Zeocin

Zeocin
Names
Systematic IUPAC name
(24R,7S,10S,11S,12R,15S,16R,182R,183S,184S,185S,186S,192R,193S,194S,195R,196R)-15-{6-Amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl]-5-methylpyrimidine-4-carboxamido}-14-({4-[(diaminomethylidene)amino]butyl}carbamoyl)-11,184,185,203,205-pentahydroxy-7-[(1R)-1-hydroxyethyl]-186,206-bis(hydroxymethyl)-16-(1H-imidazol-5-yl)-10,12-dimethyl-6,9,14-trioxo-24,25-dihydro-17,19-dioxa-5,8,13-triaza-1(2),2(4,2)-bis([1,3]thiazola)-18(2,3),20(2)-bis(oxana)icosaphan-204-yl carbamate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C55H86N20O21S2/c1-19-32(72-45(75-43(19)58)24(11-30(57)79)67-12-23(56)44(59)85)49(89)74-34(40(25-13-63-18-68-25)94-53-42(38(83)36(81)28(14-76)93-53)95-52-39(84)41(96-55(62)91)37(82)29(15-77)92-52)50(90)69-21(3)35(80)20(2)46(86)73-33(22(4)78)48(88)65-10-7-31-70-27(17-97-31)51-71-26(16-98-51)47(87)64-8-5-6-9-66-54(60)61/h13,16,18,20-24,27-29,33-42,52-53,67,76-78,80-84H,5-12,14-15,17,56H2,1-4H3,(H2,57,79)(H2,59,85)(H2,62,91)(H,63,68)(H,64,87)(H,65,88)(H,69,90)(H,73,86)(H,74,89)(H2,58,72,75)(H4,60,61,66)
    Key: CWCMIVBLVUHDHK-UHFFFAOYSA-N
  • InChI=1/C55H86N20O21S2/c1-19-32(72-45(75-43(19)58)24(11-30(57)79)67-12-23(56)44(59)85)49(89)74-34(40(25-13-63-18-68-25)94-53-42(38(83)36(81)28(14-76)93-53)95-52-39(84)41(96-55(62)91)37(82)29(15-77)92-52)50(90)69-21(3)35(80)20(2)46(86)73-33(22(4)78)48(88)65-10-7-31-70-27(17-97-31)51-71-26(16-98-51)47(87)64-8-5-6-9-66-54(60)61/h13,16,18,20-24,27-29,33-42,52-53,67,76-78,80-84H,5-12,14-15,17,56H2,1-4H3,(H2,57,79)(H2,59,85)(H2,62,91)(H,63,68)(H,64,87)(H,65,88)(H,69,90)(H,73,86)(H,74,89)(H2,58,72,75)(H4,60,61,66)
    Key: CWCMIVBLVUHDHK-UHFFFAOYAG
  • CC1=C(N=C(N=C1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@@H]([C@H](C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC5=N[C@H](CS5)C6=NC(=CS6)C(=O)NCCCCN=C(N)N)O
Properties
C55H86N20O21S2
Molar mass 1427.53 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Zeocin is a trade name for a formulation of phleomycin D1, a glycopeptide antibiotic and one of the phleomycins from Streptomyces verticillus belonging to the bleomycin family of antibiotics.[1] It is a broad-spectrum antibiotic that is effective against most aerobic organisms including bacteria, filamentous fungi, yeast, plant, and animal cells. It causes cell death by intercalating into DNA and inducing double stranded breaks of the DNA.[2][3]

Zeocin is a registered trademark belonging to InvivoGen. [4]

  1. ^ InvivoGen. "Technical Data Sheet for Zeocin" (PDF).
  2. ^ Ehrenfeld GM, Shipley JB, Heimbrook DC, Sugiyama H, Long EC, van Boom JH, van der Marel GA, Oppenheimer NJ, Hecht SM (1987). "Copper-dependent cleavage of DNA by bleomycin". Biochemistry. 26 (3): 931–42. doi:10.1021/bi00377a038. PMID 2436656.
  3. ^ Chankova SG, Dimova E, Dimitrova M, Bryant PE (2007). "Induction of DNA double-strand breaks by zeocin in Chlamydomonas reinhardtii and the role of increased DNA double-strand breaks rejoining in the formation of an adaptive response". Radiation and Environmental Biophysics. 46 (4): 409–16. doi:10.1007/s00411-007-0123-2. PMID 17639449. S2CID 40973182.
  4. ^ "ZEOCIN Trademark of INVIVOGEN - Registration Number 6366745 - Serial Number 79285216 :: Justia Trademarks".