Synthesis of a Novel Cysteine-Incorporated Anthraquinone Derivative and Its Structural Properties

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2015 Jun 6

PMID 26046319

Authors

Akihiro Nomoto

Toshihide Taniguchi

Yuta Minatobe

Syouhei Katao

Kiyomi Kakiuchi

Shigenobu Yano

Akiya Ogawa

Affiliations

Soon will be listed here.

Abstract

A novel cysteine-incorporated anthraquinone derivative was synthesized, and its molecular structure was determined by X-ray crystal analysis. Each mercapto group was located separately and did not form a disulfide bond, and hydrogen bondings and π-π interaction were observed from the packing structure.

References

Rudolph J, Theis H, Hanke R, Endermann R, Johannsen L, Geschke F . seco-Cyclothialidines: new concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties. J Med Chem. 2001; 44(4):619-26. DOI: 10.1021/jm0010623. View

Moriuchi T, Nomoto A, Yoshida K, Ogawa A, Hirao T . Chirality organization of ferrocenes bearing podand dipeptide chains: synthesis and structural characterization. J Am Chem Soc. 2001; 123(1):68-75. DOI: 10.1021/ja002869n. View

Nakanishi W, Hayashi S, Itoh N . First linear alignment of five C-Se...O...Se-C atoms in anthraquinone and 9-(methoxy)anthracene bearing phenylselanyl groups at 1,8-positions. Chem Commun (Camb). 2003; (1):124-5. DOI: 10.1039/b209261a. View

Jacob C, Giles G, Giles N, Sies H . Sulfur and selenium: the role of oxidation state in protein structure and function. Angew Chem Int Ed Engl. 2003; 42(39):4742-58. DOI: 10.1002/anie.200300573. View

Suzuki A, Hasegawa M, Ishii M, Matsumura S, Toshima K . Anthraquinone derivatives as a new family of protein photocleavers. Bioorg Med Chem Lett. 2005; 15(20):4624-7. DOI: 10.1016/j.bmcl.2005.05.137. View

Utsuno M, Yutaka T, Murata M, Kurihara M, Tamai N, Nishihara H . Synthesis of pendant-type anthraquinone-bridged cofacial dinuclear platinum(II) complexes and their emission properties. Inorg Chem. 2007; 46(26):11291-6. DOI: 10.1021/ic700953k. View

Iwaoka M, Ooka R, Nakazato T, Yoshida S, Oishi S . Synthesis of selenocysteine and selenomethionine derivatives from sulfur-containing amino acids. Chem Biodivers. 2008; 5(3):359-74. DOI: 10.1002/cbdv.200890037. View

Spek A . Structure validation in chemical crystallography. Acta Crystallogr D Biol Crystallogr. 2009; 65(Pt 2):148-55. PMC: 2631630. DOI: 10.1107/S090744490804362X. View

Chalker J, Bernardes G, Lin Y, Davis B . Chemical modification of proteins at cysteine: opportunities in chemistry and biology. Chem Asian J. 2009; 4(5):630-40. DOI: 10.1002/asia.200800427. View

10.

Zagotto G, Ricci A, Vasquez E, Sandoli A, Benedetti S, Palumbo M . Tuning G-quadruplex vs double-stranded DNA recognition in regioisomeric lysyl-peptidyl-anthraquinone conjugates. Bioconjug Chem. 2011; 22(10):2126-35. DOI: 10.1021/bc200389w. View

11.

Kobori Y, Fuki M . Protein-ligand structure and electronic coupling of photoinduced charge-separated state: 9,10-anthraquinone-1-sulfonate bound to human serum albumin. J Am Chem Soc. 2011; 133(42):16770-3. DOI: 10.1021/ja206898j. View