Peplomycin sulfate

    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.


Chemical Structure

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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: 1571.672
Elemental Analysis: C, 46.62; H, 5.77; N, 16.04; O, 25.45; S, 6.12

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

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

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

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.

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

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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.

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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.

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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.



Additional Information

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)