Netropsin
Title: Netropsin
CAS Registry Number: 1438-30-8
CAS Name: 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
Additional Names: N¢-(2-amidinoethyl)-4-(2-guanidinoacetamido)-1,1¢-dimethyl-N,4¢-bi[pyrrole-2-carboxamide]; sinanomycin; congocidine
Manufacturers' Codes: T-1384
Molecular Formula: C18H26N10O3
Molecular Weight: 430.46
Percent Composition: C 50.22%, H 6.09%, N 32.54%, O 11.15%
Literature 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).
 
Derivative Type: Disulfate
Molecular Formula: C18H26N10O3.2H2SO4
Molecular Weight: 626.62
Percent Composition: 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.
Melting point: mp 288°
 
Derivative Type: Dihydrochloride
Molecular Formula: C18H26N10O3.2HCl
Molecular Weight: 503.39
Percent Composition: 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).
Melting point: mp 228°
Toxicity data: LD50 in mice (mg/kg): 17 i.v.; 70 s.c.; >300 orally (Finlay)
 
Use: Non-intercalative DNA binding agent.

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