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Phloxine

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218: 143: 345: 24: 632:, the dye is unable to entere cell because of their membranes. Dead yeast cells lose membrane integrity, so phloxine B can enter and stain the intracellular cytosolic compounds. Therefore, staining is a measure of cell death. In cell counting assays, the number of fluorescent (i.e. dead) cells observed through a 100: 358: 636:
can be compared to the total number of cells to give a measure of mortality. The same principle can be applied at higher throughput by fluorescence-activated
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Cyanosin; Cyanosine; Eosine bluish; Eosine Blue; Cyanosin B; Eosin Blue; Phloxine P; Phloxin B; Eosine I Bluish; Acid red 92; C.I. 45410; D & C Red no. 28
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Leive, Loretta; Kollin, Virginia (July 1967). "Controlling EDTA treatment to produce permeable escherichia coli with normal metabolic processes".
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Duarte, Paulo; Ferreira, Diana P.; Ferreira Machado, Isabel; Filipe, Luis; Ferreira, Vieira; Rodríguez, Hernan B.; San Román, Enrique (2012).
832:"In Vitro Antibacterial Activities of Phloxine B and Other Halogenated Fluoresceins against Methicillin-Resistant Staphylococcus aureus" 1001: 515:
of 25 μM, growth is reduced by 10-fold within 2.5 hours. At concentrations of 50 μM and 100 μM, growth is stopped completely and
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Coppeta, J.; Rogers, C. (1998). "Dual emission laser induced fluorescence for direct planar scalar behavior measurements".
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are formed. These compounds cause irreversible damage to the bacteria, leading to growth arrest and cell death.
1210: 614: 1190: 138: 1205: 591: 567: 1195: 503: 1138: 1038: 793: 36: 910:"Expanding the bactericidal action of the food color additive phloxine B to gram-negative bacteria" 559: 213: 66: 809: 587: 551: 880: 1200: 1166: 1107: 1066: 1007: 997: 966: 931: 861: 766: 487: 457: 433: 1156: 1146: 1097: 1056: 1046: 989: 958: 921: 851: 843: 801: 756: 746: 713: 594:, removes the phloxine B resistance and allows gram-negative bacteria to be killed as well. 532: 323: 255: 1025:
Guérin, Renée; Beauregard, Pascale B.; Leroux, Alexandre; Rokeach, Luis A. (16 July 2009).
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creates a permeability barrier that prevents efficient uptake of the compound. Addition of
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The Code of Federal Regulations of the United States of America, Title 21, Part 74.1328
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Minois, Nadège; Frajnt, Magdalena; Wilson, Chris; Vaupel, James W. (11 January 2005).
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maximum around 564 nm. Apart from industrial use, phloxine B has functions as an
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C1=C2C(=C(C(=C1Br))Br)OC3=C(C(=C(C=C3C24C5=C(C(=C(C(=C5Cl)Cl)Cl)Cl)C(=O)O4)Br))Br..
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Proceedings of the National Academy of Sciences of the United States of America
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Noda, Takeshi (2008). "Chapter 2 Viability Assays to Monitor Yeast Autophagy".
1027:"Calnexin Regulates Apoptosis Induced by Inositol Starvation in Fission Yeast" 751: 718: 701: 385: 301: 1151: 1102: 1085: 453: 449: 397: 1170: 1111: 1070: 1011: 935: 865: 770: 970: 805: 445: 421: 417: 536: 413: 151: 1127:"Advances in measuring lifespan in the yeast Saccharomyces cerevisiae" 523:
deems phloxine B to be safe up to a daily dosage of 1.25 mg/kg.
735:"Phloxine B as a Probe for Entrapment in Microcrystalline Cellulose" 335:
Except where otherwise noted, data are given for materials in their
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Kwolek-Mirek, Magdalena; Zadrag-Tecza, Renata (September 2014).
644:), where all phloxine B-stained cells in a sample are counted. 393: 543: 389: 986:
Autophagy: Lower Eukaryotes and Non-Mammalian Systems, Part A
448:. For example, it is used in hematoxylin-phloxine-saffron ( 201: 706:
Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)
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Disodium 2′,4′,5′,7′-tetrabromo-4,5,6,7-tetrachloro-3-oxo-3
988:. Methods in Enzymology. Vol. 451. pp. 27–32. 353: 608:
Phloxine B can be used to stain dead cells of several
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Biochemical and Biophysical Research Communications
519:decrease by a factor of 10 to 10. For humans, the 702:"Thin Layer Chromatography of Synthetic Dyes (X)" 163: 45:-spirobenzofuran-1,9′-xanthene]-3′,6′-bis(olate) 75: 903: 901: 825: 823: 681:. U S Government Printing Office. p. 296 8: 914:FEMS Immunology & Medical Microbiology 570:are phloxine B-resistant due to the outer 216: 141: 15: 1160: 1150: 1101: 1060: 1050: 925: 855: 760: 750: 717: 554:. When phloxine B is subjected to light, 183: 830:Rasooly, Avraham; Weisz, Adrian (2002). 531:Bacteria exposed to phloxine B die from 416:atoms at positions 2, 4, 5 and 7 of the 653: 237: 212: 412:, but differs by the presence of four 132: 836:Antimicrobial Agents and Chemotherapy 675:Food and Drug Administration (2001). 670: 668: 119: 7: 154: 432:maximum around 540 nm and an 14: 848:10.1128/AAC.46.11.3650-3653.2002 513:minimum inhibitory concentration 343: 279: 267: 22: 908:Rasooly, Reuven (August 2005). 339:(at 25 °C , 100 kPa). 273: 586:, which is known to strip the 291: 285: 261: 1: 994:10.1016/S0076-6879(08)03202-3 1052:10.1371/journal.pone.0006244 963:10.1016/0006-291x(67)90434-2 927:10.1016/j.femsim.2005.04.004 885:Narkive Mailing List Archive 521:Food and Drug Administration 1227: 601: 574:that surrounds them. This 380:(commonly known simply as 752:10.3390/molecules17021602 719:10.3358/shokueishi.11.242 621:Schizosaccharomyces pombe 333: 248: 228: 59: 51: 35: 30: 21: 661:Phloxine B (Acid red 92) 615:Saccharomyces cerevisiae 464:Antimicrobial properties 452:) staining to color the 1152:10.1073/pnas.0408332102 1103:10.1111/1567-1364.12202 568:Gram-negative bacteria 550:to positively charged 806:10.1007/s003480050202 786:Experiments in Fluids 602:Further information: 592:membrane permeability 539:in water to become a 504:Staphylococcus aureus 408:. It is derived from 404:and coloring food in 879:Borgerink, Hermina. 700:Kamikura, M (1970). 598:Measure of viability 469:Lethal dosage levels 317:Red to brown powder 37:Preferred IUPAC name 1143:2005PNAS..102..402M 1090:FEMS Yeast Research 1043:2009PLoSO...4.6244G 798:1998ExFl...25....1C 588:lipopolysaccharides 552:cellular components 527:Mechanism of action 477:, phloxine B has a 473:In the presence of 324:Solubility in water 309: g·mol 18: 541:negatively charged 460:in shades of red. 392:used for coloring 366:Infobox references 16: 842:(11): 3650–3653. 488:Bacillus subtilis 485:strains, such as 458:connective tissue 374:Chemical compound 372: 371: 197:CompTox Dashboard 101:Interactive image 1218: 1175: 1174: 1164: 1154: 1122: 1116: 1115: 1105: 1096:(7): 1068–1079. 1081: 1075: 1074: 1064: 1054: 1022: 1016: 1015: 981: 975: 974: 946: 940: 939: 929: 905: 896: 895: 893: 891: 876: 870: 869: 859: 827: 818: 817: 781: 775: 774: 764: 754: 745:(2): 1602–1616. 730: 724: 723: 721: 697: 691: 690: 688: 686: 672: 663: 658: 533:oxidative damage 511:) strains. At a 446:biological stain 428:ring. It has an 356: 350: 347: 346: 308: 293: 287: 281: 275: 269: 263: 256:Chemical formula 221: 220: 205: 203: 187: 167: 156: 145: 134: 123: 103: 79: 26: 19: 1226: 1225: 1221: 1220: 1219: 1217: 1216: 1215: 1211:Spiro compounds 1181: 1180: 1179: 1178: 1124: 1123: 1119: 1083: 1082: 1078: 1024: 1023: 1019: 1004: 983: 982: 978: 948: 947: 943: 907: 906: 899: 889: 887: 878: 877: 873: 829: 828: 821: 783: 782: 778: 732: 731: 727: 699: 698: 694: 684: 682: 674: 673: 666: 659: 655: 650: 606: 604:Viability assay 600: 529: 494:Bacillus cereus 471: 466: 375: 368: 363: 362: 361:  ?) 352: 348: 344: 340: 326: 306: 296: 290: 284: 278: 272: 266: 258: 244: 241: 236: 235: 224: 206: 199: 190: 170: 157: 126: 106: 93: 82: 69: 55: 47: 46: 12: 11: 5: 1224: 1222: 1214: 1213: 1208: 1203: 1198: 1193: 1191:Organobromides 1183: 1182: 1177: 1176: 1137:(2): 402–406. 1117: 1076: 1017: 1002: 976: 957:(2): 229–236. 941: 920:(2): 239–244. 897: 871: 819: 776: 725: 712:(4): 242–248. 692: 664: 652: 651: 649: 646: 638:flow cytometry 634:haemocytometer 599: 596: 576:polysaccharide 564:singlet oxygen 528: 525: 497:, and several 470: 467: 465: 462: 420:ring and four 373: 370: 369: 364: 342: 341: 337:standard state 334: 331: 330: 327: 322: 319: 318: 315: 311: 310: 304: 298: 297: 294: 288: 282: 276: 270: 264: 259: 254: 251: 250: 246: 245: 243: 242: 239: 231: 230: 229: 226: 225: 223: 222: 209: 207: 195: 192: 191: 189: 188: 180: 178: 172: 171: 169: 168: 160: 158: 150: 147: 146: 136: 128: 127: 125: 124: 116: 114: 108: 107: 105: 104: 96: 94: 87: 84: 83: 81: 80: 72: 70: 65: 62: 61: 57: 56: 53: 49: 48: 40: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 1223: 1212: 1209: 1207: 1206:Fluorone dyes 1204: 1202: 1199: 1197: 1194: 1192: 1189: 1188: 1186: 1172: 1168: 1163: 1158: 1153: 1148: 1144: 1140: 1136: 1132: 1128: 1121: 1118: 1113: 1109: 1104: 1099: 1095: 1091: 1087: 1080: 1077: 1072: 1068: 1063: 1058: 1053: 1048: 1044: 1040: 1036: 1032: 1028: 1021: 1018: 1013: 1009: 1005: 1003:9780123745484 999: 995: 991: 987: 980: 977: 972: 968: 964: 960: 956: 952: 945: 942: 937: 933: 928: 923: 919: 915: 911: 904: 902: 898: 886: 882: 875: 872: 867: 863: 858: 853: 849: 845: 841: 837: 833: 826: 824: 820: 815: 811: 807: 803: 799: 795: 791: 787: 780: 777: 772: 768: 763: 758: 753: 748: 744: 740: 736: 729: 726: 720: 715: 711: 707: 703: 696: 693: 680: 679: 671: 669: 665: 662: 657: 654: 647: 645: 643: 639: 635: 631: 627: 623: 622: 617: 616: 611: 605: 597: 595: 593: 590:and increase 589: 585: 581: 580:lipid bilayer 577: 573: 572:cell membrane 569: 565: 561: 560:free radicals 557: 556:debromination 553: 549: 545: 542: 538: 535:. Phloxine B 534: 526: 524: 522: 518: 514: 510: 506: 505: 500: 496: 495: 490: 489: 484: 483:gram-positive 480: 476: 468: 463: 461: 459: 455: 451: 447: 443: 439: 438:antimicrobial 435: 431: 427: 426:carboxyphenyl 424:atoms in the 423: 419: 415: 411: 407: 403: 402:United States 399: 395: 391: 387: 386:water-soluble 383: 379: 367: 360: 355: 338: 332: 328: 325: 321: 320: 316: 313: 312: 305: 303: 300: 299: 260: 257: 253: 252: 247: 238: 234: 227: 219: 215: 214:DTXSID1031090 211: 210: 208: 198: 194: 193: 186: 182: 181: 179: 177: 174: 173: 166: 162: 161: 159: 153: 149: 148: 144: 140: 137: 135: 133:ECHA InfoCard 130: 129: 122: 118: 117: 115: 113: 110: 109: 102: 98: 97: 95: 91: 86: 85: 78: 74: 73: 71: 68: 64: 63: 58: 50: 44: 38: 34: 29: 25: 20: 1196:Chloroarenes 1134: 1130: 1120: 1093: 1089: 1079: 1037:(7): e6244. 1034: 1030: 1020: 985: 979: 954: 950: 944: 917: 913: 888:. Retrieved 884: 874: 839: 835: 789: 785: 779: 742: 738: 728: 709: 705: 695: 683:. Retrieved 677: 656: 630:growth media 619: 613: 612:, including 607: 530: 502: 492: 486: 479:bactericidal 472: 381: 377: 376: 60:Identifiers 52:Other names 42: 881:"HPS stain" 792:(1): 1–15. 558:occurs and 517:cell counts 501:-resistant 499:methicillin 440:substance, 410:fluorescein 314:Appearance 249:Properties 139:100.038.490 121:CHEBI:87192 1185:Categories 648:References 481:effect on 430:absorption 378:Phloxine B 302:Molar mass 185:767IP0Y5NH 88:3D model ( 77:18472-87-2 67:CAS Number 739:Molecules 628:in yeast 454:cytoplasm 442:viability 398:cosmetics 17:Phloxine 1201:Lactones 1171:15625107 1112:25154541 1071:19606215 1031:PLOS ONE 1012:19185710 936:15949926 890:18 April 866:12384384 814:37649159 771:22314381 685:15 April 578:-coated 444:dye and 434:emission 422:chlorine 418:xanthene 382:phloxine 329:Soluble 1139:Bibcode 1062:2705804 1039:Bibcode 971:4166571 794:Bibcode 762:6268435 626:diluted 624:. When 537:ionizes 414:bromine 400:in the 384:) is a 359:what is 357: ( 165:6433718 152:PubChem 1169:  1162:544282 1159:  1110:  1069:  1059:  1010:  1000:  969:  934:  864:  857:128710 854:  812:  769:  759:  610:yeasts 354:verify 351:  307:829.63 233:SMILES 31:Names 810:S2CID 548:binds 546:that 475:light 406:Japan 394:drugs 112:ChEBI 90:JSmol 1167:PMID 1108:PMID 1067:PMID 1008:PMID 998:ISBN 967:PMID 932:PMID 892:2016 862:PMID 767:PMID 687:2016 642:FACS 618:and 584:EDTA 562:and 509:MRSA 456:and 396:and 388:red 176:UNII 1157:PMC 1147:doi 1135:102 1098:doi 1057:PMC 1047:doi 990:doi 959:doi 922:doi 852:PMC 844:doi 802:doi 757:PMC 747:doi 714:doi 544:ion 450:HPS 390:dye 202:EPA 155:CID 1187:: 1165:. 1155:. 1145:. 1133:. 1129:. 1106:. 1094:14 1092:. 1088:. 1065:. 1055:. 1045:. 1033:. 1029:. 1006:. 996:. 965:. 955:28 953:. 930:. 918:45 916:. 912:. 900:^ 883:. 860:. 850:. 840:46 838:. 834:. 822:^ 808:. 800:. 790:25 788:. 765:. 755:. 743:17 741:. 737:. 710:11 708:. 704:. 667:^ 491:, 286:Na 280:Cl 274:Br 265:20 1173:. 1149:: 1141:: 1114:. 1100:: 1073:. 1049:: 1041:: 1035:4 1014:. 992:: 973:. 961:: 938:. 924:: 894:. 868:. 846:: 816:. 804:: 796:: 773:. 749:: 722:. 716:: 689:. 640:( 507:( 349:N 295:5 292:O 289:2 283:4 277:4 271:2 268:H 262:C 204:) 200:( 92:) 43:H

Index


Preferred IUPAC name
CAS Number
18472-87-2
JSmol
Interactive image
ChEBI
CHEBI:87192
ECHA InfoCard
100.038.490
Edit this at Wikidata
PubChem
6433718
UNII
767IP0Y5NH
CompTox Dashboard
DTXSID1031090
Edit this at Wikidata
SMILES
Chemical formula
Molar mass
Solubility in water
standard state
verify
what is
Infobox references
water-soluble
dye
drugs
cosmetics

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