N1-[3-[(1-Phenylethyl)amino]propyl]bleomycinamide

Names

[ Name ]:
N1-[3-[(1-Phenylethyl)amino]propyl]bleomycinamide

[Synonym ]:
PLM
N1-[3-[[(S)-a-Methylbenzyl]amino]propyl]bleomycinamide
NK-631{PEP
Peplocin
Bleomycin PEP
Pepleocine
Pepreomycin
(2R,3S,4S,5R,6R)-2-{[(2R,3S,4S,5S,6S)-2-[2-{[(6-Amino-2-{3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl}-5-methyl-4-pyrimidinyl)carbonyl]amino}-3-{[3-hydroxy-5-({3-hydroxy-1-oxo-1-[(2-{4-[(3-{[(1S)-1-phenylethyl]amino}propyl)carbamoyl]-2,4'-bi-1,3-thiazol-2'-yl}ethyl)amino]-2-butanyl}amino)-4-methyl-5-oxo-2-pentanyl]amino}-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3,5-dihydroxy-6
Pepleomycin
PEP-Bleomycin
3((S)-1'-Phenylethylamino)-propylaminbleomycin
N1-[3-[(1-Phenylethyl)amino]propyl]bleomycinamide

Biological Activity

[Description]:

Peplomycin (Bleomycin PEP; Pepleomycin) is an antibiotic analogue of Bleomycin (HY-108345), with high antitumor effect and less pulmonary toxicity. Peplomycin induce apoptosis in oral squamous carcinoma cell line SSCKN cells and pulmonary fibrosis in rats[1][2][3][4].

[Related Catalog]:

Research Areas >> Cancer

[In Vitro]

Peplomycin (0-100 μM; 30 h) inhibits human oral squamous carcinoma cell line SSCKN and SCCTF cells in a dose-dependent manner[3]. Peplomycin (1 μM and 10 μM; 30 h) results nuclear fragmentation and condensation of chromatin in cells dose-dependently and induces apoptosis[3]. Peplomycin (5 mg/mL; 7 d) induces pulmonary fibrosis separated from saline-injected rats (N-Fib) by differentiating fibroblasts to alpha-SMA-positive MF[4]. Cell Viability Assay[3] Cell Line: SSCKN and SCCTF cells Concentration: 0, 1, 5, 10, 50, and 100 μM Incubation Time: 30 hours Result: Decreased SSCKN and SCCTF cells viability dose-dependently up to 50 μM, and resulted the viability of 38% and 30% that of the control group, respectively.

[In Vivo]

Peplomycin (5 mg/kg; once daily) induces rat pulmonary fibroblasts to myofibroblasts (MF), while the peripheries of lungs adjacent to the pleura reveals advanced fibrosis with a small number of alpha-smooth muscle actin (alpha-SMA)-positive MF, which ultrastructurally possessed abundant microfilaments and cellular organelles[4].

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Molecular Formula ]:
C₆₁H₈₈N₁₈O₂₁S₂

[ Molecular Weight ]:
1473.589

[ Exact Mass ]:
1472.581299

[ PSA ]:
695.58000

[ LogP ]:
0.00

[ Index of Refraction ]:
1.689

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EC5991700

CHEMICAL NAME :: Bleomycinamide, N(sup 1)-(3-((1-phenylethyl)amino)propyl)-

CAS REGISTRY NUMBER :: 68247-85-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C61-H88-N18-O21-S2

MOLECULAR WEIGHT :: 1473.79

WISWESSER LINE NOTATION :: T6OTJ BQ CQ DOVZ EQ FO- CT6OTJ DQ EQ FQ BOY- DT5M CNJ&YMV- DT6N CNJ BY1VZM1YZVZ E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 51 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 80 mg/kg/4W-I

TOXIC EFFECTS :: Behavioral - irritability Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 25 mg/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 38,1257,1985

Related Compounds

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