WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100721
CAS#: 70384-29-1 (sulfate)
Description: Peplomycin is a semisynthetic analog of Bleomycin, a mixture of several basic glycopeptide antineoplastic antibiotics isolated from the fungus Streptomyces verticillus. Peplomycin forms complexes with iron that reduce molecular oxygen to superoxide and hydroxyl radicals that cause single- and double-stranded breaks in DNA. This agent appears to show greater antitumor activity than bleomycin; its use is limited due to pulmonary toxicity.
MedKoo Cat#: 100721
Name: Peplomycin sulfate
CAS#: 70384-29-1 (sulfate)
Chemical Formula: C61H90N18O25S3
Exact Mass:
Molecular Weight: 1571.672
Elemental Analysis: C, 46.62; H, 5.77; N, 16.04; O, 25.45; S, 6.12
Peplomycin sulfate is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.
Related CAS #: 70384-29-1 (sulfate) 68247-85-8 (free base)
Synonym: NK-631, NK 631, NK631, pepleomycin, PEP
IUPAC/Chemical Name: (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-methylpyrimidine-4-carboxamido)-3-((3-hydroxy-5-((3-hydroxy-1-oxo-1-((2-(4-((3-(((S)-1-phenylethyl)amino)propyl)carbamoyl)-[2,4'-bithiazol]-2'-yl)ethyl)amino)butan-2-yl)amino)-4-methyl-5-oxopentan-2-yl)amino)-1-(1H-imidazol-5-yl)-3-oxopropoxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate sulfate
InChi Key: ZHHIHQFAUZZMTG-HBTICLRTSA-N
InChi Code: InChI=1S/C61H88N18O21S2.H2O4S/c1-24-39(76-52(79-50(24)64)31(16-37(63)83)71-17-30(62)51(65)89)56(93)78-41(47(32-18-67-23-72-32)98-60-49(45(87)43(85)35(19-80)97-60)99-59-46(88)48(100-61(66)95)44(86)36(20-81)96-59)57(94)73-27(4)42(84)25(2)53(90)77-40(28(5)82)55(92)70-15-12-38-74-34(22-101-38)58-75-33(21-102-58)54(91)69-14-9-13-68-26(3)29-10-7-6-8-11-29;1-5(2,3)4/h6-8,10-11,18,21-23,25-28,30-31,35-36,40-49,59-60,68,71,80-82,84-88H,9,12-17,19-20,62H2,1-5H3,(H2,63,83)(H2,65,89)(H2,66,95)(H,67,72)(H,69,91)(H,70,92)(H,73,94)(H,77,90)(H,78,93)(H2,64,76,79);(H2,1,2,3,4)/t25?,26-,27?,28?,30?,31?,35-,36+,40?,41?,42?,43+,44+,45-,46-,47?,48-,49-,59+,60-;/m0./s1
SMILES Code: NC(O[C@@H]1[C@H](O)[C@@H](O[C@@H]2[C@H](OC(C3=CN=CN3)C(NC(C4=NC(C(NCC(N)C(N)=O)CC(N)=O)=NC(N)=C4C)=O)C(NC(C(O)C(C)C(NC(C(O)C)C(NCCC5=NC(C6=NC(C(NCCCN[C@@H](C)C7=CC=CC=C7)=O)=CS6)=CS5)=O)=O)C)=O)O[C@@H](CO)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@H]1O)=O.O=S(O)(O)=O
The following data is based on the product molecular weight 1571.672 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Tanaka T, Toujima S, Utsunomiya T, Yukawa K, Umesaki N. Experimental characterization of recurrent ovarian immature teratoma cells after optimal surgery. Oncol Rep. 2008 Jul;20(1):13-23. PubMed PMID: 18575713.
2: Kokawa K, Mabuchi Y, Tanaka K, Yagi S, Utsunomiya T, Oba N, Yata C, Umesaki N. Apoptosis in cervical cancer after balloon-occluded arterial infusion of anticancer drugs. Anticancer Res. 2006 Mar-Apr;26(2B):1413-8. PubMed PMID: 16619552.
3: Liu TL, Shimada H, Ochiai T, Shiratori T, Lin SE, Kitagawa M, Harigaya K, Maki M, Oka M, Abe T, Takiguchi M, Hiwasa T. Enhancement of chemosensitivity toward peplomycin by calpastatin-stabilized NF-kappaB p65 in esophageal carcinoma cells: possible involvement of Fas/Fas-L synergism. Apoptosis. 2006 Jun;11(6):1025-37. PubMed PMID: 16547594.
4: Iwadate Y, Sakaida T, Saegusa T, Hiwasa T, Takiguchi M, Fujimoto S, Yamaura A. Proteome-based identification of molecular markers predicting chemosensitivity to each category of anticancer agents in human gliomas. Int J Oncol. 2005 Apr;26(4):993-8. PubMed PMID: 15753994.
5: Okamura M, Hashimoto K, Shimada J, Sakagami H. Apoptosis-inducing activity of cisplatin (CDDP) against human hepatoma and oral squamous cell carcinoma cell lines. Anticancer Res. 2004 Mar-Apr;24(2B):655-61. PubMed PMID: 15161008.
6: Ueta E, Yoneda K, Kimura T, Tatemoto Y, Doi S, Yamamoto T, Osaki T. Mn-SOD antisense upregulates in vivo apoptosis of squamous cell carcinoma cells by anticancer drugs and gamma-rays regulating expression of the BCL-2 family proteins, COX-2 and p21. Int J Cancer. 2001 Nov;94(4):545-50. PubMed PMID: 11745442.
7: Kawashiri S, Kojima K, Kumagai S, Nakagawa K, Yamamoto E. Effects of chemotherapy on invasion and metastasis of oral cavity cancer in mice. Head Neck. 2001 Sep;23(9):764-71. PubMed PMID: 11505487.
8: Ueta E, Tanida T, Yoneda K, Yamamoto T, Osaki T. Increase of Candida cell virulence by anticancer drugs and irradiation. Oral Microbiol Immunol. 2001 Aug;16(4):243-9. PubMed PMID: 11442850.
9: Okamura H, Morimoto H, Haneji T. Peplomycin-induced apoptosis in oral squamous carcinoma cells depends on bleomycin sensitivity. Oral Oncol. 2001 Jun;37(4):379-85. PubMed PMID: 11337271.
10: Kawanishi S, Oikawa S, Kawanishi M, Sugiyama H, Saito I, Strekowski L, Wilson WD. Amplification of pepleomycin-mediated DNA cleavage and apoptosis by unfused aromatic cations. Biochemistry. 2000 Oct 31;39(43):13210-5. PubMed PMID: 11052673.
Peplomycin is a semisynthetic analog of Bleomycin, a mixture of several basic glycopeptide antineoplastic antibiotics isolated from the fungus Streptomyces verticillus. Peplomycin forms complexes with iron that reduce molecular oxygen to superoxide and hydroxyl radicals that cause single- and double-stranded breaks in DNA. This agent appears to show greater antitumor activity than bleomycin; its use is limited due to pulmonary toxicity. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)
