Deamido bleomycin A2 | 65154-36-1 | Antitumor Agent

MedKoo Cat#: 581621 | Name: Deamido bleomycin A2

Description:

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

Deamido Bleomycin A 2 is the Major Catabolite of the Antitumor Agent Bleomycin. Metabolic inactivation of the antitumor antibiotic bleomycin is be mediated exclusively via the action of bleomycin hydrolase, a cysteine proteinase that is widely distributed in nature.

Chemical Structure

Deamido bleomycin A2

CAS#65154-36-1

Theoretical Analysis

MedKoo Cat#: 581621

Name: Deamido bleomycin A2

CAS#: 65154-36-1

Chemical Formula: C55H83N16O22S3+

Exact Mass: 1415.5024

Molecular Weight: 1416.54

Elemental Analysis: C, 46.64; H, 5.91; N, 15.82; O, 24.85; S, 6.79

Price and Availability

This product was removed for the commercial reasons.

Related CAS #

No Data

Synonym

Deamido bleomycin A2; Deamido Bleomycin A2; Deamido Bleomycin A 2; Deamido Bleomycin A (2).

IUPAC/Chemical Name

(3-(2'-((3S,6R,7S,8S,11S)-1-(6-amino-2-((S)-3-amino-1-(((S)-2-amino-2-carboxyethyl)amino)-3-oxopropyl)-5-methylpyrimidin-4-yl)-3-((R)-(((2R,3S,4S,5S,6S)-3-(((2R,3S,4S,5R,6R)-4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)(1H-imidazol-5-yl)methyl)-7-hydroxy-11-((R)-1-hydroxyethyl)-6,8-dimethyl-1,4,9,12-tetraoxo-2,5,10,13-tetraazapentadecan-15-yl)-[2,4'-bithiazole]-4-carboxamido)propyl)dimethylsulfonium

InChi Key

LEWBSQHVMFJVKL-FSFWWQNWSA-O

InChi Code

1S/C55H82N16O22S3/c1-20-33(68-45(71-44(20)58)25(12-31(57)75)63-13-24(56)52(86)87)49(84)70-35(41(26-14-60-19-64-26)91-54-43(39(79)37(77)29(15-72)90-54)92-53-40(80)42(93-55(59)88)38(78)30(16-73)89-53)50(85)65-22(3)36(76)21(2)46(81)69-34(23(4)74)48(83)62-10-8-32-66-28(18-94-32)51-67-27(17-95-51)47(82)61-9-7-11-96(5)6/h14,17-19,21-25,29-30,34-43,53-54,63,72-74,76-80H,7-13,15-16,56H2,1-6H3,(H12-,57,58,59,60,61,62,64,65,68,69,70,71,75,81,82,83,84,85,86,87,88)/p+1/t21-,22?,23+,24-,25-,29-,30+,34-,35-,36-,37+,38+,39-,40-,41-,42-,43-,53+,54?/m0/s1

SMILES Code

O1[C@@H]([C@H]([C@@H]([C@@H]([C@H]1O[C@@H]1[C@@H](O[C@@H](CO)[C@H]([C@@H]1O)O)O[C@H]([C@H](NC(c1c(C)c(N)nc([C@@H](NC[C@@H](C(O)=O)N)CC(N)=O)n1)=O)C(=O)N[C@@H]([C@H]([C@@H](C(N[C@H](C(NCCc1nc(cs1)c1scc(n1)C(NCCC[S+](C)C)=O)=O)[C@H](O)C)=O)C)O)C)c1[nH]cnc1)O)OC(N)=O)O)CO

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,416.54 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: Crnovcic I, Gan F, Yang D, Dong LB, Schultz PG, Shen B. Activities of recombinant human bleomycin hydrolase on bleomycins and engineered analogues revealing new opportunities to overcome bleomycin-induced pulmonary toxicity. Bioorg Med Chem Lett. 2018 Sep 1;28(16):2670-2674. doi: 10.1016/j.bmcl.2018.04.065. Epub 2018 Apr 30. PubMed PMID: 29730026. 2: Zou Y, Fahmi NE, Vialas C, Miller GM, Hecht SM. Total synthesis of deamido bleomycin a(2), the major catabolite of the antitumor agent bleomycin. J Am Chem Soc. 2002 Aug 14;124(32):9476-88. PubMed PMID: 12167044. 3: Pei Z, Calmels TP, Creutz CE, Sebti SM. Yeast cysteine proteinase gene ycp1 induces resistance to bleomycin in mammalian cells. Mol Pharmacol. 1995 Oct;48(4):676-81. PubMed PMID: 7476893. 4: Morris G, Mistry JS, Jani JP, Mignano JE, Sebti SM, Lazo JS. Neutralization of bleomycin hydrolase by an epitope-specific antibody. Mol Pharmacol. 1992 Jul;42(1):57-62. PubMed PMID: 1378925. 5: Jani JP, Mistry JS, Morris G, Davies P, Lazo JS, Sebti SM. In vivo circumvention of human colon carcinoma resistance to bleomycin. Cancer Res. 1992 May 15;52(10):2931-7. PubMed PMID: 1374681. 6: Mahdadi R, Kenani A, Pommery N, Pommery J, Hénichart JP, Lhermitte M. High-performance liquid chromatography assay of bleomycin in human plasma and rat hepatocytes in culture. Cancer Chemother Pharmacol. 1991;28(1):22-6. PubMed PMID: 1710176. 7: Mistry JS, Sebti SM, Lazo JS. Separation of bleomycins and their deamido metabolites by high-performance cation-exchange chromatography. J Chromatogr. 1990 Aug 10;514(1):86-90. PubMed PMID: 1698802. 8: Lazo JS, Braun ID, Labaree DC, Schisselbauer JC, Meandzija B, Newman RA, Kennedy KA. Characteristics of bleomycin-resistant phenotypes of human cell sublines and circumvention of bleomycin resistance by liblomycin. Cancer Res. 1989 Jan 1;49(1):185-90. PubMed PMID: 2461797. 9: Seki T, Muraoka Y, Takahashi K, Horinishi H, Umezawa H. Radioimmunoassay of bleomycins. J Antibiot (Tokyo). 1985 Sep;38(9):1251-6. PubMed PMID: 2415502. 10: Huang CH, Mirabelli CK, Jan Y, Crooke ST. Single-strand and double-strand deoxyribonucleic acid breaks produced by several bleomycin analogues. Biochemistry. 1981 Jan 20;20(2):233-8. PubMed PMID: 6162480.