Aclacinomycin Y

Aclacinomycin Y

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Category Antibiotics
Catalog number BBF-00012
CAS 66789-14-8
Molecular Weight 809.85
Molecular Formula C42H51NO15

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Description

Aclacinomycin Y is an anthrone antitumor antibiotic isolated from Streptomyces galilaeus.

Specification

IUPAC Name methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
Canonical SMILES CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7C=CC(=O)C(O7)C)O)N(C)C)O
InChI InChI=1S/C42H51NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-14,18-20,24,27-31,35,39-40,45-46,49,51H,8,15-17H2,1-7H3/t18-,19-,20-,24-,27-,28-,29-,30-,31-,35-,39+,40+,42+/m0/s1
InChI Key ADCDIHNCUQOKFP-SVEJIMAYSA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Melting Point 153-155 °C

Reference Reading

1. Directed Biosynthesis of Iso-aclacinomycins with Improved Anticancer Activity
Yu Hu, Zhuan Zhang, Yue Yin, Gong-Li Tang Org Lett. 2020 Jan 3;22(1):150-154. doi: 10.1021/acs.orglett.9b04069. Epub 2019 Dec 12.
A four-enzyme catalyzed hydroxy regioisomerization of anthracycline was integrated into the biosynthetic pathway of aclacinomycin A (ALM-A), to generate a series of iso-ALMs via directed combinatorial biosynthesis combined with precursor-directed mutasynthesis. Most of the newly acquired iso-ALMs exhibit obviously (1-5-fold) improved antitumor activity. Therefore, we not only developed iso-ALMs with potential as clinical drugs but also demonstrated the utility of this tailoring tool for modification of anthracycline antibiotics in drug discovery and development.
2. Modifications of aclacinomycin T by aclacinomycin methyl esterase (RdmC) and aclacinomycin-10-hydroxylase (RdmB) from Streptomyces purpurascens
Y Wang, J Niemi, K Airas, K Ylihonko, J Hakala, P Mäntsälä Biochim Biophys Acta. 2000 Jul 14;1480(1-2):191-200. doi: 10.1016/s0167-4838(00)00089-3.
The genes rdmB and rdmC of Streptomyces purpurascens encoding aclacinomycin modifying enzymes RdmB and RdmC were expressed in Streptomyces lividans TK24. In contrast to the earlier suggestion that RdmC may be an esterase that causes the removal of the carbomethoxy group from the 10 position of aclacinomycins, RdmC functions as an aclacinomycin methyl esterase and catalyzes the removal of the methoxy group from the C-15 position of aclacinomycin T producing 15-demethoxyaclacinomycin T. RdmB acts upon C-10 of 15-demethoxyaclacinomycin T and is able to remove the carboxylic group from the C-10 position. It functions also as an aclacinomycin-10-hydroxylase being able to add a hydroxyl group at the same, C-10 position in vitro. Aclacinomycin methyl esterase was purified to apparent homogeneity from S. lividans carrying the rdmC and aclacinomycin-10-hydroxylase as a glutathione S-transferase fusion construct from Escherichia coli carrying the rdmB gene, respectively. Aclacinomycin methyl esterase functions as a monomer and aclacinomycin-10-hydroxylase as a tetramer. Aclacinomycin methyl esterase has an exceptionally high temperature stability and has an apparent K(m) for aclacinomycin T of 15.5 microM. The introduction of rdmC and rdmB in a Streptomyces galilaeus mutant HO38 produced the same modifications of aclacinomycin T in vivo as aclacinomycin methyl esterase and aclacinomycin-10-hydroxylase in vitro.
3. [Cardiooncology: Current Aspects of Prevention of Anthracycline Toxicity]
Y A Vasyuk, E L Shkolnik, V V Nesterov, L D Shkolnik, G V Varlan Kardiologiia. 2016 Dec;56(12):72-79.
Anthracyclines including doxorubicin, epirubicin, daunorubicin, aclarubicin are extensively used as chemotherapeutic agents for treatment of hematological and other malignancies. In cancer therapy anthracyclines are often used in combinations with other chemotherapeutic drugs and agents for molecularly targeted therapy. Anthracyclines are effective and powerful antineoplastic drugs with wide spectrum of application but active use of preparations of this group is limited because of such side effects as cardiotoxicity, myelotoxicity, thromboembolism, alopecia, etc. Cardiotoxicity is the most severe side effect of anthracycline administration. Clinical studies have shown that it is progressive and irreversible. Therefore, early detection and prevention of anthracycline cardiotoxicity has become an important trend in cardiology.

Bio Calculators

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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