Zorbamycin

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

MedKoo CAT#: 462867

CAS#: 11056-20-5

Description: Antibiotic related to bleomycin & phleomycin. It has a different DNA sequence selectivity compared with bleomycin and analogues and has been studied for its antitumor properties.


Chemical Structure

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Zorbamycin
CAS# 11056-20-5

Theoretical Analysis

MedKoo Cat#: 462867
Name: Zorbamycin
CAS#: 11056-20-5
Chemical Formula: C55H85N19O21S2
Exact Mass: 1411.5609
Molecular Weight: 1412.517
Elemental Analysis: C, 46.77; H, 6.07; N, 18.84; O, 23.79; S, 4.54

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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Synonym: U-30,604; U-30604; Zorbamycin;

IUPAC/Chemical Name: (2R,3S,4S,5R,6R)-2-(((2R,3S,4S,5S,6S)-2-((1R,2S)-2-(6-amino-2-((S)-3-amino-1-(((S)-2,3-diamino-3-oxopropyl)amino)-3-oxopropyl)-5-methylpyrimidine-4-carboxamido)-3-(((3R,4S,5S)-6-(((S)-1-((2-((R)-4-((3-amino-3-iminopropyl)carbamoyl)-4',5'-dihydro-[2,4'-bithiazol]-2'-yl)ethyl)amino)-3-hydroxy-3-methyl-1-oxobutan-2-yl)amino)-1,4-dihydroxy-5-methyl-6-oxohexan-3-yl)amino)-1-(1H-imidazol-4-yl)-3-oxopropoxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate

InChi Key: UJKRUPHWCPAJIL-CPLCKGKLSA-N

InChi Code: InChI=1S/C55H85N19O21S2/c1-19-32(71-45(74-43(19)60)24(12-30(59)77)66-13-22(56)44(61)83)48(86)72-33(39(25-14-63-18-67-25)93-53-41(37(81)35(79)21(3)91-53)94-52-38(82)40(95-54(62)89)36(80)28(15-76)92-52)49(87)69-23(8-11-75)34(78)20(2)46(84)73-42(55(4,5)90)50(88)65-10-7-31-68-27(17-96-31)51-70-26(16-97-51)47(85)64-9-6-29(57)58/h14,16,18,20-24,27-28,33-42,52-53,66,75-76,78-82,90H,6-13,15,17,56H2,1-5H3,(H3,57,58)(H2,59,77)(H2,61,83)(H2,62,89)(H,63,67)(H,64,85)(H,65,88)(H,69,87)(H,72,86)(H,73,84)(H2,60,71,74)/t20-,21-,22-,23+,24-,27+,28+,33-,34-,35+,36+,37-,38-,39-,40-,41-,42+,52+,53-/m0/s1

SMILES Code: C[C@H](C(N[C@@H](C(C)(O)C)C(NCCC1=N[C@@H](c2scc(C(NCCC(N)=N)=O)n2)CS1)=O)=O)[C@@H]([C@H](NC([C@H]([C@H](c3nc[nH]c3)O[C@@H]4O[C@H]([C@H]([C@@H]([C@@H]4O[C@H]5O[C@@H]([C@H]([C@@H]([C@@H]5O)OC(N)=O)O)CO)O)O)C)NC(c6c(C)c(N)nc([C@@H](NC[C@@H](C(N)=O)N)CC(N)=O)n6)=O)=O)CCO)O

Appearance: 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

Shelf Life: >3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 1412.517 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: Murray V, Chen JK, Yang D, Shen B. The genome-wide sequence specificity of DNA cleavage by bleomycin analogues in human cells. Bioorg Med Chem. 2018 Aug 7;26(14):4168-4178. doi: 10.1016/j.bmc.2018.07.006. Epub 2018 Jul 5. PMID: 30006142.

2: Yang D, Hindra, Dong LB, Crnovcic I, Shen B. Engineered production and evaluation of 6'-deoxy-tallysomycin H-1 revealing new insights into the structure-activity relationship of the anticancer drug bleomycin. J Antibiot (Tokyo). 2017 Aug 23. doi: 10.1038/ja.2017.93. Epub ahead of print. PMID: 28831149.

3: Chen JK, Yang D, Shen B, Murray V. Bleomycin analogues preferentially cleave at the transcription start sites of actively transcribed genes in human cells. Int J Biochem Cell Biol. 2017 Apr;85:56-65. doi: 10.1016/j.biocel.2017.02.001. Epub 2017 Feb 3. PMID: 28167289.

4: Chen JK, Yang D, Shen B, Neilan BA, Murray V. Zorbamycin has a different DNA sequence selectivity compared with bleomycin and analogues. Bioorg Med Chem. 2016 Nov 15;24(22):6094-6101. doi: 10.1016/j.bmc.2016.09.072. Epub 2016 Sep 30. PMID: 27745992; PMCID: PMC5466353.

5: Rudolf JD, Bigelow L, Chang C, Cuff ME, Lohman JR, Chang CY, Ma M, Yang D, Clancy S, Babnigg G, Joachimiak A, Phillips GN Jr, Shen B. Crystal Structure of the Zorbamycin-Binding Protein ZbmA, the Primary Self-Resistance Element in Streptomyces flavoviridis ATCC21892. Biochemistry. 2015 Nov 17;54(45):6842-51. doi: 10.1021/acs.biochem.5b01008. Epub 2015 Nov 5. PMID: 26512730; PMCID: PMC4809751.

6: Coughlin JM, Rudolf JD, Wendt-Pienkowski E, Wang L, Unsin C, Galm U, Yang D, Tao M, Shen B. BlmB and TlmB provide resistance to the bleomycin family of antitumor antibiotics by N-acetylating metal-free bleomycin, tallysomycin, phleomycin, and zorbamycin. Biochemistry. 2014 Nov 11;53(44):6901-9. doi: 10.1021/bi501121e. Epub 2014 Oct 23. PMID: 25299801; PMCID: PMC4230324.

7: Huang SX, Feng Z, Wang L, Galm U, Wendt-Pienkowski E, Yang D, Tao M, Coughlin JM, Duan Y, Shen B. A designer bleomycin with significantly improved DNA cleavage activity. J Am Chem Soc. 2012 Aug 15;134(32):13501-9. doi: 10.1021/ja3056535. Epub 2012 Aug 6. PMID: 22831455; PMCID: PMC3422780.

8: Galm U, Wendt-Pienkowski E, Wang L, Huang SX, Unsin C, Tao M, Coughlin JM, Shen B. Comparative analysis of the biosynthetic gene clusters and pathways for three structurally related antitumor antibiotics: bleomycin, tallysomycin, and zorbamycin. J Nat Prod. 2011 Mar 25;74(3):526-36. doi: 10.1021/np1008152. Epub 2011 Jan 6. PMID: 21210656; PMCID: PMC3064724.

9: Galm U, Wendt-Pienkowski E, Wang L, George NP, Oh TJ, Yi F, Tao M, Coughlin JM, Shen B. The biosynthetic gene cluster of zorbamycin, a member of the bleomycin family of antitumor antibiotics, from Streptomyces flavoviridis ATCC 21892. Mol Biosyst. 2009 Jan;5(1):77-90. doi: 10.1039/b814075h. Epub 2008 Nov 12. PMID: 19081934; PMCID: PMC3086045.

10: Wang L, Yun BS, George NP, Wendt-Pienkowski E, Galm U, Oh TJ, Coughlin JM, Zhang G, Tao M, Shen B. Glycopeptide antitumor antibiotic zorbamycin from Streptomyces flavoviridis ATCC 21892: strain improvement and structure elucidation. J Nat Prod. 2007 Mar;70(3):402-6. doi: 10.1021/np060592k. Epub 2007 Feb 21. PMID: 17311457; PMCID: PMC2579990.

11: Sermonti G, Lanfaloni L, Micheli MR. Where are the antibiotic producing genes? Riv Biol. 1982 Spring;75(1):67-85. English, Italian. PMID: 7100780.

12: Krueger WC, Pschigoda LM, Reusser F. Interactions of DNA with zorbamycin, phleomycin and bleomycin; ultraviolet absorption and circular dichroism measurements. J Antibiot (Tokyo). 1973 Aug;26(8):424-8. doi: 10.7164/antibiotics.26.424. PMID: 4134738.

13: Reusser F. Mode of action of zorbamycin. J Bacteriol. 1971 Oct;108(1):30-7. doi: 10.1128/JB.108.1.30-37.1971. PMID: 4107810; PMCID: PMC247028.

14: Argoudelis AD, Bergy ME, Pyke TR. Zorbamycin and related antibiotics. I. Production, isolation and characterization. J Antibiot (Tokyo). 1971 Aug;24(8):543-57. doi: 10.7164/antibiotics.24.543. PMID: 5092789.

15: Coats JH, Roeser J. Genetic recombination in Streptomyces bikiniensis var. zorbonensis. J Bacteriol. 1971 Mar;105(3):880-5. doi: 10.1128/JB.105.3.880-885.1971. PMID: 5547993; PMCID: PMC248513.