6481. Netropsin

Nomenclature

CAS number: 1438-30-8
4-[[[(Aminoiminomethyl)amino]acetyl]amino]-N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-pyrrole-2-carboxamide; N′-(2-amidinoethyl)-4-(2-guanidinoacetamido)-1,1′-dimethyl-N,4′-bi[pyrrole-2-carboxamide]; sinanomycin; congocidine; T-1384.
C18H26N10O3; mol wt 430.46.
C 50.22%, H 6.09%, N 32.54%, O 11.15%.

Description and references

Basic oligopeptide antibiotic produced by Streptomyces netropsis with wide range of antimicrobial activity. Prepn and antibacterial spectrum: A. C. Finlay et al., J. Am. Chem. Soc. 73, 341 (1951); and trypanocidal activity: C. Cosar et al., Compt. Rend. 234, 1498 (1952). Antiviral activity: F. M. Schabel et al., Proc. Soc. Exp. Biol. Med. 83, 1 (1953). Identity with sinanomycin: K. Watanabe, J. Antibiot. 9A, 102 (1956). Structural studies: M. Julia, N. Joseph, Compt. Rend. 243, 961 (1956). Structure: C. W. Waller et al., J. Am. Chem. Soc. 79, 1265 (1957). Revised structure: M. Julia, N. Préau-Joseph, Compt. Rend. 257, 1115 (1963); eidem, Bull. Soc. Chim. Fr. 1967, 4348. Specific binding to DNA: Ch. Zimmer et al., J. Mol. Biol. 58, 329 (1971); K. Zakrzewska et al., Nucleic Acids Res. 11, 8825, 8841 (1983). Use in gradient separation of DNA: K. M. Tatti et al., Anal. Biochem. 89, 561 (1978). Selective blocking of DNAase I cleavage: Ch. Zimmer et al., Nucleic Acids Res. 8, 2999 (1980). Review of activity: F. E. Hahn in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 79-100. Review of effect on DNA structure and function: Ch. Zimmer, Prog. Nucleic Acid Res. Mol. Biol. 15, 285-318 (1975).

Chemical structure

Derivative

Disulfate.
C18H26N10O3.2H2SO4; mol wt 626.62.
C 34.50%, H 4.83%, N 22.35%, O 28.09%, S 10.23%.

Properties

Needles, mp 288°. Soly in water ≈30 mg/ml at 80°, <0.5 mg/ml at 25°. Practically insol in the common organic solvents.

Derivative

Dihydrochloride.
C18H26N10O3.2HCl; mol wt 503.39.
C 42.95%, H 5.61%, N 27.82%, O 9.53%, Cl 14.09%.

Properties

Prisms, mp 228°. LD50 in mice (mg/kg): 17 i.v.; 70 s.c.; >300 orally (Finlay).

Use

Non-intercalative DNA binding agent.