Thiocoraline

Thiocoraline is a microbial natural product of the depsipeptide class. Thiocoraline was isolated from the mycelium cake of a marine actinomycete strain L-13-ACM2-092.[1] In vitro, thiocoraline causes an arrest in G1 phase of the cell cycle and decreases the rate of S phase progression towards G2/M phase.[2] Thiocoraline is likely to be a DNA replication inhibitor. Thiocoraline is produced on a nonribosomal peptide synthetase (NRPS) assembly line.[3]

Thiocoraline
Names
IUPAC name
N,N′-{(1R,7S,11S,14R,20S,24S)-2,12,15,25-Tetramethyl-11,24-bis[(methylsulfanyl)methyl]-3,6,10,13,16,19,23,26-octaoxo-9,22,28,29-tetrathia-2,5,12,15,18,25-hexaazabicyclo[12.12.4]triacontane-7,20-diyl}bis(3-hydroxy-2-quinolinecarboxamide)
Other names
Thiocoraline A
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C48H56N10O12S6/c1-55-31-23-75-76-24-32(46(68)58(4)34(22-72-6)48(70)74-19-29(41(63)49-17-37(55)61)53-43(65)39-35(59)15-25-11-7-9-13-27(25)51-39)56(2)38(62)18-50-42(64)30(20-73-47(69)33(21-71-5)57(3)45(31)67)54-44(66)40-36(60)16-26-12-8-10-14-28(26)52-40/h7-16,29-34,59-60H,17-24H2,1-6H3,(H,49,63)(H,50,64)(H,53,65)(H,54,66)/t29-,30-,31+,32+,33+,34+/m1/s1
    Key: UPGGKUQISSWRJJ-ZRBWWFCKSA-N
  • CN1[C@H]2CSSC[C@@H](C(=O)N([C@H](C(=O)SC[C@H](C(=O)NCC1=O)NC(=O)C3=NC4=CC=CC=C4C=C3O)CSC)C)N(C(=O)CNC(=O)[C@@H](CSC(=O)[C@@H](N(C2=O)C)CSC)NC(=O)C5=NC6=CC=CC=C6C=C5O)C
Properties
C48H56N10O12S6
Molar mass 1157.39 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Romero F, Espliego F, Pérez Baz J, García de Quesada T, Grávalos D, de la Calle F, Fernández-Puentes JL (September 1997). "Thiocoraline, a new depsipeptide with antitumor activity produced by a marine Micromonospora. I. Taxonomy, fermentation, isolation, and biological activities". The Journal of Antibiotics. 50 (9): 734–7. doi:10.7164/antibiotics.50.734. PMID 9360617.
  2. Erba E, Bergamaschi D, Ronzoni S, Faretta M, Taverna S, Bonfanti M, Catapano CV, Faircloth G, Jimeno J, D'Incalci M (June 1999). "Mode of action of thiocoraline, a natural marine compound with anti-tumour activity". British Journal of Cancer. 80 (7): 971–80. doi:10.1038/sj.bjc.6690451. PMC 2363046. PMID 10362104.
  3. Lombó F, Velasco A, Castro A, de la Calle F, Braña AF, Sánchez-Puelles JM, Méndez C, Salas JA (February 2006). "Deciphering the biosynthesis pathway of the antitumor thiocoraline from a marine actinomycete and its expression in two Streptomyces species". ChemBioChem. 7 (2): 366–76. doi:10.1002/cbic.200500325. PMID 16408310.
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