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MedKoo Cat#: 414287 | Name: NB-506 glucuronide

Description:

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

NB-506 glucuronide is an indolocarbazole antitumor agent; a DNA topoisomerase I inhibitor.

Chemical Structure

NB-506 glucuronide
NB-506 glucuronide
CAS#217187-87-6 (glucuronide)

Theoretical Analysis

MedKoo Cat#: 414287

Name: NB-506 glucuronide

CAS#: 217187-87-6 (glucuronide)

Chemical Formula: C33H30N4O16

Exact Mass: 738.1657

Molecular Weight: 738.62

Elemental Analysis: C, 53.66; H, 4.09; N, 7.59; O, 34.66

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
217187-87-6 (glucuronide) 151069-12-4 (free base)
Synonym
NB-506 glucuronide; NB506 glucuronide; NB-506 glucuronide; ED594; ED-594; ED 594
IUPAC/Chemical Name
6-(Formylamino)-12-beta-D-glucopyranosyl-6,7,12,13-tetrahydro-11-hydroxy-5,7-dioxo-5H-indolo(2,3-a)pyrrolo(3,4-C)carbazol-1-yl beta-D-glucopyranosiduronic acid
InChi Key
FSEPVVMERYDPRB-ZLNMQOEFSA-N
InChi Code
InChI=1S/C33H30N4O16/c38-7-13-22(41)23(42)26(45)31(51-13)36-20-10(4-1-5-11(20)40)15-17-16(29(47)37(30(17)48)34-8-39)14-9-3-2-6-12(18(9)35-19(14)21(15)36)52-33-27(46)24(43)25(44)28(53-33)32(49)50/h1-6,8,13,22-28,31,33,35,38,40-46H,7H2,(H,34,39)(H,49,50)/t13-,22-,23+,24+,25+,26-,27-,28+,31-,33-/m1/s1
SMILES Code
O[C@H]([C@H]([C@@H]([C@@H](C(O)=O)O1)O)O)[C@@H]1OC2=CC=CC3=C2NC4=C3C5=C(C(N(NC=O)C5=O)=O)C6=C4N([C@H]7[C@@H]([C@H]([C@@H]([C@@H](CO)O7)O)O)O)C8=C6C=CC=C8O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 738.62 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.

Recalculate based on batch purity %
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: Lansiaux A, Bailly C. Le NB-506 [NB 506]. Bull Cancer. 1999 Mar;86(3):255-8. French. PMID: 10210758. 2: Kanzawa F, Nishio K, Kubota N, Saijo N. Antitumor activities of a new indolocarbazole substance, NB-506, and establishment of NB-506-resistant cell lines, SBC-3/NB. Cancer Res. 1995 Jul 1;55(13):2806-13. PMID: 7796407. 3: Ren J, Bailly C, Chaires JB. NB-506, an indolocarbazole topoisomerase I inhibitor, binds preferentially to triplex DNA. FEBS Lett. 2000 Mar 31;470(3):355-9. doi: 10.1016/s0014-5793(00)01335-1. PMID: 10745096. 4: Urasaki Y, Laco G, Takebayashi Y, Bailly C, Kohlhagen G, Pommier Y. Use of camptothecin-resistant mammalian cell lines to evaluate the role of topoisomerase I in the antiproliferative activity of the indolocarbazole, NB-506, and its topoisomerase I binding site. Cancer Res. 2001 Jan 15;61(2):504-8. PMID: 11212241. 5: Facompre M, Goossens JF, Bailly C. Apoptotic response of HL-60 human leukemia cells to the antitumor drug NB-506, a glycosylated indolocarbazole inhibitor of topoisomerase 1. Biochem Pharmacol. 2001 Feb 1;61(3):299-310. doi: 10.1016/s0006-2952(00)00553-0. PMID: 11172734. 6: Vanhoefer U, Voigt W, Hilger RA, Yin MB, Harstrick A, Seeber S, Rustum YM. Cellular determinants of resistance to indolocarbazole analogue 6-N-formylamino-12,13-dihydro-1,11-dihydroxy-13(beta-D-glucopyranosyl)- 5H-indolo[2,3-alpha]pyrrolo[3,4-c]carbazole-5,7(6H)-dione (NB-506), a novel potent topoisomerase I inhibitor, in multidrug-resistant human tumor cells. Oncol Res. 1997;9(9):485-94. PMID: 9495454. 7: Fukuda M, Nishio K, Kanzawa F, Ogasawara H, Ishida T, Arioka H, Bojanowski K, Oka M, Saijo N. Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells. Cancer Res. 1996 Feb 15;56(4):789-93. PMID: 8631015. 8: Komatani H, Kotani H, Hara Y, Nakagawa R, Matsumoto M, Arakawa H, Nishimura S. Identification of breast cancer resistant protein/mitoxantrone resistance/placenta-specific, ATP-binding cassette transporter as a transporter of NB-506 and J-107088, topoisomerase I inhibitors with an indolocarbazole structure. Cancer Res. 2001 Apr 1;61(7):2827-32. PMID: 11306452. 9: Pilch B, Allemand E, Facompré M, Bailly C, Riou JF, Soret J, Tazi J. Specific inhibition of serine- and arginine-rich splicing factors phosphorylation, spliceosome assembly, and splicing by the antitumor drug NB-506. Cancer Res. 2001 Sep 15;61(18):6876-84. PMID: 11559564. 10: Bailly C, Qu X, Chaires JB, Colson P, Houssier C, Ohkubo M, Nishimura S, Yoshinari T. Substitution at the F-ring N-imide of the indolocarbazole antitumor drug NB-506 increases the cytotoxicity, DNA binding, and topoisomerase I inhibition activities. J Med Chem. 1999 Jul 29;42(15):2927-35. doi: 10.1021/jm990108t. PMID: 10425102.