CAS 11116-32-8

Bleomycin A5

Description:

Bleomycin A5 is a glycopeptide antibiotic derived from the bacterium *Streptomyces verticillus*. It is primarily known for its antitumor properties and is used in the treatment of various cancers, including testicular cancer and Hodgkin's lymphoma. The compound exhibits a unique mechanism of action, which involves the induction of DNA strand breaks through the formation of free radicals, ultimately leading to cell death. Bleomycin A5 is characterized by its ability to bind to DNA, particularly at guanine residues, and its efficacy is influenced by factors such as oxygen concentration and the presence of metal ions. The substance is typically administered via injection and can cause side effects, including pulmonary toxicity and skin reactions. Its structure includes a distinctive metal-binding domain, which is crucial for its biological activity. Overall, Bleomycin A5 is a significant agent in oncological therapy, with ongoing research aimed at optimizing its use and minimizing adverse effects.

Formula: C₅₇H₈₉N₁₉O₂₁S₂

InChI: InChI=1S/C57H89N19O21S2/c1-22-35(73-48(76-46(22)61)27(14-33(60)80)68-15-26(59)47(62)86)52(90)75-37(43(28-16-65-21-69-28)95-56-45(41(84)39(82)31(17-77)94-56)96-55-42(85)44(97-57(63)92)40(83)32(18-78)93-55)53(91)70-24(3)38(81)23(2)49(87)74-36(25(4)79)51(89)67-13-8-34-71-30(20-98-34)54-72-29(19-99-54)50(88)66-12-7-11-64-10-6-5-9-58/h16,19-21,23-27,31-32,36-45,55-56,64,68,77-79,81-85H,5-15,17-18,58-59H2,1-4H3,(H2,60,80)(H2,62,86)(H2,63,92)(H,65,69)(H,66,88)(H,67,89)(H,70,91)(H,74,87)(H,75,90)(H2,61,73,76)/t23-,24+,25+,26-,27-,31-,32+,36-,37-,38-,39+,40+,41-,42-,43-,44-,45-,55-,56-/m0/s1

InChI key: InChIKey=QYOAUOAXCQAEMW-DDZPZTJXSA-N

SMILES: [C@H]([C@H](NC(=O)C1=NC([C@@H](NC[C@@H](C(N)=O)N)CC(N)=O)=NC(N)=C1C)C(N[C@@H]([C@H]([C@@H](C(N[C@H](C(NCCC2=NC(=CS2)C3=NC(C(NCCCNCCCCN)=O)=CS3)=O)[C@@H](C)O)=O)C)O)C)=O)(O[C@H]4[C@@H](O[C@H]5[C@@H](O)[C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O5)[C@@H](O)[C@H](O)[C@H](CO)O4)C6=CN=CN6

Synonyms:

• 2-({2-[2-{[(6-amino-2-{3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl}-5-methylpyrimidin-4-yl)carbonyl]amino}-3-[(5-{[1-({2-[4-({3-[(4-aminobutyl)amino]propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)-3-hydroxy-1-oxobutan-2-yl]amino}-3-hydroxy-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 (non-preferred name)
• 2-({2-[2-{[(6-amino-2-{3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl}-5-methylpyrimidin-4-yl)carbonyl]amino}-3-[(5-{[1-({2-[4-({3-[(4-aminobutyl)amino]propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)-3-hydroxy-1-oxobutan-2-yl]amino}-3-hydroxy-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 hydrochloride (1:1) (non-preferred name)
• 2-{[2-{[(1R,2S)-2-[({6-amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl]-5-methylpyrimidin-4-yl}carbonyl)amino]-3-{[(1R,2S,3S)-2-hydroxy-4-{[(1S,2R)-2-hydroxy-1-({2-[4-({3-[(3-pyridin-2-ylpropyl)amino]propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}carbamoyl)propyl]amino}-1,3-dimethyl-4-oxobutyl]amino}-1-(1H-imidazol-5-yl)-3-oxopropyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate (non-preferred name)
• BLM A₅
• Bleomycetin
• Bleomycin A₅
• Bleomycinamide, N¹-[3-[(4-aminobutyl)amino]propyl]-
• N¹-[3-[(4-Aminobutyl)amino]propyl]bleomycinamide
• NSC 350895
• Pingyangmycin A₅
• Zhengguangmycin A₅
• Bleomycin A5
• N1-[3-[(4-Aminobutyl)amino]propyl]bleomycinamide
• Bleomycinamide, N1-[3-[(4-aminobutyl)amino]propyl]-

Bleomycin A5

CAS: 11116-32-8

Bleomycin A5, or Pingyangmycin, is an oral glycopeptide antibiotic and acts as an antineoplastic and apoptosis inducer.

Formula: C₅₇H₈₉N₁₉O₂₁S₂

Color and Shape: Solid

Molecular weight: 1440.56

Ref: TM-T75508

Bleomycin A5

CAS: 11116-32-8

Bleomycin A5 is an antitumor antibiotic, which is derived from the bacterium *Streptomyces verticillus*. Its mode of action involves the induction of DNA strand breaks, primarily by forming complexes with metal ions such as iron, which can generate reactive oxygen species. These species cause oxidative damage to the DNA, leading to single- and double-strand breaks. This DNA cleavage is crucial for its efficacy in inhibiting the proliferation of cancer cells.

Formula: C₅₇H₈₉N₁₉O₂₁S₂

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 1,440.56 g/mol

Ref: 3D-FB152633

Bleomycin A5 hydrochloride

CAS: 11116-32-8

Bleomycin A5 hydrochloride is an antineoplastic antibiotic, which is derived from the bacterium Streptomyces verticillus. Its mode of action involves binding to DNA and inducing strand breaks through the generation of free radicals, specifically targeting deoxyribose units. This leads to the inhibition of DNA synthesis and cell division, ultimately resulting in cell death.

Formula: C₅₇H₈₉N₁₉O₂₁S₂•HCl

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 1,177.03 g/mol

Ref: 3D-AB183381