Porfiromycin

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Porfiromycin
Category Antineoplastic
Catalog number BBF-02583
CAS 801-52-5
Molecular Weight 348.35
Molecular Formula C16H20N4O5
Purity >98%

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Description

Porfiromycin is a quinone antibiotic produced by Str. ardus NRRL 2817. It has anti-Gram-positive and negative bacteria activity. It can inhibit sarcoma-180, Ehrlich ascites carcinoma, L-1210, H leukemia (solid type). The dose of inhibiting KB cell protein synthesis is 0.5 μg/mL. It is a bioreductive DNA alkylating agent that preferentially kills hypoxic tumor cells relative to other aerobic counterparts.

Specification

Synonyms N-Methylmitomycin C; NSC-56410; U-14743; Methylmitomycin; Methyl mitomycin C; Regamycin; Mitiromycin D; Porphyromycin; (1aS,8S,8aR,8bS)-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione
Storage Store at -20°C
IUPAC Name [(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
Canonical SMILES CC1=C(C(=O)C2=C(C1=O)N3CC4C(C3(C2COC(=O)N)OC)N4C)N
InChI InChI=1S/C16H20N4O5/c1-6-10(17)13(22)9-7(5-25-15(18)23)16(24-3)14-8(19(14)2)4-20(16)11(9)12(6)21/h7-8,14H,4-5,17H2,1-3H3,(H2,18,23)/t7-,8+,14+,16-,19?/m1/s1
InChI Key HRHKSTOGXBBQCB-VFWICMBZSA-N

Properties

Appearance Dark Purple Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor)
Boiling Point 560.9±50.0°C at 760 mmHg
Melting Point 204-206°C (dec.)
Density 1.5±0.1 g/cm3
Solubility Soluble in Chloroform, DMSO, Methanol

Reference Reading

1.Concurrent chemo-radiotherapy with mitomycin C compared with porfiromycin in squamous cell cancer of the head and neck: final results of a randomized clinical trial.
Haffty BG1, Wilson LD, Son YH, Cho EI, Papac RJ, Fischer DB, Rockwell S, Sartorelli AC, Ross DA, Sasaki CT, Fischer JJ. Int J Radiat Oncol Biol Phys. 2005 Jan 1;61(1):119-28.
PURPOSE: Previous randomized trials have shown a benefit with concurrent use of the hypoxic cell cytotoxin mitomycin C (MC) and radiation (RT) in the management of squamous cell cancer of the head and neck (SCCHN). We conducted a randomized trial comparing MC with porfiromycin (POR) in combination with RT in the management of SCCHN.
2.Cyclic disulfide C8 iminoporfiromycin: nucleophilic activation of a porfiromycin.
Lee SH1, Kohn H. J Am Chem Soc. 2004 Apr 7;126(13):4281-92.
The clinical success of mitomycin C (1) and its associated toxicities and resistance have led to efforts to prepare semisynthetic analogues (i.e., KW-2149 (3), BMS-181174 (4)) that have improved pharmacological profiles. In this study, we report the preparation and evaluation of the novel 7-N-(1'-amino-4',5'-dithian-2'-yl)porfiromycin C(8) cyclized imine (6) and its reference compound, 7-N-(1'-aminocyclohex-2'-yl)porfiromycin C(8) cyclized imine (13). Porfiromycin 6 contains a disulfide unit that, upon cleavage, may provide thiol(s) that affect drug reactivity. We demonstrated that phosphines dramatically accelerated 6 activation and solvolysis in methanolic solutions ("pH 7.4") compared with 13. Porfiromycins 6 and 13 efficiently cross-linked EcoRI-linearized pBR322 DNA upon addition of Et3P. We found enhanced levels of interstrand cross-link (ISC) adducts for 6 and 13 compared with porfiromycin (7) and that 6 was more efficient than 13.

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