MedKoo Cat#: 100721 | Name: Peplomycin sulfate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Peplomycin sulfate
Peplomycin sulfate
CAS#70384-29-1 (sulfate)

Theoretical Analysis

MedKoo Cat#: 100721

Name: Peplomycin sulfate

CAS#: 70384-29-1 (sulfate)

Chemical Formula: C61H90N18O25S3

Exact Mass:

Molecular Weight: 1571.67

Elemental Analysis: C, 46.62; H, 5.77; N, 16.04; O, 25.45; S, 6.12

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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
Appearance
Light yellow to yellow solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
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)    
Certificate of Analysis
Safety Data Sheet (SDS)

Preparing Stock Solutions

The following data is based on the product molecular weight 1,571.67 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.

Recalculate based on batch purity %
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.