KW 2149 | CAS#118359-59-4 | mitomycin C derivative

MedKoo Cat#: 597293 | Name: KW 2149

Description:

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

KW 2149 is a derivative of mitomycin C.

Chemical Structure

KW 2149

CAS#118359-59-4

Theoretical Analysis

MedKoo Cat#: 597293

Name: KW 2149

CAS#: 118359-59-4

Chemical Formula: C24H34N6O8S2

Exact Mass: 598.1880

Molecular Weight: 598.69

Elemental Analysis: C, 48.15; H, 5.72; N, 14.04; O, 21.38; S, 10.71

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 #

No Data

Synonym

KW 2149; KW-2149; KW2149; KT6149;

IUPAC/Chemical Name

(2-((2-(((1aS,8S,8aR,8bS)-8-((carbamoyloxy)methyl)-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-6-yl)amino)ethyl)disulfanyl)ethyl)-L-glutamine

InChi Key

WAPQQYLIKWNWHP-CYUGEGSCSA-N

InChi Code

InChI=1S/C24H34N6O8S2/c1-11-17(28-6-8-40-39-7-5-27-13(22(34)35)3-4-15(25)31)20(33)16-12(10-38-23(26)36)24(37-2)21-14(29-21)9-30(24)18(16)19(11)32/h12-14,21,27-29H,3-10H2,1-2H3,(H2,25,31)(H2,26,36)(H,34,35)/t12-,13+,14+,21+,24-/m1/s1

SMILES Code

O=C(N)CC[C@@H](C(O)=O)NCCSSCCNC(C(C1=C2N3[C@@]([C@](N4)([H])[C@]4([H])C3)(OC)[C@@H]1COC(N)=O)=O)=C(C)C2=O

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

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 598.69 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.

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: Lee SH, Kohn H. 7-N,7'-N'-(1",2"-Dithianyl-3",6"-dimethylenyl)bismitomycin C: synthesis and nucleophilic activation of a dimeric mitomycin. Org Biomol Chem. 2005 Feb 7;3(3):471-82. Epub 2005 Jan 6. PubMed PMID: 15678185. 2: Lee SH, Kohn H. Cyclic disulfide C8 iminoporfiromycin: nucleophilic activation of a porfiromycin. J Am Chem Soc. 2004 Apr 7;126(13):4281-92. PubMed PMID: 15053618. 3: van Acker FA, van Acker SA, Haenen GR, Bast A, van der Vijgh WJ. In vitro screening of antitumour agents for cardiotoxicity by means of isolated mouse left atria. Anticancer Res. 2000 Nov-Dec;20(6B):4483-7. PubMed PMID: 11205292. 4: Takaba K, Furumoto H, Ikegami J, Suzuki K, Takahashi J, Hara T, Ishii A. Inhibitory effects of subcutaneous dexamethasone treatment on rat pulmonary toxicity of KW-2149, a new mitomycin C analogue. Arch Toxicol. 2000 Apr;74(2):106-11. PubMed PMID: 10839478. 5: Zhang ZD, Guetens G, De Boeck G, Van Cauwenberghe K, Maes RA, Ardiet C, van Oosterom AT, Highley M, de Bruijn EA, Tjaden UR. Simultaneous determination of the peptide-mitomycin KW-2149 and its metabolites in plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 2000 Mar 10;739(2):281-9. PubMed PMID: 10755372. 6: Harada T, Takaba K, Hara T, Yamamoto N, Tamura T, Saijo N, Ishii A. Inhibitory effects of repeated intravenous injections of dexamethasone on pulmonary toxicity of a new mitomycin C analogue, KW-2149, in a novel rat model. J Toxicol Sci. 2000 Feb;25(1):11-5. PubMed PMID: 10736785. 7: Schrijvers D, Catimel G, Highley M, Höppener FJ, Dirix L, De Bruijn E, Droz JP, Van Oosterom AT. KW-2149-induced pulmonary toxicity is not prevented by corticosteroids: a phase I and pharmacokinetic study. Anticancer Drugs. 1999 Aug;10(7):633-9. PubMed PMID: 10507312. 8: Highley MS, van Oosterom AT, Maes RA, De Bruijn EA. Intravesical drug delivery. Pharmacokinetic and clinical considerations. Clin Pharmacokinet. 1999 Jul;37(1):59-73. Review. PubMed PMID: 10451783. 9: Wang S, Kohn H. Studies on the mode of action of mitomycin C(7) aminoethylene disulfides (BMS-181174 and KW-2149): reactivity of 7-N-(mercaptoethyl)mitomycin C. J Med Chem. 1999 Mar 11;42(5):788-90. PubMed PMID: 10072677. 10: Rohde D, Raffenberg G, Kaviani S, Wolff J, Jakse G. 7-N-(2-([2-(gamma-L-glutamylamino)-ethyl]-dithio)-ethyl)-mitomycin C (KW-2149) is more active than mitomycin C on chemonaive and drug-resistant urothelial carcinoma cells. Urol Res. 1998;26(4):243-7. PubMed PMID: 9759997. 11: McAdam SR, Knox RJ, Hartley JA, Masters JR. KW-2149 (7-N-[2-[gamma-L-glutamylamino]ethyldithioethyl] mitomycin C): DNA interactions and drug uptake following serum activation. Biochem Pharmacol. 1998 Jun 1;55(11):1777-83. PubMed PMID: 9714295. 12: Tomasz M, Palom Y. The mitomycin bioreductive antitumor agents: cross-linking and alkylation of DNA as the molecular basis of their activity. Pharmacol Ther. 1997 Oct-Dec;76(1-3):73-87. Review. PubMed PMID: 9535170. 13: Saijo N. New chemotherapeutic agents for the treatment of non-small cell lung cancer: the Japanese experience. Chest. 1998 Jan;113(1 Suppl):17S-23S. Review. PubMed PMID: 9438685. 14: Dirix LY, Libura M, Libura J, Vermeulen PB, De Bruijn EA, Van Oosterom AT. In vitro toxicity studies with mitomycins and bleomycin on endothelial cells. Anticancer Drugs. 1997 Oct;8(9):859-68. PubMed PMID: 9402313. 15: Mikami K, Shirakusa T, Tsuruo T. [DT-diaphorase]. Gan To Kagaku Ryoho. 1997 Sep;24(11):1606-10. Review. Japanese. PubMed PMID: 9309161. 16: Ishida T, Nishio K, Kurokawa H, Arioka H, Fukumoto H, Fukuoka K, Nomoto T, Yokote H, Hasegawa S, Saijo N. Circumvention of glutathione-mediated mitomycin C resistance by a novel mitomycin C analogue, KW-2149. Int J Cancer. 1997 Sep 4;72(5):865-70. PubMed PMID: 9311606. 17: Yasuzawa T, Tomer KB. Structural determination of the conjugate of human serum albumin with a mitomycin C derivative, KW-2149, by matrix-assisted laser desorption/ionization mass spectrometry. Bioconjug Chem. 1997 May-Jun;8(3):391-9. PubMed PMID: 9177846. 18: Masters JR, Know RJ, Hartley JA, Kelland LR, Hendriks HR, Connors T. KW-2149 (7-N-[2-[gamma-L-glutamylamino]ethyldithioethyl]mitomycin C). A new mitomycin C analogue activated by serum. Biochem Pharmacol. 1997 Feb 7;53(3):279-85. PubMed PMID: 9065731. 19: Nishio K, Kurokawa H, Ishida T, Fukuoka K, Saijo N. [gamma-Glutamylcysteine synthetase and chemosensitivity]. Gan To Kagaku Ryoho. 1997 Feb;24(4):418-23. Review. Japanese. PubMed PMID: 9063478. 20: Egelmeers A, Dirix LY, Lyczek J, De Bruijn EA, Van Oosterom AT, Scalliet P. The influence of hypoxia on the cytotoxicity of concomitant KW-2149 and ionizing irradiation in Chinese hamster fibroblasts. Anticancer Drugs. 1996 Jul;7(5):586-90. PubMed PMID: 8862727.