Aclarubicin - CAS 57576-44-0
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
Aclarubicin
Catalog Number:
57576-44-0
Synonyms:
11-Dioxo-4-((2,3,6-trideoxy-4-o-(2,6-dideoxy-4-o-((2r-trans)-tetrahydro-6-met;1-naphthacenecarboxylicacid,2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6;(1R,2R,4S)-methyl 4-(((2R,5S,6S)-4-(dimethylamino)-5-(((2S,4S,5S,6S)-4-hydroxy-6-methyl-5-(((2R,6S)
CAS Number:
57576-44-0
Description:
Aclarubicin is an oligosaccharide anthracycline antineoplastic antibiotic isolated from the bacterium Streptomyces galilaeus. It intercalates into DNA and interacts with topoisomerases I and II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. It is antagonistic to other agents that inhibit topoisomerase II, such as etoposide, teniposide and amsacrine. It has potent antineoplastic activity. It is used in the treatment of cancer. It can induce histone eviction from chromatin upon intercalation. It has been listed.
Molecular Weight:
811.87
Molecular Formula:
C42H53NO15
Quantity:
Kilograms to Tons
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CCC1(CC(C2=C(C1C(=O)OC)C=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O
InChI:
InChI=1S/C42H53NO15/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/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,
InChIKey:
USZYSDMBJDPRIF-SVEJIMAYSA-N
Targets:
Topoisomerase
Current Developer:
Aclarubicin has been listed.
Chemical Structure
CAS 57576-44-0 Aclarubicin

Related Topoisomerase Products


CAS 867063-97-6 Atiratecan

Atiratecan
(CAS: 867063-97-6)

Atiratecan is a topoisomerase inhibitor. It has potential anticancer activity.

CAS 211100-13-9 Sabarubicin

Sabarubicin
(CAS: 211100-13-9)

Sabarubicina, a disaccharide analogue of doxorubicin, is an antineoplastic agent which can intercalate into the DNA of tumor cells and interact with topoisomera...

CAS 72496-41-4 Pirarubicin

Pirarubicin
(CAS: 72496-41-4)

Pirarubicin is an anthracycline antibiotic, and also a DNA/RNA synthesis inhibitor by intercalating into DNA and interacts with topoisomerase II, used as an ant...

CAS 56390-09-1 Epirubicin Hydrochloride

Epirubicin Hydrochloride
(CAS: 56390-09-1)

Epirubicin HCl, a semisynthetic L-arabino derivative of doxorubicin, is an antineoplastic agent by inhibiting Topoisomerase.

CP 117227
(CAS: 154531-78-9)

CP 117227, a dibenzocyclohepten derivative, has been found to be a Type II DNA topoisomerase inhibitor that was once developed in studies of anticancer.

CAS 4707-32-8 β-Lapachone

β-Lapachone
(CAS: 4707-32-8)

β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae), exhibiting anti-inflammatory properties by suppr...

CAS 51264-14-3 Amsacrine

Amsacrine
(CAS: 51264-14-3)

Amsacrine is an antineoplastic agent which can intercalate into the DNA of tumor cells. It also expresses topoisomerase inhibitor activity, specifically inhibit...

CAS 33419-42-0 Etoposide

Etoposide
(CAS: 33419-42-0)

Etoposide is a semisynthetic derivative of podophyllotoxin, which inhibits DNA synthesis via topoisomerase II inhibition activity.

SW044248
(CAS: 522650-83-5)

SW044248 is a potent and selective Topoisomerase I inhibitor. SW044248 killed approximately 15% of a panel of 74 NSCLC cell lines and was nontoxic to immortaliz...

CAS 123948-87-8 Topotecan

Topotecan
(CAS: 123948-87-8)

Topotecan has been used as a positive control for the identification and analysis of HIF-1α and VEGF inhibitors in human glioma cells under hypoxic conditions. ...

CAS 151271-53-3 UK-1

UK-1
(CAS: 151271-53-3)

UK-1, a benzoxazol derivative, has been found to a Streptomyces metabolite that could exhibit anticancer activity and topoisomerase II restraination activity.

Elomotecan HCl salt
(CAS: 220997-99-9)

Elomotecan, also referred to BN 80927 and R 1559, characterized by a stable seven-membered beta-hydroxylactone ring, is a DNA topoisomerase inhibitor. In vivo e...

CAS 95343-20-7 Pirarubicin Hydrochloride

Pirarubicin Hydrochloride
(CAS: 95343-20-7)

Pirarubicin Hydrochloride is an analogue of the anthracycline anti-neoplastic doxorubicin, which is an inhibitor of Topo II. It intercalates into DNA and intera...

CAS 70476-82-3 Mitoxantrone HCl

Mitoxantrone HCl
(CAS: 70476-82-3)

Mitoxantrone is a type II topoisomerase inhibitor with IC50 of 2.0 μM, 0.42 mM for HepG2 and MCF-7/wt cells, respectively.

CAS 119413-54-6 Topotecan Hydrochloride

Topotecan Hydrochloride
(CAS: 119413-54-6)

Topocecan is a semisynthetic derivative of camptothecin with antineoplastic activity. During the S phase of the cell cycle, topotecan selectively stabilizes top...

CAS 69408-81-7 Amonafide dihydrochloride

Amonafide dihydrochloride
(CAS: 69408-81-7)

Amonafide dihydrochloride is the dihydrochloride salt of amonafide, an imide derivative of naphthalic acid. Amonafide intercalates into DNA and inhibits topoiso...

ABT-719 HCl
(CAS: 162763-53-3)

The hydrochloride salt form of ABT-719, a fluoroquinolone derivative, has been found to be a DNA topoisomerase inhibitor that was once developed in antibacteria...

CAS 65271-80-9 Mitoxantrone

Mitoxantrone
(CAS: 65271-80-9)

Mitoxantrone is a type II topoisomerase inhibitor with IC50 of 2.0 μM, 0.42 mM for HepG2 and MCF-7/wt cells, respectively. It is used in the treatment of certai...

CAS 78186-34-2 Bisantrene Dihydrochloride

Bisantrene Dihydrochloride
(CAS: 78186-34-2)

Bisantrene Dihydrochloride is the hydrochloride salt of Bisantrene. Bisantrene, also referred to CL-216942, Cyabin or NSC-337766, an anthracene bishydrazone der...

CAS 174634-09-4 TAS-103

TAS-103
(CAS: 174634-09-4)

TAS-103, also known as BMS-247615, is a quinoline derivative that displays antitumor activity in murine and human tumor models. TAS-103 has been reported to be ...

Reference Reading


1.Generation of hydroxyl radical by anticancer quinone drugs, carbazilquinone, mitomycin C, aclacinomycin A and adriamycin, in the presence of NADPH-cytochrome P-450 reductase.
Komiyama T, Kikuchi T, Sugiura Y. Biochem Pharmacol. 1982 Nov 15;31(22):3651-6.
The generation of hydroxyl free radicals in the system consisting of purified NADPH-cytochrome P-450 reductase and anticancer quinone drugs, such as carbazilquinone, mitomycin C, aclacinomycin A and adriamycin, has been confirmed by two methods. In the spin trapping study, using N-tert-butyl-alpha-phenylnitrone as the spin trapping agent, four drugs generated hydroxyl radical-trapped signals, and the formation of the spin adduct was dependent on time and the enzyme concentration. Among the four drugs, the generation time of signal was in the order of carbazilquinone, aclacinomycin A, adriamycin and mitomycin C, but the magnitude of signal intensity was different. In both aclacinomycin A and adriamycin, the signal disappeared in a few minutes. Catalase completely inhibited the formation of the spin adduct, while superoxide dismutase did not significantly inhibit, but effected in some manner. The generation of hydroxyl radical was also confirmed by the ethylene production from methional.
2.Antitumor activity of mitoxantrone against murine experimental tumors: comparative analysis against various antitumor antibiotics.
Fujimoto S, Ogawa M. Cancer Chemother Pharmacol. 1982;8(2):157-62.
1,4-Dihydroxy-5,8-bis(((2-[(2-hydroxyethyl) amino] ethyl)amino))-9,10-anthracenedione dihydrochloride (mitoxantrone) was tested for antitumor activity against experimental tumors in mice and the results were compared with those of seven antitumor antibiotics: adriamycin (ADM), daunomycin (DM), aclarubicin, mitomycin C (MNC), bleomycin, neocarzinostatin, and chromomycin A3. The drugs were given IP or IV, in general on days 1, 5, and 9 following tumor inoculation. Mitoxantrone given IP at the optimal dose (1.6 mg/kg/day; as a free base) produced a statistically significant number of 60-day survivors (curative effect) in mice with IP implanted L1210 leukemia. The curative effect was not observed with any of the other antibiotics. In the case of IV implanted L1210 leukemia, there was an increase in lifespan (ILS) by more than 100% in the mice following IV treatment with mitoxantrone or DM. In IP implanted P388 leukemia, the curative effect was elicited by IP treatment with mitoxantrone or MMC.
3.Interactions of anticancer quinone drugs, aclacinomycin A, adriamycin, carbazilquinone, and mitomycin C, with NADPH-cytochrome P-450 reductase, xanthine oxidase and oxygen.
Komiyama T, Kikuchi T, Sugiura Y. J Pharmacobiodyn. 1986 Aug;9(8):651-64.
The properties of the interactions of anticancer quinone drugs, aclacinomycin A, adriamycin, carbazilquinone, and mitomycin C with nicotinamide adenine dinucleotide phosphate (NADPH)-cytochrome P-450 reductase and xanthine oxidase under anaerobic and aerobic conditions were studied. Km values of NADPH-cytochrome P-450 reductase for these drugs were in the range of 40-227 microM, and that of deflavo xanthine oxidase in the range of 39-over 200 microM. Under anaerobic conditions, when xanthine was used as an electron donor, deflavo xanthine oxidase catalyzed the reductive glycosidic cleavage reaction of anthracyclines and nicotinamide adenine dinucleotide was ineffective as an electron donor. In the electron spin resonance study, the formation of the semiquinone or free radical state of the quinone drugs in both enzyme systems were evidenced. A weak and symmetric signal was obtained from aclacinomycin A, and a symmetric signal from adriamycin was changed into an asymmetric and strong.
4.Thermodynamics of the anthracycline-nuclei interactions in drug-resistant and drug-sensitive K562 cells.
Tarasiuk J1, Garnier-Suillerot A. Biochem Pharmacol. 1992 Jun 23;43(12):2575-80.
Fluorescence emission spectra from anthracycline-treated cells suspended in buffer have been used to measure the uptake of three anthracycline derivatives: Adriamycin (ADR), 4'-o-tetrahydropyranyl-Adriamycin (THP-ADR) and aclacinomycin (ACM) in drug-sensitive and drug-resistant K562 cells. The concentration of drug bound to the nucleus and free in the cytoplasm, at steady state, as well as the concentration of drug bound to the nucleus at equilibrium state have been determined at temperatures ranging from 6 degrees to 40 degrees. The enthalpies for the binding of ADR, THP-ADR and ACM to nuclei equal -35 +/- 3, -35 +/- 3 and -30 +/- 3 kJ/mol, respectively. These values compare with the enthalpies of binding of these drugs to naked DNA.