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A22 (antibiotic)

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binding. As a consequence, A22 inhibits MreB polymerization and thus disrupts the cytoskeleton of bacteria, causing defects of morphology and
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Bonez PC, Ramos AP, Nascimento K, Copetti PM, Souza ME, Rossi GG, Agertt VA, Sagrillo MR, Santos RC, Campos MM (October 2016).
365: 189: 438:"Antibacterial, cyto and genotoxic activities of A22 compound ((S-3, 4 -dichlorobenzyl) isothiourea hydrochloride)" 295: 376:
Despite its cytotoxic effects in human cells, A22 has been used as a research tool to investigate the bacterial
479:"A22 disrupts the bacterial actin cytoskeleton by directly binding and inducing a low-affinity state in MreB" 116: 153: 170: 385: 347: 542: 532: 72: 36: 174: 8: 477:
Bean GJ, Flickinger ST, Westler WM, McCully ME, Sept D, Weibel DB, Amann KJ (June 2009).
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InChI=1S/C8H8Cl2N2S/c9-6-2-1-5(3-7(6)10)4-13-8(11)12/h1-3H,4H2,(H3,11,12)
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homolog MreB in its nucleotide-binding pocket, blocking simultaneous
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cells. The antibiotic activity of A22 has been studied primarily in
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Except where otherwise noted, data are given for materials in their
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However, A22 does not seem to be useful as an antibiotic in
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A22 acts as a reversible inhibitor of the bacterial
524: 140: 71: 341:, causing bacterial rod-shaped cells to form 41:(3,4-Dichlorophenyl)methyl carbamimidothioate 431: 429: 173: 502: 453: 426: 371: 169: 525: 328: 201:Key: LZTCFLDZLBOLDW-UHFFFAOYSA-N 115: 50:3,4-Dichlorobenzyl carbamimidothioate 131: 13: 366:peripheral blood mononuclear cells 14: 554: 315:-(3,4-dichlorobenzyl) isothiourea 261: 255: 249: 22: 292:(at 25 °C , 100 kPa). 470: 410:"MreB Perturbing Compound A22" 402: 317:, is a chemical compound with 267: 243: 1: 455:10.1016/j.micpath.2016.07.007 395: 380:. A22 binds directly to the 7: 321:activity. It is colorless, 222:C1=CC(=C(C=C1CSC(=N)N)Cl)Cl 10: 559: 286: 230: 210: 185: 55: 47: 35: 30: 21: 325:, and light-sensitive. 442:Microbial Pathogenesis 372:A22 as a research tool 348:Pseudomonas aeruginosa 414:www.emdmillipore.com 37:Preferred IUPAC name 329:Antibiotic activity 282: g·mol 18: 296:Infobox references 16: 495:10.1021/bi900014d 364:effects on human 304:Chemical compound 302: 301: 154:CompTox Dashboard 97:Interactive image 550: 517: 516: 506: 474: 468: 467: 457: 433: 424: 423: 421: 420: 406: 310:, also known as 281: 269: 263: 257: 251: 245: 238:Chemical formula 178: 177: 162: 160: 144: 133: 119: 99: 75: 26: 19: 15: 558: 557: 553: 552: 551: 549: 548: 547: 523: 522: 521: 520: 475: 471: 434: 427: 418: 416: 408: 407: 403: 398: 374: 331: 305: 298: 293: 279: 266: 260: 254: 248: 240: 226: 223: 218: 217: 206: 203: 202: 199: 193: 192: 181: 163: 156: 147: 134: 122: 102: 89: 78: 65: 51: 43: 42: 12: 11: 5: 556: 546: 545: 540: 535: 519: 518: 489:(22): 4852–7. 469: 425: 400: 399: 397: 394: 373: 370: 330: 327: 303: 300: 299: 294: 290:standard state 287: 284: 283: 277: 271: 270: 264: 258: 252: 246: 241: 236: 233: 232: 228: 227: 225: 224: 221: 213: 212: 211: 208: 207: 205: 204: 200: 197: 196: 188: 187: 186: 183: 182: 180: 179: 171:DTXSID10324845 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: 9: 6: 4: 3: 2: 555: 544: 541: 539: 536: 534: 531: 530: 528: 514: 510: 505: 500: 496: 492: 488: 484: 480: 473: 465: 461: 456: 451: 447: 443: 439: 432: 430: 415: 411: 405: 401: 393: 392:segregation. 391: 387: 383: 379: 369: 367: 363: 359: 355: 351: 349: 344: 340: 336: 326: 324: 320: 316: 314: 309: 297: 291: 285: 278: 276: 273: 272: 242: 239: 235: 234: 229: 220: 219: 216: 209: 195: 194: 191: 184: 176: 172: 168: 167: 165: 155: 151: 150: 143: 139: 138: 136: 130: 126: 125: 118: 117:ChEMBL1229059 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: 543:Chloroarenes 486: 483:Biochemistry 482: 472: 445: 441: 417:. Retrieved 413: 404: 378:cytoskeleton 375: 346: 332: 312: 311: 307: 306: 56:Identifiers 48:Other names 533:Antibiotics 356:due to its 323:hygroscopic 231:Properties 527:Categories 419:2018-02-14 396:References 390:chromosome 319:antibiotic 275:Molar mass 84:3D model ( 73:22297-13-8 63:CAS Number 538:Thioureas 448:: 14–18. 368:(PBMCs). 362:genotoxic 358:cytotoxic 335:cell wall 513:19382805 464:27427089 337:protein 504:3951351 343:coccoid 129:PubChem 511:  501:  462:  354:humans 280:235.13 215:SMILES 142:348494 108:ChEMBL 31:Names 382:actin 190:InChI 86:JSmol 509:PMID 460:PMID 360:and 339:MreB 17:A22 499:PMC 491:doi 450:doi 386:ATP 308:A22 159:EPA 132:CID 529:: 507:. 497:. 487:48 485:. 481:. 458:. 446:99 444:. 440:. 428:^ 412:. 256:Cl 515:. 493:: 466:. 452:: 422:. 350:. 313:S 268:S 265:2 262:N 259:2 253:8 250:H 247:8 244:C 161:) 157:( 88:)

Index


Preferred IUPAC name
CAS Number
22297-13-8
JSmol
Interactive image
ChEMBL
ChEMBL1229059
PubChem
348494
CompTox Dashboard
DTXSID10324845
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InChI
SMILES
Chemical formula
Molar mass
standard state
Infobox references
antibiotic
hygroscopic
cell wall
MreB
coccoid
Pseudomonas aeruginosa
humans
cytotoxic
genotoxic
peripheral blood mononuclear cells
cytoskeleton

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