Knowledge (XXG)

Distamycin

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137: 24: 296: 737:
Vaijayanthi, Thangavel; Bando, Toshikazu; Pandian, Ganesh N.; Sugiyama, Hiroshi (2012). "Progress and Prospects of Pyrrole-Imidazole Polyamide-Fluorophore Conjugates as Sequence-Selective DNA Probes".
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Baraldi, Pier Giovanni; Preti, Delia; Fruttarolo, Francesca; Tabrizi, Mojgan Aghazadeh; Romagnoli, Romeo (2007). "Hybrid molecules between distamycin a and active moieties of antitumor agents".
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InChI=1S/C22H27N9O4/c1-29-9-13(26-12-32)6-17(29)21(34)28-15-8-18(31(3)11-15)22(35)27-14-7-16(30(2)10-14)20(33)25-5-4-19(23)24/h6-12H,4-5H2,1-3H3,(H3,23,24)(H,25,33)(H,26,32)(H,27,35)(H,28,34)
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Pagano, Bruno; Fotticchia, Iolanda; De Tito, Stefano; Mattia, Carlo A.; Mayol, Luciano; Novellino, Ettore; Randazzo, Antonio; Giancola, Concetta (2010).
602:
Majumder, Parijat; Banerjee, Amrita; Shandilya, Jayasha; Senapati, Parijat; Chatterjee, Snehajyoti; Kundu, Tapas K.; Dasgupta, Dipak (2013).
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N-{5-carbamoyl}-1-methyl-1H-pyrrol-3-yl)carbamoyl]-1-methyl-1H-pyrrol-3-yl}-4-formamido-1-methyl-1H-pyrrole-2-carboxamide
169: 457:
Barrett, Michael P.; Gemmell, Curtis G.; Suckling, Colin J. (2013). "Minor groove binders as anti-infective agents".
663:"Mammalian topoisomerase II activity is modulated by the DNA minor groove binder distamycin in simian virus 40 DNA" 338: 376: 132: 367: 36: 791: 615: 505: 801: 60: 365:. As opposed to netropsin, distamycin contains three N-methyl-pyrrole units. It is harvested from 762: 806: 786: 754: 719: 684: 643: 584: 533: 474: 553:"Selective Binding of Distamycin a Derivative to G-Quadruplex Structure [d(TGGGGT)]4" 746: 711: 674: 633: 623: 574: 564: 523: 513: 466: 380: 240: 178: 811: 392: 136: 114: 70: 619: 509: 638: 603: 579: 552: 371:
that also produces netropsin. Distamycin prefers AT-rich DNA-sequences and tetrades of
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Proceedings of the National Academy of Sciences of the United States of America
715: 604:"Minor Groove Binder Distamycin Remodels Chromatin but Inhibits Transcription" 403: 399: 330: 267: 105: 424: 358: 326: 758: 750: 723: 647: 588: 518: 478: 688: 569: 537: 494:"The molecular origin of DNA-drug specificity in netropsin and distamycin" 492:
Kopka, M. L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R. E. (1985).
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Except where otherwise noted, data are given for materials in their
93: 83: 434: 225:/N=C(/CCNC(=O)c1cc(cn1C)NC(=O)c2cc(cn2C)NC(=O)c3cc(cn3C)NC=O)\N 157: 452: 450: 410:is 37,000 M cm at a wavelength of 303 nm. 69: 8: 135: 113: 15: 678: 637: 627: 578: 568: 527: 517: 177: 383:. Derivates from distamycin are used as 446: 222: 197: 126: 337:, binding to the small furrow of the 204:Key: UPBAOYRENQEPJO-UHFFFAOYSA-N 48:Distamycin A, Herperetin, Stallimycin 7: 704:Bioorganic & Medicinal Chemistry 402:, and sensible to light, freeze and 667:The Journal of Biological Chemistry 148: 387:to combat tumours. Derivates with 379:and increases the activity of the 14: 471:10.1016/j.pharmthera.2013.03.002 385:alkylating antineoplastic agents 294: 22: 661:Fesen, M.; Pommier, Y. (1989). 459:Pharmacology & Therapeutics 290:(at 25 °C , 100 kPa). 1: 680:10.1016/S0021-9258(18)60471-5 408:molar attenuation coefficient 629:10.1371/journal.pone.0057693 357:antibiotic and analogous to 272:481.508 g/mol 828: 375:. Distamycin inhibits the 716:10.1016/j.bmc.2006.07.004 395:for double-stranded DNA. 284: 233: 213: 188: 53: 45: 35: 30: 21: 557:Journal of Nucleic Acids 797:DNA-binding substances 751:10.1002/cbic.201200451 519:10.1073/pnas.82.5.1376 368:Streptomyces netropsis 620:2013PLoSO...857693M 570:10.4061/2010/247137 510:1985PNAS...82.1376K 335:minor groove binder 18: 333:, which acts as a 311:Infobox references 16: 745:(15): 2170–2185. 361:and the class of 319:Chemical compound 317: 316: 95:Interactive image 819: 771: 770: 734: 728: 727: 699: 693: 692: 682: 658: 652: 651: 641: 631: 599: 593: 592: 582: 572: 548: 542: 541: 531: 521: 489: 483: 482: 454: 398:The compound is 393:fluorescent tags 381:topoisomerase II 349:Distamycin is a 301: 298: 297: 241:Chemical formula 181: 161: 150: 139: 128: 117: 97: 73: 26: 19: 827: 826: 822: 821: 820: 818: 817: 816: 777: 776: 775: 774: 736: 735: 731: 701: 700: 696: 673:(19): 11354–9. 660: 659: 655: 601: 600: 596: 550: 549: 545: 491: 490: 486: 456: 455: 448: 443: 416: 374: 347: 320: 313: 308: 307: 306:  ?) 299: 295: 291: 261: 257: 253: 249: 243: 229: 226: 221: 220: 209: 206: 205: 202: 196: 195: 184: 164: 151: 120: 100: 87: 76: 63: 49: 41: 12: 11: 5: 825: 823: 815: 814: 809: 804: 799: 794: 789: 779: 778: 773: 772: 729: 694: 653: 594: 543: 504:(5): 1376–80. 484: 445: 444: 442: 439: 438: 437: 432: 427: 422: 415: 412: 372: 346: 343: 318: 315: 314: 309: 293: 292: 288:standard state 285: 282: 281: 278: 274: 273: 270: 264: 263: 259: 255: 251: 247: 244: 239: 236: 235: 231: 230: 228: 227: 224: 216: 215: 214: 211: 210: 208: 207: 203: 200: 199: 191: 190: 189: 186: 185: 183: 182: 174: 172: 166: 165: 163: 162: 154: 152: 144: 141: 140: 130: 122: 121: 119: 118: 110: 108: 102: 101: 99: 98: 90: 88: 81: 78: 77: 75: 74: 66: 64: 59: 56: 55: 51: 50: 47: 43: 42: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 824: 813: 810: 808: 805: 803: 800: 798: 795: 793: 790: 788: 785: 784: 782: 768: 764: 760: 756: 752: 748: 744: 740: 733: 730: 725: 721: 717: 713: 709: 705: 698: 695: 690: 686: 681: 676: 672: 668: 664: 657: 654: 649: 645: 640: 635: 630: 625: 621: 617: 614:(2): e57693. 613: 609: 605: 598: 595: 590: 586: 581: 576: 571: 566: 562: 558: 554: 547: 544: 539: 535: 530: 525: 520: 515: 511: 507: 503: 499: 495: 488: 485: 480: 476: 472: 468: 464: 460: 453: 451: 447: 440: 436: 433: 431: 430:Hoechst 33258 428: 426: 423: 421: 418: 417: 413: 411: 409: 405: 401: 396: 394: 390: 386: 382: 378: 377:transcription 370: 369: 364: 360: 356: 352: 344: 342: 340: 336: 332: 328: 324: 312: 305: 289: 283: 280:White powder 279: 276: 275: 271: 269: 266: 265: 245: 242: 238: 237: 232: 223: 219: 212: 198: 194: 187: 180: 176: 175: 173: 171: 168: 167: 160: 156: 155: 153: 147: 143: 142: 138: 134: 131: 129: 127:ECHA InfoCard 124: 123: 116: 112: 111: 109: 107: 104: 103: 96: 92: 91: 89: 85: 80: 79: 72: 68: 67: 65: 62: 58: 57: 52: 44: 38: 34: 29: 25: 20: 742: 738: 732: 710:(1): 17–35. 707: 703: 697: 670: 666: 656: 611: 607: 597: 560: 556: 546: 501: 497: 487: 465:(1): 12–23. 462: 458: 397: 391:are used as 389:fluorophores 366: 363:lexitropsins 348: 339:double helix 322: 321: 54:Identifiers 46:Other names 792:Antibiotics 739:ChemBioChem 420:Lexitropsin 400:hygroscopic 277:Appearance 234:Properties 133:100.026.823 17:Distamycin 802:Imidazoles 781:Categories 441:References 404:hydrolysis 345:Properties 331:antibiotic 323:Distamycin 268:Molar mass 179:F6010N240F 106:ChemSpider 82:3D model ( 61:CAS Number 37:IUPAC name 425:Netropsin 359:netropsin 327:polyamide 71:6576-51-8 807:Pyrroles 787:Peptides 759:23023993 724:17081759 648:23460895 608:PLOS ONE 589:20725616 479:23507040 414:See also 159:24894001 767:1491900 689:2544590 639:3584068 616:Bibcode 580:2915651 563:: 1–7. 538:2983343 506:Bibcode 355:amidine 351:pyrrole 304:what is 302: ( 262: 146:PubChem 812:Amines 765:  757:  722:  687:  646:  636:  587:  577:  536:  529:397264 526:  477:  406:. Its 218:SMILES 31:Names 763:S2CID 325:is a 193:InChI 84:JSmol 755:PMID 720:PMID 685:PMID 644:PMID 585:PMID 561:2010 534:PMID 475:PMID 435:DAPI 170:UNII 115:3003 747:doi 712:doi 675:doi 671:264 634:PMC 624:doi 575:PMC 565:doi 524:PMC 514:doi 467:doi 463:139 149:CID 783:: 761:. 753:. 743:13 741:. 718:. 708:15 706:. 683:. 669:. 665:. 642:. 632:. 622:. 610:. 606:. 583:. 573:. 559:. 555:. 532:. 522:. 512:. 502:82 500:. 496:. 473:. 461:. 449:^ 341:. 252:27 248:22 769:. 749:: 726:. 714:: 691:. 677:: 650:. 626:: 618:: 612:8 591:. 567:: 540:. 516:: 508:: 481:. 469:: 373:4 353:- 329:- 300:N 260:4 258:O 256:9 254:N 250:H 246:C 86:)

Index


IUPAC name
CAS Number
6576-51-8
JSmol
Interactive image
ChemSpider
3003
ECHA InfoCard
100.026.823
Edit this at Wikidata
PubChem
24894001
UNII
F6010N240F
InChI
SMILES
Chemical formula
Molar mass
standard state
what is
Infobox references
polyamide
antibiotic
minor groove binder
double helix
pyrrole
amidine
netropsin
lexitropsins

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