Cat. No.: HY-19825

Rebeccamycin

Rebeccamycin, an antitumor antibiotic, inhibits DNA topoisomerase I. Rebeccamycin appears to exert its primary antineoplastic effect by poisoning topoisomerase I and has negligible effect on protein kinase C and topoisomerase II.

For research use only. We do not sell to patients.

CAS No.: 93908-02-2
Formula: C₂₇H₂₁Cl₂N₃O₇
Molecular Weight:570.38

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (278 KB)

Rebeccamycin Chemical Structure

CAS No.: 93908-02-2

Size

Price

Stock

Quantity

Amount: USD 0.00

* Please select Quantity before adding items.

Top Publications Citing

Use of MCE Products

One-stop CDMO Service

One-Stop Platform：From Independent R&D to Pilot-Scale Production

Biological Activity
- Description
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Bioz

Biological Activity

Description

IC₅₀ & Target^[1]

Topoisomerase I

Traditional Cytotoxic Agents

All Topoisomerase Isoforms :

All ADC Payloads Isoforms :

All Antibiotic Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	0.3 μM Compound: 1 ; Rebeccamycin	Antiproliferative activity in vitro against A549 (human non-small lung carcinoma) cell line. Antiproliferative activity in vitro against A549 (human non-small lung carcinoma) cell line.	[PMID: 11882002]
B16	IC₅₀	0.48 μM Compound: 1	Inhibition of murine B16 Melanoma cell proliferation Inhibition of murine B16 Melanoma cell proliferation	[PMID: 9341921]
B16	IC₅₀	0.48 μM Compound: 1 (Rebeccamycin)	Antiproliferative activity measured against murine B16 melanoma cells Antiproliferative activity measured against murine B16 melanoma cells	[PMID: 9572888]
B16	IC₅₀	0.48 μM Compound: 1 ; Rebeccamycin	Antiproliferative activity against B16 mouse melanoma cells Antiproliferative activity against B16 mouse melanoma cells	[PMID: 8893841]
CEM-SS	CC₅₀	1.05 μM Compound: 1	The cytotoxicity was evaluated in in HIV -I Lai infected CEM-SS cells. The cytotoxicity was evaluated in in HIV -I Lai infected CEM-SS cells.	[PMID: 10346933]
CEM-SS	CC₅₀	1.05 μM Compound: 1 (Rebeccamycin)	Cytotoxicity against HIV-1 Lai infected CEM-SS cells Cytotoxicity against HIV-1 Lai infected CEM-SS cells	[PMID: 10052965]
CEM-SS	CC₅₀	1.05 μM Compound: 1 (Rebeccamycin)	Cytotoxic concentration is tested against CEM-SS cells Cytotoxic concentration is tested against CEM-SS cells	[PMID: 9572888]
CEM-SS	IC₅₀	0.52 μM Compound: 1 (Rebeccamycin)	Anti-HIV-1 activity in CEM-SS cells was measured by the quantification of the reverse transcriptase activity, associated with the virus particles released from HIV-1 infected cells in the culture medium. Anti-HIV-1 activity in CEM-SS cells was measured by the quantification of the reverse transcriptase activity, associated with the virus particles released from HIV-1 infected cells in the culture medium.	[PMID: 10052965]
CEM-SS	IC₅₀	0.52 μM Compound: 1	Compound was tested for anti-HIV activity in HIV -I Lai infected CEM-SS cells. Compound was tested for anti-HIV activity in HIV -I Lai infected CEM-SS cells.	[PMID: 10346933]
CEM-SS	IC₅₀	0.52 μM Compound: 1 (Rebeccamycin)	Inhibitory concentration is tested in HIV-1 Lai-infected CEM-SS cells Inhibitory concentration is tested in HIV-1 Lai-infected CEM-SS cells	[PMID: 9572888]
HT-29	IC₅₀	0.3 μM Compound: 1 ; Rebeccamycin	Antiproliferative activity in vitro against HT-29 (human colon carcinoma) cell line. Antiproliferative activity in vitro against HT-29 (human colon carcinoma) cell line.	[PMID: 11882002]
HT-29	IC₅₀	0.3 μM Compound: Rebeccamycin	In vitro antiproliferative activity against human colon carcinoma HT-29 cells In vitro antiproliferative activity against human colon carcinoma HT-29 cells	[PMID: 15743184]
K562	IC₅₀	0.2 μM Compound: 1 ; Rebeccamycin	Antiproliferative activity in vitro against K-562 (human leukemia) cell line. Antiproliferative activity in vitro against K-562 (human leukemia) cell line.	[PMID: 11882002]
K562	IC₅₀	4 μM Compound: Reb	Anticancer activity against human K562 cells Anticancer activity against human K562 cells	[PMID: 18653350]
K562	IC₅₀	6 μM Compound: Rebeccamycin	Inhibitory concentration against K5662 leukemia cell line in MTS assay Inhibitory concentration against K5662 leukemia cell line in MTS assay	[PMID: 15801850]
L1210	IC₅₀	0.1 μM Compound: 1 ; Rebeccamycin	Antiproliferative activity tested in vitro against L1210 (murine leukemia) cell line. Antiproliferative activity tested in vitro against L1210 (murine leukemia) cell line.	[PMID: 11882002]
L1210	IC₅₀	0.14 μM Compound: Rebeccamycin	Cytotoxicity activity against mouse L1210 cells by MTT assay Cytotoxicity activity against mouse L1210 cells by MTT assay	[PMID: 20566289]
L1210	IC₅₀	0.14 μM Compound: Rebeccamycin	In vitro antiproliferative activity against murine leukemia L1210 cells In vitro antiproliferative activity against murine leukemia L1210 cells	[PMID: 15743184]
P388	IC₅₀	0.3 μM Compound: 1 ; Rebeccamycin	Antiproliferative activity against P388 Murine Leukemia cells Antiproliferative activity against P388 Murine Leukemia cells	[PMID: 8893841]
P388	IC₅₀	0.5 μM Compound: 1	Inhibition of P388 murine leukemia cell proliferation Inhibition of P388 murine leukemia cell proliferation	[PMID: 9341921]
P388	IC₅₀	1.22 μM Compound: 1	In vitro inhibitory concentration against murine P388 leukemia cell proliferation In vitro inhibitory concentration against murine P388 leukemia cell proliferation	[PMID: 10346933]
P388	IC₅₀	1.22 μM Compound: 1 (Rebeccamycin)	Cytotoxicity against P388 leukemia cells Cytotoxicity against P388 leukemia cells	[PMID: 10052965]
P388	IC₅₀	1.22 μM Compound: 1 (Rebeccamycin)	Antiproliferative activity measured against P388 Leukemia cells Antiproliferative activity measured against P388 Leukemia cells	[PMID: 9572888]
P388	IC₅₀	10.5 μM Compound: 1 (Rebeccamycin)	Cytotoxicity against P388/CPT5 leukemia cells. Cytotoxicity against P388/CPT5 leukemia cells.	[PMID: 10052965]
P388CPT5	IC₅₀	10.5 μM Compound: 1	In vitro inhibitory concentration against murine P388CPT5 leukemia cell proliferation In vitro inhibitory concentration against murine P388CPT5 leukemia cell proliferation	[PMID: 10346933]
P388CPT5	IC₅₀	10.5 μM Compound: 1 (Rebeccamycin)	Antiproliferative activity measured against P388CPT5 cells resistant to Topoisomerase I inhibitor Camptothecin Antiproliferative activity measured against P388CPT5 cells resistant to Topoisomerase I inhibitor Camptothecin	[PMID: 9572888]
SW-620	IC₅₀	4 μM Compound: Reb	Anticancer activity against human SW620 cells Anticancer activity against human SW620 cells	[PMID: 18653350]
SW-620	IC₅₀	4 μM Compound: Rebeccamycin	Inhibitory concentration against SW620 colorectal carcinoma cell line in MTS assay Inhibitory concentration against SW620 colorectal carcinoma cell line in MTS assay	[PMID: 15801850]

In Vitro

Rebeccamycin is an antitumor antibiotic produced by the actinomycete Saccharotrix aerocolonigenes with activity against several human tumor cell lines, including A549 (lung adenocarcinoma), HCT-116 (colon carcinoma), and KB (nasopharyngeal carcinoma) ^[1].
Rebeccamycin shows antibacterial activity against several Gram-positive bacteria, including Staphylococcus aureus and Streptococcus faecalis^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Rebeccamycin (2-256 mg/kg; i.p.; daily for 9 days) prolongs survival in B16 melanoma, L1210 leukemia^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

CDF1 mice (B16 melanoma, L1210 leukemia)^[2]
Dosage:

2, 4, 8, 16, 32, 64, 128, 256 mg/kg
Administration:

I.p.; daily for 9 days
Result:

Prolongation of survival of the mice at dose levels ranging from 8 to 256 mg/kg.

Chemical Information

CAS No. 93908-02-2
Molecular Weight 570.38
Formula C₂₇H₂₁Cl₂N₃O₇
SMILES

O=C(N1)C(C2=C3N([C@@H]([C@@H]([C@@H](O)[C@@H]4OC)O)O[C@@H]4CO)C5=C2C=CC=C5Cl)=C(C(C6=CC=C7)=C3NC6=C7Cl)C1=O
Structure Classification
- Antibiotics
- Other Antibiotics
Initial Source
- Microorganisms
the mycelium
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (278 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Merchant J, et al. Phase I clinical and pharmacokinetic study of NSC 655649, a rebeccamycin analogue, given in both single-dose and multiple-dose formats. Clin Cancer Res. 2002 Jul;8(7):2193-201. [Content Brief]

[2]. Bush JA, et al. Production and biological activity of rebeccamycin, a novel antitumor agent. J Antibiot (Tokyo). 1987 May;40(5):668-78. [Content Brief]

[3]. Sánchez C, et al. The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem Biol. 2002 Apr;9(4):519-31. [Content Brief]

Calculators

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Dilution Calculator

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Keywords

Product Name:
Cat. No.:
Quantity:
MCE Japan Authorized Agent:

Product Name:
CAS No.:
Species:
Purity:
Quantity:

Rebeccamycin

All Topoisomerase Isoforms

All ADC Payloads Isoforms

All Antibiotic Isoforms