-21-61-27(3)49)35(11-25)58-9-10-59-36-12-31-13-37(43-45-15-38(71-43)44(57)69-24-64-30(6)52)70-34(31)14-33(36)47(18-41(55)67-22-62-28(4)50)19-42(56)68-23-63-29(5)51/h7-8,11-15H,9-10,16-24H2,1-6H3
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Oakes, S. G; Martin Wj, 2nd; Lisek, C. A; Powis, G (1988). "Incomplete hydrolysis of the calcium indicator precursor fura-2 pentaacetoxymethyl ester (fura-2 AM) by cells".
398: 500: 224: 456: 41:(Acetyloxy)methyl 2-(5-{2-ethoxy}-6-(2,6,10,14-tetraoxo-3,5,11,13-tetraoxa-8-azapentadecan-8-yl)-1-benzofuran-2-yl)-1,3-oxazole-5-carboxylate 189: 480: 475: 315: 232:
O=C(OCOC(=O)CN(c4ccc(cc4OCCOc3cc1c(oc(c1)c2ncc(o2)C(=O)OCOC(=O)C)cc3N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)C)CC(=O)OCOC(=O)C)C
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Except where otherwise noted, data are given for materials in their
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used in biochemistry to measure cellular calcium concentrations by
95: 85: 158: 430: 334:, is a membrane-permeant derivative of the ratiometric 303: 140: 71: 450: 8: 397:: CS1 maint: numeric names: authors list ( 457: 443: 173: 115: 15: 355: 229: 194: 169: 390: 501:Benzofuran ethers at the benzene ring 201:Key: VPSRLGDRGCKUTK-UHFFFAOYSA-N 7: 411: 409: 211:Key: VPSRLGDRGCKUTK-UHFFFAOYAI 131: 429:. You can help Knowledge (XXG) by 14: 413: 293: 22: 289:(at 25 °C , 100 kPa). 1: 377:10.1016/0003-2697(88)90267-9 17:Fura-2-acetoxymethyl ester 542: 408: 328:Fura-2-acetoxymethyl ester 283: 240: 220: 185: 55: 47: 35: 30: 21: 365:Analytical Biochemistry 481:Cell culture reagents 279:1001.85 476:Biochemistry methods 330:, often abbreviated 37:Preferred IUPAC name 18: 526:Biochemistry stubs 316:Infobox references 16: 438: 437: 324:Chemical compound 322: 321: 154:CompTox Dashboard 97:Interactive image 533: 491:Fluorescent dyes 459: 452: 445: 417: 410: 403: 402: 396: 388: 360: 306: 300: 297: 296: 248:Chemical formula 178: 177: 162: 160: 144: 133: 119: 99: 75: 26: 19: 541: 540: 536: 535: 534: 532: 531: 530: 466: 465: 464: 463: 407: 406: 389: 362: 361: 357: 352: 325: 318: 313: 312: 311:  ?) 302: 298: 294: 290: 268: 264: 260: 256: 250: 236: 233: 228: 227: 216: 213: 212: 209: 203: 202: 199: 193: 192: 181: 163: 156: 147: 134: 122: 102: 89: 78: 65: 51: 43: 42: 12: 11: 5: 539: 537: 529: 528: 523: 518: 513: 508: 506:Acetate esters 503: 498: 493: 488: 483: 478: 468: 467: 462: 461: 454: 447: 439: 436: 435: 418: 405: 404: 354: 353: 351: 348: 323: 320: 319: 314: 292: 291: 287:standard state 284: 281: 280: 277: 271: 270: 266: 262: 258: 254: 251: 246: 243: 242: 238: 237: 235: 234: 231: 223: 222: 221: 218: 217: 215: 214: 210: 207: 206: 204: 200: 197: 196: 188: 187: 186: 183: 182: 180: 179: 171:DTXSID50148784 166: 164: 152: 149: 148: 146: 145: 137: 135: 127: 124: 123: 121: 120: 112: 110: 104: 103: 101: 100: 92: 90: 83: 80: 79: 77: 76: 68: 66: 61: 58: 57: 53: 52: 49: 45: 44: 40: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 538: 527: 524: 522: 519: 517: 516:Glycol ethers 514: 512: 509: 507: 504: 502: 499: 497: 494: 492: 489: 487: 484: 482: 479: 477: 474: 473: 471: 460: 455: 453: 448: 446: 441: 440: 434: 432: 428: 425:article is a 424: 419: 416: 412: 400: 394: 386: 382: 378: 374: 371:(1): 159–66. 370: 366: 359: 356: 349: 347: 345: 341: 337: 333: 329: 317: 310: 305: 288: 282: 278: 276: 273: 272: 252: 249: 245: 244: 239: 230: 226: 219: 205: 195: 191: 184: 176: 172: 168: 167: 165: 155: 151: 150: 143: 139: 138: 136: 130: 126: 125: 118: 114: 113: 111: 109: 106: 105: 98: 94: 93: 91: 87: 82: 81: 74: 70: 69: 67: 64: 60: 59: 54: 46: 38: 34: 29: 25: 20: 486:Cell imaging 431:expanding it 423:biochemistry 420: 393:cite journal 368: 364: 358: 344:fluorescence 331: 327: 326: 56:Identifiers 48:Other names 241:Properties 73:108964-32-5 470:Categories 350:References 338:indicator 275:Molar mass 108:ChemSpider 84:3D model ( 63:CAS Number 521:Anilines 496:Oxazoles 332:Fura-2AM 50:Fura-2AM 511:Formals 385:3369679 336:calcium 309:what is 307: ( 269: 142:3364574 129:PubChem 117:2610364 383:  340:Fura-2 304:verify 301:  225:SMILES 31:Names 421:This 190:InChI 86:JSmol 427:stub 399:link 381:PMID 373:doi 369:169 159:EPA 132:CID 472:: 395:}} 391:{{ 379:. 367:. 267:24 259:47 255:44 458:e 451:t 444:v 433:. 401:) 387:. 375:: 299:Y 265:O 263:3 261:N 257:H 253:C 161:) 157:( 88:)

Index


Preferred IUPAC name
CAS Number
108964-32-5
JSmol
Interactive image
ChemSpider
2610364
PubChem
3364574
CompTox Dashboard
DTXSID50148784
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
standard state
verify
what is
Infobox references
calcium
Fura-2
fluorescence
doi
10.1016/0003-2697(88)90267-9
PMID
3369679
cite journal
link

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