Development of anti-HIV agents targeting dynamic supramolecular mechanism: Entry and fusion inhibitors based on CXCR4/CCR5 antagonists and gp41-C34-remodeling peptides

Current HIV Research

Volumn 3, Issue 4, 2005, Pages 289-301

  Tamamura, Hirokazu ^a   Otaka, Akira ^b   Fujii, Nobutaka ^c  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

AIDS; Artificial remodeling; Cancer metastasis; Chemokine; Fusion inhibitor; Low molecular weight CXCR4 antagonist; Rheumatoid arthritis; X4 HIV 1 entry

Indexed keywords

1 ACETYL N [3 [4 (4 CARBAMOYLBENZYL) 1 PIPERIDINYL]PROPYL] N (3 CHLORO 4 METHYLPHENYL) 4 PIPERIDINECARBOXAMIDE; 1,1' [1,4 PHENYLENEBIS(METHYLENE)]BIS(1,4,8,11 TETRAAZACYCLOTETRADECANE); 4,4' [CARBONYLBIS[IMINO 1H PYRROLE 4,2 DIYLCARBONYLIMINO(1 METHYL 1H PYRROLE 4,2 DIYL)CARBONYLIMINO]]BIS(1,7 NAPHTHALENESULFONIC ACID); AMD 070; AMD 3465; AMD 8665; AMPELOPSIN; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTINEOPLASTIC AGENT; APLAVIROC; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CXCR4; CHEMOKINE RECEPTOR CXCR4 ANTAGONIST; CHEMOKINE RECEPTOR CXCR5; CHEMOKINE RECEPTOR CXCR5 ANTAGONIST; DISTAMYCIN A DERIVATIVE; ENDOTHELIN RECEPTOR ANTAGONIST; ENFUVIRTIDE; FC 131; FLAVONOID; GLYCOPROTEIN GP 120; GLYCOPROTEIN GP 41; KRH 1636; N [4 [[[6,7 DIHYDRO 2 (4 METHYLPHENYL) 5H BENZOCYCLOHEPTEN 8 YL]CARBONYL]AMINO]BENZYL] N,N DIMETHYL 2H TETRAHYDROPYRAN 4 AMINIUM CHLORIDE; PEPTIDE DERIVATIVE; PROTEINASE INHIBITOR; RNA DIRECTED DNA POLYMERASE INHIBITOR; T 140; T 22; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; CANCER INHIBITION; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG TARGETING; HIGHLY ACTIVE ANTIRETROVIRAL THERAPY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IN VITRO STUDY; METASTASIS; MOLECULAR MECHANICS; MOLECULAR WEIGHT; NONHUMAN; PHARMACOLOGICAL BLOCKING; PROTEIN INTERACTION; REVIEW; RHEUMATOID ARTHRITIS; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE; VIRUS STRAIN;

AMINO ACID SEQUENCE; HIV ENVELOPE PROTEIN GP41; HIV FUSION INHIBITORS; HUMANS; MOLECULAR SEQUENCE DATA; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; RECEPTORS, CCR5; RECEPTORS, CXCR4;

EID: 27844544370     PISSN: 1570162X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016205774370429     Document Type: Review

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84. Tamamura H, Hiramatsu K, Ueda S, Wang Z, Kusano S, Terakubo S, Trent JO, Peiper SC, Yamamoto N, Nakashima H, Otaka A, Fujii N. (2005). Stereoselective synthesis of [L-Arg-L/D-3-(2-naphthyl)alanine]-type (E)-alkene dipeptide isosteres and its application to the synthesis and biological evaluation of pseudopeptide analogues of the CXCR4 antagonist FC131. Journal of Medicinal Chemistry. 48: 380-391.
85. Tamamura H, Hori A, Kanzaki N, Hiramatsu K, Mizumoto M, Nakashima H, Yamamoto N, Otaka A, Fujii N. (2003). T140 analogs as CXCR4 antagonists identified as anti-metastatic agents in the treatment of breast cancer. FEBS Letters. 550: 79-83.
86. Tamamura H, Koh Y, Ueda S, Sasaki Y, Yamasaki T, Aoki M, Maeda K, Watai Y, Arikuni H, Otaka A, Mitsuya H, Fujii N. (2003). Reduction of peptide character of HIV protease inhibitors that exhibit nanomolar potency against multidrug resistant HIV-1 strains. Journal of Medicinal Chemistry. 46: 1764-1768.
87. Tamamura H, Omagari A, Hiramatsu K, Gotoh K, Kanamoto T, Xu Y, Kodama E, Matsuoka M, Hattori T, Yamamoto N, Nakashima H, Otaka A, Fujii N. (2001). Development of specific CXCR4 inhibitors possessing high selectivity indexes as well as complete stability in serum based on an anti-HIV peptide T140. Bioorganic & Medicinal chemistry Letters. 11: 1897-1902.
88. Tamamura H, Omagari A, Oishi S, Kanamoto T, Yamamoto N, Peiper SC, Nakashima H, Otaka A, Fujii N. (2000). Pharmacophore identification of a specific CXCR4 inhibitor, T140, leads to development of effective anti-HIV agents with very high selectivity indexes. Bioorganic & Medicinal chemistry Letters. 10: 2633-2637.
89. Tamamura H, Otaka A, Murakami T, Ishihara T, Ibuka T, Waki M, Matsumoto A, Yamamoto N, Fujii N. (1996). Interaction of an anti-HIV peptide, T22, with GP120 and CD4. Biochemical and Biophysical Research Communications. 219: 555-559.
90. Tamamura H, Sugioka M, Odagaki Y, Omagari A, Kan Y, Oishi S, Nakashima H, Yamamoto N, Peiper SC, Hamanaka N, Otaka A, Fujii N. (2001). Conformational study of a highly specific CXCR4 inhibitor, T140, disclosing the close proximity of its intrinsic pharmacophores associated with strong anti-HIV activity. Bioorganic & Medicinal Chemistry Letters. 11: 359-362 and 2409.
91. Tamamura H, Xu Y, Hattori T, Zhang X, Arakaki R, Kanbara K, Omagari A, Otaka A, Ibuka T, Yamamoto N, Nakashima H, Fujii N. (1998). A low-molecular-weight inhibitor against the chemokine receptor CXCR4: A strong anti-HIV peptide T140. Biochemical and Biophysical Research Communications. 253: 877-882.
92. Tamamura H, Yamashita M, Muramatsu H, Ohno H, Ibuka T, Otaka A, Fujii N. (1997). Regiospecific ring-opening reactions of aziridines bearing an α,β-unsaturated ester group with trifluoroacetic acid or methanesulfonic acid: application to the stereoselective synthesis of (E)-alkene dipeptide isosteres. Chemical Communications. 2327-2328.
93. Tamamura H, Yamashita M, Nakajima Y, Sakano K, Otaka A, Ohno H, Ibuka T, Fujii N. (1999). Regiospecific ring-opening reactions of β-aziridinyl α,β-enoates with acids: application to the stereoselective synthesis of a couple of diastereoisomeric (E)-alkene dipeptide isosteres from a single β-aziridinyl α,β-enoate and to the convenient preparation of amino alcohols bearing α,β-unsaturated ester groups. Journal of the Chemical Society-Perkin Transactions 1 2983-2996.
94. Tashiro K, Tada H, Heilker R, Shirozu M, Nakano T, Honjo T. (1993). Signal sequence trap - a cloning strategy for secreted proteins and type-I membrane-proteins. Science. 261: 600-603.
95. Trent JO, Wang Z, Murray JL, Shao W, Tamamura H, Fujii N, Peiper SC. (2003). Lipid bilayer simulations of CXCR4 with inverse agonists and weak partial agonists. Journal of Biological Chemistry. 278: 47136-47144.
96. Tsukada N, Burger JA, Zvaifler NJ, Kipps TJ. (2002). Distinctive features of "nurselike" cells that differentiate in the context of chronic lymphocytic leukemia. Blood. 99: 1030-1037.
97. Vermeire K, Hatse S, Princen K, De Clercq E, Calandra G, Skerlj R, Bridger G, Schols D. (2004). Virus resistance to the CXCR4 inhibitor AMD070 develops slowly and does not induce a co-receptor switch. Antiviral Research. 62: A42-A43.
98. Wermuth J, Goodman SL, Jonczyk A, Kessler H. (1997). Stereoisomerism and biological activity of the selective and superactive αvβ3 integrin inhibitor cyclo(-RGDfV-) and its retro-inverso peptide. Journal of the American Chemical Society. 119: 1328-1335.
99. Wild CT, Greenwell TK, Matthews TJ. (1993). A synthetic peptide from HIV-1 gp41 is a potent inhibitor of virus-mediated cell-cell fusion. AIDS Research and Human Retroviruses. 9: 1051-1053.
100. Wipf P, Fritch PC. (1994). SN2′-Reactions of peptide aziridines - a cuprate-based approach to (E)-alkene isosteres. Journal of Organic Chemistry. 59: 4875-4886.
101. Xu Y, Tamamura H, Arakaki R, Nakashima H, Zhang X, Fujii N, Uchiyama T, Hattori T. (1999). Marked increase in anti-HIV activity, as well as inhibitory activity against HIV entry mediated by CXCR4, linked to enhancement of the binding ability of tachyplesin analogs to CXCR4. AIDS Research and Human Retroviruses. 15: 419-427.
102. Zhang W, Navenot JM, Haribabu B, Tamamura H, Hiramatu K, Omagari A, Pei G, Manfredi JP, Fujii N, Broach JR, Peiper SC. (2002). A point mutation that confers constitutive activity to CXCR4 reveals that T140 is an inverse agonist and that AMD3100 and ALX40-4C axe weak partial agonists. Journal of Biological Chemistry. 277: 24515-24521.